Sarasota Homes with Sailboat Water Water Frontage

2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code

This beautifully renovated 2-bedroom, 2-bath condominium overlooking the bay was freshly painted on 9/8/2026 and is truly move-in ready. Turnkey furnished with an open kitchen featuring granite countertops, stainless-steel appliances, and solid-wood cabinets. The thoughtfully reconfigured layout is ideal for entertaining or relaxing while taking in spectacular views of the bay and nature preserve. Both bathrooms have been nicely remodeled, with tile flooring throughout, recessed lighting, and solid-wood interior doors. Wake each morning to breathtaking sunrises from your bed with a cup of coffee or tea. The spacious air-conditioned lanai, with full-width sliding glass doors, is perfect for watching dolphins and manatees, boaters and kayakers, or simply enjoying a good book. In-unit washer and dryer plus a separate lower-level storage area for beach chairs, fishing gear, golf equipment, and more. Simple paradise! *** THE POINTE is a pet-friendly gated community that offers the best of both worlds — activity and exercise alongside peace and tranquility. Surrounded by water on three sides and set on 5+ acres of prime waterfront, residents enjoy boat docks with electricity and water, outdoor walkways to each unit, a heated outdoor lap pool, spa, sauna, kayak/canoe/SUP launches, tennis and pickleball courts, dog walk, open-air gazebo with BBQ grills, clubhouse, entertaining/party rooms, fitness centers in each building, a non-smoking environment, butterfly garden, and more. Advantageously located near fine and casual dining, Turtle Beach, shopping, coffee shops, nightlife, entertainment, Siesta Key Beach, a full-service marina, public transportation, and everything else this island paradise has to provide A rare opportunity to own a true piece of Siesta Key.

9393 Midnight Pass Road Unit 205, Sarasota

$77,900

Phillippi Harbor Club SubDv. ⋅ 34231 Zip Code

OWNER FINANCING AVAILABLE! This inside boat storage rack measures 32' L x 10'W x 9.5'H and can accommodate a boat with dimensions UP TO APPROXIMATELY: 32'L x 9'W x 8'H. Height is measured from the bottom of the keel up to the highest fixed point on the boat. Phillippi Harbor Club is your answer to truly enjoying boating on our beautiful Sarasota waters! This is a boating gamechanger! Simply call the friendly PHC staff and ask them to "splash" your boat, show up and enjoy your day on the water. Return to the dock where the staff will pull your boat, wash & rinse the outside, flush the engine(s), and store it back in your rack for next time. The marina has fuel on site, and an inside storage locker is included. There are plenty of work racks and on-site mechanics almost daily. This is a hurricane category 3-rated building with the latest in fire equipment and enhanced security monitoring. Phillippi Creek is around 4' at mean high tide and is about a 6-minute ride to the Intracoastal Waterway. The racks are in incredible rental demand! Stop towing your boat and own your own rack today...Stop on down and see the operation! Ask about owner financing.

1780 Phillippi Shores Drive Unit A3-5, Sarasota

$4,795,000

Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$995,000

3 Beds ⋅ 2 Baths ⋅ Hudson Landings SubDv. ⋅ 34236 Zip Code

Bring your boat and live downtown. West of the trail waterfront condo on the Hudson Bayou. Beautifully renovated 3 bedrooms, 2 bathrooms, a deeded dock and a garage, this condo is an incredible opportunity to live downtown with water view overlooking the Hudson Bayou. Offering a unique lifestyle, you can walk to downtown Sarasota, the Selby garden and the Marina. Enjoy other features such as skylights, custom closets, tile flooring, newer italian style shower, vaulted ceilings, newer granite countertops and top of the line stainless appliances. South exposition, enjoy morning coffee or the perfect ending of the day with amazing water view from your open balcony. Hudson Landings is a 12 units residence, tucked in a private, calm and secluded location. An absolute must see with wow factor. Tenant occupied until November 31st 2026.

