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1445 Gulf Of Mexico Drive Unit 101, Longboat Key

Step into this highly desirable corner residence featuring three bedrooms, three full baths, and a 36’ x 11’ sunroom at The Players Club. Unique to this residence is a private garage, offering rare security and convenience plus an additional covered under-building parking space. You’ll immediately be drawn to the impressive 31’ balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. An open, white eat-in kitchen is designed with custom cabinetry and extra storage that flows seamlessly into the main living and dining areas. Just off the kitchen, French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The primary bedroom, a private sanctuary with an en-suite bath offers a soaking tub, separate glass-enclosed shower, dual vanities, and a fitted walk-in closet. A second bedroom functions as an additional master with a fitted walk-in closet and en-suite bath with dual sinks. A true third bedroom with two separate fitted closets and an adjacent full bathroom adds flexibility for additional guests. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves and is located Just minutes from St. Armands Circle, downtown Longboat Key, and the Longboat Key Club - with championship golf, premier tennis, and a deep-water marina. One of the largest floor plans available in the community, this residence blends privacy, convenience, and resort-style beachfront living. Offered partially furnished.

3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code

Step into this highly desirable corner residence featuring three bedrooms, three full baths, and a 36’ x 11’ sunroom at The Players Club. Unique to this residence is a private garage, offering rare security and convenience plus an additional covered under-building parking space. You’ll immediately be drawn to the impressive 31’ balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. An open, white eat-in kitchen is designed with custom cabinetry and extra storage that flows seamlessly into the main living and dining areas. Just off the kitchen, French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The primary bedroom, a private sanctuary with an en-suite bath offers a soaking tub, separate glass-enclosed shower, dual vanities, and a fitted walk-in closet. A second bedroom functions as an additional master with a fitted walk-in closet and en-suite bath with dual sinks. A true third bedroom with two separate fitted closets and an adjacent full bathroom adds flexibility for additional guests. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves and is located Just minutes from St. Armands Circle, downtown Longboat Key, and the Longboat Key Club - with championship golf, premier tennis, and a deep-water marina. One of the largest floor plans available in the community, this residence blends privacy, convenience, and resort-style beachfront living. Offered partially furnished.

1445 Gulf Of Mexico Drive Unit 101, Longboat Key

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

$698,765

Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, but also has a space where one could be installed inside. There are also accordion storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. The condo is approx. 1175 Square Feet and this building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

2 Beds ⋅ 2 Baths ⋅ Arbomar Apts SubDv. ⋅ 34228 Zip Code

Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, but also has a space where one could be installed inside. There are also accordion storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. The condo is approx. 1175 Square Feet and this building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

1591 Gulf Of Mexico Drive Unit 618, Longboat Key

$12,500,000

Experience an extraordinary standard of beachfront luxury from this spectacular penthouse residence at the prestigious St. Regis Longboat Key. Showcasing breathtaking panoramic views of the Gulf of Mexico and Sarasota Bay, this exceptional home offers an unparalleled blend of sophistication, privacy, and world-class design. Spanning approximately 5,320 square feet, the residence features four spacious bedrooms, five full baths, and one half bath, thoughtfully designed to provide the ultimate in comfort and elegance. Expansive walls of glass frame mesmerizing water views from nearly every room, while the spectacular 1736 square foot wraparound terrace creates seamless indoor-outdoor living. Enjoy your own private plunge pool, outdoor gas grill, and multiple entertaining areas perfectly positioned to capture stunning sunrises over the bay and unforgettable sunsets across the Gulf. The interiors have been exquisitely curated by award-winning interior designer Kurt Lucas, with every detail reflecting impeccable craftsmanship, timeless elegance, and refined coastal luxury. The residence is offered fully furnished, allowing for an effortless transition into an exceptional waterfront lifestyle. Additional features include a private three-car garage. The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in fractional luxury living at The St. Regis Longboat Key.

4 Beds ⋅ 6 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code

Experience an extraordinary standard of beachfront luxury from this spectacular penthouse residence at the prestigious St. Regis Longboat Key. Showcasing breathtaking panoramic views of the Gulf of Mexico and Sarasota Bay, this exceptional home offers an unparalleled blend of sophistication, privacy, and world-class design. Spanning approximately 5,320 square feet, the residence features four spacious bedrooms, five full baths, and one half bath, thoughtfully designed to provide the ultimate in comfort and elegance. Expansive walls of glass frame mesmerizing water views from nearly every room, while the spectacular 1736 square foot wraparound terrace creates seamless indoor-outdoor living. Enjoy your own private plunge pool, outdoor gas grill, and multiple entertaining areas perfectly positioned to capture stunning sunrises over the bay and unforgettable sunsets across the Gulf. The interiors have been exquisitely curated by award-winning interior designer Kurt Lucas, with every detail reflecting impeccable craftsmanship, timeless elegance, and refined coastal luxury. The residence is offered fully furnished, allowing for an effortless transition into an exceptional waterfront lifestyle. Additional features include a private three-car garage. The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in fractional luxury living at The St. Regis Longboat Key.

1591 Gulf Of Mexico Drive Unit 618, Longboat Key

1975 Gulf Of Mexico Drive Unit G4-203, Longboat Key

$795,000

Wake up to breathtaking, unobstructed views of the Gulf of Mexico from this two-bedroom, two-bath condominium in beautiful Seaplace. The screened-in lanai provides the perfect setting to relax, take in spectacular sunsets and enjoy the azure waters of the Gulf. On the lanai there is an additional large retractable screen for protection from the sun along with a hurricane impact sliding glass door. Offered unfurnished and a clean slate ready for updating, this residence presents a wonderful opportunity to bring your own style and vision to a prime Gulf-facing property. This residence offers spacious and comfortable living space, while the spectacular views provide a backdrop that is truly hard to replicate. Additional features include electric hurricane shutters on the bedroom windows, two assigned parking spaces, including one covered space, offering convenience and value. The Seaplace community on Longboat Key has 42 acres of magnificent grounds, 1/2 mile of beautiful beach and a mile walking trail around the property. Included in the amenities are two swimming pools with spas, kiddie pool, fitness room, sauna, fire pit and kiddie playground. Located very close to famous Saint Armand's Circle and downtown Sarasota where you will find an abundance of restaurants, boutique shopping, art galleries, live theatre, ballet and an opera house. Don't miss this chance to live in paradise on unique Longboat Key. BE SURE TO SEE THE VIRTUAL TOUR!

2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code

Wake up to breathtaking, unobstructed views of the Gulf of Mexico from this two-bedroom, two-bath condominium in beautiful Seaplace. The screened-in lanai provides the perfect setting to relax, take in spectacular sunsets and enjoy the azure waters of the Gulf. On the lanai there is an additional large retractable screen for protection from the sun along with a hurricane impact sliding glass door. Offered unfurnished and a clean slate ready for updating, this residence presents a wonderful opportunity to bring your own style and vision to a prime Gulf-facing property. This residence offers spacious and comfortable living space, while the spectacular views provide a backdrop that is truly hard to replicate. Additional features include electric hurricane shutters on the bedroom windows, two assigned parking spaces, including one covered space, offering convenience and value. The Seaplace community on Longboat Key has 42 acres of magnificent grounds, 1/2 mile of beautiful beach and a mile walking trail around the property. Included in the amenities are two swimming pools with spas, kiddie pool, fitness room, sauna, fire pit and kiddie playground. Located very close to famous Saint Armand's Circle and downtown Sarasota where you will find an abundance of restaurants, boutique shopping, art galleries, live theatre, ballet and an opera house. Don't miss this chance to live in paradise on unique Longboat Key. BE SURE TO SEE THE VIRTUAL TOUR!

