South Sarasota Homes with Pool

South Sarasota Homes with Pool

Welcome to South Sarasota, a hidden gem nestled in the heart of Florida's stunning Gulf Coast. Known for its picturesque landscapes, vibrant communities, and a wealth of recreational opportunities, South Sarasota is the perfect blend of relaxation and adventure. This charming area boasts a rich cultural scene, with art galleries, theaters, and a variety of dining options that cater to every palate. The nearby beaches, such as Siesta Key and Lido Beach, are famed for their powdery white sands and crystal-clear waters, making them ideal for sunbathing, swimming, and water sports.

For those seeking a home in this idyllic locale, South Sarasota offers a fantastic selection of properties, particularly homes with pools. Imagine stepping out into your own backyard oasis, where you can unwind in the refreshing waters of your private pool, surrounded by lush tropical landscaping. These homes are perfect for entertaining friends and family or simply enjoying a peaceful afternoon under the Florida sun.

The real estate market in South Sarasota is diverse, featuring everything from charming single-family homes to luxurious estates. Many of these properties are designed with open floor plans that seamlessly blend indoor and outdoor living, allowing you to embrace the beautiful weather year-round. With the added benefit of a pool, you can create lasting memories with loved ones, host summer barbecues, or simply enjoy a serene swim after a long day.

Come discover the allure of South Sarasota, where the sun shines bright, and your dream home with a pool awaits!

Newest South Sarasota Homes with Pool

$1,444,900
4 Beds ⋅ 4 Baths ⋅ A4702501 MLS
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, South Sarasota
$2,950,000
5 Beds ⋅ 4 Baths ⋅ A4703560 MLS
Furnished 5-bedroom, 4-bath residence with 3,871 sq. ft., a deep-water dock with 13,000-lb boat lift, and direct access to the Intracoastal Waterway and Little Sarasota Bay. Crescent Beach is approximately one mile away. The home features high ceilings, an upper-level loft with wet bar, a three-car garage and gated driveway. Designed for coastal entertaining, the outdoor living area includes a private pool, covered lanai, covered outdoor kitchen and dining area, and covered balcony with partial bay view.

1662 Anchorage Street, South Sarasota
$350,000
2 Beds ⋅ 2 Baths ⋅ A4703135 MLS ⋅ 14 BLDG.
Location, Location, Location! Only 3.5 miles to the World Famous Siesta Key Beach with its fine sugary sands. Close to I-75 and rte.41, hospitals, shopping, schools, restaurants and downtown Sarasota. There is a storage closet by the front door, ideal to store bikes & beach chairs. This STUNNING & Elegant 2-bedroom 2 bath GROUNDFLOOR unit is TURNKEY furnished and totally renovated in 2021 with 20" ceramic tiles throughout the unit along with CROWN MOLDING as well. The open layout of the kitchen boasts a wraparound granite countertop. Custom built kitchen cabinets and pantry with modern hardware. Updated bathrooms with floor to ceiling tiles. Elegantly furnished. There is a storage closet in the living room. The Master bedroom features king size bed, walk-in closet and walk-in shower. The Guest bedroom features queen size bed, closet and the guest bathroom has a tub/shower combo. Fully updated for immediate occupancy. All you need are your personal belongings and your bathing suit! Unit is bright, airy and very welcoming. There is also a screened lanai featuring electric hurricane shutters, a Jenn-Aire electric grill and a great view of the lake. Be entertained by our Florida wildlife. We are located on 33 acres of luscious greenery, with 4 lakes, 2 heated pools,7 grilling stations, one large pool with lap lane, a combination of 2 tennis courts and 4 pickleball courts, shuffleboard, clubhouse and various other amenities. We are also connected to Merchants Mart by a foot bridge, consisting of CVS, ACE hardware, liquor store, take-outs, and the famous Detwiler's Farm market. Come be a part of this friendly welcoming community...

