Winding Creek Real Estate

Welcome to Winding Creek, a charming subdivision nestled in the heart of sunny Florida. Located in the vibrant state of FL, Winding Creek offers the perfect blend of tranquility and convenience for its residents.

Winding Creek is known for its lush greenery, winding streets, and a strong sense of community. The neighborhood boasts a variety of home styles, from cozy bungalows to spacious family homes, ensuring there is something for everyone. With well-maintained sidewalks and beautiful landscaping, Winding Creek is an inviting place for evening strolls or morning jogs.

Residents of Winding Creek enjoy easy access to a range of amenities, including shopping centers, dining options, and top-rated schools. The close-knit community often hosts events and gatherings, fostering a sense of belonging among neighbors.

Nature enthusiasts will appreciate the proximity of Winding Creek to parks, lakes, and nature trails, providing ample opportunities for outdoor activities. Whether you enjoy birdwatching, fishing, or simply taking in the scenic views, Winding Creek has something for everyone.

If you are looking for a peaceful retreat that is still close to all the action, consider making Winding Creek your new home. Experience the best of Florida living in this welcoming subdivision where neighbors become friends and every day feels like a vacation.

Newest Listings in Winding Creek

$157,900

2 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code ⋅ TB8521581 MLS ⋅ Active Status ⋅ 20a BLDG.

Virtually Staged. This rare ground floor corner 2BR/2BA condo is ideally located in the sought-after community of Winding Creek. It sits on high ground in a NON flood zone and is centrally located with access roads leading to all parts of the county. The unit has a bright, spacious, split bedroom plan that includes the following: welcoming foyer, spacious great room, eat-in kitchen, master bedroom with private bath & walk-in closet, office or guest bedroom, 2nd full bath, utility closet with full size washer & dryer, bonus area, PLUS a rear paved patio perfect for your morning coffee & evening glass of wine. As an end unit, additional windows allow natural light to shine in the great room. Updates include, MASTER BATH: vanity with dual sinks - stone counters and soft close drawers & doors, faucets, mirror, light fixture, toilet, showerhead & custom tiled walk-in shower, HALL BATH: vanity with stone counters, faucet, mirror, light fixture, showerhead, and custom tiled tub, INTERIOR: luxury vinyl flooring, new water heater (2026), and AC system (2021), EXTERIOR: newer roof (2021), and painted parking spots - condo assn takes care of exterior including roof. Unit includes an assigned parking spot footsteps from the front door as well as ample guest parking. This building is non-age restricted, pet friendly, and adjacent to the pool & clubhouse. Winding Creek is a well maintained community with mature plants-shrubs-palms-majestic trees & green lawns. Amenities include: active clubhouse with kitchen - social area - meeting & game rooms, heated pool & spa, tennis/pickleball court, and BBQ picnic area. It is conveniently located a short drive from major shopping hubs, Countryside Mall, Historic Downtown Dunedin, Eclectic Safety Harbor, and Award Winning Clearwater Beach. Enjoy Florida living at its finest with countless activities nearby: beaches, water sports, boating, parks, casual & fine dining, trendy bars, micro-breweries, cafes, festivals, concerts, art shows, theaters, spring training baseball, championship golf & more. This is a MUST SEE for buyers seeking maintenance free living in a desirable community.

