Sarasota County Homes with Sailboat Water Water Frontage

Sarasota County Homes with Sailboat Water Water Frontage

Welcome to Sarasota County, Florida, a stunning coastal paradise that perfectly blends the charm of small-town living with the vibrancy of a bustling arts scene. Nestled along the Gulf of Mexico, Sarasota is renowned for its picturesque beaches, cultural attractions, and outdoor recreational opportunities. With its warm climate, beautiful parks, and numerous golf courses, it's no wonder that this area has become a sought-after destination for both residents and visitors alike.

One of the most alluring features of Sarasota County is its waterfront properties, particularly homes with sailboat water frontage. Imagine waking up each day to breathtaking views of the water, where your private dock awaits you for leisurely afternoons spent sailing the shimmering waves. These homes offer direct access to the Gulf, allowing for endless adventures on the water, whether you’re fishing, cruising, or simply soaking up the sun.

Sarasota’s sailboat water properties are not just about the lifestyle; they also embody luxury and comfort. Many of these homes boast modern designs, spacious layouts, and high-end finishes, creating an ideal sanctuary for families and retirees alike. The vibrant neighborhoods surrounding these waterfront gems are filled with friendly neighbors, boutique shops, and delightful dining options, making it easy to enjoy the best of coastal living.

Whether you're looking for a year-round residence or a vacation retreat, Sarasota County's sailboat water homes offer an unparalleled lifestyle that celebrates the beauty of Florida's sun-soaked shores. Come explore the possibilities and discover your dream home in this idyllic coastal community!

Newest Sarasota County Homes with Sailboat Water Water Frontage

1313 Dockside Place Unit 120, Sarasota
$1,090,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
RARE BOATER’S OPPORTUNITY! 45' BOAT SLIP with NEW 27,000-lb IMM/Quality Platinum Series boat lift on deep, sailboat water! Completely renovated waterfront townhouse-style residence with the slip directly behind the unit—a highly desirable and rarely available location. Ultimate Beach lifestyle with easy access to Siesta #1 Beach & Siesta Village, just a few minutes' walk away. Enjoy mornings on the beach, afternoons on the boat, and evenings sunsets & exploring the Village. With many restaurants, music & shops. Fully remodeled down to the block walls with new plumbing, electrical, HVAC and ductwork, drywall, raised ceilings, LED lighting, and beautiful wood-look porcelain tile throughout. Gourmet kitchen features custom cabinetry, GE Profile appliances, natural quartzite, and abundant storage. Both baths offer easy-entry showers, and the primary suite includes a walk-in closet with custom organization. Private one-car garage, additional parking, attic storage, and newly screened lanai for entertaining. Elevated to 11.5' floor level remained free of stormwater during the 2024 storms. The dock features new pilings, full-length finger pier, fresh water, 30-amp/120V service, remote-controlled lift with auto-stop, and approximately 7' of water depth. Protected harbor approximately 100 yards from the ICW and just 10 minutes to Sarasota Big Pass. HOA permits boats up to 45' feet. Complex is getting a look and remodel! See photos Beach. Boating. Village life. All from one exceptional Siesta Key location. Community is going through a major face lift!! Scope of renovations • Siding/Trim/Facia with Stain-paint • Railings • Stairs • Gutter/Downspouts • Lighting

