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 within Sarasota County that boasts a unique blend of coastal charm and vibrant community spirit. Known for its stunning waterfront views and laid-back lifestyle, South Sarasota is the perfect place for those seeking a slice of paradise.

One of the most sought-after features of this enchanting area is the availability of homes with sailboat water frontage. Imagine waking up to the gentle sound of waves lapping against your dock, with direct access to the sparkling waters of the Gulf of Mexico. These homes not only offer breathtaking views but also provide an unparalleled lifestyle for boating enthusiasts and beach lovers alike. Whether you're setting sail for a day of fishing, exploring nearby islands, or simply enjoying a sunset cruise, living on sailboat water ensures that adventure is just a few steps away.

South Sarasota is also rich in amenities, boasting an array of dining options, shopping venues, and recreational activities. From picturesque parks to pristine beaches, residents can indulge in outdoor activities year-round. The community is known for its friendly atmosphere, making it easy to connect with neighbors and foster lasting relationships.

With a diverse selection of homes available, from charming bungalows to luxurious waterfront estates, South Sarasota has something for everyone. If you’re looking for a place where you can enjoy the best of Florida living, with the added bonus of sailboat water access, South Sarasota is the perfect destination to call home. Come explore this vibrant community and discover your dream waterfront property today!

Newest South Sarasota Homes with Sailboat Water Water Frontage

$390,000
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
It's easy to enjoy the beauty of coastal waterfront living in Pelican Cove and this 3-bedroom end unit condo is centrally located within the complex. Everything in this condo is exquisitely done and no expense was spared with new flooring, new lighting, updated bathrooms, new kitchen with all new appliances, sink, lighting, counters and backsplash. Enjoy volume ceilings and the open floor plan that this three-bedroom unit provides. Pelican Cove is a magical place with lush landscaping that sits on gorgeous acres overlooking the Little Sarasota Bay. This is what Florida living is all about, stroll to the Pelican Point Observation deck, the bird sanctuary or the through the gardens. This community is a boaters dream with more than 87 boat harbor slips with each slip having water and electric. There are six heated pools to choose from, pickle ball, kayak and canoe launch and storage, gym, 4 lighted tennis courts, shuffleboard, basketball, 5 miles of amazing walking trails and Musical concerts. Pelican University offers classes and clubs for all including woodworking, photography, and clay sculpture, to name a few.

1508 Pelican Cove Road Unit 235, Sarasota
$2,890,000
4 Beds ⋅ 3 Baths ⋅ Southpointe Shores SubDv. ⋅ 34231 Zip Code
Imagine having your own private outdoor paradise designed for a relaxing life on the water. This custom designed Key West style residence in Southpointe Shores offers deep sailboat water on a rare wide natural bayou with more than 100 feet of waterfront, complemented by a new Atkins seawall, a 30 foot Cool Touch dock, a 27,000 pound boat lift, second wet slip capability, and a fish cleaning station. Built by Graber Homes and extensively and beautifully renovated, the residence features an open floor plan with living and dining areas that transition naturally to the kitchen and waterfront. Renewal by Andersen sliding doors frame the canal and provide direct access to the outdoor living spaces. Travertine flooring extends throughout the entire first level. The kitchen includes fine wood custom Campbell Cabinetry, Calacatta marble countertops and backsplash, a large entertaining island, a walk in pantry, and gourmet appliances featuring a new Sub Zero refrigerator, a Wolf wall oven, two Miele dishwashers, a Wolf coffee station, and a 48 inch Fulgor Milano induction range. Additionally, the first floor offers a roomy primary suite with two walk in closets and an updated Campbell Cabinetry bath with dual vanities, a walk in shower, and a clawfoot tub, along with a pool bath and an oversized laundry room. The second level offers three guest bedrooms, a full bath with a marble walk in shower and Campbell Cabinetry, and a large bonus room currently arranged as a home gym. New wood look tile flooring extends throughout the second floor. Outdoor spaces include a 7 foot deep saltwater pool and deep seat gas heated spa, a built in 48 inch Lynx outdoor kitchen, professionally designed Artistic paver patios and walkways, a gas fire pit in a private seating area, a second patio for sunbathing, and a stunning landscaped pond with waterfalls inspired by Marie Selby Botanical Gardens. The home also features a 14 speaker indoor and outdoor NHT sound system for entertaining. The entirely fenced backyard provides privacy with direct access to the dock and waterfront. Recent improvements include a whole house 26KW Generac generator, three new Bryant HVAC systems with new ductwork and Knauf insulation, an Aprilaire whole home fresh air and dehumidification system, whole house water filtration, new Starlink internet, two 48 amp Tesla charging stations, and a large air conditioned three car garage with hanging rack storage along the ceiling. Located West of the Trail, Southpointe Shores offers a friendly optional HOA, a private gated neighborhood boat ramp and park, and easy access to Midnight Pass, Sarasota Bay, Siesta Key, downtown Sarasota, shopping, and dining.