870 Hudson Avenue Unit 870, Sarasota

$4,795,000

2 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$6,990,000

5 Beds ⋅ 6 Baths ⋅ Bird Key Sub SubDv. ⋅ 34236 Zip Code

Breathtaking Bird Key Bayfront Estate | 5 Bedrooms | 5.5 Bathrooms | 5,176 SF | 0.69 Acre Experience the ultimate in Sarasota Bayfront living at this extraordinary Bird Key estate, where timeless coastal elegance meets modern luxury. Set on a private 0.69-acre homesite, the 5,176-square-foot residence is perfectly positioned to showcase sweeping bay views, spectacular sunsets and an unparalleled waterfront lifestyle. A grand paver driveway leads to oversized glass double doors, opening to an impressive, light-filled interior defined by soaring tray ceilings, intricate crown molding, designer finishes and expansive walls of impact glass. The open-concept design creates a seamless connection between the refined interiors and the breathtaking outdoor surroundings. At the heart of the home, the gourmet chef’s kitchen is both stylish and functional, featuring top-of-the-line appliances, custom cabinetry, a generous island, 2 butler’s pantries and temperature-controlled wine cellar—ideal for intimate dinners or effortless entertaining. Additional living spaces include a dedicated office, elegant formal and casual gathering areas, and a sophisticated game room designed for relaxed enjoyment. Each of the five spacious bedrooms offers a private retreat of comfort and serenity. Thoughtfully designed and beautifully appointed, the accommodations provide exceptional privacy for family and guests alike. Walls of glass pocket open to a spectacular resort-style outdoor oasis. A sparkling pool with sun shelves and spa is surrounded by a luxurious travertine deck overlooking tranquil Sarasota Bay. The expansive outdoor living area includes a full kitchen, covered lounge and dining spaces, creating the perfect setting for year-round entertaining, sunset cocktails and relaxing waterfront days. Enjoy direct access to the bay from your private beach, dock and boat lift, or take a leisurely stroll to the shops and restaurants of St. Armands Circle and the cultural attractions of downtown Sarasota. With its rare blend of privacy, sophistication and premier bayfront access, this exceptional Bird Key estate offers a truly unparalleled coastal lifestyle.

101 Seagull Lane, Sarasota

$859,000

2 Beds ⋅ 2 Baths ⋅ Harbor House West SubDv. ⋅ 34236 Zip Code

****WATER VIEWS GALORE**** Breathtaking views of the Sarasota Bay, Fabulous sunsets, and unobstructed views of John Ringling Bridge from every 4th Floor window. Don't worry there is an elevator. END UNIT CONDO WITH EXTRA WINDOWS. FURNISHED Condo on Golden Gate Point. Remodeled 2-bedroom, 2-bathroom waterfront condo has classic style with modern conveniences. This open floor plan design has functionality, comfort, and is aesthetic pleasing. Perfect setting for everyday living and special occasions. Whirlpool stainless steel appliances (Refrigerator, Microwave, Dishwasher and Range). Laminate flooring throughout main living area. Chef's delight as well as an entertainer's dream. The gourmet kitchen has custom cabinetry and an oversized quartz island with seating. The primary bedroom features a walk-in closet, a king-sized bed, and an updated primary bathroom. The guest bedroom features a good-sized built-in closet and a queen-size bed. The laundry room comes with a washer, dryer, and lots of storage for your convenience. Most windows have plantation shutters. The main water view windows have motorized blinds. Amenities include a fitness room, Bayfront social area, a day dock with boat slips, guest parking and one premium covered parking for your convenience. Luxurious condo close to downtown Sarasota, Marina Jacks, St. Armand’s Circle, Sarasota Memorial Hospital, Marie Selby Botanical Gardens, Bayfront Park and Van Wezel Performing Arts Hall to name a few. Only 3 miles or less to Lido Beach, St. Armand’s Circle and Longboat Key. Only 4 miles to Sarasota Bradenton International Airport. Easy to show and priced to sell. Condo is also on the market for rent. Don't worry owner says whatever happens first. Tenant in place till December 31st 2026. Easy to show.