1313 Dockside Place Unit 120, Sarasota
315 S Shore Drive, Sarasota
$4,950,000
4 Beds ⋅ 4 Baths ⋅ Sapphire Shores SubDv. ⋅ 34234 Zip Code
House never flooded, including during Hurricanes Milton and Helene, and protected by a generator! Built as a solid concrete structure on concrete pilings, this home was engineered for the Florida waterfront. Lavishly embellished with Old World authenticity, this exceptional waterfront estate evokes the grandeur of a 17th century Tuscan farmhouse. Custom built by John Cannon, the home is set on what was once Ringling’s personal yacht basin, offering protected sailboat water, 178 feet of seawall, a private dock, two boat lifts (24,000 lbs & 10,000 lbs), and a dedicated kayak lift platform, all framed by sweeping panoramic water views. From the moment of arrival, the level of craftsmanship is unmistakable. Walls are finished in aged plaster, hand made terra cotta floors have been acid washed and stained to reflect centuries of wear, and authentic frescoes and ceiling beams inspired by the Renaissance period add depth and character throughout. The great room provides a dramatic setting for entertaining with soaring 22 foot ceilings, a gas fireplace, and a wet bar accented by a hammered copper sink. The chef’s kitchen is equipped with an Italian eight burner gas range and Brazilian soapstone countertops, while the dining room features a rare brick vaulted ceiling that reinforces the home’s Mediterranean soul and creates a truly immersive dining experience. The primary suite is a romantic retreat with his and hers walk in closets and a spa like bath wrapped in rich wood and stone finishes. Additional spaces include two to three guest bedrooms, dual offices, a bonus room, and a wine room. A private elevator connects every level, offering effortless access from the garage to the living spaces above. A true 2,500 square foot ground level garage offers tandem parking for four plus vehicles, making it a dream for car collectors. Outdoor living is exceptional, with stone and wrought iron terraces, an outdoor kitchen and bar on the main level, all designed to capture natural breezes and expansive water views. The newly completed infinity edge pool and spa create a striking visual effect, with the water appearing to seamlessly spill into the bay. This storybook residence is ideally located near Sarasota’s beaches, dining, and cultural attractions, offering a rare blend of architectural artistry, privacy, and timeless elegance.

315 S Shore Drive, Sarasota
894 Freeling Drive, Sarasota
$3,695,000
Bay Island Shores SubDv. ⋅ 34242 Zip Code
Zoning confirmation letter in from City of Sarasota. Ready for permitting and your custom dream home. This waterfront gem fronts Roberts Bay, facing Edwards Island, and offers unobstructed 180-degree views of dolphins, various bird species, and manatees. It's a perfect canvas for creating your customized residence. Located on the prized northern tip of Siesta Key, nestled on the Freeling Drive peninsula, this exquisite parcel blends sophistication with coastal living. Bay Island is renowned for its admired homes and architectural beauty, redefining island luxury along one of the area’s most pristine waterways. The oversized homesite is just under 15,000 square feet and features an impressive 155 feet of brand-new two-foot-elevated seawall, offering stunning panoramas. This location is ideal for boating and fishing enthusiasts, or for simply enjoying breathtaking sunrises and sunsets in unmatched natural beauty. Access on and off the island is easy, with Siesta Key Village's vibrant shops and restaurants, as well as the world-renowned Siesta Key Beach, just minutes away. Downtown Sarasota, with its galleries, theater, and fine dining, is also a short drive. Opportunities like this are rare, making this property a true gem for anyone seeking the ultimate waterfront address where privilege and prestige are embedded in an affluent lifestyle. I highly recommend experiencing the magic of this property for yourself. Choose any architect or builder to make your dreams come true. Owner will consider financing.

894 Freeling Drive, Sarasota
4050 Higel Avenue, Sarasota
$25,000,000
5 Beds ⋅ 7 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. To be complete in a few months. An unmatched luxury beach estate, this Gulf-front upcoming masterpiece offers sweeping ocean views and a private stretch of sand on Siesta Key. Designed and built by Pham Development, the iconic Mid-Century Modern residence is privately gated and designed to deliver resort-level living on one of Florida’s most coveted coastlines, with breathtaking views of the Gulf’s sparkling waters. Spanning 14,943 sq. ft. under roof, with 6,301 sq. ft. of air-conditioned interiors, the home features 5 bedrooms, 6 full baths, and 1 half bath. Engineered for longevity, it rests on a fortified foundation with a planned riprap seawall installation, complemented by a luxurious infinity pool and hot tub overlooking the gorgeous Gulf waters. Lifestyle amenities rival the finest resorts: a rooftop with spectacular ocean views and a full personal fitness center with a yoga studio. Entertainment spaces abound, with opportunities for a movie theater room, an ocean-view office, a gun and jewelry safe room, and an enclosed garage accommodating up to 16 cars. Paddle board and kayak access lead directly to the Gulf, with options for a beach volleyball or pickleball court. The grand primary suite features an expansive Gulf-facing terrace, his-and-hers walk-in closets, and spa-inspired baths, with stunning water views creating a serene coastal retreat. Multiple terraces, a Wolf-equipped outdoor kitchen, a chef’s kitchen, and a butler’s pantry add to the all-inclusive luxury lifestyle of this home. The chef’s kitchen will feature a 72-inch Sub-Zero refrigerator, Cove dishwasher, and Wolf range, coffee maker, and microwave. More than a residence, this estate is a legacy home crafted for generations, with an indoor-outdoor footprint tailored for both grand entertaining and intimate coastal living, all framed by extraordinary Gulf views. One or more photos have been virtually staged. Private showings are available upon request.