1975 Gulf Of Mexico Drive Unit G4-203, Longboat Key

$1,999,000

MODERN BEACH LUXURY | OCEAN VIEWS | PRIVATE BOAT DOCK & LIFT | LAGUNA YACHT VILLAGE Aggressively Priced for a Motivated Sale — Owners Relocating! Discover an extraordinary opportunity to own a beautifully modernized beach residence in Laguna Yacht Village, one of Longboat Key’s most private and closely held coastal communities. Perfectly positioned between the Gulf of Mexico and Sarasota Bay, this exclusive gated enclave encompasses just 8 residences across 9 lots, offering a level of privacy, boating access, and beach lifestyle that is exceptionally difficult to replicate. Elevated approximately 16 feet, this sophisticated 3-bedroom, 3-bath residence offers the flexibility of a possible 4th bedroom and an expansive 3+ car garage, all thoughtfully designed for effortless coastal living. From the home’s elevated vantage point, enjoy ocean views and the unmistakable sense of being surrounded by water, while your deeded private dock with 10,000-lb. boat lift places Sarasota Bay and the Gulf lifestyle literally at your doorstep. The current owners substantially modernized and expanded the residence in 2019–2020, creating a home that feels exceptionally fresh, refined and move-in ready. Improvements include a new 25-year aluminum roof, pre-painted HardiePlank exterior, expanded and enclosed upper deck, enlarged primary suite, completely renovated kitchen and bathrooms, new solid-panel interior doors, 16-foot-wide glass slider doors, refinished hardwood flooring on the main level and newly installed matching hardwood flooring throughout the upper level. The designer kitchen is appointed with premium Sub-Zero and Bosch appliances, complemented by an integrated 180-bottle wine refrigerator—perfectly suited for entertaining after a day on the water or at the beach. Additional major updates include a new water heater in 2025, 5-ton HVAC system, washer and dryer, and a host of upscale architectural and finish details. Much of the extensive renovation was completed by Greyhawk of Bradenton, reflecting the quality and craftsmanship found throughout. The generous upper-level loft offers exceptional versatility and could readily be transformed into a fourth bedroom, private office, media room or additional living space, depending upon your lifestyle needs. Outside, the true magic of Laguna Yacht Village unfolds. Relax on your expansive deck while taking in the coastal surroundings, launch your boat from your private dock and 10,000-lb. lift, walk to the beach, or unwind beside the community’s private heated and chilled pool. Even better, the HOA maintains the grounds, pool and dock infrastructure, allowing you to enjoy the lifestyle without the burden of extensive exterior maintenance. An oversized 3+ car garage provides abundant room for vehicles, a golf cart, water toys and all the equipment that comes with a true Florida coastal lifestyle. This is more than a home—it is a private coastal retreat with deeded boating, beach access, ocean views and an exceptionally rare sense of exclusivity. Laguna Yacht Village remains one of Longboat Key’s best-kept secrets, and opportunities within this intimate community are seldom available. Priced aggressively to sell due to the owners’ relocation. For the discerning buyer seeking privacy, boating, beach access and turnkey modern luxury on Longboat Key, this is an opportunity not to be missed.

3 Beds ⋅ 3 Baths ⋅ Laguna Yacht Village SubDv. ⋅ 34228 Zip Code

MODERN BEACH LUXURY | OCEAN VIEWS | PRIVATE BOAT DOCK & LIFT | LAGUNA YACHT VILLAGE Aggressively Priced for a Motivated Sale — Owners Relocating! Discover an extraordinary opportunity to own a beautifully modernized beach residence in Laguna Yacht Village, one of Longboat Key’s most private and closely held coastal communities. Perfectly positioned between the Gulf of Mexico and Sarasota Bay, this exclusive gated enclave encompasses just 8 residences across 9 lots, offering a level of privacy, boating access, and beach lifestyle that is exceptionally difficult to replicate. Elevated approximately 16 feet, this sophisticated 3-bedroom, 3-bath residence offers the flexibility of a possible 4th bedroom and an expansive 3+ car garage, all thoughtfully designed for effortless coastal living. From the home’s elevated vantage point, enjoy ocean views and the unmistakable sense of being surrounded by water, while your deeded private dock with 10,000-lb. boat lift places Sarasota Bay and the Gulf lifestyle literally at your doorstep. The current owners substantially modernized and expanded the residence in 2019–2020, creating a home that feels exceptionally fresh, refined and move-in ready. Improvements include a new 25-year aluminum roof, pre-painted HardiePlank exterior, expanded and enclosed upper deck, enlarged primary suite, completely renovated kitchen and bathrooms, new solid-panel interior doors, 16-foot-wide glass slider doors, refinished hardwood flooring on the main level and newly installed matching hardwood flooring throughout the upper level. The designer kitchen is appointed with premium Sub-Zero and Bosch appliances, complemented by an integrated 180-bottle wine refrigerator—perfectly suited for entertaining after a day on the water or at the beach. Additional major updates include a new water heater in 2025, 5-ton HVAC system, washer and dryer, and a host of upscale architectural and finish details. Much of the extensive renovation was completed by Greyhawk of Bradenton, reflecting the quality and craftsmanship found throughout. The generous upper-level loft offers exceptional versatility and could readily be transformed into a fourth bedroom, private office, media room or additional living space, depending upon your lifestyle needs. Outside, the true magic of Laguna Yacht Village unfolds. Relax on your expansive deck while taking in the coastal surroundings, launch your boat from your private dock and 10,000-lb. lift, walk to the beach, or unwind beside the community’s private heated and chilled pool. Even better, the HOA maintains the grounds, pool and dock infrastructure, allowing you to enjoy the lifestyle without the burden of extensive exterior maintenance. An oversized 3+ car garage provides abundant room for vehicles, a golf cart, water toys and all the equipment that comes with a true Florida coastal lifestyle. This is more than a home—it is a private coastal retreat with deeded boating, beach access, ocean views and an exceptionally rare sense of exclusivity. Laguna Yacht Village remains one of Longboat Key’s best-kept secrets, and opportunities within this intimate community are seldom available. Priced aggressively to sell due to the owners’ relocation. For the discerning buyer seeking privacy, boating, beach access and turnkey modern luxury on Longboat Key, this is an opportunity not to be missed.

6330 Laguna Drive, Longboat Key

2600 Harbourside Drive Unit C3, Longboat Key

$275,000

Experience the luxury boating lifestyle on Longboat Key. This 62' x 21' deeded boat slip is positioned on serene deep water at Longboat Key Club Moorings, a full-service, world-class Marina with every desirable amenity. This NON-COVENANT slip does not require the new owner to join the Longboat Key Club although club membership is an available option. C Dock is especially desirable due to the unique design of the finger piers which allow boarding on most vessels without the need for an additional boarding ladder. Owners of boat slips have the option to join the Bay Isles Beach Club for a small annual fee. This is a deeded live aboard slip, a rarity in today’s market, with great rental potential making this a unique opportunity for investors and boaters alike. Currently rented with income in place until a new owner is ready to occupy.

1 Beds ⋅ 1 Baths ⋅ Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Experience the luxury boating lifestyle on Longboat Key. This 62' x 21' deeded boat slip is positioned on serene deep water at Longboat Key Club Moorings, a full-service, world-class Marina with every desirable amenity. This NON-COVENANT slip does not require the new owner to join the Longboat Key Club although club membership is an available option. C Dock is especially desirable due to the unique design of the finger piers which allow boarding on most vessels without the need for an additional boarding ladder. Owners of boat slips have the option to join the Bay Isles Beach Club for a small annual fee. This is a deeded live aboard slip, a rarity in today’s market, with great rental potential making this a unique opportunity for investors and boaters alike. Currently rented with income in place until a new owner is ready to occupy.

2600 Harbourside Drive Unit C3, Longboat Key

5055 Gulf Of Mexico Drive Unit 532, Longboat Key

$799,000

Location, Location , Location FULL GULF & BEACH VIEWS. Building 5 is the rare and coveted building in the Club Longboat Complex. This Penthouse 3rd floor unit is the only Building in the community with sensational full beach and gulf views with the perfect Horizon in the distance. Built in 1976 and going strong, this 3rd floor unit offers the sounds of the surf overlooking the beautiful Sea grapes. . ... Very few people have ever experienced this combination and is a Must See to experience. You can always change or renovate inside any unit but, you can’t change the location. This original unit has never been available for sale. Hard to find a 3 bedroom ( with movable partition), you can enclose the screened patio for added square footage. This is the lowest priced 3 bedroom Elevator Building on the beaches of Longboat Key. Hurricane shutters are in place in addition to two open patios. New hurricane rated sliding doors for easy and secure access and energy efficiency. One of only 6 units on the 3rd floor. Newer kitchen and Primary walk in shower. Club Longboat has wonderful amenities to enjoy, 8 Har-Tru tennis courts, 2 heated pools, large fitness center, and a sauna and spa to help you relax. A newly renovated clubhouse has an expansive bar for everyone to enjoy all those fun seasonal activities together with a game room, library, full catering kitchen and views of that azure blue waters of the Gulf of Mexico. Very Dog Friendly" 2 Large allowed. On site management caters to the owner's every need, with only 80 units ensconced by mature landscaping and meticulously maintained, this complex is highly sought after with mid-key location and fabulous amenities. Come live the dream now here on the white sugar sand beaches in Longboat Key. Being sold as-is. Ready for immediate occupancy. Priced to give the new lucky Owner many possibilities.

