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 shines bright and the waters beckon. This vibrant community is renowned for its stunning waterfront properties, particularly those with sailboat water frontage, making it a paradise for boating enthusiasts and nature lovers alike.

Imagine waking up to breathtaking views of the shimmering waters, where the gentle sound of waves lapping against your dock creates a soothing soundtrack to your mornings. Homes in South Sarasota with sailboat water frontage offer direct access to the beautiful Gulf of Mexico, allowing you to sail away into endless adventures right from your backyard. Whether you're an experienced sailor or a weekend warrior, this area is designed for those who appreciate the beauty of life on the water.

Beyond its stunning homes, South Sarasota boasts a rich tapestry of amenities. Explore the nearby beaches, indulge in world-class dining, and immerse yourself in the vibrant arts scene that Sarasota is famous for. With lush parks and recreational facilities, families will find plenty of opportunities for outdoor fun and community engagement.

The charm of South Sarasota lies not just in its picturesque landscapes but also in its welcoming community spirit. Residents take pride in their neighborhoods, creating a warm and inviting atmosphere for newcomers and long-time locals alike. If you’re seeking a slice of paradise where luxury meets leisure, look no further than South Sarasota – where your dream waterfront home awaits!

Newest South Sarasota Homes with Sailboat Water Water Frontage

6723 Avenue C, Sarasota
$1,650,000
3 Beds ⋅ 3 Baths ⋅ Bay View Acres SubDv. ⋅ 34231 Zip Code
LOCATION, LOCATION, LOCATION! SIESTA KEY LIVING WITH A PRIVATE BOAT SLIP! Located on Avenue C, just before the South Siesta Key Bridge, this beautifully updated 3-bedroom, 3-bathroom pool home offers the perfect mix of coastal living, boating, and convenience! Enjoy being less than a mile from the world-famous Siesta Key Beach, where Florida sand, beautiful sunsets, and relaxing days by the water are all within reach. Boaters will love having their own PRIVATE BOAT SLIP, one of only TWO in the entire neighborhood! With quick access to the Intracoastal Waterway and approximately 15 minutes to the Gulf, spending the day on the boat couldn't be easier. Inside, this home has been beautifully updated with major improvements completed in 2020, including a 2020 ROOF, tile flooring throughout, a completely remodeled kitchen, and updated bathrooms. The spacious floor plan features three bedrooms, including a SECOND PRIMARY SUITE, three full bathrooms, and an oversized two-car garage. Whether you're hosting guests or enjoying everyday life, this home offers plenty of space and comfort. Step outside to your own private Florida retreat! The backyard features a LARGE HEATED POOL, a spacious covered lanai, and NEW PANORAMIC SCREENING that opens up the beautiful outdoor views. The pool was resurfaced in 2025, and the dock was also completed in 2025. Whether you're relaxing by the pool, entertaining friends, or heading out for a sunset boat ride, this outdoor space is made for enjoying the Florida lifestyle! What truly makes this property special is its LOCATION! Tucked away in a peaceful bird sanctuary, you'll enjoy a quiet setting while still being within minutes of beaches, restaurants, and local favorites. Spend your evenings at Daiquiri Deck, Siesta Key Oyster Bar, Captain Curt's Crab & Oyster Bar, The Old Salty Dog, or Abel's Ice Cream. Ruth's Chris Steak House and Carrabba's Italian Grill are also nearby, along with Publix, shopping, and everything you need for everyday living. With its rare private boat slip, beautiful updates, and incredible location just minutes from Siesta Key, this home offers the coastal lifestyle so many dream of! Schedule your own personal tour today!