7631 Cove Terrace, Sarasota
$1,925,000
3 Beds ⋅ 2 Baths ⋅ Bay View Acres SubDv. ⋅ 34231 Zip Code
ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly opened Midnight Pass where pristine waters flow freely into the Gulf. 10,000 pound boat lift - gorgeous trex decking - 45+ foot dock with fish stand. Walk to Siesta Key. This beautifully updated waterfront residence offers refined Florida coastal living in a truly exceptional setting. Positioned on a picturesque “Y” intersection of two canals, the property provides serene water views, privacy, and effortless access for deep water boating and outdoor enjoyment—just minutes from Siesta Key’s renowned white sand beaches. A stately approach framed by mature oaks and professional landscaping leads to a custom paver drive and striking hurricane-impact glass entry. Inside, the open, light-filled floor plan showcases original terrazzo and travertine flooring, PGT impact windows, and seamless indoor-outdoor flow. Impact French doors open to expansive gardens, tranquil fountains, a private pool, and classic Chicago brick pavers. Designed for entertaining, the home features multiple outdoor living spaces, including an expansive Trex deck overlooking the canal, a pergola, screened patio, boat dock and covered cabana. The kitchen is appointed with quartz countertops, ceiling-height shaker cabinetry, stainless steel appliances, reverse-osmosis water, and generous windows overlooking the backyard. Living and dining spaces flow effortlessly, complemented by a separate family room, opening to a screened lanai. Renovated guest accommodations complete the main level with 2 bedrooms including sun-drenched guest room, office with Murphy bed and full bath. The second level is devoted entirely to the primary suite, a private retreat with resort quality features as: hardwood floors, water views in every direction, French doors with retractable screens, a private balcony, and a spa-inspired bath with dual vanities, a Carrara-tiled walk-in shower, and custom walk-in closets. Ideally located near Siesta Key, downtown Sarasota, and the region’s cultural, dining, and shopping destinations. Evening relaxation - picture this: you’ve had an amazing day on the water and now you’re ready to cook up your catch right in your own backyard. Perfect sunset dinner awaits! This waterfront gem offers everything you need for the ultimate boaters lifestyle – easy access, premium amenities, and the perfect set up for enjoying your evenings. Ready to make waves in your new home? **No hurricane damage. HOME NOT IN A FLOOD ZONE.