3 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Location, Location , Location FULL GULF & BEACH VIEWS. Building 5 is the rare and coveted building in the Club Longboat Complex. This Penthouse 3rd floor unit is the only Building in the community with sensational full beach and gulf views with the perfect Horizon in the distance. Built in 1976 and going strong, this 3rd floor unit offers the sounds of the surf overlooking the beautiful Sea grapes. . ... Very few people have ever experienced this combination and is a Must See to experience. You can always change or renovate inside any unit but, you can’t change the location. This original unit has never been available for sale. Hard to find a 3 bedroom ( with movable partition), you can enclose the screened patio for added square footage. This is the lowest priced 3 bedroom Elevator Building on the beaches of Longboat Key. Hurricane shutters are in place in addition to two open patios. New hurricane rated sliding doors for easy and secure access and energy efficiency. One of only 6 units on the 3rd floor. Newer kitchen and Primary walk in shower. Club Longboat has wonderful amenities to enjoy, 8 Har-Tru tennis courts, 2 heated pools, large fitness center, and a sauna and spa to help you relax. A newly renovated clubhouse has an expansive bar for everyone to enjoy all those fun seasonal activities together with a game room, library, full catering kitchen and views of that azure blue waters of the Gulf of Mexico. Very Dog Friendly" 2 Large allowed. On site management caters to the owner's every need, with only 80 units ensconced by mature landscaping and meticulously maintained, this complex is highly sought after with mid-key location and fabulous amenities. Come live the dream now here on the white sugar sand beaches in Longboat Key. Being sold as-is. Ready for immediate occupancy. Priced to give the new lucky Owner many possibilities.

5055 Gulf Of Mexico Drive Unit 532, Longboat Key

3808 Gulf Of Mexico Drive Unit E412, Longboat Key

$1,175,000

Rarely available penthouse living at Beach Harbor Club pairs sweeping Sarasota Bay views with deeded access to the white sands of the Gulf of Mexico. Set on the top floor of Building E, Residence #E412 is an exceptionally spacious three-bedroom, three-bath retreat offering more than 2,500 square feet, captivating water views from nearly every room and the relaxed indoor-outdoor lifestyle that makes Longboat Key so desirable. This residence also includes two premium covered parking spaces. From the moment you arrive, the water takes center stage. A private screened front patio creates an inviting outdoor perch overlooking the bay, while inside, an expansive, light-filled floor plan unfolds through generous living, dining and family spaces. Walls of glass frame the sparkling bay, surrounding tropical landscape and boating activity below, creating a constant connection to the waterfront setting. The oversized living room flows naturally into the enclosed bayfront terrace, now incorporated as a comfortable family room for additional year-round living space. Impact-rated sliding glass doors open to a Juliet balcony, inviting refreshing bay breezes inside while preserving the protection and comfort of an enclosed space. It is an ideal setting for morning coffee, reading, entertaining or simply watching the ever-changing colors of the water. Designed for both everyday living and entertaining, the formal dining room is surrounded by windows and enjoys beautiful bay views. The adjacent eat-in kitchen, renovated in 2018, features abundant cabinetry and workspace, a breakfast nook and its own picturesque outlook across the water. Three generously sized bedrooms are arranged in a desirable split plan, providing privacy for owners and overnight guests. The spacious primary suite is positioned to take advantage of the waterfront setting and includes a sitting area and an updated en-suite bath renovated in 2023. The additional bedroom suites offer exceptional flexibility for visiting family, guests or a home office. Beyond the residence, Beach Harbor Club delivers the quintessential Longboat Key lifestyle from bay to beach. Residents enjoy a bayfront clubhouse with social room, bar and catering kitchen, library, fitness center, heated swimming pool, Tiki hut and barbecue area, shuffleboard, car wash station, fish-cleaning station and outdoor shower. Boaters and paddlers will especially appreciate Beach Harbor Club's on-site marina, where assigned boat slips and kayak storage racks are available on a first-come basis. Just across Gulf of Mexico Drive, the community's deeded Gulf beach access puts the turquoise waters and soft sands of Longboat Key only moments from home—offering the rare opportunity to spend the morning boating on Sarasota Bay and the afternoon along the Gulf. Ideally positioned on the southern end of Longboat Key, #E412 is convenient to the boutiques, restaurants and cafés of St. Armands Circle, while Downtown Sarasota is just beyond the Ringling Bridge for acclaimed dining, galleries, theaters, the Sarasota Opera, Marina Jack and the city's celebrated arts and cultural scene. Longboat Key's waterfront restaurants, golf, tennis, parks and miles of shoreline are also close at hand.

3 Beds ⋅ 3 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code

Rarely available penthouse living at Beach Harbor Club pairs sweeping Sarasota Bay views with deeded access to the white sands of the Gulf of Mexico. Set on the top floor of Building E, Residence #E412 is an exceptionally spacious three-bedroom, three-bath retreat offering more than 2,500 square feet, captivating water views from nearly every room and the relaxed indoor-outdoor lifestyle that makes Longboat Key so desirable. This residence also includes two premium covered parking spaces. From the moment you arrive, the water takes center stage. A private screened front patio creates an inviting outdoor perch overlooking the bay, while inside, an expansive, light-filled floor plan unfolds through generous living, dining and family spaces. Walls of glass frame the sparkling bay, surrounding tropical landscape and boating activity below, creating a constant connection to the waterfront setting. The oversized living room flows naturally into the enclosed bayfront terrace, now incorporated as a comfortable family room for additional year-round living space. Impact-rated sliding glass doors open to a Juliet balcony, inviting refreshing bay breezes inside while preserving the protection and comfort of an enclosed space. It is an ideal setting for morning coffee, reading, entertaining or simply watching the ever-changing colors of the water. Designed for both everyday living and entertaining, the formal dining room is surrounded by windows and enjoys beautiful bay views. The adjacent eat-in kitchen, renovated in 2018, features abundant cabinetry and workspace, a breakfast nook and its own picturesque outlook across the water. Three generously sized bedrooms are arranged in a desirable split plan, providing privacy for owners and overnight guests. The spacious primary suite is positioned to take advantage of the waterfront setting and includes a sitting area and an updated en-suite bath renovated in 2023. The additional bedroom suites offer exceptional flexibility for visiting family, guests or a home office. Beyond the residence, Beach Harbor Club delivers the quintessential Longboat Key lifestyle from bay to beach. Residents enjoy a bayfront clubhouse with social room, bar and catering kitchen, library, fitness center, heated swimming pool, Tiki hut and barbecue area, shuffleboard, car wash station, fish-cleaning station and outdoor shower. Boaters and paddlers will especially appreciate Beach Harbor Club's on-site marina, where assigned boat slips and kayak storage racks are available on a first-come basis. Just across Gulf of Mexico Drive, the community's deeded Gulf beach access puts the turquoise waters and soft sands of Longboat Key only moments from home—offering the rare opportunity to spend the morning boating on Sarasota Bay and the afternoon along the Gulf. Ideally positioned on the southern end of Longboat Key, #E412 is convenient to the boutiques, restaurants and cafés of St. Armands Circle, while Downtown Sarasota is just beyond the Ringling Bridge for acclaimed dining, galleries, theaters, the Sarasota Opera, Marina Jack and the city's celebrated arts and cultural scene. Longboat Key's waterfront restaurants, golf, tennis, parks and miles of shoreline are also close at hand.