6723 Avenue C, Sarasota
Sarasota
$4,750,000
4 Beds ⋅ 6 Baths ⋅ Aqualane Estates 3rd SubDv. ⋅ 34231 Zip Code
Experience Sarasota waterfront living from a truly exceptional vantage point, completely surrounded by water on three sides giving you the utmost privacy protected by mangroves. Set on a rare 17,298-square-foot point lot, this custom John Cannon estate captures sweeping, unobstructed 270-degree water views, creating an extraordinary sense of openness and connection to the water. Watch dolphins glide past, fish right from your private dock, or head out for a day on the bay with direct, no-bridge access. Private dockage within a protected basin, along with the potential to accommodate a larger vessel, makes this property especially compelling for boating enthusiasts. This raised, three-level residence combines refined craftsmanship with everyday convenience, featuring an ELEVATOR, WHOLE HOME SOLAR, a 4½-car garage, and a recently installed tile roof (2025). The home offers 5,197 square feet of living space with four bedrooms, drop room perfect for yoga or small office/den, a bonus room, a theater room, a gym and 4 full and 2 half baths. As you enter through the dramatic double-door entry you enter the great room with soaring ceilings, full wall entertainment center, elegant finishes, and light-filled living spaces that keep the water views front and center. The gourmet kitchen features Wolf stainless steel appliances and granite countertops, while inviting gathering spaces provide a beautiful setting for entertaining or simply enjoying the waterfront surroundings. On the first level, you'll fall in love with the theatre room to escape from the day to day. Outdoors, the expansive patio and summer kitchen overlook a large lap pool, lagoon and grotto area with a waterfall, and spa, accented by stone decking and framed panoramic water vistas and gas firepit. Spend your mornings watching for dolphins, your afternoons fishing or relaxing poolside, and your evenings departing from your own dock for a sunset cruise. With its distinctive point-lot setting, uninterrupted views, protected dockage, and effortless access to the bay, this estate offers a rare opportunity to make the water the centerpiece of everyday life.

Sarasota
1518 Pelican Point Drive Unit 257, Sarasota
$525,000
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Little Sarasota Bay, right outside your living room. This light-filled, second-floor, 2-bedroom, 2-bath condo in Pelican Cove captures unobstructed views of Little Sarasota Bay through huge glass sliders, bringing the beauty of the water into your everyday living space. The updated kitchen opens to the living and dining areas, creating an inviting space for entertaining while keeping those beautiful water views in sight. Both bathrooms have been updated, and built-in cabinetry in the laundry room provides valuable additional storage. The split-bedroom layout offers privacy and comfortable accommodations for owners and guests alike. Set along the Intracoastal Waterway, Pelican Cove is a 75-acre gated and guarded community surrounded by lush tropical landscaping and an impressive collection of amenities. Residents enjoy an 87-slip harbor with no fixed bridges to the Gulf, a kayak and canoe launch, six heated pools, three clubhouses, lighted tennis and pickleball courts, a fitness center, art studios, and more than five miles of scenic walking trails and boardwalks. The location is another standout. Just west of the Tamiami Trail, Pelican Cove is conveniently located near a revitalized shopping plaza bringing Whole Foods, the highly anticipated Trader Joe's, additional shopping and dining options to the area. Siesta Key and Turtle Beach are just minutes away, with downtown Sarasota a short drive north. Whether you're looking for a full-time residence, seasonal retreat, or easy lock-and-leave getaway, this is an opportunity to enjoy waterfront living in one of Sarasota's most established and amenity-rich communities.

1518 Pelican Point Drive Unit 257, Sarasota
5848 Tidewood Avenue, Sarasota
$7,199,000
4 Beds ⋅ 5 Baths ⋅ Baywood Colony Westport SubDv. ⋅ 34231 Zip Code
Under Construction. Exceptional New Construction | Sarasota Bayfront Living. Experience extraordinary waterfront living in this stunning new-construction residence, perfectly positioned directly on Sarasota Bay to capture breathtaking, unobstructed water views and spectacular sunsets. Combining sophisticated coastal architecture, expansive living spaces, and exceptional boating amenities, this remarkable home has been thoughtfully designed to embrace the very best of Florida's waterfront lifestyle. Offering over 4,000 square feet of air-conditioned living space, the residence features four generously sized ensuite bedrooms, including a luxurious first-floor primary suite. A dedicated office and spacious bonus room provide exceptional flexibility, with the office offering the potential to serve as a fifth bedroom when additional accommodations are needed. The home's impressive open-concept design features soaring ceilings, abundant natural light, and expansive gathering spaces that flow effortlessly between indoor and outdoor living. Thoughtfully designed for both everyday comfort and gracious entertaining, the residence takes full advantage of its spectacular waterfront setting. More than 900 square feet of covered outdoor living space creates an extraordinary extension of the home, complete with a summer kitchen and generous areas for dining, entertaining, and relaxation. Beyond the covered terrace, an expansive pool deck features a beautiful swimming pool and heated spa, all overlooking the sparkling waters of Sarasota Bay. Whether hosting family and friends or enjoying a quiet evening, the setting provides a front-row seat to some of Sarasota's most magnificent sunsets. For boating enthusiasts, the property offers direct Sarasota Bay frontage, deep-water access, a private dock, and a 16,000-pound boat lift. With the bay just steps from your backyard, endless opportunities for cruising, fishing, and exploring Southwest Florida's beautiful waterways await. Additional highlights include a spacious three-car garage, thoughtfully designed outdoor terraces, tropical landscaping, and a versatile floor plan that seamlessly blends luxury, functionality, and coastal elegance. A rare opportunity to enjoy the finest in new-construction bayfront living, where unobstructed panoramic water views, spectacular sunsets, exceptional boating, and inspired architectural design come together in one extraordinary Sarasota residence.

