Winding Creek Real Estate

Winding Creek Real Estate

Welcome to Winding Creek, a picturesque subdivision nestled in the heart of Florida, where nature and modern living harmoniously converge. This charming community offers an idyllic escape from the hustle and bustle of city life while providing convenient access to all the amenities you desire.

Winding Creek is characterized by its lush landscapes, winding pathways, and serene water features that create a tranquil atmosphere for residents. The subdivision is designed with families in mind, featuring spacious homes that boast contemporary designs and energy-efficient amenities. Whether you’re a first-time homebuyer or looking to upgrade, Winding Creek has something for everyone.

One of the standout features of this community is its commitment to outdoor living. Residents can enjoy leisurely strolls along scenic trails, picnics in beautifully landscaped parks, and family-friendly playgrounds that foster a sense of community and connection. The nearby waterways also offer opportunities for kayaking, fishing, and nature watching, making it a perfect spot for outdoor enthusiasts.

Winding Creek is conveniently located, with easy access to major highways, shopping centers, and top-rated schools. Families will appreciate the proximity to recreational facilities, dining options, and cultural attractions that the vibrant Florida lifestyle has to offer.

As you explore Winding Creek, you'll find a welcoming community that values connection, comfort, and quality of life. Discover your dream home in this enchanting subdivision, where every day feels like a vacation in paradise. Welcome to Winding Creek—your new home awaits!

Newest Listings in Winding Creek

$130,000
1 Beds ⋅ 1 Baths ⋅ TB8536998 MLS ⋅ 17 BLDG.
Short Sale. Short Sale. Welcome to 2400 Winding Creek Blvd #17-203, a well-maintained condo in the Winding Creek community of Clearwater. This 2nd floor unit offers a comfortable layout, practical updates, and a convenient location close to shopping, dining, beaches, and everyday essentials. Inside, the living area feels open and bright, with plenty of natural light. The kitchen features granite countertops, 2 tone cabinets, and modern appliances, making it functional for both everyday meals and entertaining. The washer and dryer are located inside the unit and will convey with the sale, adding extra convenience. The bedroom offers good storage with 2 large closets, and the large updated bathroom gives the home a clean, refreshed feel with plenty of space to get ready. Residents of Winding Creek can enjoy the community pool and spa, tennis courts, and shuffleboard court while still being close to everything Clearwater has to offer. Clearwater Beach, local parks, restaurants, shopping, and entertainment are all within easy reach, with the Gulf beaches less than 20 minutes away. Whether you're looking for a full-time home, seasonal Florida getaway, or low-maintenance Clearwater condo, this property offers a practical combination of location, updates, and convenience.

2400 Winding Creek Boulevard Unit 17-203, Clearwater
$342,500
3 Beds ⋅ 2 Baths ⋅ O6431576 MLS
GREAT STARTER HOME IN MOVE IN READY CONDITION. THIS 3/2 SPLIT BEDROOM PLAN HAS A SPACIOUS GREAT ROOM WITH VAULTED CEILINGS AND MANY OPTIONS FOR LIVING & DINING ROOM FURNITURE ARRANGEMENT. BEAUTIFUL STAGGERD TILE THROUGHOUT – NO CARPET. CUTE KITCHEN WITH EATING SPACE & NEW REFRIGERATOR (6/23), NEW DISHWASHER (9/23). ROOF WAS REPLACED IN 2023 AND AIR CONDITIONER IN 7/26. PUT THIS HOME ON YOUR MUST SEE LIST.

930 Rivecon Avenue, Orlando
$299,000
A4702323 MLS
Nestled within the sought-after equestrian community of Winding Creek, this breathtaking 9.33-acre vacant homesite offers the perfect canvas to create the custom country estate you've always envisioned. Featuring a picturesque lake, brand-new fencing along the front property line, and a beautiful blend of open pasture and mature woods, this property provides the ideal balance of privacy, natural beauty, and functionality. Whether you're dreaming of a custom home, barndominium, or private equestrian retreat, this exceptional parcel offers endless possibilities. The wooded rear portion of the property creates a peaceful backdrop while the cleared acreage provides ample space for your home, barn, workshop, riding arena, or additional outbuildings. Winding Creek is a deed-restricted, agricultural community where country living meets modern convenience. Horses, farm animals, barns, outbuildings, and off-road vehicles are all permitted, making it an ideal setting for those seeking an active rural lifestyle. Residents enjoy access to over 150 acres of private equestrian and walking trails, along with the renowned Winding Trails Equestrian Center, home to rodeos, barrel racing events, and a vibrant equestrian community. Despite its tranquil setting, Winding Creek is conveniently located just 30 minutes from I-75 via SR 64 East, offering easy access to top-rated schools, shopping, dining, and everyday amenities. With low HOA fees and a rare combination of privacy, flexibility, and scenic beauty, this extraordinary property presents an exceptional opportunity to design and build the custom home of your choosing in one of the area's premier equestrian communities.

