South Sarasota Homes with Pickleball Court(s) Amenities

South Sarasota Homes with Pickleball Court(s) Amenities

Welcome to South Sarasota, a hidden gem nestled in the heart of Florida's sun-kissed Sarasota County. Known for its stunning beaches, vibrant arts scene, and lush landscapes, South Sarasota is the perfect blend of relaxation and recreation. Whether you're wandering through the picturesque parks or enjoying a day at the nearby Siesta Key Beach, this charming city offers an idyllic lifestyle that attracts both families and retirees alike.

One of the standout features of homes in South Sarasota is the growing popularity of properties equipped with pickleball courts. This dynamic sport, which combines elements of tennis, badminton, and ping-pong, has taken the community by storm, making it easy for residents to stay active and socialize. Imagine stepping out of your backyard and onto your own private court, ready to challenge friends and neighbors to a friendly match. These homes not only provide a space for exercise but also foster a sense of community and camaraderie among residents.

In South Sarasota, you can find a variety of homes that cater to different tastes and budgets, all while enjoying the luxury of having a pickleball court at your fingertips. From modern single-family homes to charming villas, each property is designed with comfort and convenience in mind. Living here means embracing an active lifestyle, surrounded by warm weather, beautiful scenery, and friendly faces.

Come discover the magic of South Sarasota, where your dream home with a pickleball court awaits!

Newest South Sarasota Homes with Pickleball Court(s) Amenities

$350,000
2 Beds ⋅ 2 Baths ⋅ Ashton Lakes SubDv. ⋅ 34231 Zip Code
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, Sarasota
$325,000
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
$655,000
3 Beds ⋅ 3 Baths ⋅ The Landings SubDv. ⋅ 34231 Zip Code
Escape to your own private retreat nestled amongst the trees in the desirable Landings Treehouse community! This stunning residence offers the perfect blend of modern elegance and comfort, just moments from Sarasota Bay and the area's beautiful beaches. Relax on the expansive screened deck overlooking lush greenery, or step inside to discover a spacious 3-bedroom, 2.5-bath layout featuring vaulted ceilings, skylights, a custom arched window, and an updated wood-burning fireplace. The beautifully renovated kitchen boasts premium appliances, sleek countertops, and a cozy breakfast area with tranquil views from both sides of the home. Neutral tones and elegant tile flooring create a warm and inviting atmosphere throughout. Upstairs, the spacious primary suite features high ceilings, a private balcony, and a fully renovated en-suite bath. Two additional guest bedrooms, each with its own balcony, share an updated bathroom. Enjoy the community's scenic tree-lined streets and nature trails leading to the Intracoastal Waterway, with optional membership available at The Landings Racquet Club, offering tennis, fitness, pool, spa, and social events. Conveniently located near shopping, dining, parks, and major highways.

1479 Landings Circle Unit 41, Sarasota
$234,788
2 Beds ⋅ 2 Baths ⋅ Woodside Village East SubDv. ⋅ 34231 Zip Code
This 2-bedroom, 2-bath villa nestled beneath tropical oak canopy in Woodside Village East, Sarasota, offers a blend of tranquil living and convenient access to local attractions. This villa features an updated interior with an open floor plan and cathedral ceilings. The clerestory windows flood the interior with natural light. A Florida room provides an additional 117 sq ft of living space. Recent updates include quartz countertops, new cabinets, brand new stainless steel appliances, luxury vinyl flooring throughout, and updated bathrooms. The community of Woodside Village East provides residents with a heated pool and tennis/pickleball courts, set within a tropical landscape. The property is situated just a few miles from Siesta Key Beach, known for its Powdered-Sugar sands. Downtown Sarasota, with its cultural venues, dining, and shopping options, is also easily accessible. Cultural attractions in downtown Sarasota include the Van Wezel Performing Arts Hall, the Sarasota Opera House, and various art galleries along Palm Avenue, also known as "Gallery Row". The shops of Gulf Gate, offering a mix of local businesses and national chains, are nearby for daily needs and entertainment. This villa presents an opportunity for those seeking a getaway near the beach and cultural attractions, or a permanent residence in Southwest Florida. Virtually Staged

6947 Woodwind Drive Unit 77, Sarasota
$364,900
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
$180,000
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
$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
$240,000
1 Beds ⋅ 1 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Located in the gated waterfront community of Pelican Cove, nestled along Little Sarasota Bay with direct access to the Intracoastal Waterway, this updated 1-bedroom, 1-bath first floor condo offers the perfect blend of comfort and coastal lifestyle. The residence features updated kitchen appliances, a modernized bathroom, and a spacious bedroom with an oversized walk-in closet. Relax and unwind on the enclosed lanai, complete with sliding doors and screens, where you’ll enjoy peaceful tropical views year-round. Set on 75 acres of lush, tropical landscaping, Pelican Cove is rich in natural beauty with miles of scenic walking paths and an impressive array of amenities. Residents enjoy four boat ramps, 85 marina slips accommodating boats up to 40 feet, plentiful kayak and paddleboard storage, multiple unique clubhouses, swimming pools, a fitness center, tennis and pickleball courts, and an active calendar of social gatherings. Whether you’re seeking a full-time residence, seasonal retreat, or waterfront lifestyle opportunity, this condo delivers exceptional value in one of Sarasota’s most sought-after bayfront communities.

