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 sun-kissed beaches, vibrant culture, and a laid-back lifestyle converge. This charming city is renowned for its stunning waterfront properties, particularly those boasting sailboat water frontage. Imagine stepping out of your backyard and onto your sailboat, ready to explore the picturesque waters of the Gulf of Mexico at a moment's notice.

South Sarasota is not just about breathtaking waterfront views; it offers a rich tapestry of community life. Residents enjoy a plethora of outdoor activities, from kayaking and fishing to leisurely strolls along the pristine beaches. With an average of 251 sunny days a year, outdoor enthusiasts find endless opportunities to embrace the Florida lifestyle. The nearby Siesta Key, known for its powdery white sands and vibrant nightlife, is just a short drive away.

The homes in South Sarasota with sailboat water frontage are truly remarkable. These properties often feature expansive docks, allowing for easy access to the water and creating a seamless blend of indoor and outdoor living. Many homes are designed with an open concept, maximizing views of the tranquil waterways and lush landscapes. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset, these waterfront homes provide an idyllic backdrop for your Florida dreams.

In South Sarasota, you’ll find a welcoming community, top-rated schools, and an array of dining and shopping options, making it an ideal place for families, retirees, and everyone in between. Discover the charm of South Sarasota and the unparalleled lifestyle that comes with owning a sailboat waterfront home today!

Newest South Sarasota Homes with Sailboat Water Water Frontage

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
1780 Phillippi Shores Drive Unit A3-5, 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
5544 Dinah 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
1761 Sandalwood Drive, 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
1720 Glenhouse Drive Unit 328, Sarasota
$319,900
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
1650 Assisi Drive Unit 16, Sarasota
$1,425,000
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
1601 Pelican Point Drive Unit 215, Sarasota
$497,800
2 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
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