1827 Baywood Drive, Sarasota
$2,997,000
4 Beds ⋅ 4 Baths ⋅ Coral Cove SubDv. ⋅ 34231 Zip Code
Fully renovated waterfront estate in Coral Cove, one of Sarasota’s most desirable West of Trail communities. Set on an elevated 0.59-acre corner lot directly across from the private neighborhood park and boat launch, this British West Indies-style residence offers over 5,012 square feet of updated living space, rare privacy, and the ultimate Sarasota coastal lifestyle. This 4-bedroom, 3.5-bath home has been extensively renovated and thoughtfully redesigned with modern luxury finishes throughout. Major updates include a new metal roof, impact-rated windows and doors, engineered hardwood flooring, solid core interior doors, custom organized closets, two fireplaces, and no flooding during recent hurricanes. The home offers dual primary suites, including a spacious upstairs retreat with a spa-inspired bathroom, freestanding tub, dual vanities, walk-in shower, and oversized custom closet. The chef’s kitchen is the centerpiece of the home, featuring Café Series appliances, Dolomite countertops, soft-close cabinetry, walk-in pantry, waterfall-edge peninsula seating, and a fluted designer range hood. Large living areas, tall ceilings, French doors, and expansive sliders create a bright, open layout designed for seamless indoor-outdoor living. Step outside to a private resort-style backyard with a large pool, limestone pool deck, lush lawn, mature landscaping, new dock, and floating jet ski pad. With the neighborhood boat launch just across the street, this property is ideal for boating, kayaking, paddleboarding, waterfront entertaining, and enjoying the best of Florida living. Located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, dining, marinas, and Sarasota’s arts and culture scene, this Coral Cove waterfront home offers a rare combination of size, elevation, renovation quality, and location.

1707 Caribbean Drive, Sarasota
$2,000,000
3 Beds ⋅ 3 Baths ⋅ Ridgewood SubDv. ⋅ 34231 Zip Code
Modern Waterfront Living on Phillippi Creek with 170 Ft Water Frontage: this stunning residence was completely rebuilt down to the studs in 2023, this move-in ready modern contemporary waterfront residence sits on a rare 0.36-acre lot with 170 feet of water frontage and complete privacy across the creek—offering open water views, and breathtaking westerly Sarasota sunsets. Home has never had water intrusion from any storms due to its elevation. Located on a quiet cul-de-sac just 5 miles to Downtown Sarasota and 3 miles to Siesta Key, the property combines convenience with a peaceful waterfront setting. The home has never flooded and was thoughtfully renovated with long-term durability and quality construction in mind. Boating enthusiasts will appreciate the 5ft +/- water depth at the dock, with additional dredging happening along the creek and an expansive boat dock with new flow-through composite decking, boat lift, and separate double jet ski lift. Enjoy direct access to Sarasota Bay and the Gulf of America just minutes from your backyard. Inside, soaring ceilings and expansive PGT impact windows and sliders fill the home with natural light while framing serene water views. The open-concept living space is centered around a chef’s kitchen featuring a dramatic oversized quartz waterfall island, sleek quartz countertops & backsplash, custom cabinetry, and premium appliances— designed for both daily living and entertaining. The primary bedroom suite offers generous proportions and a fully customized walk-in closet with boutique-level organization the size of its own bedroom. The comprehensive 2023 renovation included full re-plumbing, all new electrical wiring, and fully remodeled bathrooms. Additional upgrades since then include a handcrafted iron front entry door, modern 4 panel garage door with side mounted motor, epoxy flooring and metal standing seam roof. Outdoor living rivals a private resort with a heated saltwater pool and a 2025 custom outdoor kitchen equipped with gas grill, flat-top hibachi grill, built-in TV, refrigerators, and wine cooler. Exterior enhancements include motorized screen, artificial turf for low maintenance, oversized 5 car paver driveway, landscape lighting, leaf guard gutters, and a 12x34 ft shed on an extended concrete pad down to the water's edge. A rare combination of modern construction, deep water access, wide water frontage, and close proximity to Sarasota’s top destinations—this is move in ready waterfront living without settling. It's not just renovated; it's a rare package. All furnishings are negotiable.

