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$379,900
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave so special, paired with the fresh, move-in-ready updates. Behind the arched front entry and crisp white stucco exterior with its white tile roof, a bright open interior welcomes you, where neutral tile floors run throughout and natural light pours through plantation-shuttered windows. The renovated kitchen is the heart of the home, outfitted with white shaker cabinetry, quartz countertops, a waterfall-edged peninsula, a soft glass-tile backsplash, and crisp white appliances, all opening to a generous living and dining area finished with crown molding and an easy coastal feel. A versatile bonus room wrapped in windows, with a door to the back patio, makes a wonderful sunroom, reading retreat, or home office. Both bedrooms are comfortable and well-appointed, served by two beautifully updated bathrooms, one with a tub and shower framed in subway tile, the other a glass walk-in shower with a mosaic floor and designer fixtures. A covered carport with room for a golf cart, plus interior storage for kayaks and beach gear, adds everyday ease. Brick paver walkways and lush tropical landscaping wrap the home, and the concrete tile roof is just over five years young. Life at Spanish Main is built around the water and the warmth of neighbors. Residents enjoy a heated pool overlooking the basin, a clubhouse, shuffleboard courts, kayak storage and launch, and a deep-water marina with boat slips available for a monthly fee, offering quick access to Sarasota Bay and the Gulf beyond. Best of all is the community's private Gulf beach access, just a short stroll away, along with shaded benches lining the lagoon and a waterfront green where slow mornings and golden evenings by the water become a way of life. Beyond the community, the white sand of Longboat Key's Gulf beaches is moments away, with the boutiques and dining of St. Armands Circle, downtown Sarasota's culture, and the laid-back charm of Anna Maria Island all within easy reach. Come experience the rare blend of comfort, community, and coastal beauty that makes this villa a place to call home. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

602 Spanish Drive S Unit 115, Longboat Key
$1,225,277
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code
A rare opportunity to own a beautifully reimagined Gulf-front residence at the prestigious Islander Club on South Longboat Key. Completely renovated with sophisticated coastal elegance, this exceptional beachfront condominium offers the convenience of first-floor walk-out living with direct access to the resort-style beachfront pool and the pristine white sands of the Gulf of Mexico. Walls of glass frame breathtaking panoramic Gulf views while filling the residence with natural light and spectacular sunsets. Thoughtfully redesigned with high-end finishes, the residence features a luxurious open-concept floor plan, a stunning chef's kitchen, beautifully appointed baths, and seamless indoor-outdoor living. The private beachfront terrace serves as an extension of the living space, creating the perfect setting for morning coffee, sunset cocktails, and effortless entertaining. Ideally positioned on the coveted south end of Longboat Key, this residence offers the privacy and comfort of a beachfront home with the convenience of luxury condominium living. Residents enjoy an impressive collection of amenities including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and vibrant downtown Sarasota, this exceptional residence places world-class dining, boutique shopping, cultural attractions, and marina amenities within easy reach. An extraordinary opportunity to experience refined Gulf-front living at one of Longboat Key's most sought-after beachfront addresses.

2301 Gulf Of Mexico Drive Unit 12N, Longboat Key
$1,225,277
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code
Experience the tranquility of Gulf-front living from this beautifully updated residence at the prestigious Islander Club on South Longboat Key. Ideally positioned on the highly desirable north side of the building, this exceptional beachfront condominium enjoys a uniquely private setting with expansive views, abundant natural light, and a peaceful atmosphere rarely found in condominium living. Offering the convenience of first-floor walk-out access, the residence lives much like a private beachfront home, with direct access from the terrace to the lush grounds, beachfront pool, and the pristine white sands of the Gulf of Mexico. Floor-to-ceiling glass showcases sparkling Gulf views, breathtaking sunsets, and refreshing coastal breezes throughout the day. Thoughtfully updated and impeccably maintained, the residence offers comfortable and elegant living spaces ready to be enjoyed immediately . The open layout seamlessly connects indoor and outdoor living, creating an ideal setting for both relaxing and entertaining. Residents of The Islander Club enjoy an exceptional collection of amenities, including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, library, conference facilities, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and downtown Sarasota, this residence offers convenient access to world-class dining, boutique shopping, cultural attractions, marinas, and the very best of Florida's Gulf Coast lifestyle. A rare opportunity to enjoy privacy, beachfront living, and the unmatched beauty of Longboat Key at one of the island's most sought-after addresses.