3808 Gulf Of Mexico Drive Unit E412, Longboat Key

4525 Gulf Of Mexico Drive Unit 204, Longboat Key

$1,125,000

Direct Gulf-front living, uninterrupted beach views and spectacular sunsets define this furnished retreat at The Castillian on Longboat Key. Positioned in the South Building, Residence #204 offers a front-row perspective of the Gulf of Mexico, with expansive water views from nearly every room. Thoughtfully maintained and updated, this two-bedroom residence offers 1,362 square feet of interior living space, including an enclosed Gulf-front terrace that creates a comfortable extension of the residence. From the moment you enter, the Gulf becomes the focal point. A light-filled, open living and dining area leads directly to the enclosed terrace, where floor-to-ceiling glass frames turquoise water, the natural dune landscape and the beach beyond. Impact sliding glass doors open to welcome refreshing Gulf breezes, creating a versatile space for enjoying the ever-changing coastal scenery and everyday living. The east-facing eat-in kitchen, updated in 2017, combines functionality with a fresh coastal aesthetic. Quartz countertops, a breakfast bar, stainless steel appliances and shaker-style cabinetry complement the generous workspace, while a convenient laundry closet adds everyday practicality. The kitchen connects naturally to the living and dining areas, creating an easy flow for entertaining. A split-bedroom floor plan provides privacy for owners and guests. The Gulf-facing primary suite offers beautiful water views, a walk-in closet and an en-suite bath updated in 2017 with quartz finishes and a glass-enclosed shower. The guest bedroom is comfortably separated from the primary suite and is served by a similarly updated second bath. Offered turnkey furnished, the residence is ready for immediate enjoyment as a full-time island home or seasonal getaway. Additional conveniences include deeded under-building parking and a separate storage unit. Beyond the residence, The Castillian offers the intimate atmosphere of a 60-residence beachfront community, with two buildings overlooking the Gulf. Its beautifully maintained grounds and collection of amenities encourage an easygoing coastal lifestyle. Spend afternoons beside the heated Gulfside swimming pool, unwind in the hot tub or gather with friends at the clubhouse and outdoor grilling area. Tennis, kayak storage and opportunities for walking and biking add to the appeal, while more than 700 feet of beachfront places Longboat Key’s soft sand and sparkling Gulf waters just steps from your front door. The community is pet-friendly, subject to association restrictions. The Castillian’s central Longboat Key location also provides convenient access to the island’s waterfront restaurants, golf, tennis and marinas. To the south, St. Armands Circle offers boutique shopping, restaurants and cafés, while Downtown Sarasota is home to acclaimed dining, galleries, theaters, Sarasota Opera, Marie Selby Botanical Gardens and the scenic Bayfront. To the north, Anna Maria Island and the charming coastal communities of Manatee County offer additional opportunities for exploring Southwest Florida.

2 Beds ⋅ 2 Baths ⋅ Castillian The SubDv. ⋅ 34228 Zip Code

Direct Gulf-front living, uninterrupted beach views and spectacular sunsets define this furnished retreat at The Castillian on Longboat Key. Positioned in the South Building, Residence #204 offers a front-row perspective of the Gulf of Mexico, with expansive water views from nearly every room. Thoughtfully maintained and updated, this two-bedroom residence offers 1,362 square feet of interior living space, including an enclosed Gulf-front terrace that creates a comfortable extension of the residence. From the moment you enter, the Gulf becomes the focal point. A light-filled, open living and dining area leads directly to the enclosed terrace, where floor-to-ceiling glass frames turquoise water, the natural dune landscape and the beach beyond. Impact sliding glass doors open to welcome refreshing Gulf breezes, creating a versatile space for enjoying the ever-changing coastal scenery and everyday living. The east-facing eat-in kitchen, updated in 2017, combines functionality with a fresh coastal aesthetic. Quartz countertops, a breakfast bar, stainless steel appliances and shaker-style cabinetry complement the generous workspace, while a convenient laundry closet adds everyday practicality. The kitchen connects naturally to the living and dining areas, creating an easy flow for entertaining. A split-bedroom floor plan provides privacy for owners and guests. The Gulf-facing primary suite offers beautiful water views, a walk-in closet and an en-suite bath updated in 2017 with quartz finishes and a glass-enclosed shower. The guest bedroom is comfortably separated from the primary suite and is served by a similarly updated second bath. Offered turnkey furnished, the residence is ready for immediate enjoyment as a full-time island home or seasonal getaway. Additional conveniences include deeded under-building parking and a separate storage unit. Beyond the residence, The Castillian offers the intimate atmosphere of a 60-residence beachfront community, with two buildings overlooking the Gulf. Its beautifully maintained grounds and collection of amenities encourage an easygoing coastal lifestyle. Spend afternoons beside the heated Gulfside swimming pool, unwind in the hot tub or gather with friends at the clubhouse and outdoor grilling area. Tennis, kayak storage and opportunities for walking and biking add to the appeal, while more than 700 feet of beachfront places Longboat Key’s soft sand and sparkling Gulf waters just steps from your front door. The community is pet-friendly, subject to association restrictions. The Castillian’s central Longboat Key location also provides convenient access to the island’s waterfront restaurants, golf, tennis and marinas. To the south, St. Armands Circle offers boutique shopping, restaurants and cafés, while Downtown Sarasota is home to acclaimed dining, galleries, theaters, Sarasota Opera, Marie Selby Botanical Gardens and the scenic Bayfront. To the north, Anna Maria Island and the charming coastal communities of Manatee County offer additional opportunities for exploring Southwest Florida.

4525 Gulf Of Mexico Drive Unit 204, Longboat Key

$2,100,000

Virtually Staged. Tucked within the highly sought after Queens Harbour enclave of Bay Isles, this exceptional residence captures the effortless elegance and relaxed sophistication of the Longboat Key lifestyle. Queens Harbour offers the rare combination of single-family living with a low-maintenance lifestyle, including landscaping, irrigation, and exterior painting. Grand double entry doors open to nearly 3,000 square feet of beautifully refreshed interiors, where soaring 12- to 15-foot ceilings, abundant natural light, serene water views, and refined architectural details create an immediate sense of space and tranquility. Newly installed wood-look porcelain tile flows throughout the living and dining rooms, den, and first-floor bedrooms, bringing warmth and continuity to the home. At the heart of the residence, the newly renovated kitchen pairs sophisticated design with exceptional functionality. Quartz countertops, a dramatic waterfall island, second prep sink, new backsplash, and stainless steel appliances create an inviting space for cooking and entertaining. An adjoining breakfast nook is framed by a bay window overlooking the pool and lake. The thoughtfully designed split floor plan features three private en-suite bedrooms, a powder room, and an elegant den or office with custom cabinetry that may also serve as a fourth bedroom. The first-floor owner’s suite enjoys direct lanai access and tranquil lake views, complemented by a spa-inspired bath with dual vanities, soaking tub, and spacious walk-in shower. A second en-suite bedroom on the main level provides privacy and comfort for guests. The upper level features an additional en-suite bedroom and flexible living area, creating a secluded retreat ideal for guests, extended stays, or multigenerational living. Outdoors, the expansive screened lanai embraces the home’s peaceful waterfront setting. A heated pool and spa overlook the lake and fountain, while a generous covered sitting area with tongue-and-groove ceiling and coordinating accent wall provides an inviting setting for entertaining or relaxing. A 2023 tile roof adds to the home’s thoughtful updates and long-term appeal. Ownership in Bay Isles includes access to the private Bay Isles Beach Club and its pristine Gulf shoreline. Optional membership to the Longboat Key Club offers golf, tennis, dining, resort amenities, and access to Harbourside Marina. Ideally situated in the heart of Longboat Key, the home is convenient to the shops and everyday amenities of Bay Isles, with St. Armands Circle and downtown Sarasota’s acclaimed dining, arts, and cultural offerings just a scenic drive away. Boating, kayaking, fishing, waterfront dining, and some of Florida’s most beautiful beaches are all within easy reach. A refined island residence offering the privacy of a single-family home, the ease of low-maintenance living, and the exceptional lifestyle that defines Bay Isles and Longboat Key.