4050 Higel Avenue, Sarasota
100 Circuit Road Unit N108, Nokomis
$99,500
Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code
Own your own rack at beautiful Gulf Harbor Marina on the Intercoastal Waterway in Nokomis. Just 10 minutes from the South Jetty between Casey Key and Venice Island. No bridges to the Gulf! The marina is FULL SERVICE and offers unlimited splashes and retrievals each month using the convenient speedy dock app. Fuel, ice, and bait available for purchase on site as added time saver. Available items include REC 90 ethanol-free marine gasoline, MDO marine diesel, ice - 10lb or 20lb bags, live shrimp, and frozen bait - shrimp, sardines, squid, and chum block all available. Additional amenities include outdoor work racks for cleaning your boat or minor maintenance projects, a fish-cleaning station for your catch of the day, and rolling carts to make transporting your gear between your boat and personal vehicle easier. The marina includes designated parking. Buy for your own boat or for an investment. This slip is located 2nd rack up in the north building and the slip dimensions are 10'8" W X 32' D X 11' H. The maximum vessel dimensions for this rack are 9'8" W X 32' D X 9'6" H. End the hassle of trailers and boat ramps — secure a full-service marina slip that gives you easy access, safe storage, and stress-free boating all season.

100 Circuit Road Unit N108, Nokomis
5300 Ocean Boulevard Unit 301, Sarasota
$1,195,000
2 Beds ⋅ 2 Baths ⋅ Terrace East SubDv. ⋅ 34242 Zip Code
RELISTED WITH AN ALMOST $200,000 PRICE ADJUSTMENT. This unique beach condo with sunrise, sunset and 270-degree views is an excellent opportunity. A beachy 1,446 square-foot, 2-bedroom 2-bath corner residence with extra space for a den boasts a special sunny, oversized corner, south-facing wraparound balcony with views of the beach, Gulf of Mexico, heated pool and Siesta Village. The unusual 1,130 square foot terrace adds extra space and is very useful for romantic alfresco dining, entertaining family and friends, special parties, kid's play space, put-put golf, shuffleboard, Florida sunning and more, which is not available in other condos. From this incredible Siesta Key location, you just walk out to the sugar-white sands of #1 Siesta Key beach for a relaxing swim in the azure-blue Gulf of Mexico or get some exercise walking the 3 miles of beachfront, snorkel, paddleboard, or take your beach bike for a spin on the beach. Enjoy your morning coffee or a cocktail from your extensive terrace balconies while watching the colorful hues of the Florida sunrise and sunset without having to leave your condo. For an entertaining experience, you are steps from quaint Siesta Village to indulge in fun shopping, dining and live music. The floor plan flows from the balcony on the beachside through to the back of the building with views looking east over Siesta Village and west over the Gulf of Mexico. This delightful light & bright larger corner residence features tile throughout perfect for beach living, a covered parking space and is just waiting for your personal touch. The elevator serves only two condos per floor with an updated private foyer and private laundry facilities shared by two condos. Private & exclusive Terrace East has a modern updated lobby and social room, newly refinished pool with new grills & refrigerator, new pool furniture, new roof in 2025, and equipped fitness center. All the fixed windows in all the condos will be replaced by the association by January 2028. This is a secure gated building with onsite full-time manager and maintenance man, very well-run association with active board and no current special assessments, and a secure surveillance system. Amenities include a heated pool for laps, a tennis court, pickleball, active fitness center, beautifully landscaped garden and grounds, and bicycle & paddleboard storage. Come make this your future Florida home!