226 Golden Gate Point Unit 44, Sarasota

$22,000,000

4 Beds ⋅ 7 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Virtually Staged. Pre-Construction. To be built. Welcome to 3200 Higel Avenue, an extraordinary new waterfront residence by Pham Development, nearing completion on one of North Siesta Key’s most exceptional stretches of shoreline, with construction anticipated to be complete within the next few months. Commanding approximately 190 feet of sailboat-water frontage along two sides, this two-story contemporary estate overlooks Sarasota Bay and Big Pass, with sweeping views toward South Lido Beach Park, Bird Key, and the Downtown Sarasota Skyline. Encompassing approximately 5,453 square feet under air and 6,852 square feet under roof, the residence features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed to embrace its spectacular waterfront setting. Rare Big Pass dockage, protected access along Bayou Louise, and private boating infrastructure—including a 30,000-pound boat lift for deep-water boating and a separate 10,000-pound jet-ski/kayak lift—provide effortless access to Sarasota Bay and the Gulf. Designed with a refined contemporary aesthetic, the interiors pair dramatic scale with refined materials and meticulous attention to detail. Soaring ceilings and expansive walls of glass frame the water and skyline, while engineered hardwood flooring, level-five finishes, and custom built-in walk-in closets elevate the home throughout. A striking glass elevator offers water views as it connects the home’s living spaces and rooftop level. The chef’s kitchen is centered around an oversized island and complemented by a walk-in pantry, high-end finishes, a Sub-Zero refrigerator, and Wolf oven, creating a beautifully appointed space for living and entertaining. The primary suite is a private waterfront sanctuary, capturing panoramic views and featuring a spa-inspired bath with dual vanities, a rain shower, and separate soaking tub. The primary-suite level also features its own private secondary living room, creating an intimate retreat separate from the main entertaining spaces, while a dedicated indoor gym provides space for wellness and fitness. Multiple balconies and covered lanais extend the living spaces outdoors, while a private saltwater pool and spa create a resort-inspired setting at the water’s edge. Crowning the residence, an expansive rooftop deck offers breathtaking panoramic views across Sarasota Bay, Big Pass, Bird Key, South Lido, and the downtown Sarasota skyline—an unforgettable setting for sunset cocktails and evening entertaining. Dolphins, manatees, fish, and native coastal birds are part of the remarkable natural setting almost daily, while the surrounding waterways invite paddleboarding, fishing, snorkeling, windsurfing, and boating directly from home. The residence remains just minutes from the powder sand of Siesta Key Beach and the restaurants, boutiques, and energy of Siesta Village. Downtown Sarasota’s acclaimed dining, galleries, performing arts, and cultural attractions are also easily accessible, providing a rare combination of privacy and proximity to the best of Sarasota. With approximately 190 feet of waterfront, exceptional deep-water boating capabilities, dedicated lifts for boating and watersports, a glass elevator with water views, an incredible rooftop deck, private wellness and living spaces, panoramic views spanning some of Sarasota’s most iconic landmarks, and a newly constructed residence just months from completion, 3200 Higel Avenue represents a rare opportunity to experience an elevated level of waterfront living on Siesta Key.

3200 Higel Avenue, Sarasota

$2,900,000

Siesta SubDv. ⋅ 34242 Zip Code

INCREDIBLE LOCATION!....INCREDIBLE BOATING WATER!....INCREDIBLE SIZED LOT!.....Rarely Available EXPANSIVE 18,000+ square foot SAILBOAT WATERFRONT property with nearly 80' Seawall providing, for the Boating Enthusiast, easy access to Hansen Bayou, Sarasota Bay & the Gulf!.......Nestled on a Quiet Street near the North Bridge of Siesta, allowing Privacy as well as Quick and Easy Proximity to both all the Arts/Dining/Shopping of downtown Sarasota Bayfront as well just MOMENTS to TOP RATED SIESTA KEY BEACH!....Nearly 80' wide x 258' Deep this rectangular parcel provides the PERFECT OPPORTUNITY to Design/Build your Custom Island Estate and ENJOY the Ideal Beach and Boating Florida Lifestyle..

3601 White Lane, Sarasota

$1,650,000

6 Beds ⋅ 5 Baths ⋅ Terra Bea Sub SubDv. ⋅ 34231 Zip Code

BOATING LIFESTYLE . . . ENTERTAINER’S DREAM . . . WATERFRONT . . . CENTRAL SARASOTA LOCATION . . . NO HOA! Virtually staged with before-and-after photos. What if one of Sarasota’s most unexpected waterfront homes was hiding in plain sight? Tucked at the end of an unassuming street is an incredible waterfront retreat offering more than 4,400 square feet of living space, 100 feet of waterfront, a 13,000-pound boat lift, two Jet Ski floating docks, pool and spa, 6 bedrooms, and room for all the toys. No country club fees and NO HOA—just an incredibly fun Sarasota waterfront lifestyle. Designed for those who love to boat, entertain and gather with family and friends, this spacious home offers exceptional versatility across three levels, with beautiful water views and unforgettable sunsets. Step inside to high ceilings, abundant natural light and an impressive main living area anchored by a beautiful coral stone fireplace. Walls of sliding glass doors draw your eye toward the water and open to a spacious main-level patio—the perfect setting for morning coffee, evening cocktails and spectacular Sarasota sunsets. The primary suite is conveniently located on the main living level and features its own fireplace, direct patio access, a generous walk-in closet with custom built-ins and a spacious bath with separate vanities. A second bedroom on this level offers flexibility as a guest suite, private office or den. Upstairs, exceptionally spacious bedrooms provide plenty of room for family and overnight guests while creating privacy away from the main living areas. Downstairs is where the fun really begins. The fully built-out lower level transforms the home into an entertainer’s dream with a bar, game room, additional bedroom or workout space, full pool bath and direct access to the pool, patio and waterfront. Guests can move effortlessly from indoors to the pool, fire pit and dock without passing through the main living areas. Outside, the property truly embraces the Florida lifestyle. The fenced yard is ideal for pets, while the waterfront pool and patio create your own private resort. Head to the composite dock, where the 13,000-pound boat lift and two Jet Ski floating docks make it easy to get out on the water and return home for an evening by the pool or around the fire pit. With approximately 4,433 square feet, 6 bedrooms, multiple gathering spaces, generous garage and driveway space, and exceptional indoor-outdoor living, this is anything but a cookie-cutter Florida home. Whether entertaining a houseful of friends, accommodating extended family, working from home, boating, swimming or simply watching the sun disappear over the water, every level offers something special and every day can feel like vacation. Come discover the surprise at the end of the street. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.

