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 stunning Gulf Coast. This vibrant community is renowned for its beautiful landscapes, rich cultural scene, and an array of recreational activities that cater to every lifestyle. With its warm climate, pristine beaches, and lush parks, South Sarasota is not just a place to live; it's a lifestyle choice that invites you to enjoy the best of Florida year-round.

One of the standout features of homes in South Sarasota is the increasing popularity of properties equipped with pickleball courts. This fast-paced, fun-filled sport has taken the community by storm, offering residents a unique way to stay active and socialize. Imagine stepping out of your beautifully designed home and onto your very own pickleball court, ready for a friendly match with neighbors or family. These homes provide not just a place to live, but a lifestyle enriched with health, wellness, and community spirit.

In addition to pickleball, South Sarasota boasts a plethora of amenities that enhance the living experience. From scenic walking trails and serene parks to world-class dining and shopping options, you’ll find everything you need just a stone’s throw away. Whether you’re a retiree seeking tranquility, a family looking for adventure, or a young professional eager to connect, South Sarasota offers a welcoming environment for all.

Discover your dream home in South Sarasota and embrace a life filled with sunshine, community, and the joy of pickleball!

Newest South Sarasota Homes with Pickleball Court(s) Amenities

$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
$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
$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
$373,750
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
$339,000
2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code
Enjoy the coastal Sarasota lifestyle just minutes from world-famous Siesta Key Beach! Located in the waterfront community of Castel Del Mare, this turnkey furnished 2-bedroom, 2-bath condo combines comfort, convenience, and scenic surroundings in one of Sarasota’s most desirable locations. Inside, the condo features over 1,000 sqft of space with an open living and dining area, laminate flooring, and direct access to the spacious glass-enclosed lanai overlooking lush greenery and the community tennis court. The updated kitchen is designed for both function and style, with solid surface counters, stainless steel appliances, generous cabinet storage, and tiled backsplash. The primary suite offers a spacious walk-in closet and private en-suite bath, while the secondary bedroom includes simple closet space and easy access to the second full bathroom. This residence is ready for immediate enjoyment as a full-time home, seasonal retreat, or investment opportunity. Castel Del Mare is a beautifully maintained intracoastal waterfront community featuring resort-style amenities including two heated pools, tennis courts, kayak storage and launch access, a club house, grilling areas, walking paths, and scenic waterfront seating areas perfect for watching sunsets over Sarasota Bay. Residents also enjoy elevator access, assigned parking, and easy access to a variety of shopping, dining, and boating opportunities. Positioned just over the south bridge to Siesta Key, this location places you moments from powder-soft Gulf beaches, waterfront restaurants, marinas, and vibrant entertainment options. Whether enjoying a day at the beach, exploring nearby nature preserves, or dining along the water, this property delivers the ideal blend of relaxation and access!

1624 Stickney Point Road Unit 1624-208, 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
$369,900
2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code
Experience the best of Sarasota living in this beautifully furnished 2-bedroom, 2-bath condominium in the sought-after community of Castel Del Mare.  Perfectly positioned at the south bridge to Siesta Key, this community offers a rare combination of waterfront ambiance and everyday convenience just minutes from world-famous Siesta Key Beach.  Inside, the open-concept floor plan is bright and inviting, with generous living and dining areas designed for comfort and ease.  Large sliding doors lead to a screened lanai and frame serene views of lush tropical landscaping, tennis courts and the intracoastal waterway. The updated kitchen features granite countertops, elegant wood cabinetry, tile flooring and a stylish back splash.  The spacious primary suite offers a peaceful retreat with access to the screened lanai, views of the Intracoastal Waterway, an en-suite bath and walk in closet with custom built-ins.  A comfortable guest bedroom and second full bath provide privacy for family and visitors.  Additional features include impact rated windows and sliders, assigned parking and tasteful furnishings. Castel Del Mare is beloved for its exceptional amenities and unbeatable location.  Residents enjoy two heated pools, tennis and pickleball courts, shuffleboard, kayak storage, a fishing pier, bayside gazebo, clubhouse, grilling areas, bike storage and beautifully landscaped grounds.  This community offers direct access to the scenic waterfront boardwalk and is just a short stroll to restaurants, shops, marinas and boating options nearby.  Whether you are seeking a full-time residence, seasonal escape or investment opportunity, this condo offers outstanding flexibility, strong lifestyle appeal and the relaxed coastal atmosphere that makes Sarasota so desirable.  Enjoy sunrise walks, sunset views, dolphins along the bay, and the convenience of being close to everything Siesta Key has to offer.

1624 Stickney Point Road Unit 206, 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
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