5300 Ocean Boulevard Unit 301, Sarasota
19 Oakwood Drive N, Englewood
$399,000
2 Beds ⋅ 2 Baths ⋅ Englewood Isles SubDv. ⋅ 34223 Zip Code
The Privacy of a Single-Family Home, The Convenience of Maintenance-Free Livng, AND The Freedom of Florida's Waterfront Lifestyle — All In One Exceptional Property! Welcome to this beautifully updated FREESTANDING, DETACHED, 2-bedroom, 2-bathroom home with a 2-car garage, nestled within the highly desirable boating community of Englewood Isles. Although part of a condominium community, this residence offers the independence and privacy of a single-family home, combined with the ease of maintenance-free living — a rare and highly appealing combination! Boating Enthusiasts, Take Notice! Enjoy your own deeded 42 foot seawall, offering the opportunity to install a custom dock or boat lift and experience direct boating access to Lemon Bay, the Intracoastal Waterway, and the Gulf — WITH NO BRIDGES! Imagine setting out for a day on the water, exploring the beautiful coastline, or simply enjoying the tranquility of waterfront living right outside your door. Inside, a bright, welcoming, open floor plan creates an inviting atmosphere, complemented by beautiful terrazzo flooring throughout the main living areas. Extensive improvements completed in 2022–2023 include fresh interior paint, a beautifully renovated kitchen featuring custom wood cabinetry with soft-close features, updated quartz countertops and appliances, tastefully remodeled bathrooms, and custom window treatments. Additional highlights include hurricane-impact windows installed in 2017 and 2023 and an A/C system replaced in 2019. A delightful bonus room, surrounded by windows and filled with natural light, offers additional flexibility — perfect for a home office, reading retreat, or simply a peaceful place to unwind. Outside, enjoy beautifully maintained tropical landscaping without the burden of constant yard work. The association takes care of lawn and landscape maintenance, allowing you more time to enjoy everything Southwest Florida has to offer. A heated community pool just steps away adds another wonderful opportunity for relaxation and recreation. Ideally situated near the charming shops, restaurants, and entertainment of historic Dearborn Street, downtown Venice, golf courses, and the stunning Gulf beaches, this home offers the perfect balance of convenience, recreation, and coastal charm. Whether you are searching for a full-time residence, seasonal Florida getaway, or a low-maintenance waterfront retreat, this property delivers an exceptional lifestyle. Why Settle for a Condo When You Can Enjoy the Privacy of a Detached Home, Your Own Waterfront Access, and the Luxury of Maintenance-Free Living? Your Florida Paradise Awaits!

19 Oakwood Drive N, Englewood
321 Bayshore Road, Nokomis
$3,700,000
4 Beds ⋅ 4 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
EXCEPTIONAL INTERCOASTAL WATERFRONT PROPERTY Discover a rare waterfront opportunity featuring 100 feet of Intracoastal Waterway frontage, deep-water access, and a private dock. This unique property includes a main residence and two separate cottages, offering excellent potential for rental income, multigenerational living, or a private waterfront retreat. With ample outdoor space and plenty of room to add a pool, the possibilities are endless. The property is zoned RMF-2, presenting potential redevelopment opportunities for up to 6–7 residential units (buyer to verify zoning, density, and development requirements with Sarasota County). Ideally located just minutes from Nokomis Beach, the property offers sailboat-friendly water access, breathtaking sunsets, and convenient access to the Gulf. Jump on your boat and take a sunset cruise ride to Pops, snake island, or even head up to Sarasota and enjoy your day on the water. Whether you’re seeking a waterfront residence, income-producing investment, or development opportunity, this property offers exceptional versatility in a highly desirable location.

