South Sarasota Homes with Sailboat Water Water Frontage

South Sarasota Homes with Sailboat Water Water Frontage

Welcome to South Sarasota, Florida—a hidden gem nestled in the heart of Sarasota County, where the sun-kissed shores meet serene waterways. This vibrant community is renowned for its picturesque landscapes, lush greenery, and a laid-back lifestyle that perfectly embodies the spirit of coastal living. With its proximity to world-class beaches, fine dining, and an array of cultural attractions, South Sarasota offers an idyllic setting for families, retirees, and anyone looking to embrace the Florida lifestyle.

One of the most alluring features of South Sarasota is its stunning homes with sailboat waterfront access. Imagine waking up to the gentle lapping of waves and the soft glow of the sunrise reflecting off the water. These exquisite properties not only boast breathtaking views but also provide direct access to the tranquil waters of the Gulf of Mexico. Whether you’re an avid sailor or simply enjoy the beauty of waterfront living, these homes cater to your every whim.

The neighborhoods here are designed to foster a sense of community while offering a range of amenities, from parks and recreational facilities to boutique shops and local eateries. With a strong emphasis on outdoor activities, residents can indulge in boating, fishing, and kayaking right from their backyards.

In South Sarasota, the fusion of luxury and leisure creates an unparalleled lifestyle. Discover your dream home with sailboat water frontage and immerse yourself in the beauty and charm of this enchanting coastal paradise. Your waterfront oasis awaits!

Newest South Sarasota Homes with Sailboat Water Water Frontage

2 Beds ⋅ 2 Baths ⋅ Phillippi Landings SubDv. ⋅ 34231 Zip Code

Welcome to this fully updated Coastal Modern 2 bedroom + DEN , 2 bath dream WATERFRONT condo in sought-after gated Phillippi Landings! You’ll enjoy gorgeous sunsets from your private screened-in balcony overlooking Phillippi Creek, the Intracoastal Waterway and a glimpse of the Gulf of Mexico just beyond. Starting with the kitchen, you’ll be impressed by the quartz waterfall countertop, sleek appliances, crisp stylish cabinets, and a custom pantry with pull-out shelves. The primary bedroom enjoys beautiful waterfront views and a luxurious en-suite bathroom featuring a soaking tub, walk-in shower and dual sinks. The layout is designed for both entertaining and relaxation, secluding the guest bedroom and bathroom from the main living spaces offering privacy and separation for visitors. The den offers flexibility for adding more room for guests or as your home office. The open layout features engineered hardwood floors, crown molding, and updated designer lighting. Expansive windows frame spectacular, elevated water views right from the main living area and bedroom areas. Superbly located, you are just minutes from Sarasota’s vibrant cultural hub, world-famous Siesta Key Beach, and an array of premier dining and shopping destinations. Enjoy the heated community pool, fitness center, and dog park. Plus, an on-site kayak launch, kayak storage, and a scenic walkway. As well as a dedicated side-gate entrance to the neighboring Phillippi Harbor marina for boating enthusiasts. Make this gem your home today!

5531 Cannes Circle Unit 403, Sarasota

2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

Welcome to your fully furnished, TURNKEY water view condo. Simply move-in and take in the tranquil Little Sarasota Bay and marvel at the dolphins, manatees, birds, and other wildlife. This remodeled 2 bed/2 bath condo features soaring cathedral ceilings, clerestory windows, generous open floor plan and luxury vinyl flooring throughout. This bright and peaceful second-floor unit is centrally located within the 75-acre, botanic garden-like setting of Pelican Cove. Across the way is the private picturesque 87-boat slip harbor. Boat and kayak to Midnight Pass and have direct access to the gulf. Residents gain entry to the unique blend of natural habitats, miles of scenic trails, a fitness room, multiple heated pools and hot tub. There are six new pickle-ball courts and resurfaced tennis courts with active clubs for play. Many more recreational and cultural events are hosted year around. Robust live music, art and culture, and educational seminars are abundant in season. The community is also conveniently located with shopping and restaurants nearby. Siesta Key and downtown Sarasota are in very close proximity as well.