3 Beds ⋅ 4 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code

Virtually Staged. Tucked within the highly sought after Queens Harbour enclave of Bay Isles, this exceptional residence captures the effortless elegance and relaxed sophistication of the Longboat Key lifestyle. Queens Harbour offers the rare combination of single-family living with a low-maintenance lifestyle, including landscaping, irrigation, and exterior painting. Grand double entry doors open to nearly 3,000 square feet of beautifully refreshed interiors, where soaring 12- to 15-foot ceilings, abundant natural light, serene water views, and refined architectural details create an immediate sense of space and tranquility. Newly installed wood-look porcelain tile flows throughout the living and dining rooms, den, and first-floor bedrooms, bringing warmth and continuity to the home. At the heart of the residence, the newly renovated kitchen pairs sophisticated design with exceptional functionality. Quartz countertops, a dramatic waterfall island, second prep sink, new backsplash, and stainless steel appliances create an inviting space for cooking and entertaining. An adjoining breakfast nook is framed by a bay window overlooking the pool and lake. The thoughtfully designed split floor plan features three private en-suite bedrooms, a powder room, and an elegant den or office with custom cabinetry that may also serve as a fourth bedroom. The first-floor owner’s suite enjoys direct lanai access and tranquil lake views, complemented by a spa-inspired bath with dual vanities, soaking tub, and spacious walk-in shower. A second en-suite bedroom on the main level provides privacy and comfort for guests. The upper level features an additional en-suite bedroom and flexible living area, creating a secluded retreat ideal for guests, extended stays, or multigenerational living. Outdoors, the expansive screened lanai embraces the home’s peaceful waterfront setting. A heated pool and spa overlook the lake and fountain, while a generous covered sitting area with tongue-and-groove ceiling and coordinating accent wall provides an inviting setting for entertaining or relaxing. A 2023 tile roof adds to the home’s thoughtful updates and long-term appeal. Ownership in Bay Isles includes access to the private Bay Isles Beach Club and its pristine Gulf shoreline. Optional membership to the Longboat Key Club offers golf, tennis, dining, resort amenities, and access to Harbourside Marina. Ideally situated in the heart of Longboat Key, the home is convenient to the shops and everyday amenities of Bay Isles, with St. Armands Circle and downtown Sarasota’s acclaimed dining, arts, and cultural offerings just a scenic drive away. Boating, kayaking, fishing, waterfront dining, and some of Florida’s most beautiful beaches are all within easy reach. A refined island residence offering the privacy of a single-family home, the ease of low-maintenance living, and the exceptional lifestyle that defines Bay Isles and Longboat Key.

3617 Fair Oaks Place, Longboat Key

$4,699,999

Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities. Designed for effortless coastal living, this sophisticated home combines coastal contemporary architecture, elevated construction above current flood requirements, an oversized homesite, and beautifully curated tropical gardens creating a private, resort-like setting. Inside, exceptional craftsmanship is evident throughout. The chef’s kitchen features a waterfall quartzite island, brass-strapped custom hood, panel-front refrigeration with fridge, freezer, and wine tower, vaulted beamed ceiling with concealed cove lighting and Thermador appliances. Designed to be a true masterpiece sure to impress. The great room showcases a walnut-clad fireplace wall, custom built-ins, wide-plank engineered wood floors, backlit tray ceiling, and expansive sliding glass doors opening to the outdoor living areas. The primary suite overlooking the tranquil back yard, offers a spa-inspired bath with freestanding soaking tub, rain shower, dual vanity, and customized walk-in closets. This floor plan also allows for an additional first floor primary or guest bedroom suite with custom full bath. The second floor offers three additional bedroom suites providing beautifully appointed accommodations for family and guests. Outdoors, the home becomes its own private resort. A covered lanai opens to a heated saltwater pool and spa, beautifully landscaped backyard with its own private putting green, and stainless-steel outdoor kitchen with built-in gas grill—an exceptional setting for entertaining, relaxing, or perfecting your short game at home. The location completes the experience. Set in south Longboat Key, the home is within walking distance of the Longboat Key Club, with golf, tennis, marina, dining, and beach club amenities nearby. Bay Isles residents also enjoy access to their own private Gulf-front Beach Club with powder-soft sand and spectacular Gulf waters. The Beach Club also provides bbq grills, pavilion, locker rooms, storage, and ice machine. New construction, exceptional design and quality, private beach access, and one of Longboat Key’s premier locations—this home offers a rare opportunity to enjoy the Bay Isles lifestyle from day one. Close to Sarasota International Airport, downtown dining and entertainment, and everything wonderful offered by the beloved St Armands Circle.

5 Beds ⋅ 5 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities. Designed for effortless coastal living, this sophisticated home combines coastal contemporary architecture, elevated construction above current flood requirements, an oversized homesite, and beautifully curated tropical gardens creating a private, resort-like setting. Inside, exceptional craftsmanship is evident throughout. The chef’s kitchen features a waterfall quartzite island, brass-strapped custom hood, panel-front refrigeration with fridge, freezer, and wine tower, vaulted beamed ceiling with concealed cove lighting and Thermador appliances. Designed to be a true masterpiece sure to impress. The great room showcases a walnut-clad fireplace wall, custom built-ins, wide-plank engineered wood floors, backlit tray ceiling, and expansive sliding glass doors opening to the outdoor living areas. The primary suite overlooking the tranquil back yard, offers a spa-inspired bath with freestanding soaking tub, rain shower, dual vanity, and customized walk-in closets. This floor plan also allows for an additional first floor primary or guest bedroom suite with custom full bath. The second floor offers three additional bedroom suites providing beautifully appointed accommodations for family and guests. Outdoors, the home becomes its own private resort. A covered lanai opens to a heated saltwater pool and spa, beautifully landscaped backyard with its own private putting green, and stainless-steel outdoor kitchen with built-in gas grill—an exceptional setting for entertaining, relaxing, or perfecting your short game at home. The location completes the experience. Set in south Longboat Key, the home is within walking distance of the Longboat Key Club, with golf, tennis, marina, dining, and beach club amenities nearby. Bay Isles residents also enjoy access to their own private Gulf-front Beach Club with powder-soft sand and spectacular Gulf waters. The Beach Club also provides bbq grills, pavilion, locker rooms, storage, and ice machine. New construction, exceptional design and quality, private beach access, and one of Longboat Key’s premier locations—this home offers a rare opportunity to enjoy the Bay Isles lifestyle from day one. Close to Sarasota International Airport, downtown dining and entertainment, and everything wonderful offered by the beloved St Armands Circle.

3360 Bayou Sound, Longboat Key

$2,695,000

Waterfront living takes center stage at this impressive Queens Harbour residence, offering 3 bedrooms plus a den and 3½ bathrooms across more than 3,000 square feet of indoor living. The home opens to a tropical pool and spa, covered outdoor living, and a private dock with boat lift on a navigable canal with convenient access to Sarasota Bay. Set behind the gates of Bay Isles, the home offers generous living spaces and an exceptional Longboat Key lifestyle. A paver drive framed by mature tropical landscaping leads to the striking two-story entrance and double glass doors. Inside, soaring tray ceilings, plantation shutters, architectural details and abundant glass create a bright, open feel. A private office sits just off the foyer before the floor plan opens to the main living areas. The great room features a dedicated bar and flows into adjoining living spaces, with sliders opening to the covered lanai, summer kitchen and pool. The kitchen offers abundant white cabinetry, contrasting stone countertops, a large center island with second sink and paneled refrigerator. A light-filled dining area opens directly to the outdoor living space. The first-floor primary suite overlooks the pool and features an aquarium-glass sitting area, tray ceiling, spacious walk-in closet and bath with split vanities, spa tub and glass-enclosed shower. A second en suite bedroom completes the main level. Upstairs, a generous guest suite can serve as a second primary retreat with a walk-in closet and updated en suite bath. Outside, the pool and spa with cascading waterfall are surrounded by paver decking and tropical landscaping. The covered lanai and summer kitchen create an inviting entertaining space, while the private dock and boat lift provide direct canal access to Sarasota Bay. Ownership in Bay Isles includes membership in the private Gulf-front Bay Isles Beach Club, offering residents direct beach access, covered gathering areas, picnic and barbecue facilities and other conveniences for enjoying the Gulf. Separate optional membership to the Longboat Key Club offers additional golf, tennis, dining, fitness, spa, beach and social amenities depending on membership category.