5848 Tidewood Avenue, Sarasota
2320 Aquabluff Place Unit V274, Sarasota
$248,000
2 Beds ⋅ 2 Baths ⋅ Strathmore Riverside SubDv. ⋅ 34231 Zip Code
One or more photo(s) was virtually staged. This vibrant 55+ maintenance-free coastal living (4.4 miles from Siesta Key Beach) awaits in the highly sought-after waterfront community of Strathmore Riverside Villas! This immaculate 1,120 sq. ft. villa boasts modern structural peace of mind, featuring impact glass windows, a new roof, and updated HVAC. An absolute dream for boaters and anglers alike, the community showcases a Private Marina, fishing pier with a cleaning station and a newly updated concrete seawall.. Two boat spots available accommodate up to a (24ft x 8ft) watercraft (available on a first-come, first-served basis, wait list-2 currently available) for just $1,400 annually, offering direct, single-bridge navigable access down Phillippi Creek (15 min to ICW )straight to the Intracoastal Waterway (1.4 miles/15 min). The comprehensive $725/mo condo fee bundles premium value, covering your water, sewer, trash, internet, master building insurance, grounds maintenance, on-site manager, and fully funded escrow reserves. Steps away, enjoy a lavish waterfront clubhouse complete with a fitness center, billiards, card rooms, saunas, and a sprawling geothermally heated outdoor pool. Two pets are welcome (dogs restricted to 15? shoulder height).

2320 Aquabluff Place Unit V274, Sarasota
5424 America Drive, Sarasota
$1,350,000
3 Beds ⋅ 3 Baths ⋅ Phillippi Gardens SubDv. ⋅ 34231 Zip Code
New Roof and New AC!! Updated Kitchen and Bathrooms!!! Nestled on a quiet cul-de-sac in Sarasota, this stunning three-bedroom, three-bath waterfront home offers the perfect blend of tranquility and lifestyle. Enjoy your own private pool with sweeping views over the water, plus direct Intracoastal Waterway access via Philippi Creek. Deep water and a nine-foot bridge clearance make it easy for most 30-foot center console boats to come and go. Just across the creek lies a protected Sarasota watercourse barrier and wildlife refuge, preserving breathtaking, unobstructed views. Recent updates include a brand-new roof, AC unit, updated kitchen and bathrooms, a freshly painted exterior, and the timeless charm of a paver-brick driveway. It also features a 1.5 car garage, perfect for parking a full-size vehicle and a golf cart, bikes, or beach gear. From your private waterfront retreat, every day feels like a vacation. Best of all, it's in an X500 flood zone and you’re just a five-minute drive from world-famous Siesta Key Beach. Call the listing agent today to schedule your private showing!

5424 America Drive, Sarasota
LOT 12 Montclair Drive, Sarasota
$1,800,000
Monticello SubDv. ⋅ 34231 Zip Code
Rare opportunity to build your dream waterfront home on this approximately ¼-acre vacant lot with direct access to Sarasota Bay. Located on desirable Montclair Drive, this property features a newer seawall and offers the perfect setting for a custom residence with water views and boating access. Enjoy the best of Sarasota waterfront living while creating a home designed specifically for your lifestyle. Conveniently located near Sarasota's beaches, dining, shopping, and downtown amenities. Bring your builder and start planning your waterfront retreat!