2400 Winding Creek Boulevard Unit 20A-109, Clearwater

$1,190,000

4 Beds ⋅ 3 Baths ⋅ Winding Creek SubDv. ⋅ 34251 Zip Code ⋅ A4694907 MLS ⋅ Active Status

Welcome to a different kind of Florida living — where wide-open skies, room to roam, and luxury comforts all come together on nearly 6 FENCED ACRES in Myakka City. Behind the PRIVATE CODED MOTORIZED ENTRY GATE, you’ll find a custom-built Mark Cahill home designed for both everyday comfort and the kind of lifestyle people move to the country to enjoy. Whether you’re bringing horses, outdoor toys, or simply looking for more privacy and freedom, this property gives you the space to live the way you want. Inside, soaring 14-foot ceilings, 8-foot doors, crown molding with accent lighting, and a double tray ceiling create an impressive yet comfortable atmosphere. The living room features built-in shelving and flows toward an aquarium window overlooking the pool, giving you peaceful, unobstructed backyard views from the kitchen nook and main living areas. Gorgeous chandeliers elevate both the formal dining room and kitchen, while ALL TILE FLOORING THROUGHOUT means no carpet anywhere in the home. The flexible floor plan offers 4 bedrooms, 3 baths, formal dining, formal living room, a dedicated office and oversized kitchen with breakfast bar & island. Step outside and you’ll understand what makes this property special. The SALTWATER pool features PebbleTec coating, SOLAR HEAT, and a RESISTANCE SWIM SYSTEM that allows you to swim against the current for exercise and training right from home. Additional features include a WINTER SAFETY COVER, cool deck surfacing, RETRACTABLEMOTORIZED AWNING, sunshade, pool bath access and an OUTDOOR SHOWER nearby. You can relax in privacy while enjoying the peaceful surroundings that make country living so appealing. A dedicated FENCED-IN DOG RUN adjacent to the pool adds convenience for pets. For buyers needing space for hobbies, equipment, recreational vehicles, or business use, the 900 SQ FT WORKSHOP is a standout feature with WATER, POWER, & approximately half the space under AIR CONDITIONING. Attached COVERED PARKING provides additional room for boats, trailers, or equipment, while the home itself includes a 3-CAR GARAGE. Nearby recreational opportunities include equestrian trails, boating areas, parks, bow hunting, and a nearby motorsports facility for those who enjoy the active outdoor lifestyle. This home was built with long-term durability and efficiency in mind, including HURRICANE-IMPACT windows and garage doors, ICYNENE INSULATION for energy efficiency, a GENERAC GENERATOR with buried 250-GALLON PROPANE TANK, security system with sensors on all doors and windows, and a BRAND NEW (2026) $30,000 WELL SYSTEM with SULFUR FILTRATION and CHLORINATED PIPES for clean drinking water. The barrel tile roof adds timeless curb appeal, while the property has had no flooding and no hurricane damage. An OWNED 9.5 kW grid-tied SOLAR ENERGY SYSTEM positioned on the property conveys with the home and helps keep energy costs remarkably low — with no lease to assume. AVG ELECTRIC IS $75 -100 PER MO!!! The community itself offers an equestrian park, riding opportunities, picnic areas near the lake, planned events, and a low HOA fee of just $800 per year. If you’ve been searching for a property where you can spread out, enjoy nature, entertain friends, keep horses, store your toys, and still enjoy upscale finishes and amenities, this is exactly what you’ve been waiting for. Schedule your private showing TODAY and come experience the space, privacy, and lifestyle this exceptional property has to offer!

1210 408th Court E, Myakka City

$444,900

4 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 32825 Zip Code ⋅ O6409891 MLS ⋅ Active Status

Dual-Income Potential or Perfect Multigenerational Living with Private In-Law Suite & pool! Welcome to 1008 Old Barn Rd, a flexible and beautifully maintained property designed for modern Florida living. With 1,815 square feet, 4 bedrooms, 2 bathrooms, and a private in-law suite with separate entrance, this home is ideal for multigenerational households, investors, or traveling professionals seeking privacy and convenience. Inside, you’ll find a spacious layout filled with functionality and comfort. The upgraded kitchen features gourmet KitchenAid appliances, granite countertops, abundant cabinet space, and room to gather for everyday living or entertaining. The flexible floor plan creates multiple living possibilities while maintaining warmth and flow throughout the home. Step outside to your private pool area, perfect for relaxing, entertaining guests, or enjoying sunny Orlando afternoons year-round. Additional highlights include a 2-car garage, driveway parking, low yearly HOA of just $221, and a location convenient to shopping, dining, parks, and major commuter routes throughout Central Florida. Located just minutes from Waterford Lakes Town Center, the University of Central Florida, SR 408, and SR 417, this home offers easy access to top shopping, restaurants, entertainment, and commuting options across Orlando and surrounding areas. Built in 1997, this home combines timeless functionality with features buyers continue to search for today: private guest accommodations, flexible living space, upgraded kitchen finishes, and outdoor enjoyment. Whether you're a family needing extra room, an investor exploring rental potential, or a buyer seeking versatility in Orlando, this property delivers exceptional value at $444,900. Don’t miss the opportunity to tour this versatile Orlando property and discover the possibilities waiting at 1008 Old Barn Rd. Schedule a showing today!