5726 Ashton Lake Drive Unit 11, South Sarasota
$769,500
3 Beds ⋅ 2 Baths ⋅ A4701521 MLS
Welcome home to paradise in Riverwood Estates one of Sarasota’s most desirable and established communities! Nestled on an expansive over half an acre lot adorned with newly installed lush landscaping, this 3-bedroom, 2-bathroom residence effortlessly combines long-term peace of mind with sensational resort-style living. Major recent upgrades provide complete reassurance, including a brand-new roof installed in 2025 and a top-of-the-line HVAC system added in 2026. From the moment you step inside, you will love the airy feel created by grand cathedral ceilings and bright skylight that fill the main living areas with natural sunlight. Cool tile flooring stretches throughout the entire home, complemented by ceiling fans in every room for maximum year-round comfort. The central living space centers around a classic wood-burning fireplace, while the updated kitchen (remodeled in 2022) serves as the heart of the home with modern finishes and effortless functionality. Step through the sliding glass doors into your private outdoor oasis! The outdoor living space is an absolute crown jewel! Expanded in 2022, the spectacular backyard features an incredible pavilion with a custom outdoor kitchen and bar, making poolside entertaining an absolute dream. Relax on the screened patio or step out into the refreshing swimming pool, which was converted to a low-maintenance saltwater system in 2025. The spacious owner’s suite serves as a true sanctuary, featuring direct access to the patio and pool area so you can wake up to refreshing water views every morning. Its modern ensuite bathroom boasts a tranquil soaking tub alongside a separate, beautifully updated shower. Location is everything, and this property delivers access to the very best of Sarasota! Situated just minutes from top-rated schools, vibrant shops and dining at the Landings Shopping Center, the world-famous white sands of Siesta Key Beach, and the bustling arts scene of downtown Sarasota, you are perfectly positioned to enjoy world-class coastal living. Whether you are splashing in the pool or relaxing under the shady trees on your massive lot, this remarkable property is ready to welcome you home!

4711 Placid Circle, South Sarasota
$210,000
2 Beds ⋅ 1 Baths ⋅ A4703376 MLS ⋅ C BLDG.
Ideally located just minutes from world-famous Siesta Key Beach. This beautifully renovated condo located at 4035 S School Ave, Unit C- 5 in Sarasota was completely updated in 2022/2023. It features a modern kitchen with quartz counter tops, additional bar storage, and all-new appliances including refrigerator, stove, microwave, dishwasher, and garbage disposal. Enjoy the new waterproof laminate flooring throughout, a tank-less hot water heater, and ceiling fans in both bedrooms. The bathroom has been fully refreshed with new vanities. A newly screened porch was added in 2025. Community amenities include a sparkling pool, plus convenient access to Trader Joe's, Sarasota Bayfront, downtown shops, restaurants, and waterfront parks. This move-in-ready unit offers contemporary style and the best of Florida Suncoast living. The Association fees include water, sewer, trash, internet and pest control. Don’t miss this opportunity!