321 Bayshore Road, Nokomis
862 Hudson Avenue Unit 862, Sarasota
$850,000
3 Beds ⋅ 2 Baths ⋅ Hudson Landings SubDv. ⋅ 34236 Zip Code
WATERFRONT LIVING + DEEDED 34-FT BOAT SLIP | WEST OF TRAIL | FULLY FURNISHED Live the Sarasota waterfront lifestyle you’ve been dreaming about in Hudson Landings, a sought-after West of Trail community where tranquil waterfront living meets the energy and convenience of downtown. Now confirmed: the deeded boat slip accommodates a vessel up to 34 feet—a rare and valuable opportunity for boating enthusiasts with direct access to Sarasota Bay and the Gulf of Mexico. Privately tucked along a peaceful canal, this beautifully maintained ground-floor residence offers an exceptional blend of comfort, style and effortless Florida living. The 1,362-square-foot floor plan features three bedrooms and two baths, with an inviting open-concept layout designed for both relaxed everyday living and easy entertaining. Natural light pours through expansive windows, while elevated ceilings create an airy, spacious feel. At the heart of the home, the updated kitchen showcases granite countertops, stainless steel appliances and casual seating, opening seamlessly to the living and dining areas. Step outside and enjoy serene waterfront surroundings, lush tropical landscaping and views of the bayou and community pool. The peaceful primary suite provides a private retreat, while two additional bedrooms offer plenty of space for guests, family, a home office or flexible living arrangements. Thoughtful upgrades and amenities add to the appeal, including hurricane-rated windows and sliders, a detached one-car garage and a heated community pool. And with the residence offered fully furnished, you can settle in and start enjoying the Sarasota lifestyle immediately. Spend your days on the water, relax poolside, explore downtown Sarasota’s celebrated restaurants, galleries and cultural attractions, or simply savor the tranquility of your own waterfront retreat. A deeded 34-foot boat slip, West of Trail location, garage and fully furnished turnkey residence make this a truly special Sarasota opportunity. Come experience the lifestyle for yourself—your waterfront escape is ready.

862 Hudson Avenue Unit 862, Sarasota
5012 Higel Avenue, Sarasota
$2,149,000
4 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Discover the best of Siesta Key waterfront living in this beautifully renovated canal-front residence, where modern comfort, thoughtful design, and an exceptional island lifestyle come together on nearly half an acre. Extensively renovated (2024 - 2025), this four-bedroom, three-bath home offers 3,541 square feet of inviting air-conditioned living space, a private dock and a west-facing backyard retreat designed for enjoying Florida's beautiful sunsets. The spacious open-concept interior features a beautifully updated kitchen with new appliances, generous living and dining areas, and expansive views of the pool and canal beyond. A thoughtfully designed split floor plan includes two private primary suites with ensuite baths, ideal for family and guests. The main primary retreat overlooks the water and features a luxurious bath with a soaking tub, walk-in shower, dual vanities, and access to an outdoor shower. Two additional bedrooms provide flexibility for guests, a home office or den, including one with a private courtyard entrance. Extensive improvements completed in 2024/2025 include beautifully updated interiors and major home systems, two HVAC systems, a replaced roof with storm-code strapping, impact-resistant windows, sliding doors and garage door. Outdoors, the heated pool, coral stone lanai and expansive fenced backyard create an inviting setting for entertaining or simply relaxing in the island sunshine. Boating enthusiasts will appreciate the private Trex dock, 112-foot seawall and canal access with just one higher fixed bridge to Sarasota Bay. A two-car garage and extended driveway add convenience. Ideally located just moments from Siesta Village's restaurants, boutiques and entertainment, and minutes from the world-renowned powdery white sands of Siesta Beach, this beautifully updated waterfront home offers the perfect balance of relaxed island living, boating adventures and modern coastal comfort. Your Siesta Key lifestyle awaits.