2102 411th Street E, Myakka City
$149,900
2 Beds ⋅ 1 Baths ⋅ TB8534466 MLS ⋅ 24-102 BLDG.
This furnished condo is move in ready and a charming first floor unit in the heart of delightful Clearwater /Countryside area and the coastal destinations of Honeymoon Island State Park and other beloved coastal towns. The condo has many updates including new roof in 2025, HVAC system is 2022, new lanai windows 2024, new water heater and new flooring. The condo has two bedrooms and one bath with plenty of space for large furniture. The kitchen has plenty of cabinet space and countertops, pantry and has a breakfast bar overlooking the dining room. This unit is a cozy split floor plan with a fully enclosed lanai area with views of the courtyard and sidewalks leading to the pool area. There is an laundry room with washer and dryer included. This community is located in a non-evacuation zone, no flood zone and is conveniently located to shopping centers, grocery stores, restaurants and the St. Pete/Clearwater airport. The amenities include a heated pool, hot tub, pickleball, clubhouse and barbecue area. The HOA fee includes water, sewer, trash, cable, internet, the roof, building maintenance and landscaping so you can enjoy the freedom of maintenance fee living. Whether your seeking a primary residence, a vacation second home or investment opportunity this property checks all the boxes. Contact me today to schedule a showing or I can do a walkthrough of the property on video if your interested in this property and are out of state.

2400 Winding Creek Boulevard Unit 24-102, Clearwater
$649,900
4 Beds ⋅ 3 Baths ⋅ B26058378 MLS
Discover this exceptional 4-bedroom, 3-bathroom single-family, lakeside, pool residence in the desirable Winding Creek community of Fort Pierce. This lake front property spans 2,293 square feet of finished living space on one story, offering an efficient and comfortable layout. Several new appliances and fresh paint. 2.5 garage, with ample parking, a wall a/c unit and a generator with hook up to main panel. The thoughtful floor plan provides plenty of room for various lifestyles and entertaining needs. Located in Winding Creek, this 48 lot, gated community presents a wonderful opportunity to enjoy living in Fort Pierce. This house is listed "Coming Soon" as owners have ungrades, painting and landscapling done.

2108 Winding Creek Lane, Fort Pierce
$675,000
4 Beds ⋅ 3 Baths ⋅ B26047211 MLS
Welcome to this well-appointed single-story residence in Winding Creek, an exclusive gated community with only 45-custom homes. This four-bedroom, three-bathroom, two-and-a-half car garage home offers 3,319 square feet of finished living space, including formal living, dining, family room and a giant Florida room providing tons of space for the whole family to spread out and enjoy Florida living. Inside you will find high vaulted ceilings, plantation shutters throughout, ceiling fans in every room and tile and wood floors. The open kitchen is well appointed with granite countertops, a breakfast area, wood cabinets and two pantries. With just under a half-acre you will love the privacy of your screened lanai overlooking a lush, tree-lined backyard. Roof 2021, A/C 2025 H2O 2026

2305 Winding Creek Lane, Fort Pierce
$157,900
2 Beds ⋅ 2 Baths ⋅ TB8521581 MLS ⋅ 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
$2,300,000
5 Beds ⋅ 4 Baths ⋅ A4697701 MLS
Melissa’s Hope is a custom barndominium-style home built by Homes by Laura, Inc. and a 2026 Parade of Homes Winner. Designed to blend everyday comfort, equestrian functionality, and long-term flexibility, the main level features an open great room, kitchen, walk-in pantry, office, primary suite, two guest bedrooms, and an expansive porch. A drive-through breezeway, tack and feed room, and three stalls create a seamless connection between the home and outdoor living. Upstairs, a private two-bedroom apartment with a kitchen, living room, bathroom, and generous closet space offers flexibility for guests, extended family, or multigenerational living. Located on 5.86 acres in the wonderful, peaceful community of Winding Creek. Within the community, Winding Trails Ranch often hosts barrel races and other events. Far enough away from the crowded city life and only an hour drive down state road 64 to Anna Maria Island Beach. This lifestyle is one you will quickly fall in love with.