2500 Monterey Street, Sarasota
$899,900
3 Beds ⋅ 2 Baths ⋅ Phillippi Gardens SubDv. ⋅ 34231 Zip Code
Opportunities like this are becoming increasingly difficult to find. Situated on nearly half an acre along a wide, scenic stretch of Phillippi Creek, this property offers the perfect combination of waterfront living, privacy, and an unbeatable central Sarasota location. Tucked behind a fenced driveway, the classic Sarasota ranch-style home welcomes you with its timeless charm. But the true showstopper is the backyard, a sprawling park-like setting with mature trees, expansive green space, and peaceful water views that create a private retreat right in the middle of town. This solid block home has been thoughtfully updated with a 2024 metal roof, laminate flooring throughout, stainless steel appliances, recessed lighting, and fresh exterior paint. The functional floor plan features a dedicated dining area, oversized laundry room, and a spacious two-car garage. For boating and water enthusiasts, the possibilities are exceptional. Subject to permitting, there may be an opportunity to add a dock and boat lift, providing direct access to Phillippi Creek, Sarasota Bay, and ultimately the Gulf of Mexico. Enjoy kayaking, paddleboarding, fishing, wildlife viewing, or simply relaxing while watching the water drift by. Located just minutes from Siesta Key, Downtown Sarasota, shopping, dining, and everyday conveniences, this property offers a lifestyle that is increasingly hard to replicate. Whether you're looking for a waterfront residence, a property to expand and customize, or simply a unique piece of Sarasota waterfront land, this is an opportunity you won't want to mis- schedule your private showing today!

2103 Lusitania Drive, Sarasota
$5,500,000
5 Beds ⋅ 6 Baths ⋅ Coral Cove SubDv. ⋅ 34231 Zip Code
Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best of Sarasota’s luxury lifestyle. Encompassing over 6,100 square feet, the residence was thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. A dramatic two-story living room, sweeping staircase, extensive custom millwork, and walls of glass create a sense of timeless elegance while framing breathtaking water views throughout the home. The gourmet kitchen serves as the heart of the residence, seamlessly connecting to multiple gathering spaces and opening effortlessly to the expansive waterfront terrace. Corner sliding glass doors dissolve the boundaries between indoors and out, revealing a resort-style infinity-edge pool, summer kitchen, covered entertaining areas, and sparkling bay views beyond. The luxurious primary suite is a private waterfront retreat featuring a separate dressing room, generous dual closets, and serene water vistas. Additional guest suites provide exceptional comfort and privacy for family and visitors alike. Designed for both recreation and relaxation, the home also features a private office/library, elevator access, media and game room with full bar, and a four-car split garage. Outside, the lifestyle continues with a private dock, boat lift, fishing pier, and immediate access to Sarasota Bay. Whether enjoying sunset cruises, waterfront dining, or simply relaxing poolside while watching dolphins and boats pass by, every day feels like a vacation. Rarely does a property combine this level of space, waterfront presence, boating access, and location. Just minutes from downtown Sarasota, St. Armands Circle, and the area’s renowned beaches, this is a home designed for those who expect the very best.

1541 Caribbean Drive, Sarasota
$1,795,000
6 Beds ⋅ 5 Baths ⋅ Terra Bea Sub SubDv. ⋅ 34231 Zip Code
You’ll love entertaining guests and embracing the tranquility of waterfront living in this one-of-a-kind classic Key West home on Philippi Creek Bayou. Enter through mahogany doors to soaring cathedral ceilings that fill the home with natural light and create an open, airy atmosphere. Expansive water views can be enjoyed in most rooms, while the outdoor deck provides the perfect setting to relax and take in stunning sunset skies. Inside, the Key West coral fireplace, luxury vinyl plank flooring and thoughtful architectural details create warmth and character throughout. The kitchen is designed for gathering and entertaining, featuring stainless steel appliances, a stainless-steel chef’s cooking area, quartz countertops and a wraparound bar that encourages memorable moments with family and friends. The enormous primary suite serves as a private retreat with its own water-view balcony, charming gas fireplace and bay windows. The spa-inspired en suite bath offers dual vanities and a relaxing spa tub. Dedicated office space provides flexibility for working from home or creating a quiet study area for the kids. Upstairs, you’ll find four bedrooms, a balcony and two full baths. The lower level features an expansive entertaining area ideal for a growing family, game room, gym or play space, along with a convenient pool bath for hosting guests. Outside, enjoy the private open pool area positioned at the water’s edge with long, peaceful canal views. The waterfront lifestyle continues with a kayak launch, Jet Ski floats and a newer composite boat dock with a 13,000-pound lift ready for boating adventures. Adding even more appeal for boating enthusiasts, the county is currently dredging the canal to further improve water access and navigation. The home has also been thoughtfully updated with a newer roof and freshly repainted interior and the property has been well maintained with no known storm-related damage or water intrusion. Just minutes from Philippi Shores Elementary and Riverview High School, this exceptional property is ideal for a growing family that loves the outdoors. A treasured Suncoast oasis where privacy, comfort and waterfront living come together beautifully.