5012 Higel Avenue, Sarasota
108 Sunrise Drive, Nokomis
$1,369,999
4 Beds ⋅ 3 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
RARE GULF WATERFRONT GEM ON ROBERTS BAY! Welcome to 108 Sunrise Drive, where sparkling bay waters, coastal breezes, lush tropical landscaping, and an exceptional waterfront setting come together to create a truly unique opportunity in Nokomis. Offering approximately 75 feet of waterfront, an existing dock, Gulf-access boating with no bridges, and a beautifully paved and landscaped shoreline, this property delivers the kind of coastal setting that is increasingly difficult to replicate. Just minutes from beautiful Gulf Coast beaches, with boating access leading toward the open Gulf, the location captures everything buyers love about Florida waterfront living — peaceful water views, boating from your own backyard, warm coastal sunsets, and easy access to the sand and sea. The waterfront area is one of the property’s standout features, with attractive paving, established landscaping, dock access, and a serene setting overlooking Roberts Bay. Imagine morning coffee beside the water, afternoons on the boat, and evenings enjoying glowing sunsets and gentle coastal breezes from your own property. For builders and buyers with vision, the opportunity is substantial. Renovate and reimagine the existing residence, explore the flexibility of the additional rear living spaces, or create a spectacular custom waterfront residence designed to fully take advantage of the setting. For the buyer searching for a Florida vacation home, boating retreat, investment, or forever home, this is a chance to create something extraordinary — a custom coastal residence with expansive outdoor living, a resort-style front yard, sweeping water views, and your boat just steps from the door. The main residence is currently gutted and ready for renovation, reconfiguration, or complete redevelopment to maximize this exceptional waterfront site. The true value lies in what cannot easily be recreated: waterfront land, dockage, boating access, proximity to the open Gulf and beaches, mature landscaping, and an incredible canvas for renovation or new construction. Bring your builder. Bring your architect. Bring your vision. 108 Sunrise Drive Nokomis — where waterfront living, coastal beauty, and exceptional potential meet.

108 Sunrise Drive, Nokomis
280 Golden Gate Point Unit 600, Sarasota
$5,250,000
4 Beds ⋅ 4 Baths ⋅ Aqua Subdivision SubDv. ⋅ 34236 Zip Code
Architectural distinction meets breathtaking bayfront living at AQUA. Designed by renowned, award-winning Sarasota architect Guy Peterson, this exceptional full-floor residence is one of just eight residences in AQUA, an exclusive boutique tower on Golden Gate Point. Positioned on the sixth floor, this 4,100+ square-foot condominium captures sweeping 180-degree views of Sarasota Bay and the iconic Ringling Bridge through expansive floor-to-ceiling glass throughout, creating a seamless connection between the sophisticated interiors and the surrounding waterfront landscape. A private elevator opens directly into a welcoming foyer, revealing clean architectural lines, dramatic natural light, and a refined contemporary aesthetic. With more than $500,000 in carefully curated owner upgrades and barely lived in, this extraordinary residence offers a level of customization and sophistication rarely found in Sarasota. The open-concept floor plan lives like a single-family home, with generous entertaining spaces, a waterfront dining area, and a beautifully appointed custom wet bar. The chef’s kitchen blends exceptional design with luxury appliances, including a Wolf cooktop and ovens, two Miele dishwashers, and a Sub-Zero refrigerator. Custom Cuisines Laurier cabinetry and an expansive nine-foot island topped with striking Cielo quartzite complete this impressive culinary space. The private primary suite serves as a peaceful retreat, with captivating bay views and custom walk-in closets featuring sleek Cuisimax poly-gloss doors, two separate wardrobe sections, and a dedicated packing station. The spa-inspired primary bath features dual vanities topped with stunning azure crystal marble, a soaking tub, and an oversized glass-enclosed shower. Two additional guest suites offer en-suite privacy, while a separate office provides flexibility as a potential fourth bedroom. AQUA delivers an exceptional collection of boutique amenities, including discreet concierge services, an oversized enclosed private two-car garage with EV charging and a dehumidifier, a private boat dock accommodating a 36-foot vessel, a flat kayak lift, temperature-controlled wine storage and tasting room, fitness studio, heated pool and spa, and meeting room. Ideally situated on Golden Gate Point, this remarkable residence offers the best of both worlds: a quiet, private waterfront setting just moments from the restaurants, galleries, and cultural attractions of downtown Sarasota.

280 Golden Gate Point Unit 600, Sarasota
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