2301 Gulf Of Mexico Drive Unit 11N, Longboat Key
$1,199,000
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code
Experience breathtaking beachfront living in this rare direct Gulf-front residence at the prestigious Islander Club on Longboat Key. This two-bedroom, two-bath condominium showcases panoramic Gulf of Mexico views from every room, including the living room, primary suite and guest bedroom, creating a spectacular coastal backdrop throughout the home. One of the exceptional features of this residence is its oversized deeded beachfront terrace, a rare offering within the community. Only a select few residences at the Islander Club enjoy this expansive outdoor space, which enhances the home's connection to the beach and provides an unparalleled vantage point for taking in sweeping Gulf views and spectacular sunsets. Wake up to the sound of the waves, enjoy stunning water views from nearly every location and embrace the relaxed luxury of Longboat Key beachfront living. The Islander Club is a sought-after community with 400 feet of private beach frontage. Islander Club offers residents on-site management, a heated pool, renovated clubhouse, billiards and table tennis room, fitness center, saunas and two Har-Tru tennis courts. The shopping, dining and cultural attractions of St. Armands Circle and downtown Sarasota are just a short drive away.

2301 Gulf Of Mexico Drive Unit 33N, Longboat Key
$2,125,000
3 Beds ⋅ 3 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code
Virtually Staged. Sweeping sunrise to sunset views define this beautifully reimagined 7th floor residence at the Promenade on Longboat Key. Fully renovated in 2026, this three-bedroom, three full bath home offers floor to ceiling windows, abundant natural light, and 180- degree views of both the Gulf of Mexico and Sarasota Bay. The double door entry opens to a freshly painted residence with new luxury plank flooring, nine-foot ceilings and modern lighting throughout. This residence is designed for entertaining with a large open living area and a full wet bar and wine refrigerator. The kitchen features quartz countertops and full quartz backsplash, Sub-Zero refrigerator, Cafe stove and double convection oven, and matching panel dishwasher. The custom modern white soft closed cabinetry with polished nickel hardware provides a stylish look as well as large amounts of storage and pantry space. A reimagined kitchen layout allows for a separate island that can be used for morning coffee, workspace or meal preparation all while enjoying gorgeous bay views. The primary suite features a spa-like oasis with new enlarged glass enclosed shower featuring waterfall and wall shower-heads, all quartz countertops, dual sinks, polished nickel faucets, fully backlit electric mirrors, separate water closet, linen storage and a custom designed walk-in closet. The two additional bedrooms each offer private bathrooms, one with a dazzling walk-in shower and the other with a new bathtub/shower. The renovations included removing all popcorn ceilings, updates to electrical and plumbing systems, all new fire sprinkler hardware and base boards. The full-sized laundry room includes new storage cabinetry, full sized washer/dryer and a wash-sink. All new interior doors fitted with Emtek polished nickel door hardware. The residence includes a private storage locker that is humidity and temperature controlled and a deeded underground parking space. The Promenade has undergone significant renovation over the past few years and features elegant marble foyer, 24-hour gate security, manned concierge desk, his and hers fitness rooms with shower and sauna, luxurious party rooms, EV charging station, a well-maintained pool deck and hot tub, verdant tropical landscaping and dual BBQ areas. The beach is located directly behind the building and features a secure entrance and beach chairs. There are also 4 Har-Tru tennis courts to complete the Longboat Key lifestyle. The Promenade is located near the south end of Longboat Key, minutes from St. Armand's Circle and the restaurants and arts offerings of downtown Sarasota. The Longboat Key Club and its golf, tennis and marina offerings is available for membership and just outside the property.

1211 Gulf Of Mexico Drive Unit 701, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
The lifestyle stays premium. The price just got friendlier. Tucked within the waterfront community of Spanish Main Yacht Club on the north end of Longboat Key, this fully renovated detached villa offers a timeless coastal flair just steps from the beach. A true hidden gem and slice of paradise, residents enjoy private deeded beach access to the Gulf of America, a deep water marina with affordable boat slips, and the ultimate boating lifestyle with easy access to waterfront restaurants and open waters. This light and bright 2-bedroom, 2-bath residence is being offered turnkey furnished. Featuring an open floorplan with luxury vinyl plank flooring, impact windows and doors, custom window shades throughout, and a spacious Florida room ideal for additional living or entertaining space. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant custom cabinetry with soft-close drawers, and a large seating island perfect for gathering. Additional highlights include an interior laundry room with stackable washer and dryer, water softener system, stone paver patio, covered parking, and private driveway. Spanish Main Yacht Club is a vibrant and active 55+ community offering a heated waterfront pool, shuffleboard, social events, pet-friendly policies, maintenance-free living, and one of the most desirable 40-slip marinas on Longboat Key. Ideally located just minutes from St. Armands Circle, Sarasota, and Anna Maria Island, this exceptional Longboat Key retreat is ready for immediate enjoyment.