4035 S School Avenue Unit C5, South Sarasota
$225,000
1 Beds ⋅ 2 Baths ⋅ A4702605 MLS ⋅ V-107 BLDG.
Welcome to Strathmore Riverside Villas, a waterfront 55+ community in South Sarasota just east of the Tamiami Trail. This is a free standing villa, one of only a handful in the community that stands entirely on its own, with no shared walls and windows on all four sides. The one bedroom, one and a half bath floor plan is open and adaptable. The living room, dining area, and family room run together as one connected space finished in bamboo flooring with crown molding, giving you room to set up a den, home office, game room, or second seating area depending on how you use the home. The updated kitchen sits at the center with white raised panel cabinetry, quartz countertops, subway tile backsplash, stainless appliances, floating shelves, and a window over the sink. The Florida room off the kitchen is wrapped in windows with its own exterior door and light wood look plank flooring. The primary bedroom is set on its own side of the home with wood look plank flooring, a reclaimed wood accent wall, a walk in closet, and an ensuite bath with a frameless glass walk in shower. The interior laundry room doubles as a half bath for guests and includes a full size washer and dryer, vanity sink, and built in storage. Hurricane glass windows and energy efficient appliances are already in place, and the villa has been well maintained throughout. A private driveway leads to a covered carport and a tiled entry patio, with an exterior storage closet for beach gear and bikes. Mature landscaping and open lawn surround the home. Community amenities include a waterfront clubhouse with a heated pool, saunas, exercise room, billiard room, and library, along with an active social calendar. The 33 slip marina has an on site dockmaster, and slips are available on a first come basis for $20 a month, with canal access to Phillippi Creek, the Intracoastal Waterway, and the Gulf a few miles beyond. Siesta Key is minutes away, along with downtown Sarasota, Gulf Gate dining and shopping, and quick access to US 41. Schedule a visit to see the villa and the community in person. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2740 Riverbluff Parkway Unit V107, South Sarasota
$11,375,000
4 Beds ⋅ 8 Baths ⋅ A4703378 MLS
Some properties offer a view. This extraordinary 1.41 acre Oyster Bay estate offers an entire waterfront world of its own and is one of the best waterfront locations that Sarasota has to offer, with more than 430 feet along Sarasota Bay and a setting that feels virtually irreplaceable. Spanish and Mediterranean inspired architecture lends warmth, character, and timeless sophistication to this remarkable six bedroom residence, while its expansive shoreline creates a front row seat to spectacular sunsets, passing boats, and the natural beauty of Sarasota’s coastal landscape. With access to the Intracoastal Waterway and Gulf of Mexico, this is a rare opportunity for the luxury buyer who believes life is best lived on the water. Spanning more than 10,000 total square feet, with nearly all principal living areas on one level, the home was created for both grand entertaining and relaxed waterfront living. Dramatic ceilings, distinctive architectural details, expansive windows, and a spectacular gallery space with an interior fountain establish a sense of occasion, while multiple intimate gathering areas make the estate equally comfortable for everyday life. A commercial grade chef’s kitchen with professional appliances is equipped for effortless entertaining, from elegant dinners to large celebrations. The primary suite is a private sanctuary framed by beautiful bay views, featuring an expansive custom wardrobe and an indulgent bath with soaking tub, oversized shower, and dedicated massage and sauna room. Five additional bedroom suites provide exceptional privacy for family and guests, each with its own bath and generous storage. Beyond the interiors, the estate unfolds like a private resort. A swimming pool, tennis court, fitness room, billiard room, private office, three car garage, abundant storage, and permitted dock replacement create a property designed for recreation, relaxation, and life on the water. A new roof completed in 2024 adds further value and peace of mind. The address is equally exceptional. Oyster Bay Estates places you near The Field Club, Siesta Key, Southside Village, Sarasota Memorial Hospital, and Downtown Sarasota, offering remarkable access to world class beaches, boating, fine dining, shopping, arts, and culture while remaining tucked within a prestigious waterfront enclave. For those with an even greater vision, the magnificent acreage and extraordinary bay frontage also present the opportunity to create a completely new custom waterfront estate. The property may offer potential for division into two buildable homesites if the existing residence is removed, subject to verification and applicable approvals. With its commanding Sarasota Bay frontage, boating access, acreage, privacy, and coveted location, 1136 N Lake Shore Drive is not simply a place to live. It is the opportunity to claim an extraordinary piece of Sarasota’s waterfront lifestyle.

