South Sarasota Homes with Maintenance Free Community Extras

South Sarasota Homes with Maintenance Free Community Extras

Welcome to South Sarasota, Florida—an enchanting gem nestled within the vibrant Sarasota County. Known for its stunning beaches, lush landscapes, and a rich cultural scene, South Sarasota is a haven for those seeking a blend of relaxation and excitement. This charming area boasts a warm, welcoming atmosphere, making it an ideal spot for families, retirees, and anyone in between.

One of the standout features of South Sarasota is its array of maintenance-free communities. Imagine living in a beautifully designed home where the worries of yard work and exterior upkeep are a thing of the past. These maintenance-free residences provide homeowners with the ultimate convenience, allowing you to spend your time enjoying the sun-soaked beaches, exploring the local art galleries, or savoring delicious cuisine at nearby restaurants.

In addition to the carefree living experience, these communities are often equipped with fantastic amenities, including sparkling swimming pools, state-of-the-art fitness centers, and lush walking trails. Many neighborhoods are also conveniently located near shopping centers, parks, and recreational facilities, ensuring that everything you need is within reach.

South Sarasota is not just a place to live; it’s a lifestyle. With its friendly community vibe, diverse activities, and the allure of Florida's natural beauty, you’ll find that this area offers the perfect backdrop for creating lasting memories. Whether you’re looking for a cozy retreat or a vibrant community to call home, South Sarasota’s maintenance-free homes provide the perfect opportunity to enjoy a stress-free and fulfilling Florida lifestyle. Welcome home!

Newest South Sarasota Homes with Maintenance Free Community Extras

2 Beds ⋅ 2 Baths ⋅ Lakeside Club Of Sarasota SubDv. ⋅ 34231 Zip Code

ONLY 5 MILES TO GORGEOUS SIESTA KEY BEACH! Welcome to effortless Florida living in this beautifully updated END-UNIT condo in Sarasota’s desirable Gulf Gate area, complete with a convenient carport and just minutes from Downtown Sarasota, shopping, dining, and entertainment. Offering a wonderful combination of character, modern updates, privacy, and low-maintenance living, this move-in-ready home is ideal as a full-time residence or seasonal Florida escape. A covered entry and front storm door welcome you into the original brick foyer, adding timeless character the moment you step inside. Enjoy peace of mind with a new roof, new flooring, new lighting throughout, a brand-new dishwasher, plus newer HVAC and hot water heater. The kitchen offers plenty of storage, stainless steel appliances, a quaint dining nook, and a convenient serving window opening to the formal dining area. The spacious open-concept family room is filled with natural light from double sliding glass doors that open to a large covered rear patio—perfect for relaxing, entertaining, or enjoying Florida’s beautiful weather. The desirable split-bedroom floor plan provides excellent privacy and functionality for owners and guests. Tucked away at the rear of the home, the primary suite offers a peaceful retreat with an updated tiled walk-in shower, spacious vanity, and private access to the rear patio. The second bedroom is located at the front of the home and features its own private patio, with a full guest bathroom conveniently located nearby. Both patio areas are fenced for added privacy and maintained by the community, along with the yard maintenance, making it easy to enjoy a truly low-maintenance lifestyle. Residents also enjoy a variety of community amenities, including a swimming pool, clubhouse, meeting room, tennis courts, pickleball courts, and more. The Gulf Gate location puts you close to Gulf Gate Village, Gulf Gate Library, shopping, restaurants, entertainment, Downtown Sarasota, and approximately 5 miles from the sugary cool quartz sand and turquoise waters of Siesta Key Beach. With so much of Sarasota within easy reach, this updated end-unit condo offers the perfect combination of location, comfort, privacy, and easy Florida living. Whether you're looking for a year-round home or a seasonal getaway, this one is ready to welcome you home!