546 Spanish Drive S, Longboat Key
$1,995,000
3 Beds ⋅ 2 Baths ⋅ Villa Di Lancia SubDv. ⋅ 34228 Zip Code
Discover elevated Gulf-front living in this rarely available 3BR/3BA residence spanning 2,448 square feet in the prestigious Villa Di Lancia on Longboat Key. Perfectly positioned to capture panoramic Gulf views, this spacious condominium offers the ideal blend of privacy, security, and effortless coastal luxury. Expansive glass sliders, transom windows, and high ceilings fill the interiors with natural light, enhancing open living spaces designed for both relaxed living and entertaining. The great room flows seamlessly to a generous covered terrace, creating a year-round indoor-outdoor lifestyle. A unique private walk-out with spiral staircase provides direct access to the lush grounds, resort-style pool, and the pristine Gulf beach just steps away—an exceptional feature rarely found in condominium living. The well-appointed kitchen features a center island, solid surface countertops, and a casual dining area, perfectly suited for hosting family and guests. The primary suite serves as a tranquil retreat with terrace access, a sitting area, and a spacious bath with dual vanities, soaking tub, and glass-enclosed shower. Two additional guest bedrooms offer comfort and privacy. Villa Di Lancia is one of Longboat Key’s most sought-after beachfront communities, offering 440 feet of private beach, gated security, a beachfront lap pool and spa, fitness center, clubhouse, Har-Tru tennis courts, and pet-friendly living. The residence includes two climate-controlled garage parking spaces. Turnkey furnishings are available. Enjoy a lifestyle defined by convenience and sophistication—just minutes to the Longboat Key Club’s golf, tennis, and marina, the world-class shopping and dining of St. Armands Circle, and the vibrant cultural scene of downtown Sarasota, including fine dining, theaters, opera, ballet, and art galleries. Schedule your private showing today and experience the best of Longboat Key Gulf-front living.

2185 Gulf Of Mexico Drive Unit 212, Longboat Key
$1,648,000
2 Beds ⋅ 2 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to own this beautifully reimagined first-floor residence at The Promenade on Longboat Key, where luxury coastal living meets sophisticated modern design. Completely gutted and renovated from top to bottom, this stunning condominium offers nearly 400 feet of private beach frontage and partial Gulf of Mexico views from almost every room. This spacious two-bedroom, two-bath split floor plan showcases a bright, open-concept design ideal for both entertaining and relaxed everyday living. The designer kitchen flows seamlessly into the expansive living and dining areas and features custom cabinetry, premium countertops with full-height backsplash, and top-tier appliances. A custom dry bar with built-in wine cooler and under-shelf lighting adds an elegant touch for effortless entertaining. Enjoy breathtaking northwest sunset views from the great room or unwind on the private balcony overlooking the Gulf. The luxurious primary suite offers direct balcony access, a large custom walk-in closet, and a spa-inspired en-suite bath complete with a soaking tub, rain shower system, and large-format designer tile creating a true retreat-like atmosphere. The generously sized guest bedroom provides comfort and flexibility for visitors. Every inch of this residence has been thoughtfully curated with exceptional craftsmanship and attention to detail, balancing modern sophistication with everyday comfort. The Promenade offers a true resort-style lifestyle with a 24-hour staffed gatehouse, concierge services, secure under-building assigned parking, heated Gulf-front pool and spa, expansive sundeck with gazebo and grilling area, four Har-Tru tennis courts, fitness center, craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes this extraordinary Longboat Key experience. Rarely does a completely renovated residence of this caliber become available in one of Longboat Key’s most desirable Gulf-front communities. Experience the ultimate in beachfront living, where every day feels like a vacation.