1519 Pelican Point Drive Unit 288, Sarasota

3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

Move-in and take in the tranquil Little Sarasota Bay and marvel at the dolphins, manatees, birds, and other wildlife. Enjoy incredible sunsets and star gazing in the evenings from your private porch. This 3 bed/2 bath townhome condo features soaring cathedral ceilings, clerestory windows, generous open floor plan with a high-capacity AC system and water heater. This bright and peaceful second & third floor unit is centrally located within the 75-acre, botanic garden-like setting of Pelican Cove. The historic Wilbanks clubhouse and pool are only steps away, where the main heated resort-style pool awaits. Across the way is the private picturesque 87-boat slip harbor. Boat and kayak to Midnight Pass and have direct access to the gulf! Residents gain entry to the unique blend of natural habitats, miles of scenic trails, a fitness room, multiple heated pools and hot tub. There are six new pickle-ball courts and resurfaced tennis courts with active clubs for play. Many more recreational and cultural events are hosted year around. Robust live music, art and culture, and educational seminars are abundant in season. The community is also conveniently located with shopping and restaurants near by. Siesta Key and downtown Sarasota are in very close proximity as well. You will love this phenomenal unit in this one-of-the-kind, gated, maintenance-free living community of Pelican Cove!

1601 Bayhouse Point Drive Unit 204, Sarasota

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

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

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

2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

COMPLETELY RENOVATED AND MOVE-IN READY IN PELICAN COVE! Almost everything inside this spacious 2-bedroom, 2-bath condo has been updated, giving you the opportunity to move in and immediately start enjoying one of Sarasota's most unique gated waterfront communities. Step inside to a bright, open living and dining area featuring new flooring throughout, fresh interior paint, new lighting and ceiling fans and a beautifully renovated kitchen overlooking the main living space. The kitchen features new quartz countertops, cabinetry, stainless steel appliances, subway-tile backsplash and updated fixtures. Both bathrooms have been beautifully updated with new vanities, countertops, fixtures and finishes, including a newly tiled tub/shower surround. The bedrooms feature the same new flooring and fresh, neutral finishes found throughout the home. The closets have also been upgraded with new shelving, providing plenty of useful storage. Enjoy the large screened lanai, surrounded by Pelican Cove's lush tropical landscaping, with the added convenience of an in-unit washer and dryer located just off the lanai. Another feature you'll appreciate every day is the covered parking located right by the unit — no long walk from your car to your condo. And then there's Pelican Cove. This gated, approximately 75-acre waterfront community offers a lifestyle that's difficult to duplicate in Sarasota, with a private harbor and boat slips, direct access to the Intracoastal Waterway, kayak/canoe/paddleboard facilities, fishing areas, multiple heated swimming pools, tennis and pickleball courts, fitness facilities, three clubhouses, and miles of scenic walking paths and boardwalks winding through lush tropical landscaping. Pelican Cove is also known for its exceptionally active community, offering numerous resident clubs, art and creative programs, educational opportunities, concerts, fitness activities and year-round social events. All of this is tucked away in a beautiful Sarasota location, convenient to Siesta Key, shopping, restaurants, the Legacy Trail and downtown Sarasota. Everything has been done — bring your furniture and start enjoying the Pelican Cove lifestyle!

1720 Glenhouse Drive Unit 328, Sarasota

4 Beds ⋅ 4 Baths ⋅ Portofino On The Bay SubDv. ⋅ 34231 Zip Code

Nestled within the gated community of Portofino on the Bay, an intimate Mediterranean-inspired enclave of just twenty homesites in the Sarasota/Vamo area, this residence offers an inviting coastal setting and an active Florida lifestyle. Enjoy deeded access to Little Sarasota Bay, complete with a community dock, kayak storage and launch, and the potential to purchase a private boat slip with lift separate to community homeowner when available. Double entrance doors open into a two-story foyer, introducing an open-concept floor plan complemented by soft, welcoming wall tones, custom window and door trim, and crown molding across both levels. Plantation windows shutters add a classic touch throughout the entire home—including the garage, which features durable epoxy flooring. In the main living room, an accent stone floor to ceiling gas fireplace serves as a centerpiece for gathering or relaxing in the evening. The adjacent kitchen offers bright, clean-lined soft-close cabinetry, a built-in cooktop, stainless steel appliances, and a convenient closet pantry. The main-floor Owner’s Retreat provides a comfortable private wing, complete with its own dedicated A/C zone (one of three independent systems in the home). The bedroom features a tray ceiling and French doors opening directly to the pool patio. The ensuite bathroom is equipped with dual sinks, a makeup vanity, a walk-in shower, a bidet, a generous walk-in closet with custom built-ins and a tub ready for relaxation with bubbles after a day on the water. A main-floor den with tray ceilings offers flexible space for a home office or reading room, complemented by a main-level guest half bath. Upstairs via the wrought-iron staircase railing, a central loft connects to three additional bedrooms—each accented with tray ceilings. Two of the guest rooms share direct access to a private outdoor balcony, while the fourth bedroom showcases soaring ceiling height and abundant natural light, all cooled by a dedicated second-floor A/C zone. Step out back to the newly extended panoramic-screened lanai, finished with travertine tile surrounding the heated salt-water pool and spa. A convenient pool half bath and an outdoor shower make outdoor living effortless. Situated in an X Flood Zone with no prior hurricane damage, this home is also exceptionally well-located: just a 10-minute drive (6 miles) to world-renowned Siesta Key Beach and 15 minutes (9 miles) to vibrant Downtown Sarasota for premier dining, arts, and shopping. The new Sarasota Square presently being remodel led with approximately 90,000 square feet of daily-needs retail scheduled for delivery in the first quarter of 2027 plus with easy Costco shopping.