7364 Cloister Drive Unit 7364, Sarasota

2 Beds ⋅ 2 Baths ⋅ Baywood Colony SubDv. ⋅ 34231 Zip Code

Welcome to an exceptional opportunity to own a beautifully updated villa in one of Sarasota's most desirable location West of Trail in Baywood Colony. Offering an outstanding combination of location, value, and peace of mind, this may be the best-priced villa available in this sought-after area. This well-maintained residence has been thoughtfully updated with many of the big-ticket items already taken care of. The home has never flooded and features hurricane impact windows installed in 2025, a new HVAC system from 2025, and a new water heater installed in 2026. The kitchen was renovated in 2023, the electrical panel was updated in 2021, and the sewer lines were updated in 2018. The property also features a durable rubber membrane roof, plenty of storage and a quaint brick paved patio for grilling out and sunbathing! Inside, the villa offers a comfortable Florida lifestyle with an inviting layout and modernized finishes, making it easy to move right in and enjoy. With so many important improvements already completed, you can spend less time worrying about major maintenance and more time enjoying everything Sarasota has to offer. Located in Baywood Colony, this home puts you in the heart of the highly desirable West-of-Trail area, close to Phillippi Estate Park, shopping, dining, downtown Sarasota, and the world-famous beaches of Siesta Key.

5826 Driftwood Place, Sarasota

2 Beds ⋅ 2 Baths ⋅ Carrington Place SubDv. ⋅ 34231 Zip Code

Welcome to this beautifully appointed 2-bedroom, 2-bath condo offering spacious, comfortable living in the heart of Sarasota’s Gulf Gate area. This second-floor unit is easily accessible by elevator and features the convenience of an in-unit washer and dryer. The generous living and dining area provides plenty of room for relaxing and entertaining, while both bedrooms are nicely sized with great closet space. The primary suite features a private ensuite bath and a large walk-in closet. Step outside to the quiet screened lanai, a perfect spot to enjoy your morning coffee, unwind at the end of the day and take in the peaceful Florida setting. The beautifully maintained community features a sparkling pool, tranquil pond and affordable HOA fees. Ideally located close to shopping, restaurants and everyday conveniences, with world-famous Siesta Key Beach just minutes away. Whether you’re looking for a full-time residence or a Florida getaway, this condo offers comfort, convenience and an incredible Sarasota lifestyle. Paradise at an affordable price!

7294 Cloister Drive Unit 23, Sarasota

Phillippi Harbor Club SubDv. ⋅ 34231 Zip Code

OWNER FINANCING AVAILABLE! This inside boat storage rack measures 32' L x 10'W x 9.5'H and can accommodate a boat with dimensions UP TO APPROXIMATELY: 32'L x 9'W x 8'H. Height is measured from the bottom of the keel up to the highest fixed point on the boat. Phillippi Harbor Club is your answer to truly enjoying boating on our beautiful Sarasota waters! This is a boating gamechanger! Simply call the friendly PHC staff and ask them to "splash" your boat, show up and enjoy your day on the water. Return to the dock where the staff will pull your boat, wash & rinse the outside, flush the engine(s), and store it back in your rack for next time. The marina has fuel on site, and an inside storage locker is included. There are plenty of work racks and on-site mechanics almost daily. This is a hurricane category 3-rated building with the latest in fire equipment and enhanced security monitoring. Phillippi Creek is around 4' at mean high tide and is about a 6-minute ride to the Intracoastal Waterway. The racks are in incredible rental demand! Stop towing your boat and own your own rack today...Stop on down and see the operation! Ask about owner financing.

1780 Phillippi Shores Drive Unit A3-5, Sarasota

2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code

Your Slice of Paradise Awaits at Castel Del Mare! Enjoy outstanding Intracoastal Waterway views from this beautifully remodeled, first-floor 2-bedroom, 2-bath condo, perfectly positioned to capture the relaxed Sarasota waterfront lifestyle. Step inside and you’ll immediately appreciate the thoughtful redesign and stylish finishes throughout. Wood-look plank tile flooring flows through the living areas, complemented by rich wood cabinetry and striking California granite countertops. Both bathrooms have been beautifully updated with quartz countertops, sleek sliding glass shower doors and carefully selected designer flooring. Hurricane-impact windows, Samsung appliances, and fresh interior paint add comfort and peace of mind. This residence has undergone a complete transformation and is truly move-in ready. Carport and storage unit included with sale. Castel Del Mare feels like a waterfront retreat with two community swimming pools, including one directly on the Intracoastal Waterway—an incredible spot to relax poolside while watching boats cruise by. Enjoy the fishing pier, tennis, shuffleboard and beautifully maintained community surroundings. Best of all, you’re just minutes from the world-famous sands of Siesta Key Beach, along with nearby restaurants, shopping and everyday conveniences. With monthly rentals permitted, this property also offers excellent investment potential. Don't wait this is the perfect lock and go unit as everything on the outside is maintenance-free! Water views, gorgeous updates, a first-floor location and the Siesta Key lifestyle—this one checks all the boxes! Sold Turnkey Furnished!