1211 Gulf Of Mexico Drive Unit 105, Longboat Key
$1,400,000
2 Beds ⋅ 2 Baths ⋅ Privateer North SubDv. ⋅ 34228 Zip Code
Welcome to your beachfront retreat in the sky. Perched on the 9th floor of the highly desirable Privateer North community on Longboat Key, this beautifully furnished 2-bedroom, 2-bath residence offers 1,409 square feet of coastal elegance and breathtaking panoramic Gulf views from every room. Wake each morning to the sound of waves and endless turquoise water, and end each day with spectacular sunsets from the comfort of your living room, primary suite, or private balcony. The light-filled open floor plan is designed to showcase the stunning waterfront setting, featuring spacious living and dining areas that flow seamlessly to the balcony overlooking the Gulf of Mexico. The well-appointed kitchen offers quartz countertops, modern appliances, ample cabinetry, and everything needed for effortless entertaining. The spacious primary suite features direct balcony access, a king-sized sleeping area, and an updated en-suite bath, while the guest bedroom provides generous accommodations for family and friends. Both bathrooms have been tastefully updated with elegant finishes and walk-in showers. Just steps from the building, residents enjoy a secluded stretch of pristine private beach complete with beach chairs and umbrellas, as well as a large heated beachfront pool and spa with unobstructed Gulf views. Privateer North offers an exceptional resort-style lifestyle with a newly renovated fitness center, pickleball courts, shuffleboard, outdoor grilling and picnic areas, covered parking, secure entry, on-site management, and beautifully maintained grounds. Ideally located on the southern end of Longboat Key, this residence is only minutes from the upscale shopping, dining, and entertainment of St. Armands Circle and a short drive to downtown Sarasota, renowned for its arts, culture, waterfront parks, and world-class restaurants. Offering unmatched views, exceptional amenities, and one of the area’s most sought-after beachfront locations, this is coastal living at its finest. ** Seller is a licensed Florida Real Estate Agent

1050 Longboat Club Road Unit 901, Longboat Key
$649,000
2 Beds ⋅ 3 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Experience coastal living at its finest in this beautifully updated ground-floor residence at Seaplace on Longboat Key. This 2-bedroom, 2.5-bath condominium in the desirable G5 building offers northwest Gulf views and stunning sunset skies from the screened lanai, just steps from the beach. The bright, open-concept floor plan features a sleek modern kitchen with glossy cabinetry, quartz countertops, stainless steel appliances, and a spacious breakfast bar perfect for entertaining. Floor-to-ceiling mirrors enhance the natural light and create a spacious, contemporary feel throughout the living and dining areas. The primary suite offers a peaceful retreat with an updated en-suite bath, while the guest bedroom provides comfort and privacy for family and visitors. Hurricane-impact sliding glass doors and windows provide peace of mind and energy efficiency. Whether you are seeking a vacation getaway, seasonal retreat, investment property, or full-time residence, this move-in-ready condo checks every box. Seaplace is a gated Gulf-front community situated on 42 beautifully landscaped acres spanning from the Gulf to the Bay. Residents enjoy resort-style amenities including 24-hour guard-gated security, a newly remodeled clubhouse, two heated swimming pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, walking trails, fitness center, and private beach access with beach chairs and umbrellas provided. Conveniently located near the Longboat Key Club, St. Armands Circle, and Sarasota’s dining and cultural attractions. Schedule your private showing today and start enjoying the Longboat Key lifestyle!

1965 Gulf Of Mexico Drive Unit G5-103, Longboat Key
$1,790,000
2 Beds ⋅ 2 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Rare 2BR First-Floor Lockout Unit | Resort at Longboat Key Club Experience the perfect blend of luxury vacationing and rental income with this rare, first-floor lockout suite overlooking the resort pool and just steps from the beach. • Versatile Rental Options: Lockout design allows you to rent as a full 2-bedroom suite or a 1-bedroom unit to maximize revenue. • Prime Location: First-floor convenience with an oversized deck, steps away from the beach, pool bar, and restaurants. • World-Class Amenities: Access to 45 holes of golf, 21 tennis courts, 5 restaurants, a luxury spa, fitness center, and a bayside marina. Perfect for families seeking a premium getaway with built-in investment potential.

210 Sands Point Road Unit 2101, Longboat Key
$1,025,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered terrace that offers direct beach access. Positioned at the northern end of the gulf side, Building 4 provides owners with a sense of privacy from pool activities while still being close to all amenities. As an owner, you gain access to the exclusive offerings of the 410-acre Longboat Key Club, including five fine dining options, 45 holes of championship golf, the award-winning Tennis Gardens, a spa and wellness center, a pristine white sand beach with umbrellas and waitstaff, and a full-service marina. The renovated rooms, main dining area, pool, and guest services enhance the experience at this award-winning property, recognized with accolades such as the AAA Four-Diamond Award and Condé Nast Travelers' Top Florida Resorts. Embrace the Longboat Life today!

240 Sands Point Road Unit 4104, Longboat Key
$2,550,000
4 Beds ⋅ 5 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code
Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.