1650 Assisi Drive Unit 16, Sarasota

1 Beds ⋅ 1 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

Beautifully renovated in 2023 by the previous owner, this residence showcases stylish luxury vinyl plank (LVP) flooring throughout, along with fully updated kitchen and bathroom interiors (excluding kitchen appliances). A new hot water heater and full-size washer and dryer were installed in 2023. In 2024, a custom queen-size Murphy bed was added to enhance functionality and maximize space. Most furnishings were newly acquired in 2023, offering a modern and move-in-ready living experience. Awesome for a rental. Plus low fees for the boat slips. Pelican Cove is a gated pet friendly condominium community abounding with amenities, including a low-cost 86-slip boat harbor, kayak, and canoe launch, six heated swimming pools, hot-tub, three clubhouses, classrooms, gym, art, woodworking and pottery studios, lit tennis/pickleball courts, basketball, dog play area, walking trails, boardwalks, and fishing gazebos. Take classes at Pelican Cove University, yoga, tai-chi, water aerobics, painting, or photography. More than 37 clubs for arts, cycling, culinary arts, bridge, film and more. Relax at the evening jazz & classical music concerts, enjoy a stroll around 78 acres of lush grounds. Pelican Cove is hidden away yet minutes from everything! Come see for yourself! This is the lifestyle you deserve!

1647 Brookhouse Court Unit BR146, Sarasota

3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code

Welcome to Pelican Cove, one of Sarasota's most sought-after waterfront communities west of the Trail! This bright and spacious end-unit condominium offers 2 bedrooms, 2 bathrooms, plus a den that was originally a third bedroom and can easily be converted back. Located on the second floor, the home is filled with natural sunlight from every angle, creating a warm and inviting atmosphere throughout. Centrally positioned within the community, you'll enjoy picturesque, storybook views of the Pelican Cove yacht basin from your private lanai. The tropical setting provides both beauty and privacy, making it the perfect place to relax and unwind. The open floor plan features numerous upgrades and is being offered furnished, making it truly move-in ready. Easy to show and even easier to fall in love with! Nestled within more than 75 acres of lush, gated waterfront grounds, Pelican Cove offers an unmatched resort-style lifestyle. Amenities include an 86-slip marina with affordable boat dockage, kayak and canoe launch facilities, six heated swimming pools, a spa, three clubhouses, tennis and pickleball courts, basketball courts, walking trails, boardwalks, fishing gazebos, fitness facilities, water exercise programs, dog-walking areas, and much more. Creative and social opportunities abound with two art studios, a pottery workshop, Pelican Cove University classes, and more than 37 clubs covering interests such as photography, fiber arts, cycling, culinary arts, woodworking, sculpting, cards, and music. Evening jazz and classical concerts complete the vibrant community experience. Experience the perfect combination of natural beauty, waterfront living, and an active Sarasota lifestyle. Schedule your private showing today