1608 Stickney Point Road Unit 8-107, Sarasota

2 Beds ⋅ 1 Baths ⋅ Oakwood Gardens SubDv. ⋅ 34231 Zip Code

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, Sarasota

2 Beds ⋅ 1 Baths ⋅ South Winds Mobile Home Park Co-Op SubDv. ⋅ 34231 Zip Code

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, Sarasota

2 Beds ⋅ 2 Baths ⋅ Baywood Colony SubDv. ⋅ 34231 Zip Code

Light and Bright with 9' Ceilings located at the gateway to Siesta Key this Turn-Key Furnished Baywood Colony 2BR/2BA Villa just 1 unit away from Clubhouse and pool, diagonally across from bayfront sea wall with fountain and benches for enjoying tranquil bay views, fishing or sunsets over the bay. Less than 1 mile to the Siesta Key bridge and World's #1 Siesta Key Beach with amazing, so soft & cool crushed crystal white sands. For peace of mind, this unit never flooded during the hurricanes of 2024 and that is saying something for being this close to the Gulf and Bay. You will love the fact that it is concrete block construction the Open Living Room/Dining Room Floor Plan Flows out to an Oversized Lanai via Quadruple Sliding glass doors - the feeling of light and space in this Villa is simply amazing! The primary BR has a walk-in closet and en-suite bath. The second bedroom is ample in size, and the 2nd bath is just in the hallway for easy access from the entire home. The $1053 Condo Fee includes Villa Exterior Insurance, Exterior Painting, All Ground Maintenance, Water, Sewer, Clubhouse with Pool, Saunas, Kitchen, Function room, Game Room with pool table, dart board, library, etc. and the beautiful bayfront park (this seller was only paying $300/yr. for HO-6 insurance which covers you from the drywall inward). So close to shopping and restaurants too! This is an amazing property and an amazing deal - you will love all that it offers. Mainland security with easy beach access and all at an Oh-so-nice price!

5887 Tidewood Avenue Unit 2, Sarasota

2 Beds ⋅ 2 Baths ⋅ Ashton Lakes SubDv. ⋅ 34231 Zip Code

Welcome to Ashton Lakes, a maintenance-free community set on 33 acres of lush landscaping with four lakes — less than two miles from the beaches of Siesta Key. This beautifully maintained 2—bedroom, 2-bath residence has been thoughtfully updated throughout and delivers an easy blend of comfort, convenience, and coastal charm. Step inside to soaring vaulted ceilings and an abundance of natural light that gives the entire home an airy, light coastal feel. Sweeping lake views frame the living space, and a desirable one-car garage — a rarity at this price point — adds everyday practicality. The primary bath has been fully renovated, with additional updates in the guest bath, and a newly installed Murphy bed maximizes flexibility for guests, a home office, or both. Life at Ashton Lakes centers on its exceptional amenities: a recently updated clubhouse, two heated pools including a large pool with a dedicated lap lane, two tennis courts and four pickleball courts, shuffleboard, grilling stations, and more. A private footbridge connects residents directly to Merchants Mart shopping center, home to CVS, ACE Hardware, a Dollar store, restaurants, and Detwiler's Farm Market. You're also minutes from the Whole Foods anchored redevelopment at Sarasota Square and Siesta Promenade, the new 24-acre mixed-use project at the northwest corner of U.S. 41 and Stickney Point Road. Downtown Sarasota and I-75 are both an easy reach. Recent updates include: HVAC in Jan 2026, deluxe fabric roller shade throughout in Feb 2026, murphey bed in Feb 2026, smart garage open in Feb 2026, refrigerator and washer in 2023, dry bar, primary bathroom, and guest bathroom.

