Crooked Creek Homes with Trail(s) Amenities

Welcome to Crooked Creek, a charming subdivision nestled in the heart of South Sarasota, Florida. This delightful community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and everyone in between. With its lush landscapes and friendly atmosphere, Crooked Creek invites you to experience the serene lifestyle that South Sarasota has to offer.

One of the standout features of Crooked Creek is its extensive network of scenic trails. Perfect for morning jogs, evening strolls, or leisurely bike rides, these trails wind through the community’s picturesque surroundings, providing residents with an opportunity to connect with nature. Imagine starting your day with a refreshing walk, surrounded by the vibrant flora and fauna of Florida, or unwinding after a long day on the peaceful paths of Crooked Creek.

The homes in this subdivision are designed with comfort and style in mind, featuring spacious layouts, modern amenities, and beautiful outdoor spaces. Many properties boast private backyards where you can bask in the Florida sunshine or host gatherings with family and friends. With the added benefit of trail access, outdoor enthusiasts will find themselves in paradise, with ample opportunities for recreation right at their doorstep.

Crooked Creek is not just a place to live; it’s a community where neighbors become friends and memories are made. With its prime location in South Sarasota, residents enjoy easy access to shopping, dining, and the stunning beaches that this beautiful region is known for. Discover the charm of Crooked Creek and make it your new home today!

Newest Crooked Creek Homes with Trail(s) Amenities

$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

$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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