3527 Fair Oaks Lane, Longboat Key
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.

4325 Gulf Of Mexico Drive Unit 103, Longboat Key
$960,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Completely renovated first floor walkdown Junior Suite with spectacular views of Longboat Key Club’s Golf Course currently in the hotel program now available. There is an expanded deck in addition to the covered terrace, ideal for watching a wide variety of wildlife and golfing activity. Building 5 is positioned where owners value privacy from the hustle and bustle of the main entrance and pool activities but are still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Gross income realized in 2023 was $130,895 and in 2024 was $117,719. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!

250 Sands Point Road Unit 5106, Longboat Key
$995,000
2 Beds ⋅ 2 Baths ⋅ Privateer North SubDv. ⋅ 34228 Zip Code
Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this beautifully renovated corner residence blends sweeping views, refined finishes and effortless coastal living. Offered TURNKEY FURNISHED, the 2-bedroom, 2-bath home looks out across the golf course, Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline, creating a view that shifts beautifully from morning light to evening sparkle. Inside, the renovation is immediately apparent. Clean neutral finishes, recessed lighting, crisp white trim and an open, comfortable floor plan keep the focus on the scenery beyond the glass. All glass is high-impact, hurricane-rated, and the residence also includes hurricane shutters for added peace of mind. The kitchen is designed for both everyday living and easy entertaining, with quartz countertops, custom cabinetry, high-end appliances, a wine refrigerator and detailed tilework. An inviting eat-in area frames bay views, bringing the water into daily life. The living and dining areas open to a terrace overlooking manicured grounds, the golf course and the bay beyond. Both bedroom suites are generously sized with walk-in closets, and the primary suite enjoys its own private terrace. The updated baths feature tasteful finishes, including a beautifully tiled walk-in shower in the primary bath. Privateer North offers a true beachfront lifestyle with a secure lobby, on-site management, heated pool and spa, fitness center, tennis and pickleball courts, social spaces and private beach access. For those seeking an even broader resort experience, optional membership at the Longboat Key Club offers access to 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining, beach and pool facilities, spa, fitness, wellness programming, social events and marina amenities. Located on the sought-after south end of Longboat Key, the residence is just minutes from St. Armands Circle, downtown Sarasota, fine dining, shopping, arts venues and the area’s best coastal amenities.

1050 Longboat Club Road Unit 903, Longboat Key
$435,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Calling all boaters. If you have ever considered living on Longboat Key in sunny beautiful Florida, now is your chance! This amazing villa is available and ready for you to move to paradise! 711 Spanish Dr. S. is a 2 bedroom/2bath home that has been newly renovated in 2025/2026 and it is beautiful! Entering the home your eyes are immediately drawn upwards to the gorgeous open beam 10’-12’ ceiling over the kitchen and dining area. The kitchen is complete with all new wood cabinets, new stainless top of the line appliances, undermount sink, Quartz counter tops, and an oversized island with a dark blue base which brings in a beautiful pop of color. The open floor plan flows easily with luxury vinyl connecting all the rooms. The dining living combination is airy and bright. The primary bedroom is divided from the Florida room with textured glass pane sliding doors that allow the light in but keep the space quiet and private. Beautifully renovated primary bath is tastefully appointed. The guest bedroom and bath have been updated with the same quality and fine design as the entire villa. The large Florida room houses the stacked washer and dryer in their own space. A stylish glass back door leads to the brick patio perfect for your potted plants and just sitting and enjoying the perfect Florida weather. A newly installed PVC gate secures the common area shared by the adjoining villa. Perfect area for grilling, storage of bikes, beach chairs, paddle boards and more. There is also easy access to the unit's storage room. This is a must see! Make it your new home with all hurricane rated windows and doors, and so much more. This vibrant 55+ community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, and lots of amenities, shuffleboards, swimming pool, private deeded beach access to the gorgeous Longboat Key beaches and the warm Gulf waters. Fishing, boating and so much more. The expansive 40 slip Marina in the envy of all boaters as the lease is extremely inexpensive to lease, you won’t believe it. Call for details. Close to St Armands Circle and downtown Sarasota makes this location perfect for shopping, dining, theater, botanical gardens, airport and more. All 212 units in Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. All FEMA regulations completed including inspections. Come and enjoy your soft place to land in this world.