5544 Dinah Lane, Sarasota

$1,979,000

3 Beds ⋅ 2 Baths ⋅ Southpointe Shores SubDv. ⋅ 34231 Zip Code

Nestled within the desirable West of Trail Southpointe Shores Community, this home benefits from top-rated school zones and a serene, upscale waterfront atmosphere. This canal front home was fully updated with a bright open layout. Three bedrooms, two bathrooms, large updated kitchen with lots of windows and the living areas have pocket sliding doors to outdoor entertaining areas. Luxury vinyl flooring throughout. The indoor/outdoor living quality is almost unbeatable. The current owner added and enlarged the outdoor terrace (almost the width of the entire home) including roofing a section of it and having panoramic and vaulted screening installed that you barely see. Open the pocket sliding doors to create seamless entertaining. Gorgeous views of the canal and great dock space and jet ski lifts also. The canal is very wide and deep water in all tide conditions. The home is only 4 homes away from the intracoastal waterway and just 10 minutes by boat to access the Gulf and Midnight Pass. Roof was replaced in 2021, new pool equipment and air conditioning in 2021. Boat lift 2022. Oversized dock. The neighborhood's private boat ramp, available for a minimal annual fee, enhances its appeal for boating enthusiasts. Perfectly situated close to Sarasota's shopping, dining, Siesta Key beaches, and marinas, the property still offers the tranquility, water access, and elevated coastal living that define a true retreat. Come see it for yourself and bask in the waterfront views from the amazing terrace.

1761 Sandalwood Drive, Sarasota

$4,245,000

3 Beds ⋅ 5 Baths ⋅ La Bellasara SubDv. ⋅ 34236 Zip Code

FOREVER UNOBSTRUCTED BAY & DOWNTOWN SARASOTA VIEWS! Experience luxury waterfront living at La Bellasara, a gated boutique community on Golden Gate Point. This exceptional 7th-floor residence is furnished and move-in ready, offering 3 full bedrooms plus a den, 4.5 baths, a private 2-car garage and breathtaking panoramic views of Sarasota Bay & downtown City skyline from nearly every room. Thoughtfully reimagined architectural modifications and strategically reconfigured furnishings create a flowing, functional and beautifully balanced living environment. The elevator opens to a private lobby and double-door foyer entry. 3,200+ square feet of spacious living and entertaining areas with varying 9–11 ft. ceiling heights and custom built-ins. An updated gourmet kitchen features custom white cabinetry, top-tier appliances, a 6-burner gas range, center island, and walk-in pantry. The open layout effortlessly combines the kitchen, dining, breakfast and gathering areas, all oriented toward picturesque Bay and City views. The impressive 42-foot bayfront terrace, complete with a built-in gas grill, sink and food-prep area is ideal for casual outdoor celebrations. A separate library with custom built-in desk and bookcases provides flexible space for a home office or overflow guest accommodations. The primary suite features a separate entrance, two luxurious baths, one with a water view spa tub, dual walk-in closets, a morning coffee bar with refrigerator & sink and direct terrace access with Bay views. Two guest bedrooms with full en-suite baths, custom walk-in closets, and separate terraces, are thoughtfully positioned for privacy. Adding to its appeal, La Bellasara is undergoing an exciting renovation of the common areas - including the main lobby, fitness center, spa, conference room and social room, enhancing the building’s already exceptional lifestyle and creating a fresh, contemporary experience for residents. The private 2-car garage with storage space is conveniently located near the elevator. Concierge services are provided 7-days a week. Additional amenities include a heated pool and spa and a courtesy day dock. This pet-friendly downtown enclave on Golden Gate Point offers the feel of a private home with the convenience of luxury condominium living just moments from Sarasota’s dining, shopping, arts, and entertainment.

464 Golden Gate Point Unit 702, Sarasota

Sarasota Homes with Sailboat Water Water Frontage

Newest Sarasota Homes with Sailboat Water Water Frontage