Crooked Creek Homes with Pickleball Court(s) Amenities

Crooked Creek Homes with Pickleball Court(s) Amenities

Welcome to Crooked Creek, a charming subdivision nestled in the heart of South Sarasota, Florida. Known for its picturesque landscapes and inviting community spirit, Crooked Creek is an ideal destination for families, retirees, and everyone in between. This vibrant neighborhood stands out not only for its beautiful homes but also for its exceptional amenities, including the much-coveted pickleball courts.

Imagine waking up each day in a stunning home surrounded by lush greenery, where the warm Florida sun bathes your private oasis in golden light. Crooked Creek offers a variety of thoughtfully designed residences, catering to diverse tastes and lifestyles. Whether you’re searching for a cozy single-family home or a spacious property perfect for entertaining, you’ll find it here.

One of the standout features of Crooked Creek is its dedicated pickleball courts. This fast-growing sport is perfect for players of all ages and skill levels, making it a fantastic way to stay active and socialize with neighbors. The courts are well-maintained and provide an excellent environment for both casual play and competitive matches. Join in on community tournaments or simply enjoy a friendly game with friends—either way, you’ll be part of a lively and engaging community.

In addition to its recreational offerings, Crooked Creek is conveniently located near shopping, dining, and beautiful beaches, ensuring that everything you need is just a stone's throw away. Experience the perfect blend of relaxation and recreation in Crooked Creek, where your dream home awaits!

Newest Crooked Creek Homes with Pickleball Court(s) Amenities

3351 Thornwood Road Unit 3351, Sarasota
$339,000
3 Beds ⋅ 3 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
JUST REDUCED Again, WOW!!!! — AN INCREDIBLE SARASOTA VALUE! Where else can you find a 3-bedroom, 3-bath home with a 2-car garage and nearly 1,700 sq. ft. in this desirable Sarasota location—PLUS a maintenance-friendly lifestyle surrounded by nature? Welcome to Crooked Creek, one of Sarasota’s best-kept secrets. This rarely available end-unit villa offers the space and privacy you want without many of the exterior, and ground maintenance responsibilities of traditional homeownership. Your HOA fee includes roof, gutter and soffit maintenance, and replacement, exterior painting, pest control, irrigation, grounds maintenance, trash, Wi-Fi and community amenities—giving you more time to simply enjoy the Florida lifestyle. Inside, the flexible floor plan includes two spacious ensuite bedrooms, plus a third bedroom and full bath—ideal for guests, multigenerational living or a home office. With 1,683 sq. ft., a 2-car garage, no carpet, two skylights, an enclosed sunroom and 2 private outdoor patios, there is room to live comfortably without giving up the features buyers want. And then there’s the lifestyle. Crooked Creek offers a heated community pool, tennis and pickleball, gazebo and grilling areas, community kitchen, scenic walking areas and a private gated entrance to Red Bug Slough Preserve. Step outside your neighborhood and enjoy acres of natural Florida beauty with walking and biking trails, wildlife, fishing and picnic areas. LOCATION, LOCATION, LOCATION! You’re approximately 2 miles from Gulf Gate, with its popular restaurants, shopping and everyday conveniences; about 6 miles from world-famous Siesta Key Beach; approximately 6 miles from Downtown Sarasota for dining, arts, entertainment and the Bayfront; and roughly 10 miles from Sarasota-Bradenton International Airport (SRQ). It’s hard to find this combination of 3 bedrooms, 3 full baths, nearly 1,700 sq. ft., a 2-car garage, extensive HOA-covered exterior maintenance, community amenities, preserve access AND proximity to Siesta Key at this price. More home. Less maintenance. An incredible Sarasota location. Come discover why Crooked Creek deserves a closer look.

3351 Thornwood Road Unit 3351, Sarasota
3361 Cross Creek Drive Unit 3361, 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
4957 Cross Creek Road Unit 4957, 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
3363 Cross Creek Drive Unit 3363, Sarasota
$259,000
2 Beds ⋅ 2 Baths ⋅ Crooked Creek SubDv. ⋅ 34231 Zip Code
Welcome to Crooked Creek, a hidden gem in Sarasota with its own private gated access to the Red Bug Slough Preserve. This beautifully maintained 2-bedroom, 2-bath 2nd floor residence was completely updated in 2021 and offers serene views of Crooked Creek, a charming wooden bridge, and lush park-like surroundings. The open and airy floor plan features hardwood floors and tile throughout, plantation shutters, a skylight at entry, and modern finishes. The updated kitchen includes white cabinetry, solid surface countertops with a large peninsula, tile backsplash, smart stainless steel appliances ( fridge and dishwasher 2025, oven and microwave 2021), a spacious pantry, and a garden window. Additional updates are water heater 2018, and reverse osmosis for kitchen sink 2025. The primary suite enjoys peaceful water, a walk-in closet, linen closet and sliding doors to a covered screened lanai. The updated bath has a washer/ dryer (2021)in separate laundry closet, as well as tile floors, a modern vanity, and tile shower . The guest bedroom offers flexible use with a built-in workstation and queen-size Murphy bed. Additional features include two screened covered lanais, reverse osmosis water system for kitchen sink, covered carport, and ample guest parking. Crooked Creek is a 78-unit community offering a heated resurfaced pool, updated poolside kitchen, gazebo with seating, gas and charcoal grills, tennis/pickleball court, community storage with individual lockers, newer roofs (2021), new carports, and recently painted buildings. HOA fees have been reduced by $69 per month from 2025, reflecting strong reserves and excellent financial management. Conveniently located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, and dining. A true nature lover’s paradise.

3363 Cross Creek Drive Unit 3363, Sarasota
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