LOT 12 Montclair Drive, Sarasota
1515 Clower Creek Drive Unit HA158, Sarasota
$395,000
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Welcome to the award-winning waterfront community of Pelican Cove, where lush tropical grounds, an incredible array of amenities, activities, and social clubs create a truly exceptional Sarasota lifestyle. This GROUND-FLOOR WATERFRONT CONDO enjoys a prime location overlooking the entrance to beautiful Clower Creek. The light and bright END-UNIT features additional windows for added light, neutral tile flooring, updated bathrooms, a newer electrical panel, upgraded raised-panel doors throughout, modern paint colors, and a new A/C system. Step outside from the sliding glass-enclosed lanai to the oversized waterfront Trex-type deck and relax while enjoying abundant wildlife, tropical surroundings, and boats as they cruise into the canal. Offered turnkey furnished, this inviting condo is move-in ready and provides the perfect opportunity to enjoy the Pelican Cove lifestyle from day one. PELICAN COVE FEATURES includes over 28+ organized clubs including art & sculpture, active yacht club, folk music, photography & cinema clubs, social clubs, and many more. There is a for-fun “Pelican Cove University” covering several diverse subjects like politics, history, financial topics, and much more. The community has a woodworking studio, pottery studio, many card-playing clubs, water exercise & yoga, and a tennis club. There are several yearly jazz and cultural concerts and a few harborside concerts as well. Pelican Cove has a 24-hour gated and staffed entrance, 87-slip boat harbor with over 130 kayak/canoe storage racks & launch docks, fishing docks, three very active clubhouses, large exercise room, six heated pools, hot tub, basketball, dog exercise area, 5.5 miles of meandering boardwalks & nature trails, two lighted tennis courts and six lighted pickleball courts all in an award-winning community with unbelievably well-manicured tropical grounds! Welcome to Pelican Cove!

1515 Clower Creek Drive Unit HA158, Sarasota
5531 Cannes Circle Unit 403, Sarasota
$699,900
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
1637 Brookhouse Court Unit 244, Sarasota
$396,500
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Don’t miss this spacious, TURNKEY FURNISHED unit in Pelican Cove – Sarasota’s premier 75-acre, gated community along Little Sarasota Bay. Your updated 3-bedroom home is light and bright with vaulted ceilings, three balconies and water views. With a convertible 3rd bedroom with sleeper sofa, you have plenty of space for family and friends. The main balcony sliders can be opened to enjoy the sights and sounds from this lushly landscaped property. The interior has 20” tile throughout the unit. The updated eat-in kitchen has white cabinets, solid surface countertops and sliding glass doors to the 2nd balcony where you can enjoy your morning coffee. The primary bedroom has water views and sliding glass doors to the balcony. There are dual closets in the primary bedroom– one is a cedar lined walk-in. Both bathrooms have been refreshed with new vanities and granite countertops. A large laundry room is located off the balcony. Lots of closet space and attic storage is a plus. One of the communities six pools is just around the corner. Award-winning Pelican Cove has 3 Clubhouses that host year-round activities. There is a fitness room, studio space for art, photography and woodworking. The large auditorium is used for concerts, lectures and art shows. Miles of scenic pathways lead to tennis and pickleball courts and the community-friendly dog park. Pelican Cove Yacht Basin has access to Midnight Pass and the Gulf with no fixed bridges. The marina includes an 86-boat slip marina with the ability to lease slips on a first-come-first serve basis along with canoe and kayak launch facilities-including over 100 storage racks. Visit the fishing docks or spend time at the waterside gazebo. With over 35 social clubs, you can be as busy as you want. Best of all, Pelican Cove is close to Siesta Key beaches. Great shopping and restaurants are just minutes away. Feel close to everything while living in the Sarasota’s hidden gem.

1637 Brookhouse Court Unit 244, Sarasota
5381 Palos Verdes Drive, Sarasota
$1,195,000
2 Beds ⋅ 2 Baths ⋅ River Forest SubDv. ⋅ 34231 Zip Code
This beautiful Mediterranean style home offers peaceful views of Phillippi Creek, mature oak trees, privacy, and an oversized 0.39 acre lot. Inside, you’ll find two spacious bedrooms, two bathrooms, plus den, a newly remodeled kitchen with granite countertops, stainless steel appliances, and custom wood cabinetry. Designed for both relaxing and entertaining, the home features generous living spaces, tile flooring, crown molding, and large windows overlooking the lagoon style pool and serene waterfront setting. With approximately 179 feet of frontage along Phillippi Creek, this is a truly special Sarasota property. Conveniently located near Siesta Key, Downtown Sarasota, and everything Central Sarasota has to offer. OWNER FINANCING OPTIONS AVAILABLE

5381 Palos Verdes Drive, Sarasota
1519 Pelican Point Drive Unit 288, Sarasota
$375,000
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
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