3 Beds ⋅ 4 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code

Waterfront living takes center stage at this impressive Queens Harbour residence, offering 3 bedrooms plus a den and 3½ bathrooms across more than 3,000 square feet of indoor living. The home opens to a tropical pool and spa, covered outdoor living, and a private dock with boat lift on a navigable canal with convenient access to Sarasota Bay. Set behind the gates of Bay Isles, the home offers generous living spaces and an exceptional Longboat Key lifestyle. A paver drive framed by mature tropical landscaping leads to the striking two-story entrance and double glass doors. Inside, soaring tray ceilings, plantation shutters, architectural details and abundant glass create a bright, open feel. A private office sits just off the foyer before the floor plan opens to the main living areas. The great room features a dedicated bar and flows into adjoining living spaces, with sliders opening to the covered lanai, summer kitchen and pool. The kitchen offers abundant white cabinetry, contrasting stone countertops, a large center island with second sink and paneled refrigerator. A light-filled dining area opens directly to the outdoor living space. The first-floor primary suite overlooks the pool and features an aquarium-glass sitting area, tray ceiling, spacious walk-in closet and bath with split vanities, spa tub and glass-enclosed shower. A second en suite bedroom completes the main level. Upstairs, a generous guest suite can serve as a second primary retreat with a walk-in closet and updated en suite bath. Outside, the pool and spa with cascading waterfall are surrounded by paver decking and tropical landscaping. The covered lanai and summer kitchen create an inviting entertaining space, while the private dock and boat lift provide direct canal access to Sarasota Bay. Ownership in Bay Isles includes membership in the private Gulf-front Bay Isles Beach Club, offering residents direct beach access, covered gathering areas, picnic and barbecue facilities and other conveniences for enjoying the Gulf. Separate optional membership to the Longboat Key Club offers additional golf, tennis, dining, fitness, spa, beach and social amenities depending on membership category.

3578 Fair Oaks Way, Longboat Key

775 Longboat Club Road Unit 405, Longboat Key

$1,095,000

Behind the gates of the Longboat Key Club, this 2BR/2BA corner residence at The Beaches offers 1,602± sq. ft. of comfortable living space, a wraparound terrace and views extending across the golf course to the Gulf. Located on the desirable south end of Longboat Key, the residence offers convenient access to the beach and the amenities of both The Beaches and the Longboat Key Club. Double entry doors open to a foyer with tile floors, high ceilings and neutral finishes. The combined living and dining area features walls of new high impact sliding glass doors that bring in natural light and open to the wraparound terrace. With exposures along two sides of the residence, the terrace provides multiple seating areas and views across the golf course and toward the Gulf. The galley-style kitchen offers generous counter space, stainless steel appliances, a tray ceiling and an adjoining breakfast nook with direct terrace access. The guest bedroom is comfortably sized and overlooks the golf course. The primary suite includes a private bath with dual vanities, a spa tub and a separate water closet with walk-in shower. An in-residence washer and dryer add convenience. The Beaches provides 24-hour concierge service, fitness and social rooms, two private tennis courts, a heated pool and spa, private beach access, garage parking and on-site management. Optional membership opportunities at the Longboat Key Club further expand the lifestyle, with Full, Golf, Tennis and Social membership categories offering access to amenities that may include 45 holes of golf, the Tennis Gardens, private dining venues, beach and pool facilities, spa, fitness and marina privileges. Boaters also have access to Longboat Key Club Moorings, a 291-slip, full-service deep-water marina described by the resort as the largest resort marina on Florida’s west coast. The marina accommodates vessels up to 150 feet, with slips available for lease or purchase, subject to availability and applicable membership requirements.

2 Beds ⋅ 2 Baths ⋅ Beaches Of Longboat Key SubDv. ⋅ 34228 Zip Code

Behind the gates of the Longboat Key Club, this 2BR/2BA corner residence at The Beaches offers 1,602± sq. ft. of comfortable living space, a wraparound terrace and views extending across the golf course to the Gulf. Located on the desirable south end of Longboat Key, the residence offers convenient access to the beach and the amenities of both The Beaches and the Longboat Key Club. Double entry doors open to a foyer with tile floors, high ceilings and neutral finishes. The combined living and dining area features walls of new high impact sliding glass doors that bring in natural light and open to the wraparound terrace. With exposures along two sides of the residence, the terrace provides multiple seating areas and views across the golf course and toward the Gulf. The galley-style kitchen offers generous counter space, stainless steel appliances, a tray ceiling and an adjoining breakfast nook with direct terrace access. The guest bedroom is comfortably sized and overlooks the golf course. The primary suite includes a private bath with dual vanities, a spa tub and a separate water closet with walk-in shower. An in-residence washer and dryer add convenience. The Beaches provides 24-hour concierge service, fitness and social rooms, two private tennis courts, a heated pool and spa, private beach access, garage parking and on-site management. Optional membership opportunities at the Longboat Key Club further expand the lifestyle, with Full, Golf, Tennis and Social membership categories offering access to amenities that may include 45 holes of golf, the Tennis Gardens, private dining venues, beach and pool facilities, spa, fitness and marina privileges. Boaters also have access to Longboat Key Club Moorings, a 291-slip, full-service deep-water marina described by the resort as the largest resort marina on Florida’s west coast. The marina accommodates vessels up to 150 feet, with slips available for lease or purchase, subject to availability and applicable membership requirements.

775 Longboat Club Road Unit 405, Longboat Key

2525 Gulf Of Mexico Drive Unit 7B, Longboat Key

$1,450,000

Welcome to your own piece of paradise at the renowned Islands West community on Longboat Key. This desirable 7th floor Gulf-side residence offers beautiful beachfront views, a thoughtfully designed floor plan, and the added peace of mind of hurricane impact windows and doors! The spacious interior features tile flooring throughout and two generously sized master suites, positioned on opposite sides of the residence to provide privacy for owners and guests. Both suites offer ensuite baths and beautiful Gulf views. The kitchen provides ample cabinetry and plenty of space for everyday living, while the main living area offers two separate seating areas and a defined dining space. With beautiful water views from every window, the home brings the natural beauty of the Gulf into everyday living. Step outside onto the spacious balcony and enjoy the coastal breezes, breathtaking Gulf views, and beautiful surroundings. It is the perfect spot to start the morning with coffee or unwind at the end of the day. Islands West offers an impressive collection of amenities, including a newly refurbished clubhouse, heated beachfront pool and hot tub, two fitness rooms, dry sauna, tennis and pickleball court, library, outdoor patio and grilling area, and beautifully landscaped grounds. Secure key-fob entry and direct access to the sandy Gulf beach complete the relaxed beachfront lifestyle. Ideally located on Longboat Key, Bay Isles Shoppes is just across the street, offering Publix, banking, dining, and everyday conveniences. St. Armands Circle, downtown Sarasota, area marinas, golf, and the beaches of Lido Key and Anna Maria Island are all within easy reach. Whether you are looking for a full-time residence, vacation retreat, or a place to enjoy the Florida lifestyle, this Gulf-side residence offers a wonderful combination of views, privacy, amenities, and location.

2 Beds ⋅ 2 Baths ⋅ Islands West SubDv. ⋅ 34228 Zip Code

Welcome to your own piece of paradise at the renowned Islands West community on Longboat Key. This desirable 7th floor Gulf-side residence offers beautiful beachfront views, a thoughtfully designed floor plan, and the added peace of mind of hurricane impact windows and doors! The spacious interior features tile flooring throughout and two generously sized master suites, positioned on opposite sides of the residence to provide privacy for owners and guests. Both suites offer ensuite baths and beautiful Gulf views. The kitchen provides ample cabinetry and plenty of space for everyday living, while the main living area offers two separate seating areas and a defined dining space. With beautiful water views from every window, the home brings the natural beauty of the Gulf into everyday living. Step outside onto the spacious balcony and enjoy the coastal breezes, breathtaking Gulf views, and beautiful surroundings. It is the perfect spot to start the morning with coffee or unwind at the end of the day. Islands West offers an impressive collection of amenities, including a newly refurbished clubhouse, heated beachfront pool and hot tub, two fitness rooms, dry sauna, tennis and pickleball court, library, outdoor patio and grilling area, and beautifully landscaped grounds. Secure key-fob entry and direct access to the sandy Gulf beach complete the relaxed beachfront lifestyle. Ideally located on Longboat Key, Bay Isles Shoppes is just across the street, offering Publix, banking, dining, and everyday conveniences. St. Armands Circle, downtown Sarasota, area marinas, golf, and the beaches of Lido Key and Anna Maria Island are all within easy reach. Whether you are looking for a full-time residence, vacation retreat, or a place to enjoy the Florida lifestyle, this Gulf-side residence offers a wonderful combination of views, privacy, amenities, and location.