1136 N Lake Shore Drive, South Sarasota
$137,900
2 Beds ⋅ 1 Baths ⋅ A4703297 MLS
AFFORDABLE SARASOTA LIVING JUST MINUTES FROM SIESTA KEY! Opportunities like this are hard to find! Located in desirable South Winds Mobile Home Park, this well-maintained home offers an incredibly affordable lifestyle with monthly fees of only $195. Enjoy the best of Sarasota living in this friendly 55+ community, just minutes from world-renowned Siesta Key Beach! This home has been lovingly maintained and is ready for immediate occupancy. The comfortable interior features an open living and dining area along with a nicely arranged kitchen. Even better, the outdoor living space is exceptional! A newer carport and screened lanai have been added (2 nice sized lanai's ... 1 on each side!) providing additional space to relax and enjoy the Florida lifestyle. This area also includes a convenient storage room for a washer and dryer. On the opposite side is an additional covered lanai, giving you even more space for outdoor living, entertaining, or simply enjoying our beautiful Florida weather. Important improvements include an air-conditioning system installed in 2020 and re-piping completed in 2022. A termite warranty/contract will also transfer to the new owner at closing. Tucked toward the back of the community on one of its quieter streets with minimal through traffic, this home offers a peaceful setting while keeping you remarkably close to everything in Sarasota. South Winds offers a beautiful, heated community pool, shuffleboard, horseshoes, pickleball, a putting green, library, recreation hall, social activities, friendly neighbors and superb on-site management! Hop on your bike or scooter and head towards Siesta Key, or take a quick drive and have your toes in the sand in approximately five minutes! Cultural downtown Sarasota is approximately 15 minutes away, offering outstanding restaurants, shopping, theaters, opera, galleries and entertainment. Affordable fees, a fantastic location and the Siesta Key lifestyle - this one is a gem! Furniture is negotiable. Being sold As-Is with Right to Inspect. Don't miss this rare opportunity to own in one of Sarasota's affordable 55+ co-op communities but don't wait ... this one won't last long. H-U-R-R-Y!

251 Southwinds Drive, South Sarasota
$225,000
2 Beds ⋅ 2 Baths ⋅ A4702878 MLS ⋅ 5785 BLDG.
Virtually Staged. Welcome to this beautifully updated 2 bedroom, 2 bathroom condo offering a refined blend of comfort, style, and effortless Florida living. Thoughtfully updated throughout, this light-filled residence features LVP flooring throughout the main living areas, inviting indoor and outdoor living spaces, a welcoming front porch, and a private rear porch, along with access to a beautifully maintained community pool. The updated kitchen combines modern style with warm, natural accents, featuring crisp white cabinetry, stainless steel appliances, and custom Acacia wood butcher-block countertops sealed with a water-based polyurethane finish. A sliding glass door off the kitchen opens directly to the private front porch. The spacious primary suite provides a peaceful retreat with a generously sized walk in closet featuring built-in shelving for exceptional storage and organization. The beautifully updated en-suite bathroom continues the home's custom finishes with an Acacia wood butcher-block vanity countertop, also sealed with a water-based polyurethane finish, complemented by a stylish vessel sink and matte-black faucet. A glass-enclosed walk-in shower finished with wood look tile completes this inviting, spa-inspired space. The second bedroom offers excellent flexibility for guests, a home office, or a hobby room and is conveniently served by a full guest bathroom featuring a tub and shower combination with tasteful tile accents. For added everyday convenience, the home includes a full size stacked washer and dryer along with additional shelving, making laundry and storage effortless. Outdoor living is just as inviting, with both a welcoming front porch and private rear porch providing comfortable spaces to enjoy morning coffee, outdoor dining, grilling, or relaxing in the Florida breeze. Residents also enjoy access to a sparkling community pool surrounded by lush landscaping, mature shade trees, and ample lounge seating, creating a peaceful retreat just steps from home. Ideally positioned near Siesta Key, this residence puts some of Sarasota's most desirable beaches, restaurants, shopping, and local attractions within easy reach. Whether you're looking for a full-time residence, seasonal retreat, or low maintenance investment, this beautifully updated condo offers the ideal blend of thoughtful upgrades, private outdoor living, community amenities, and an unbeatable Sarasota location.