40916 11th Avenue East, Myakka City
$925,000
4 Beds ⋅ 5 Baths ⋅ B26042080 MLS
Welcome to luxury waterfront living in the exclusive gated community of Winding Creek. This custom-built estate features 4 bedrooms, 3 full bathrooms, 2 half bathrooms, a private office, and a 3-car garage, complemented by elegant finishes throughout, including a dramatic stone staircase, gourmet kitchen, and an expansive primary suite. Step outside to your private backyard oasis with a gas-heated pool and spa, outdoor kitchen, and breathtaking lake views perfect for relaxing or entertaining. Offering the ideal blend of luxury, comfort, and Florida lifestyle living, this exceptional home is a rare opportunity you won't want to miss. Schedule your private showing today and discover why this remarkable home is the perfect place to create your next chapter.

2304 Winding Creek Lane, Fort Pierce
$1,140,000
4 Beds ⋅ 3 Baths ⋅ A4694907 MLS
Luxury, privacy, & nearly 6 FENCED ACRES come together in one extraordinary custom-built Mark Cahill estate in Myakka City. Behind the PRIVATE CODED MOTORIZED ENTRY GATE, you'll discover the freedom, space, & lifestyle today's buyers are searching for. Based on current land & construction costs, recreating a comparable estate like this today could approach $2 MILLION, making this an exceptional opportunity to own a luxury country property without the wait, uncertainty, or rising costs of new construction. Inside, soaring ceilings, 8-FOOT DOORS, crown molding with accent lighting, a dramatic double tray ceiling, elegant chandeliers, & ALL TILE FLOORING create an impressive yet welcoming atmosphere. Built-in shelving anchors the living room, while an aquarium window frames peaceful views of the pool from the main living areas. The flexible floor plan offers 4 BEDROOMS, 3 BATHS, formal living & dining rooms, a dedicated office, & an oversized kitchen with breakfast bar & island. Step outside to your own private retreat featuring a SALTWATER PebbleTec pool with SOLAR HEAT, a RESISTANCE SWIM SYSTEM for year-round exercise, winter safety cover, cool deck, RETRACTABLE MOTORIZED AWNING, sunshade, pool bath access, outdoor shower, & a fenced dog run—all designed for entertaining, relaxing, & enjoying Florida's outdoor lifestyle. Need room for hobbies, horses, recreational vehicles, or a home-based business? The 900 SQ FT WORKSHOP is a standout feature, offering WATER, POWER, approximately half under AIR CONDITIONING, pass-through access, & attached COVERED PARKING for boats, trailers, or equipment. The home also includes an oversized 3-CAR GARAGE. Built with durability, efficiency, & peace of mind in mind, this home features HURRICANE-IMPACT WINDOWS & GARAGE DOORS, ICYNENE INSULATION, an OWNED 9.5 kW SOLAR SYSTEM, GENERAC GENERATOR with buried 250-GALLON PROPANE TANK, a security system with sensors on all doors & windows, & a BRAND-NEW (2026) $30,000 WELL SYSTEM with sulfur filtration & chlorinated pipes. The barrel tile roof adds timeless curb appeal, & the property has experienced no flooding or hurricane damage. Winding Creek offers a peaceful country setting with a private community park, lakefront picnic area, riding opportunities, community events, & LOW HOA FEES of just $800 per year. Nearby boating, parks, nature preserves, bow hunting, & the local motorsports facility provide endless opportunities for outdoor recreation. Be sure to explore the Matterport 3D Tour & review the complete Features Sheet to discover the many additional upgrades & amenities this remarkable estate has to offer. Schedule your private showing today & discover why this extraordinary property represents an exceptional opportunity to own a luxury estate that's difficult to replicate at today's construction costs.

1210 408th Court E, Myakka City
$669,000
3 Beds ⋅ 2 Baths ⋅ TB8499646 MLS
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
A4688367 MLS
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
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