1008 Old Barn Road, Orlando

$669,000

3 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 34251 Zip Code ⋅ TB8499646 MLS ⋅ Active Status

MAJOR PRICE IMPROVEMENT! - Set on a private, pie-shaped 7.95-acre lot, In Winding Creek, that stretches deep into the lush wooded forest, this partially fenced estate offers a rare combination of usable land, natural beauty, and thoughtful improvements. The grounds feature a private fishable pond, expansive cleared areas for recreation, and wooded sections that create privacy, including a charming enclosed treehouse with deck. The home is complemented by a detached two-story carport offering two oversized covered parking area and two heated and cooled rooms (one upstairs and one downstairs, not included in the published sq/ft), ideal for an air-conditioned workshop, hobby space, or guest overflow. Additional exterior highlights include a well-maintained and covered well system with pump, bladder tank, and filtration, a huge circular driveway, irrigation system, and beautifully manicured front and rear lawns with lush landscaping. Inside, the open floorplan features vaulted ceilings throughout the main living areas, a spacious living room with a wood-burning fireplace, and a kitchen with stainless steel appliances, breakfast bar seating, and a large dining area. The home offers three bedrooms and two fully updated bathrooms, along with an inside laundry room complete with washer, dryer, second refrigerator, and side entry access. Flooring includes hardwood and tile throughout the main living areas, bathrooms, and primary suite, with wood laminate in the secondary bedrooms. Enjoy outdoor living year-round from the 12x24 covered and screened rear patio with double door access from both the living room and primary bedroom. With a new roof in 2024 and a property that balances open space and wooded privacy, this is a truly unique opportunity to own nearly 8 acres with exceptional features and flexibility. Winding Creek is a private, nature-surrounded community featuring an equestrian center and expansive common areas ideal for walking, hiking, biking, and horseback riding, conveniently located approximately 20 minutes east of I-75 off SR 64.

1115 410th Court E, Myakka City

$325,000

Winding Creek SubDv. ⋅ 34251 Zip Code ⋅ A4688367 MLS ⋅ Active Status

Prime 5+ Acre Lot in Winding Creek community! Build your dream home or private retreat on this beautiful 5+ acre parcel, nestled in the peaceful countryside of Myakka City. Surrounded by nature, this property offers the perfect balance of privacy, space, and tranquility — ideal for a custom estate or a serene getaway. Located within the Winding Creek community, you’ll enjoy a quiet, low-density setting while still being just a short drive from Lakewood Ranch and Sarasota, with easy access to shopping, dining, and everyday conveniences. An additional adjacent 5+ acre lot, also owned by the same seller, is available for purchase — offering the rare opportunity to combine both parcels for approximately 10+ acres of space. This property is not located in a flood zone. Whether you’re looking to build now or invest for the future, this is a unique opportunity to own a piece of Florida’s natural beauty. Residents of Winding Creek also enjoy access to a 148-acre preserve, ideal for horseback riding, hiking, and bow hunting, along with a covered equestrian arena within the community

Sr-64 E, Myakka City

$325,000

Winding Creek SubDv. ⋅ 34251 Zip Code ⋅ A4690172 MLS ⋅ Active Status

41155 State Rd 64 East, Myakka City

$115,000

1 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code ⋅ TB8480990 MLS ⋅ Active Status ⋅ 26 BLDG.