2525 Gulf Of Mexico Drive Unit 7B, Longboat Key

408 Gulf Of Mexico Drive Unit 2207, Longboat Key

$49,000

Welcome to Slip #2207 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 28 feet in length, with a maximum height of 7'8" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #2207 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 28 feet in length, with a maximum height of 7'8" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2207, Longboat Key

408 Gulf Of Mexico Drive Unit 1206, Longboat Key

$65,000

Welcome to Slip #1206 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8'4" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #1206 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8'4" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 1206, Longboat Key

408 Gulf Of Mexico Drive Unit 2114, Longboat Key

$39,000

Welcome to Slip #2114 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 23.5 feet in length, with a maximum height of 7'2" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #2114 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 23.5 feet in length, with a maximum height of 7'2" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2114, Longboat Key

$840,000

Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout.The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout.The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

760 Longboat Court, Longboat Key

$639,000

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

539 Forest Way Unit 539, Longboat Key

1591 Gulf Of Mexico Drive Unit 312, Longboat Key

$4,290,000

Tucked into the Champagne Building at The Residences at The St. Regis Longboat Key, unit 312 is a fully furnished coastal residence done right. Ceilings soar, glass walls stretch floor to ceiling, and the craftsmanship shows in every corner of this thoughtfully laid-out home. Step off the private elevator and into a great room capped by a dramatic tray ceiling and a sculptural bubble chandelier, where sliding glass doors open the space up to the terrace and the greenery beyond, letting the space extend beyond the walls. The kitchen is built for chef and entertainer alike. Glossy custom cabinetry, waterfall-edge counters with a leathered finish, a book matched quartz backsplash, and a full Wolf and Sub-Zero lineup, gas cooktop, double wall ovens, paneled refrigeration all give it the look of a showroom and the function of a real working kitchen. The island is the centerpiece for memories to be made with friends and family. The primary suite feels like its own retreat, tucked away from the living space with a wall of glass framing the grounds below. The bath is spa-worthy: dual vanities under illuminated round mirrors, a frameless glass rain shower, and a walk-in closet custom-fitted with enough drawers and shelving for a serious wardrobe. A second ensuite bedroom offers privacy for guests, and a well-appointed bath handles the rest. A discreet wet bar with wine storage and ice maker sits ready for evening cocktails, and wide-plank, wood-look porcelain tile runs throughout, warming up every room without competing with the views. Outside, the private terrace comes with its own Wolf gas grill, an easy spot for dinner under Longboat Key's evening skies. This is one of only 69 residences in the first branded residential community on the Gulf of Mexico with 800 feet of private beachfront. Ownership here comes with real perks: St. Regis Butler and Concierge service on call, a private Residents' Clubhouse and fitness center, a resident-only pool and spa, and beachside cabanas set aside just for owners. Steps beyond that, the full resort opens up: a heated infinity-edge pool, a drifting lazy river, a meandering saltwater lagoon home to a family of resident Aldabra tortoises, several chef-driven restaurants, and an oceanfront spa with vitality pools and a full menu of treatments. It's the kind of amenity list that makes staying home feel like a vacation. St. Armand’s Circle and downtown Sarasota are just minutes away, but out here on this stretch of Longboat Key, the pace slows down and the world feels a little further off. Here, you're not just buying a home, you're buying into the St. Regis way of doing life, every single day.

2 Beds ⋅ 3 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code

Tucked into the Champagne Building at The Residences at The St. Regis Longboat Key, unit 312 is a fully furnished coastal residence done right. Ceilings soar, glass walls stretch floor to ceiling, and the craftsmanship shows in every corner of this thoughtfully laid-out home. Step off the private elevator and into a great room capped by a dramatic tray ceiling and a sculptural bubble chandelier, where sliding glass doors open the space up to the terrace and the greenery beyond, letting the space extend beyond the walls. The kitchen is built for chef and entertainer alike. Glossy custom cabinetry, waterfall-edge counters with a leathered finish, a book matched quartz backsplash, and a full Wolf and Sub-Zero lineup, gas cooktop, double wall ovens, paneled refrigeration all give it the look of a showroom and the function of a real working kitchen. The island is the centerpiece for memories to be made with friends and family. The primary suite feels like its own retreat, tucked away from the living space with a wall of glass framing the grounds below. The bath is spa-worthy: dual vanities under illuminated round mirrors, a frameless glass rain shower, and a walk-in closet custom-fitted with enough drawers and shelving for a serious wardrobe. A second ensuite bedroom offers privacy for guests, and a well-appointed bath handles the rest. A discreet wet bar with wine storage and ice maker sits ready for evening cocktails, and wide-plank, wood-look porcelain tile runs throughout, warming up every room without competing with the views. Outside, the private terrace comes with its own Wolf gas grill, an easy spot for dinner under Longboat Key's evening skies. This is one of only 69 residences in the first branded residential community on the Gulf of Mexico with 800 feet of private beachfront. Ownership here comes with real perks: St. Regis Butler and Concierge service on call, a private Residents' Clubhouse and fitness center, a resident-only pool and spa, and beachside cabanas set aside just for owners. Steps beyond that, the full resort opens up: a heated infinity-edge pool, a drifting lazy river, a meandering saltwater lagoon home to a family of resident Aldabra tortoises, several chef-driven restaurants, and an oceanfront spa with vitality pools and a full menu of treatments. It's the kind of amenity list that makes staying home feel like a vacation. St. Armand’s Circle and downtown Sarasota are just minutes away, but out here on this stretch of Longboat Key, the pace slows down and the world feels a little further off. Here, you're not just buying a home, you're buying into the St. Regis way of doing life, every single day.

1591 Gulf Of Mexico Drive Unit 312, Longboat Key

2800 Harbourside Drive Unit E-21, Longboat Key

$385,000

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-21, Longboat Key

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$660,000

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$645,000

LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style amenities all within your own community. Tucked into a private setting surrounded by tropical landscaping, this 2-bedroom, 2-bath second-floor end unit offers something buyers will appreciate immediately—extra natural light, added privacy, and no one living above you. Inside, the residence feels comfortable and welcoming, with an open living and dining area and a split-bedroom design that gives owners and guests their own space. The kitchen and bathrooms have been updated, the windows are newer, and a full-size washer and dryer inside the condo adds everyday convenience. The primary suite includes a walk-in closet plus a bonus area that works beautifully as a small home office, reading nook, or additional storage space. Florida living continues outdoors with two separate spaces to enjoy. Start the day on the open-air deck or relax on the screened lanai surrounded by Bayport's lush landscaping. Covered parking, guest parking, multiple storage areas, and an owner's closet provide even more functionality. But what truly sets this property apart is Bayport itself. Spanning approximately 27 acres from the Gulf of Mexico to Sarasota Bay, this distinctive Longboat Key community offers approximately 1,200 feet of private Gulf beach access along with an impressive collection of amenities. Spend the day at the heated Junior Olympic-size pool, play a match on one of four Har-Tru tennis courts, work out in the fitness center, launch a kayak onto the bay, or head to the fishing pier. When it's time for the beach, chairs and umbrellas are available for residents to enjoy. Bayport's winding pathways, mature tropical landscaping, and low-density setting create a peaceful atmosphere that feels worlds away—yet you're conveniently located to the restaurants, shopping, and attractions of Longboat Key, St. Armands Circle, and Sarasota. Beach in the morning, bay in the afternoon, and a Gulf sunset to finish the day. Whether you're looking for a full-time residence or a Longboat Key getaway, this is an opportunity to enjoy the island lifestyle from one exceptional Gulf-to-Bay community.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style amenities all within your own community. Tucked into a private setting surrounded by tropical landscaping, this 2-bedroom, 2-bath second-floor end unit offers something buyers will appreciate immediately—extra natural light, added privacy, and no one living above you. Inside, the residence feels comfortable and welcoming, with an open living and dining area and a split-bedroom design that gives owners and guests their own space. The kitchen and bathrooms have been updated, the windows are newer, and a full-size washer and dryer inside the condo adds everyday convenience. The primary suite includes a walk-in closet plus a bonus area that works beautifully as a small home office, reading nook, or additional storage space. Florida living continues outdoors with two separate spaces to enjoy. Start the day on the open-air deck or relax on the screened lanai surrounded by Bayport's lush landscaping. Covered parking, guest parking, multiple storage areas, and an owner's closet provide even more functionality. But what truly sets this property apart is Bayport itself. Spanning approximately 27 acres from the Gulf of Mexico to Sarasota Bay, this distinctive Longboat Key community offers approximately 1,200 feet of private Gulf beach access along with an impressive collection of amenities. Spend the day at the heated Junior Olympic-size pool, play a match on one of four Har-Tru tennis courts, work out in the fitness center, launch a kayak onto the bay, or head to the fishing pier. When it's time for the beach, chairs and umbrellas are available for residents to enjoy. Bayport's winding pathways, mature tropical landscaping, and low-density setting create a peaceful atmosphere that feels worlds away—yet you're conveniently located to the restaurants, shopping, and attractions of Longboat Key, St. Armands Circle, and Sarasota. Beach in the morning, bay in the afternoon, and a Gulf sunset to finish the day. Whether you're looking for a full-time residence or a Longboat Key getaway, this is an opportunity to enjoy the island lifestyle from one exceptional Gulf-to-Bay community.