5544 Dinah Lane, Sarasota
$4,500,000
5 Beds ⋅ 6 Baths ⋅ Pine Shores Est SubDv. ⋅ 34231 Zip Code
Welcome to Coucher du Soleil — French for "Sunset" — a magnificent gated waterfront estate styled after the grand French residences of New Orleans. Breathtaking views of Little Sarasota Bay, Siesta Key, and spectacular daily sunsets greet you from every room of this one-of-a-kind home. Impeccable craftsmanship is evident throughout, from the custom sapele mahogany front doors and hand-carved fireplace mantel to the handmade crown moldings and exotic sucupira hardwood floors. An elevator, exquisite lighting fixtures, exterior gas lanterns, and thoughtful hardware selections make this residence as functional as it is beautiful. The open-concept living and dining room flows seamlessly through numerous French doors onto an expansive covered balcony, also accessible from the guest suite and solarium. A custom library offers a tranquil retreat, while the entire top floor is dedicated to the primary suite, complete with a private office, morning kitchen, spacious dressing room, and private balcony with unsurpassed views. The carriage house provides an ideal in-law or guest suite with its own entrance, kitchen, bath, and balcony. Outdoors, enjoy the sprawling verandah overlooking the saltwater pool or head out on the water from your 50-foot composite dock with lift, electric, water, and sailboat access. Truly a one-of-a-kind Sarasota estate, do not miss this opportunity.

6438 Hollywood Boulevard, Sarasota
$675,000
3 Beds ⋅ 2 Baths ⋅ Schooner Bay SubDv. ⋅ 34231 Zip Code
Experience the best of Florida waterfront living in this beautifully updated turnkey furnished 3-bedroom, 2-bath condo situated on a peaceful canal with direct boating access to Sarasota Bay. This light-filled residence offers an open-concept layout, vaulted ceilings and everything you need to move right in and start enjoying the lifestyle. Step outside to your private boat slip and lift, making it effortless to spend the day cruising the bay, exploring nearby waterfront restaurants, or heading out to the Gulf. Inside, the spacious living and dining areas flow seamlessly to a enclosed lanai where you can relax and take in tranquil water views. The well-appointed kitchen features ample cabinetry and counter space, while the primary suite offers water views, generous closet space, and an en-suite bath. The split bedroom floor plan provides plenty of room for guests, family, or a home office. Whether you’re looking for a full-time residence, seasonal retreat, or investment opportunity, this exceptional canal-front condo combines comfort, convenience, and easy access to Sarasota Bay in one perfect package. This condo is located in a quiet gated community of only 36 units close to all conveniences. This second and top floor spacious unit has the largest floor plan and feels more like a single family home, vaulted ceilings and an open floor plan with split bedrooms. It's a short walk over the bridge to Siesta Key beaches. Quick access to the intercoastal and bay by boat, no bridges to navigate, makes it easy to go to the many waterfront restaurants. The huge primary ensuite overlooks the canal and has a walk in shower/closet, dual sinks, king bed, separate tub and WC. The detached 2 car garage has a separate AC unit. Seller had the 6000 lb lift refurbished in 2023. New roof in 2023. The air ducts and dryer vent were cleaned in January 2024. The condo is only steps from the heated pool. It's a 10 minute drive to downtown Sarasota. Walk or bike to the world famous Siesta Key Beach or take a trolley. You are within a mile of every convenience you can think of. This community is a hidden gem. All offers must provide proof of funds or pre-approval with offer.