711 Spanish Drive S, Longboat Key
$625,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
A rare private walk-down residence in the highly sought-after Beachplace community on Longboat Key. This property offers the convenience of direct terrace access to the beautifully landscaped grounds below, overlooking a serene pond with fountains and offering a charming peekaboo view of the Gulf. Spacious and largely original, presenting the perfect canvas for a buyer to customize and create their ideal coastal retreat while enjoying the exceptional location and layout. The light-filled interior features an open living and dining area with walls of glass that connect seamlessly to the outdoor living space, creating an inviting indoor-outdoor lifestyle just moments from the beach. The split-bedroom floor plan offers privacy and functionality, while the terrace provides a peaceful setting to relax and enjoy the lush tropical surroundings. Whether updating immediately or renovating over time, this residence offers tremendous potential within one of Longboat Key’s premier Gulf-front communities. Beachplace is renowned for its resort-style amenities and beautifully maintained grounds. Residents enjoy 24-hour guard-gated entry, on-site management, a clubhouse, fitness center, tennis and pickleball courts, heated swimming pool and spa, private beach access, walking paths, and expansive tropical landscaping throughout the community. Ideally positioned on the south end of Longboat Key, Beachplace is just minutes from the fine dining, boutiques, and waterfront charm of St. Armands Circle, as well as downtown Sarasota’s cultural attractions, marinas, golf clubs, and world-class beaches. Whether you are searching for a seasonal getaway, investment opportunity, or full-time coastal residence, this property presents exceptional value and the opportunity to create a personalized beachfront retreat in one of Longboat Key’s most desirable locations.

1095 Gulf Of Mexico Drive Unit 102, Longboat Key
$999,000
3 Beds ⋅ 2 Baths ⋅ Longboat Landing Condominium SubDv. ⋅ 34228 Zip Code
Rarely available within the intimate nine-residence bayfront community of Longboat Landing, this beautifully updated three-bedroom residence captures panoramic Sarasota Bay views and effortless waterfront living from its prized location on the north end of Longboat Key. Offered turnkey furnished and completely move-in ready, the getaway combines a refined coastal aesthetic with the rare convenience of on-site boat slips and docks (on a first-come basis) capable of accommodating up to a 26-foot vessel—creating an ideal opportunity for boating enthusiasts seeking immediate enjoyment. Spanning more than 1,300 square feet, the open-concept layout is filled with natural light and designed to maximize the calming bayfront setting. Contemporary wood-grain tile flooring flows throughout the residence, while crown molding, high ceilings, and chic modern finishes enhance the interiors. An extended foyer hallway leads to the sunlit great room, where walls of impact-rated floor-to-ceiling pocketing sliders open completely to the screened bayfront terrace, creating a seamless indoor-outdoor connection framed by sparkling blue water views. The granite kitchen overlooks the main living spaces and was thoughtfully designed for both entertaining and everyday living. Features include a wraparound breakfast bar, informal dining area, solid-wood cabinetry, granite countertops and backsplash, stainless steel appliances, and generous prep space. Recent upgrades provide added peace of mind, including a 2024 A/C replacement, 2023 Hardi Plank siding installation, impact-rated windows and sliding doors throughout, kitchen and bath renovations, updated finishes, ductwork modifications, and a newer roof. The primary suite is positioned directly along the bayfront, offering tranquil water views and private terrace access. Two additional guest bedrooms are arranged in a split plan for privacy, including one en-suite guest suite and a third bedroom currently utilized as a home office. Completing the residence are a private laundry room, two under-building parking spaces, and additional exterior storage. Outside, residents enjoy the relaxed waterfront lifestyle Longboat Landing is known for, with amenities including dock slips, fishing pier, heated community pool, and tennis court—all surrounded by lush tropical landscaping and Sarasota Bay vistas. Perfectly positioned along Gulf of Mexico Drive, this charming bayfront getaway is moments from Longboat Key’s renowned beaches, waterfront dining, boutique shopping, marinas, and scenic biking paths. St. Armands Circle and downtown Sarasota are just a short drive away, offering fine dining, galleries, theaters, Selby Gardens, and Sarasota’s vibrant cultural attractions. Rarely available, beautifully updated, and directly on Sarasota Bay, this residence offers an exceptional opportunity to embrace the best of Longboat Key waterfront living.