1601 Pelican Point Drive Unit 215, Sarasota

4 Beds ⋅ 5 Baths ⋅ Aqualane Estates SubDv. ⋅ 34231 Zip Code

Some homes are built. Others are envisioned. 1516 Ridgewood is the result of an uncompromising pursuit of excellence—a California Pacific Palisades-inspired waterfront estate where timeless architecture, extraordinary craftsmanship, and Sarasota's coveted boating lifestyle converge into one remarkable residence. Completely reimagined with virtually every surface, system, and space thoughtfully transformed, this exceptional home was designed to live as beautifully as it looks. Sunlight pours through expansive impact glass, illuminating sophisticated interiors where clean architectural lines, custom finishes, and seamless indoor-outdoor living create an atmosphere of effortless elegance. Every detail reflects a commitment to quality rarely found in today's market. Anchoring the home is a spectacular chef's kitchen designed for both culinary excellence and unforgettable entertaining. An extraordinary suite of Wolf and Sub-Zero appliances—including an eight-burner gas range with griddle, built-in coffee system, Cove dishwasher, designer refrigeration, oversized pantry, and a dramatic entertaining bar—is complemented by custom cabinetry, multiple beverage centers, ice makers, and a stunning temperature-controlled glass wine room worthy of the finest private collections. The primary suite offers a tranquil retreat inspired by the world's finest luxury resorts, while beautifully redesigned guest suites provide exceptional comfort and privacy. Throughout the residence, Turkish shell stone flooring, TruStile doors, EMTEK hardware, floating custom cabinetry, Level 5 wall finishes, and designer appointments create an understated elegance that feels both warm and sophisticated. Behind the walls lies a level of engineering that is seldom seen. A state-of-the-art Josh AI automation system seamlessly integrates lighting, climate, security, audio, and mechanical systems into one intuitive platform, placing the entire home at your fingertips. Whole-home True Audio speakers, buried fiber connectivity, dedicated IT infrastructure, multiple wireless access points, and integrated security provide technology equal to the home's extraordinary design. Constructed with longevity in mind, the residence showcases impact-rated windows and doors, concrete block construction, spray foam insulation, a standing seam metal roof, elevated mechanical systems, new electrical service, new plumbing, new water and sewer infrastructure, WiFi-enabled tankless water heaters, and countless improvements that reflect an unwavering commitment to enduring quality. Outside, the boundaries between home and resort disappear. A completely reimagined pool, expansive terraces, architectural ceilings, lush tropical landscaping, dramatic landscape lighting, and a fully appointed Wolf outdoor kitchen create an extraordinary backdrop for entertaining beneath Sarasota's spectacular sunsets. For boating enthusiasts, the experience is simply unmatched. With newly dredged water access, newer dock, and no bridges to Sarasota Bay, spontaneous afternoons on the water and unforgettable Gulf sunsets become part of everyday life. More than a luxury residence, 1516 Ridgewood is a home that inspires. It is the rare combination of visionary design, uncompromising construction, intelligent technology, and an incomparable waterfront setting—created for those who believe true luxury is measured not only by beauty, but by the extraordinary way a home makes you feel.

1516 Ridgewood Lane, Sarasota

4 Beds ⋅ 2 Baths ⋅ Coral Cove SubDv. ⋅ 34231 Zip Code

WATERFRONT * NO FLOOD ZONE * NO HOA. Positioned west of the Trail in Sarasota’s highly sought-after Coral Cove neighborhood, 1901 Upper Cove Terrace offers one of the area’s most compelling deep-water waterfront opportunities, pairing boating access, updated mid-century character, and an exceptional Sarasota lifestyle setting. Priced below appraisal. Set on an oversized 0.35-acre lot with 75 feet of canal frontage, this 4-bedroom, 2-bath residence spans 2,105 square feet and was thoughtfully updated in 2024 to enhance its mid-century modern character while preserving the spirit of its 1968 origins. For boaters, the value is exceptional. The property features deep-water dockage, no fixed bridges, direct Gulf access, a new lifetime vinyl bulkhead, 30-amp shore power, and a private dock that accommodates up to a 45-foot vessel. Outdoor living is central to the home, with a screened pool and spa, covered entertaining areas, and seamless indoor-outdoor flow. The property also offers room for boat and RV parking, plus a large attached workshop garage with two Level 2 EV chargers. Located in Coral Cove, residents enjoy access to a private neighborhood park and boat ramp through the community’s voluntary neighborhood association, adding another layer of boating, fishing, kayaking, and Gulf-access lifestyle appeal. Highlights include: west of the Trail location, Coral Cove neighborhood, private park and boat ramp, 4 bedrooms, 2 baths, 2,105 SF, 0.35-acre lot, 75’ canal frontage, deep-water dockage, no fixed bridges, direct Gulf access, new lifetime vinyl bulkhead, dock for up to a 45’ boat, screened pool and spa, boat/RV parking, workshop garage, and two Level 2 EV chargers.

1901 Upper Cove Terrace, Sarasota

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