6660 Schooner Bay Circle Unit 6660, Sarasota
$529,800
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Attention Buyers — This is the one! A rare FIRST-FLOOR condo in Pelican Cove with direct Bay Views and unbeatable indoor/outdoor living. Step into your new 2-bedroom, 2-bath home featuring an open floor plan that flows seamlessly from the kitchen through the dining and living areas straight out to your private waterfront deck. Both bathrooms offer walk-in showers, and the condo is being sold fully furnished, making your move effortless. This residence is vacant and easy to show, and the moment you walk in, the water views will grab your attention. Sit outside and enjoy boats passing by throughout the day and spectacular sunsets in the evening. It’s the perfect blend of comfort, convenience, and coastal beauty. Pelican Cove located in South Sarasota west of the trail. This community is over 80 acres in a lush gated tropical setting! Your new condominium is on the FIRST floor. Lots of natural light pours into your home. The setting at the back of the condo is a tropical paradise and it’s also private. Open floor with many upgrades throughout your home! Condo will be sold furnished and very easy to show! Pelican Cove is a 75-acre, gated, vibrant-waterfront community nestled among manicured tropical foliage. Truly offering something for everyone. Abundant amenities include the 86-slip boat harbor with excellent rates & a launch dock for kayaks and canoes, 6 heated swimming pools, hot-tub, 3 clubhouses, lighted tennis/pickleball courts, basketball, dog walk area, walking trails and boardwalks, as well as fishing gazebos, water exercise classes, exercise facility, 2 art studios and a pottery classroom. Take classes at Pelican Cove University or join one of the more than 37 clubs for photography, fiber art, bike riding, culinary arts and card clubs. Woodworking, sculpting, and evening jazz & classical music concerts round out the active lifestyle. Come and see what you have been waiting for.

1515 Pelican Point Drive Unit BA185, Sarasota
$349,800
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Pelican Cove – Turnkey Furnished First-Floor End Unit. Welcome to Pelican Cove, one of Sarasota’s most sought-after gated waterfront communities. This first-floor END unit offers the perfect blend of comfort, privacy, and Florida living at its best. Inside, the main bathroom features a walk-in shower, while the guest bath includes a convenient tub/shower combination. This residence is being sold turnkey furnished, allowing you to move right in and start enjoying the Pelican Cove lifestyle from day one. Recent upgrades include new water tank, air/heating, heavy duty garbage disposal, ceramic floor in living room and kitchen, full handicap entrance wheel chair/scooter accessible, new up to code electrical box, outside outlet, combination door lock. Step outside and explore miles of scenic walking trails that wind through a bird sanctuary and lush botanical gardens. Residents enjoy an impressive array of amenities, including: Six heated pools, well-equipped fitness center, lighted tennis/pickleball courts, three clubhouses with a full calendar of activities, 87-slip safe-harbor marina with kayak and paddleboard launch. Boaters will appreciate direct access to the Intracoastal Waterway, Little Sarasota Bay, and the sparkling Gulf Coast. This charming 2-bed/2-bath condo offers an affordable opportunity to enjoy the Pelican Cove lifestyle. Start your mornings with coffee on the private patio off the kitchen, surrounded by nature. The main living area overlooks a peaceful preserve, creating a serene indoor/outdoor experience that feels uniquely Floridian. Residents also receive a monthly community newsletter filled with special events, classes, and social gatherings—there’s always something happening in Pelican Cove.

1707 Pelican Cove Road Unit GL351, Sarasota
Start Your Search