Welcome to 2400 Winding Creek Blvd #26-203 a picture-perfect penthouse-style retreat where comfort, charm, and leisure meet in the heart of a vibrant 55+ Adult community. If you’re ready to live like every day is a vacation, this completely furnished, sun-soaked 1-bedroom, 1-bath condo is your golden opportunity to turn the page and start the next exciting chapter of your life. Perched on the top floor of a two story building with a walk-up design, this residence delivers all the low-maintenance benefits of condo living, while offering the serenity openness and privacy that comes with elevated living. As soon as you step inside, you’re welcomed by an airy open floor plan that flows effortlessly from room to room, creating a space that feels both expansive and cozy. Natural light spills through the windows, illuminating the warm, plush carpet underfoot in the living and bedroom areas, while vinyl and travertine tile finishes add a refined touch where it counts. The heart of the home — the kitchen — boasts a functional layout with timeless appeal. Whether you're cooking for one or entertaining a few close friends, you'll appreciate the spacious counters, classic cabinetry, and built-in appliances, including a microwave, range, refrigerator, and dishwasher. Everything is right where it should be, giving you the ease and confidence to enjoy everyday living. The generously-sized bedroom is your personal retreat, featuring a built-in closet’s and ample space for restful nights and relaxed mornings. But the charm doesn’t stop there. You’ll find bonus spaces like a cozy Florida Room and a bonus room that can double as an office, reading nook, or creative studio. There’s also an inside utility and laundry closet — conveniently located for your laundry / extra storage — giving you practicality without compromise. Step outside to your private screened rear porch, an inviting spot to sip your morning coffee, read a book, or watch the palm trees sway against the backdrop of a lush garden/ courtyard view. You’ll love having a front-row seat to the serene, beautifully landscaped grounds — a calming retreat from the hustle of the world outside. For those who enjoy a social lifestyle, the community delivers in every way. Dive into the sparkling community pool or unwind in the spa. Join your neighbors for a match on the tennis courts or head to the clubhouse for planned activities and recreation. Deeded, covered parking carport , along with guest spaces, means you’ll never worry about where to park, while the meticulously maintained common areas and exterior upkeep ensure everything stays as beautiful as the day you arrived. This residence is designed with deed restrictions and maintenance services that make life effortless. From cable and insurance to landscaping and sewer — it’s all taken care of. All that’s left is for you to live your best life. And let’s not forget this is a 55+ adult community, purposefully created for those who value lifestyle, ease, and connection. Whether you’re downsizing, relocating, or simply seeking a fresh start in a vibrant adult community, this condo is the kind of place that lets you slow down, breathe easy, and feel right at home from day one. Close to the world class beach’s and shopping and dining are right around the corner 2400 Winding Creek Blvd #26-203 isn’t just a condo, it’s a lifestyle. One that’s relaxed, secure, and full of possibility. Your turnkey dream home awaits.

2400 Winding Creek Boulevard Unit 26-203, Clearwater

$249,000

Winding Creek SubDv. ⋅ 34251 Zip Code ⋅ A4196499 MLS ⋅ Active Status

Almost 7 Acres with mature trees, both oaks and pines. There is a spring fed creek through the back portion of the property. Paved road frontage. This beautiful lot would make a beautiful building site. Winding Creek is located in rural Myakka City, and is a beautiful equestrian community that is deed restricted, but allows it's residents to have pets, cattle and horses The community also has a wildlife preserve. What an opportunity! Have you always dreamed of building your dream home but did not want to settle for lack of privacy. This home site is located in the sought-after development of Winding Creek. You will love the fact that you have access and full use of the 148 acre members only Preserve at Winding Creek. Perfect for a relaxing stroll, an after work bike ride or horseback ride. Build your dream home far from neighbors, noise, and the hustle and bustle of life. With almost 7 acres, you can build your own private oasis. This lot offers natural Florida beauty including an abundance of mature oaks. Plenty of room for a pool and tennis court on your equestrian estate. Horses are welcomed and the community offers a 132 acre equestrian training center plus the 148 acre preserve for riding. 4 X 4 golf carts are welcomed as well as four wheelers, and UTVs. Room for your RV, tractor. and all of your toys. Paved roads and maintained Winding Creek is located just off State Road 64 in East Manatee County. Country Living at its best!

41025 E 20th Place, Myakka City

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