Crooked Creek Real Estate

Crooked Creek Real Estate

Welcome to Crooked Creek, a hidden gem nestled in the heart of Sarasota County, Florida! This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and everyone in between.

Crooked Creek is known for its picturesque landscapes, featuring lush greenery, scenic ponds, and winding pathways that invite leisurely strolls and outdoor activities. The community is thoughtfully designed with a variety of homes that cater to diverse lifestyles, from cozy single-family residences to spacious modern designs. Each property is set against a backdrop of natural beauty, providing residents with a serene retreat from the hustle and bustle of everyday life.

One of the standout features of Crooked Creek is its commitment to community living. Residents enjoy access to well-maintained amenities, including a sparkling swimming pool, tennis courts, and playgrounds, perfect for family gatherings or friendly matches. Additionally, the subdivision hosts regular community events, fostering a strong sense of neighborhood camaraderie.

Location is key, and Crooked Creek doesn't disappoint! Just a short drive away, you'll find the vibrant downtown Sarasota, with its eclectic mix of dining, shopping, and cultural attractions. The stunning beaches of the Gulf Coast are also within easy reach, offering endless opportunities for sun-soaked relaxation and water activities.

Whether you’re looking for a peaceful sanctuary or an active lifestyle, Crooked Creek in Sarasota County is the perfect place to call home. Experience the charm and warmth of this delightful community, where every day feels like a vacation!

Newest Listings in Crooked Creek

2 Beds ⋅ 2 Baths ⋅ A4704481 MLS ⋅ Na BLDG.

A little Sarasota gem you didn't know existed. Quiet and secluded Crooked Creek is hidden near Red Bug Slough Preserve where you have a private gated entrance to the park. A laid-back community with a newer roof & carport, heated pool, gazebo, poolside kitchen, gas and charcoal grills, tennis and pickleball court, and community storage with private lockers. This adorable dog friendly 2 bedroom 2 bath condo is positioned perfectly on the first floor and near the pool with an unobstructed view of Crooked Creek. With 1,027 sf of living space, there is room to accommodate a dedicated home office space and entertaining guests comfortably. The kitchen is large with a pantry, bar seating and a garden window. The primary bedroom has windows facing the creek, a walk-in closet and a second built-in closet, and an en-suite bathroom that also hosts the washer and dryer. A spacious and versatile second bedroom is ready to suit your needs and is adjacent to the guest bath. Embrace the Sarasota lifestyle and enjoy dog friendly Red Bug Slough with over 3 miles of combined unpaved and accessible nature paths. Minutes to Siesta Key & Turtle Beach, Gulf Gate, The Legacy Trail, shopping and dining.

3365 Cross Creek Dr Unit 3365, South Sarasota

4 Beds ⋅ 2 Baths ⋅ B26070091 MLS

Welcome to this exceptional 4-bedroom, 2-bath Deer Valley Homebuilders custom Woodland Homes Series modular home, built in 2021 and offering approximately 2,280 sq. ft. under air on a private 2-acre homesite. Ideally situated high and dry on a quiet cul-de-sac, this beautifully upgraded property offers the perfect blend of quality construction, comfort, privacy, and outdoor enjoyment—while being conveniently located near I-95, beaches, shopping, and everyday amenities. Inside, you'll find 9-foot ceilings throughout, crown molding, upgraded 6-inch baseboards in the main living areas, and an inviting electric fireplace. The spacious kitchen is designed to impress, featuring quartz countertops, solid-wood soft-close cabinetry, and a separate pantry. From the durable metal roof and Hardie board siding to the solid concrete-filled block foundation, quality and durability were clearly priorities in this home. Step outside and discover your own private retreat. The fully perimeter-fenced property features a front metal entrance gate, pond, fire pit, 15x24 above-ground saltwater pool with a brand-new pump, entry-level deck, and hot tub—perfect for relaxing or entertaining family and friends.For the hobbyist, outdoor enthusiast, or recreational vehicle owner, this property offers incredible storage. The spacious 3-bay covered carport includes 50-amp electrical service and a water connection, making it ideal for a motorhome, large RV, boat, or other recreational toys. Two additional metal-roofed outbuildings, approximately 12x30 and 14x36, provide even more room for vehicles, equipment, storage, or a workshop. Buried conduit is already installed for future electrical connections. Additional upgrades include a whole-home water filtration system, complete clear hurricane panels, upgraded electrical system, and buried conduit to the street for a future communication connection. With its high-and-dry location, spacious acreage, exceptional construction, extensive upgrades and convenient access to I-95, beautiful beaches, shopping, dining, and more, this property offers a rare opportunity to enjoy privacy and functionality without sacrificing convenience. Come see everything this impressive property has to offer!

4944 NE 115th Place, Okeechobee

3 Beds ⋅ 3 Baths ⋅ A4687754 MLS

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, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4685552 MLS ⋅ 3361 BLDG.

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, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4682348 MLS ⋅ 1 BLDG.

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, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4680117 MLS ⋅ Na BLDG.

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, South Sarasota

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