5652 Ashton Lake Drive Unit 5652, Sarasota

2 Beds ⋅ 2 Baths ⋅ Baywood Colony SubDv. ⋅ 34231 Zip Code

Maintenance-Free Living Just Minutes from Siesta Key Beach! Enjoy the Florida lifestyle in this beautifully updated 2-bedroom, 2-bathroom villa, ideally located just a short bike ride from the world-famous Siesta Key Beach. This move-in-ready home has been thoughtfully updated throughout, featuring new flooring, modern appliances, renovated bathrooms, and impact-resistant windows for style, comfort, and peace of mind. The bright, open layout creates an inviting space that’s perfect for relaxing or entertaining. Whether you’re looking for a full-time residence, seasonal retreat, or investment opportunity, this maintenance-free villa offers the perfect blend of convenience and coastal living. Spend your days biking to the sugar-white sands of Siesta Key, exploring nearby shopping and dining, or simply enjoying the low-maintenance lifestyle. Don’t miss your chance to own this beautifully updated villa in one of Florida’s most desirable locations!

5865 Tidewood Avenue Unit 8, Sarasota

2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code

Live close to Siesta Key Beach, rated in the top ten beaches and in Sarasota, Florida, CNN rated as the #1 city to visit in the United States for under $375,000. This two-bedroom, one and one-half bathroom townhouse unit is just across the south bridge to Siesta Key. A short walk to Crescent Beach, restaurants, shopping, and off-island in season, do not deal with beach traffic. The 1,232 square foot townhouse has two floors, a screened and private covered lanai on the first floor and a private open balcony on the second floor. The living area and the primary upstairs bedroom both overlook a private, tranquil rear yard and greenbelt area for your relaxation and your enjoyment. This townhouse is turn-key furnished, with an inside utility closet with a stack washer/dryer, new extra under stairs, 3 x 6 storage closet and an additional 4 x 6 mechanical closet with the HVAC system, hot water heater and more storage space. This is one of the few units in the complex with inside utility. This unit has been fully renovated by the current owner with all new stainless steel appliances, all new flooring, all new shiplap walling in Dining area, and second-floor full bathroom, with new vanity, and all new stair case and wood risers. Decorated turnkey furnished, this townhouse shows extremely well for one's personal enjoyment and the Siesta Key lifestyle or as an investment property with a one-month minimum rental, three times a year. The monthly condo fee covers the barrel-tile roof which is maintained annually, and the exterior of the building, maintenance and insurance, landscaping, all amenities including on-site management, two heated community pools, one on the intercoastal with water views, a clubhouse, pickleball courts, tennis courts, shuffle board, a mangrove walk, and a gazebo on the intercoastal for fishing or watching sunset. Through the association and paid for with the monthly fees are the financial reserves, basic cable television, water, sewer, trash, recycling, and weekly pest control. Unit #101 assigned and deeded parking space, #163 is on the left of this unit's front door and two guest parking spaces are directly across the driveway from this unit. Other monthly costs are the electric (FPL) $80 a month, and internet (Frontier) $50 a month, on average. Your homeowner's interior insurance is less than $75 a month and the policy is paid through April of 2027. If you want to drive, there is the Gulf Gate Mall a the corner of US41 and Stickney Point Road with shopping, restaurants, hardware, Publix and Detwiler grocery stores. Castel Del Mare has 185 units, borders the intercostal, and owning one of only 16 townhouses is this island community could be yours. The townhouses have no one above them, so more quiet than your normal stack units with another unit above. This townhouse is vacant and easy to see.

1646 Stickney Point Road Unit 101, Sarasota

2 Beds ⋅ 2 Baths ⋅ Pinewood Village SubDv. ⋅ 34231 Zip Code

Virtually Staged. Delightful 2-bedroom, 2-bath condo in an unbeatable Sarasota location! Beautifully maintained and move-in ready, this spacious home is just 15 minutes from the world-famous Siesta Key Beach and the vibrant dining, shopping, and cultural attractions of Downtown Sarasota. The recently renovated kitchen offers a fresh, modern feel, while the generous floor plan provides comfort, convenience, and easy Florida living. Additional updates include a new A/C (2023) for added peace of mind. The current tenant is scheduled to move out in September 2026, making this an excellent opportunity for a first-time homebuyer looking to move right in, while also offering investors immediate rental income until then. To provide even greater peace of mind, the seller is including a one-year home warranty, paid at closing. Whether you're searching for your first home, a seasonal retreat, or a smart investment, this Sarasota gem is one you won't want to miss.

2763 Woodgate Lane Unit 211, Sarasota

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