5785 Summer Side Lane Unit 4A, South Sarasota
$275,000
2 Beds ⋅ 2 Baths ⋅ A4702996 MLS
BUYER INCENTIVE – RECEIVE A 1% LENDER CREDIT WITH PREFERRED LENDER! BRAND NEW ROOF WITH TRANSFERABLE WARRANTY + BRAND NEW A/C! Welcome home to this well-maintained villa located in a 55+ Sarasota community with plenty of amenities to enjoy. Inside, you'll find a bright and comfortable layout with 2 bedrooms, 2 bathrooms, spacious living and dining areas, and a functional kitchen with plenty of cabinet and counter space. The big-ticket items have already been taken care of with a brand new roof, transferable roof warranty, and brand new A/C, giving the next owner added peace of mind. Enjoy an active Florida lifestyle with community amenities including a heated pool, fitness center, shuffleboard, clubhouse, library, billiards, gathering spaces, and an on-site marina with boat docks. Conveniently located near shopping, dining, beaches, and everything Sarasota has to offer. Come see why this home and community are such a great place to call home!

2407 Riverbluff Parkway Unit V-226, South Sarasota
$180,000
2 Beds ⋅ 2 Baths ⋅ A4702960 MLS ⋅ 3427 BLDG.
Tour 1 Come see this very modern, updated 2-bedroom, 2-bath condo in Sienna Park, ideally located in the heart of Sarasota! This move-in-ready unit features an updated kitchen with granite countertops, updated bathrooms, attractive vinyl flooring, and a bright, comfortable living space. This ground floor unit has a very favorable front door, designated parking space. Also, a private fenced in back yard is included!! Sienna Park offers great community amenities, including a heated swimming pool, fitness center, clubhouse, tennis courts, and recreational areas. The central location puts you close to shopping, restaurants, grocery stores, entertainment, and everyday conveniences, with world-famous Siesta Key Beach just a short drive away. This unit has maintained great rental history for the investor.

3427 Clark Rd Unit 127, South Sarasota
$225,000
2 Beds ⋅ 2 Baths ⋅ A4702358 MLS ⋅ V-315 BLDG.
Welcome to Strathmore Riverside Villas, an active 55+ community in Sarasota where maintenance-free living meets a true boater's amenity package just minutes from Siesta Key. This move-in ready villa offers two bedrooms, two bathrooms, a flex room that works beautifully as a den, study, or office, and an enclosed lanai Florida room, giving you an abundance of flexible living arrangements all on one level. The foyer opens to the main living areas, where luxury vinyl flooring, plantation shutters, and natural light set a clean coastal tone. The spacious and open living and dining space continues into the Florida room, overlooking the green space behind the home, an inviting spot for morning coffee, reading, or casual entertaining. The updated kitchen features recycled glass countertops, a glass mosaic tile backsplash, white cabinetry, stainless appliances, recessed lighting, and pantry storage. The primary suite includes a walk-in closet and an ensuite bath with a walk-in shower, and a guest bedroom and full bath sit at the front of the home. The covered carport delivers everyday convenience, with a dedicated laundry room featuring a utility sink and shelving that doubles as extra storage for beach gear, bikes, and tools. The community's waterfront setting is what sets it apart. A resident marina offers boat slips on a first-come basis for a nominal fee, with access out to the Intracoastal Waterway and the Gulf beyond, so you can keep your boat steps from home. The waterfront clubhouse anchors a full social calendar and includes a large gathering hall, fitness room, library, and a game room with billiards, shuffleboard, and ping pong, all beside a heated pool and sun deck overlooking the water, with outdoor shuffleboard courts nearby. Grounds maintenance is handled for you, leaving more time to enjoy it all. From here you are about four miles from the sands of Siesta Key Beach, minutes from the shops and restaurants of Gulf Gate, and a short drive to downtown Sarasota's dining, arts, and bayfront. Come experience the villa and the lifestyle that comes with it. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2327 Waterbluff Place Unit V315, South Sarasota
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