5320 Gulf Of Mexico Drive Unit 101, Longboat Key
$3,850,000
3 Beds ⋅ 3 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code
Welcome to coastal luxury redefined at the Water Club on Longboat Key. This fully reimagined residence at 1241 Gulf of Mexico Dr, Unit 506 has undergone a complete, top-to-bottom renovation completed in 2025, offering a like-new living experience in one of Florida’s most sought-after beachfront communities. No detail was overlooked—featuring a brand-new designer kitchen with premium finishes, fully renovated bathrooms, new flooring throughout, updated trim, modern lighting, and fresh interior paint. The home is further elevated by a whole-home Lutron system, delivering effortless, customizable lighting control and a true smart-luxury experience. Positioned in the highly desirable south building and an even-numbered unit (ideal for sunset views over the Gulf), this residence captures some of the most breathtaking winter sunset views—where the sun sets between the buildings, creating a rare and unforgettable coastal backdrop. Residents enjoy an unparalleled resort lifestyle at The Water Club, featuring an exceptional collection of amenities including Har-Tru tennis courts, a resort-style beachfront pool and spa, state-of-the-art fitness center, saunas, locker rooms, elegant clubhouse, library, and private event spaces. With 24-hour security, concierge-level services, and meticulously maintained grounds, The Water Club offers the ultimate in privacy, comfort, and luxury coastal living. Whether as a full-time residence or seasonal retreat, this is Gulf-front living at its absolute finest.

1241 Gulf Of Mexico Drive Unit 506, Longboat Key
$670,000
2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code
This exceptionally clean and well maintained 2-bedroom, 2-bath residence in Bayport Beach and Tennis Club is ideally positioned as a bright and private second-floor end unit with no neighbors above, and is filled with natural light. Kitchen, dining, living room open design with split bedrooms for privacy. The primary suite features a walk-in closet and a dedicated office niche—perfect for today’s work-from-home lifestyle. Two inviting outdoor living spaces—a private open-air deck and a screened lanai overlooking the tropical gardens—create the perfect setting to relax and unwind. Additional highlights include newer kitchen, bathrooms, and windows. The condo includes covered parking, ample guest parking, two private storage areas plus an owner’s closet, and the convenience of an in-unit full-size washer and dryer. Set on 27 acres of beautifully landscaped grounds on Longboat Key, Bayport is a sought-after gulf-to-bay community designed by renowned architect Tim Seibert. Residents enjoy 1,200 feet of deeded private beach access along the Gulf of Mexico. Community amenities are exceptional, including a Junior Olympic-size heated pool—one of the largest on the Key—four Har-Tru tennis courts, a fitness center, fishing pier, and kayak launch. Beach chairs and umbrellas are provided by the condo association, and a full calendar of seasonal social activities fosters a vibrant yet relaxed coastal lifestyle. Meandering shell pathways and meticulously maintained tropical landscaping complete the serene setting. Experience the best of island living with breathtaking sunrises over the bay, unforgettable sunsets on the beach, and everything in between.

843 Bayport Way Unit 843, Longboat Key
$512,000
2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity. Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches. Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape. This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.

1930 Harbourside Drive Unit 122, Longboat Key
$410,000
1 Beds ⋅ 1 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code
Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and coastal-inspired design. The home offers a relaxed, airy feel perfect for full-time living, a seasonal getaway, or an investment property. This pet-friendly and rental-friendly community is vibrant and social, offering an unmatched waterfront lifestyle. Residents enjoy private beach access, two pools, tennis and shuffleboard courts, a fitness center, and kayak launch and storage. Boating and fishing enthusiasts will appreciate the boat slips and fishing dock, while outdoor living is elevated with grill stations, picnic areas, and complimentary beach chairs. Whether you are searching for a relaxing coastal escape or an active waterfront lifestyle, this exceptional Longboat Key condo delivers the very best of Florida living with breathtaking water views, abundant amenities, and endless opportunities to enjoy the beauty of marine life and island living!