1720 Glenhouse Drive Unit 326, 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
$359,000
3 Beds ⋅ 3 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Hey… have you heard about this little hidden gem called Crooked Creek? Tucked away alongside the natural beauty of Red Bug Slough, this community is one of Sarasota’s best-kept secrets—and this rarely available end-unit villa might just be the one you’ve been waiting for. Offering 3 bedrooms, 3 bathrooms, and a 2-car garage, this spacious residence just under 1,700 sq ft lives large with a flexible layout that’s hard to find. Two of the bedrooms are generous ensuites, perfect for guests or multi-generational living, while the third bedroom offers versatility as a home office or den with its own patio. Inside, you’ll love the no-carpet lifestyle with stylish vinyl plank and tile flooring throughout, complemented by two skylights that fill the home with natural light. Enjoy the large enclosed sunroom as well as an open outdoor private patio, ideal for morning coffee or unwinding in the peaceful, lush surroundings of mature Florida landscaping. This amazing community was Designed by renowned Sarasota School of Architecture architect Tim Seibert, and this villa blends timeless design with a serene, nature-inspired setting. The lifestyle? It’s just as impressive. Residents enjoy a heated pool, pergolas, large Gazebo, wooden footbridge, scenic walking paths, and the tranquility of nearby Red Bug Slough Preserve—all while being minutes from shopping, dining, and Siesta Key beaches. The HOA offers exceptional value, covering roof maintenance, exterior building care, ground maintenance, private roads, cable, and WIFI, Pest control, and trash, making for truly low-maintenance living. Plus, no age restrictions—this is NOT a 55+ community. Opportunities like this don’t come around often… especially in Crooked Creek. Come take a look—you may just fall in love.

3351 Thornwood Road Unit 3351, Sarasota
$269,000
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
A HIDDEN SARASOTA GEM — FULLY REMODELED, FIRST FLOOR & STEPS FROM THE POOL! If you’ve been waiting for a condo that feels fresh, modern and completely move-in ready, this may be the one. Beautifully updated from top to bottom, this light and bright 2-bedroom, 2-bath residence features a 2021 fully remodeled kitchen and bathrooms, new flooring, new A/C (2026), fresh interior paint and trim, and a soft modern coastal palette that feels right at home in Sarasota. And the location within the community is hard to beat. This first-floor residence is in the building right next to the heated pool, gazebo and outdoor grills — yet Crooked Creek feels tucked away from it all, surrounded by mature landscaping and nature. One of the community’s best-kept secrets? A private gated entrance directly into the 72-acre Red Bug Slough Preserve, where miles of walking trails, wildlife and peaceful natural surroundings are practically in your backyard. Residents also enjoy tennis/pickleball, bike storage and a community storage building with individual 5' x 3' storage lockers for condo residents. Just as important, Crooked Creek is a community that has continued to invest in itself. Recent improvements include roofs replaced in 2021, resurfaced heated pool (2025), freshly painted buildings and new carports (2024-2025), along with well-maintained grounds and community amenities. The HOA fee also includes full exterior maintenance, grounds maintenance and Wi-Fi. Nature outside your door. Sarasota at your fingertips. Nothing to renovate. Just move in and enjoy. At its new price of $269,000, this is one Sarasota hidden gem you’ll want to see in person.

3361 Cross Creek Drive Unit 3361, Sarasota
$269,900
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Nestled on the second floor of Sarasota's boutique Crooked Creek community, this thoughtfully updated two-bedroom, two-bath condominium offers a rare combination of refined interiors, natural surroundings, and low-maintenance living. Since 2022, the owners have invested significantly in the home. The kitchen was fully renovated in 2023 with sleek European-style cabinetry, black granite countertops, and all-new appliances , a clean, contemporary space that anchors the open living area. Underfoot, premium engineered hardwood flooring with a 4mm wear layer (refinishable) runs through the main living and dining rooms, installed in 2022. Overhead, a designer Hubbardton Forge light fixture in the dining area and a new ceiling fan with wall switch in the living room add considered detail throughout (2024). The second bathroom received a complete refresh in 2025 with a new toilet, vanity, and flooring. Fresh paint throughout ,the living and dining rooms, kitchen, master and second baths, hallway, and master bedroom ceiling ties everything together with a crisp, move-in ready finish. The functional floor plan is further enhanced by a glass-enclosed porch, offering additional living space and a seamless connection to the outdoors. The unit enjoys a private, tranquil setting with views of mature tropical landscaping and the adjacent Red Bug Slough Preserve a natural buffer that creates a true sense of retreat while keeping you centrally located. Crooked Creek is a 78-unit community with a heated pool, tennis and pickleball courts, a clubhouse, and outdoor gathering areas. Covered assigned parking and dedicated storage are included. Shopping, dining, and area beaches are all just minutes away.

4957 Cross Creek Road Unit 4957, Sarasota
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