843 Bayport Way Unit 843, Longboat Key

3453 Gulf Of Mexico Drive Unit 237, Longboat Key

$495,000

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

3453 Gulf Of Mexico Drive Unit 237, Longboat Key

$599,900

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with a recently installed hurricane-rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). This property has been a second home for current long time owners, but similair neighboring properties boasts a proven track record as a lucrative short-term rental, consistently producing roughly $50,000 in net annual revenue after platform fees. Furthermore, it offers a rare level of operational flexibility for Longboat Key, permitting up to 26 rental cycles per year. When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with a recently installed hurricane-rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). This property has been a second home for current long time owners, but similair neighboring properties boasts a proven track record as a lucrative short-term rental, consistently producing roughly $50,000 in net annual revenue after platform fees. Furthermore, it offers a rare level of operational flexibility for Longboat Key, permitting up to 26 rental cycles per year. When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front

521 Forest Way, Longboat Key

$1,050,000

Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat Key’s distinctive Gulf to Bay communities. Thoughtfully redesigned and renovated in 2023, this 2 bedroom, 2 bath residence offers approximately 1,456 square feet of sophisticated, move in ready living with virtually every detail updated. The renovation includes new flooring, countertops and windows, along with a dedicated home office that creates the perfect space for working remotely or enjoying a quiet study. The sleek, redesigned kitchen features premium JennAir appliances, crisp contemporary cabinetry, beautiful countertops, a water purification system and thoughtful finishes throughout. Designed with entertaining in mind, the residence also features a custom bar complete with a wine cooler, dedicated whisky display and built in cigar humidor, creating a distinctive space for cocktails, wine and evenings with friends. New furnishings throughout, including select pieces from Restoration Hardware, complete the refined yet relaxed coastal feel. Bayport offers an exceptional Longboat Key lifestyle, stretching from the Gulf of Mexico to Sarasota Bay and giving residents the opportunity to enjoy both beach and bay. Community amenities include private Gulf beach access, a heated swimming pool, tennis courts, fitness facilities, clubhouse, walking and nature paths, kayak facilities and access to Sarasota Bay. Start the morning with a walk along the Gulf, work from your private home office, spend the afternoon by the pool or on the water, and finish the evening entertaining at home or taking in a Longboat Key sunset. Completely remodeled, beautifully furnished and ready to enjoy from day one, 732 Bayport Way offers the opportunity to step directly into the Longboat Key lifestyle without the time, expense or inconvenience of undertaking a major renovation.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat Key’s distinctive Gulf to Bay communities. Thoughtfully redesigned and renovated in 2023, this 2 bedroom, 2 bath residence offers approximately 1,456 square feet of sophisticated, move in ready living with virtually every detail updated. The renovation includes new flooring, countertops and windows, along with a dedicated home office that creates the perfect space for working remotely or enjoying a quiet study. The sleek, redesigned kitchen features premium JennAir appliances, crisp contemporary cabinetry, beautiful countertops, a water purification system and thoughtful finishes throughout. Designed with entertaining in mind, the residence also features a custom bar complete with a wine cooler, dedicated whisky display and built in cigar humidor, creating a distinctive space for cocktails, wine and evenings with friends. New furnishings throughout, including select pieces from Restoration Hardware, complete the refined yet relaxed coastal feel. Bayport offers an exceptional Longboat Key lifestyle, stretching from the Gulf of Mexico to Sarasota Bay and giving residents the opportunity to enjoy both beach and bay. Community amenities include private Gulf beach access, a heated swimming pool, tennis courts, fitness facilities, clubhouse, walking and nature paths, kayak facilities and access to Sarasota Bay. Start the morning with a walk along the Gulf, work from your private home office, spend the afternoon by the pool or on the water, and finish the evening entertaining at home or taking in a Longboat Key sunset. Completely remodeled, beautifully furnished and ready to enjoy from day one, 732 Bayport Way offers the opportunity to step directly into the Longboat Key lifestyle without the time, expense or inconvenience of undertaking a major renovation.

732 Bayport Way, Longboat Key

$815,000

Situated on an extra large 11,250 sf waterfront lot, with a 2020 seawall, and deeded beach access, this fabulous single family home represents one of the best investments on all of Longboat Key! Completely renovated and ready for you to move right in and start enjoying island life or a dreamy location for you to earn monthly rental income while you envision building your own island getaway. Charmingly decorated, with a new kitchen and all new appliances, in an open floor plan with beautiful wood look tile that flows seamlessly from room to room. 2022 storm windows provide a full wall of light while taking in the views overlooking the canal; A day out on the boat can be a routine adventure with easy access to the intracoastal waterway and no fixed bridges to the Gulf of Mexico. When you return, the 2nd bath has a door to the back so you can come right off the boat to the showers or it also could provide a perfect location as a pool bath if you choose to put in a pool. A covered carport provides a perfect place for outdoor dining. In only a short walk or bike ride down the street, you have your deeded beach access point, and you have access to multiple restaurants, shopping, 11 miles of bike paths and the beautiful nature trails of Joan Durante Park. With this mid-key location it's just a short drive to the new St.Regis Resort, world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this island home today. At this price point, it will not last long!

2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Situated on an extra large 11,250 sf waterfront lot, with a 2020 seawall, and deeded beach access, this fabulous single family home represents one of the best investments on all of Longboat Key! Completely renovated and ready for you to move right in and start enjoying island life or a dreamy location for you to earn monthly rental income while you envision building your own island getaway. Charmingly decorated, with a new kitchen and all new appliances, in an open floor plan with beautiful wood look tile that flows seamlessly from room to room. 2022 storm windows provide a full wall of light while taking in the views overlooking the canal; A day out on the boat can be a routine adventure with easy access to the intracoastal waterway and no fixed bridges to the Gulf of Mexico. When you return, the 2nd bath has a door to the back so you can come right off the boat to the showers or it also could provide a perfect location as a pool bath if you choose to put in a pool. A covered carport provides a perfect place for outdoor dining. In only a short walk or bike ride down the street, you have your deeded beach access point, and you have access to multiple restaurants, shopping, 11 miles of bike paths and the beautiful nature trails of Joan Durante Park. With this mid-key location it's just a short drive to the new St.Regis Resort, world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this island home today. At this price point, it will not last long!

691 Tarawitt Drive, Longboat Key

2101 Harbourside Drive Unit 1103, Longboat Key

$1,495,000

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

2020 Harbourside Drive Unit 442, Longboat Key

$699,000

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

$399,000

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Beautifully located 55+ Community. Own the land you live on in Longboat Key. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 6 feet up, 2-bedroom, 2 bath, open floorplan home. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new future Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickle ball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! Hurry, Paradise Awaits!

2 Beds ⋅ 2 Baths ⋅ Twin Shores Mobile Home SubDv. ⋅ 34228 Zip Code

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Beautifully located 55+ Community. Own the land you live on in Longboat Key. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 6 feet up, 2-bedroom, 2 bath, open floorplan home. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new future Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickle ball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! Hurry, Paradise Awaits!

96 Twin Shores Boulevard, Longboat Key