6700 Gulf Of Mexico Drive Unit 143, Longboat Key
$675,000
2 Beds ⋅ 2 Baths ⋅ Longboat Arms SubDv. ⋅ 34228 Zip Code
Island Elegance on the Bay: A Turnkey Waterfront Sanctuary! Escape to the serene shores of Longboat Key and experience the pinnacle of coastal luxury at 3330 Gulf of Mexico Drive. This meticulously reimagined, two-bedroom, two-bathroom residence offers a rare "walk-out" lifestyle, where lush green lawns meet the shimmering waters of the Sarasota Bay. The Interior: Modern Luxury Meets Tropical Soul. No detail was spared in this fully renovated, turnkey-furnished masterpiece. Step inside to find an open-concept sanctuary defined by high-end finishes and a sophisticated "island chic" aesthetic. Gourmet Kitchen: Features crisp white cabinetry, designer backsplash, and premium stainless steel appliances, perfect for the culinary enthusiast. Designer Living: Relax in a sun-drenched living area adorned with organic textures, custom wood-slat feature walls, and curated furnishings that reflect the colors of the coast. Master Suite: A true retreat, the primary bedroom opens directly to the outdoors, allowing you to wake up to the gentle sounds of the bay and the rustle of palm trees. Spa-Inspired Baths: Indulge in sleek, modern bathrooms featuring frameless glass showers, backlit mirrors, and contemporary vanities. The "Florida Room" Experience: The heart of this home is the climate-controlled Florida Room. Encased in floor-to-ceiling glass, this versatile space offers an effortless transition to the outdoors. Whether you're sipping your morning coffee or hosting a sunset dinner, you'll enjoy front-row views of local wildlife, passing boats, and the sparkling bay. Unrivaled Amenities & Location: Situated within the coveted Longboat Arms community, you'll enjoy a resort-style lifestyle with access to: Waterfront Perks: Private boat slips, a boat ramp, and kayak storage for the ultimate bayfront adventure. Leisure & Sport: A heated community pool and tennis courts just steps from your door. Deeded Beach Access: Simply cross the street to sink your toes into the world-famous white sands of Longboat Key's private beaches. Prime Location: Located on the south end of the Key, you are mere minutes from the upscale dining, boutique shopping, and cultural arts of St. Armands Circle and Downtown Sarasota. Your Turnkey Paradise Awaits: Offered fully furnished with a curated selection of "Artful Living" decor, this condo is ready for immediate enjoyment. Whether you're looking for a seasonal getaway or a permanent slice of paradise, this is the coastal retreat you've been waiting for. Experience the beauty for yourself. Welcome home to Longboat Key.

3330 Gulf Of Mexico Drive Unit 107D, Longboat Key
$825,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!

4825 Gulf Of Mexico Drive Unit 504, Longboat Key
$799,000
2 Beds ⋅ 2 Baths ⋅ Mccalls Beach Castle SubDv. ⋅ 34228 Zip Code
Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.

5311 Gulf Of Mexico Drive Unit 5, Longboat Key
$599,000
2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code
Enjoy the benefits of a well-managed waterfront community with just 39 residences and attractively low condominium association fees. Set within an intimate waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.

448 Gulf Of Mexico Drive Unit A205, Longboat Key
$750,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.

900 Spanish Drive N, Longboat Key
$999,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the kitchen, dining, and living areas, creating a bright and functional space designed to maximize natural light and water views. The private balcony is the perfect place to spot dolphins, manatees and other wildlife while enjoying morning coffee or evening sunsets. With only 42 residences, Tiffany Plaza offers a more private and welcoming atmosphere than larger condominium communities, with an active clubhouse and strong sense of community among owners. Residents also enjoy close proximity to Bayfront Park, featuring dog parks, tennis, pickleball, kayak facilities, fitness classes, and beautiful bay front walking paths.

4325 Gulf Of Mexico Drive Unit 305, Longboat Key
$435,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy private deeded beach access to the powder sands and turquoise color of the Gulf of Mexico — perfect for sunrise walks, beachcombing, or sunset gatherings. Boaters will appreciate the community’s deep-water marina with boat slips priced around $1,200 annually that have direct access to the Intracoastal Waterway, and quick passage to the open Gulf, along with kayak racks and fishing right at hand. Inside, the bright open-concept 2-bedroom, 2-bath villa showcases an elevated, contemporary coastal design. The gourmet kitchen is a true entertainer’s dream, featuring sleek modern cabinetry, elegant stone countertops, a spacious island, and high-end stainless steel appliances. Sunlight pours through the generous windows and sliders, highlighting the beautiful new flooring that flows seamlessly into the living and dining areas. A sun-drenched Florida room/lanai offers flexible space, ideal for a home office, artist studio, or casual living — all overlooking lush tropical landscaping and a peaceful community setting. Both bedrooms are generously sized with ample closet space, while the updated baths feature contemporary fixtures and finishes for a spa-like feel. Additional highlights include a private outdoor shower, a spacious carport for your island toys, and thoughtful storage throughout. This vibrant, friendly 55+ community (can be under 55 to purchase) offers a heated pool, a clubhouse with marina views, shuffleboard courts, and a welcoming social atmosphere. Maintenance-free living, beautifully landscaped grounds, and covered parking complete the carefree Longboat Key lifestyle. Whether you seek a full-time waterfront residence, seasonal escape, or outstanding investment, 718 Spanish Dr N offers turnkey luxury with effortless deeded beach access and marina convenience in one of Longboat Key’s most desirable waterfront enclaves. Minutes to St. Armand's Circle, downtown Sarasota, and Anna Maria Island, yet tucked away in paradise. Don’t miss this rare opportunity to own a freshly renovated gem in Spanish Main Yacht Club — where high-end coastal living meets the best of island boating and beach life!

718 Spanish Drive N, Longboat Key