Winding Creek Real Estate

Winding Creek Real Estate

Welcome to Winding Creek, a picturesque subdivision nestled in the heart of Florida, where tranquility meets modern living. This charming community is designed for those who appreciate the beauty of nature while enjoying the conveniences of contemporary life. Winding Creek boasts beautifully landscaped streets, vibrant green spaces, and a welcoming atmosphere that makes it feel like home from the moment you arrive.

One of the standout features of Winding Creek is its diverse range of homes, catering to families of all sizes and lifestyles. From spacious single-family residences to cozy townhomes, each property is thoughtfully designed to provide comfort and style. Residents can enjoy well-appointed interiors, modern amenities, and private outdoor spaces perfect for entertaining or relaxation.

Nature lovers will find their haven here, with nearby parks and nature trails that invite exploration and adventure. Whether it's a leisurely stroll or an invigorating hike, the lush surroundings of Winding Creek offer plenty of opportunities to connect with the great outdoors. Additionally, the community is conveniently located near shopping centers, dining options, and top-rated schools, making it an ideal location for families and professionals alike.

With a strong sense of community, Winding Creek hosts various events and activities throughout the year, fostering connections among neighbors and creating lasting friendships. Whether you're looking to buy your first home, downsize, or invest in a property, Winding Creek is a wonderful choice for those seeking a vibrant and inviting community in sunny Florida. Come discover your new home in Winding Creek, where every day feels like a getaway!

Newest Listings in Winding Creek

$149,900
2 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv.
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
$157,900
2 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv.
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 ⋅ Winding Creek SubDv.
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
$1,140,000
4 Beds ⋅ 3 Baths ⋅ Winding Creek SubDv.
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 ⋅ Winding Creek SubDv.
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.
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.
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

41155 State Rd 64 East, Myakka City
$115,000
1 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv.
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
$179,000
2 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv.
This condo has a great vibe! Move-in ready, updated, immaculate and fully furnished! This beautiful updated 2 bedroom split floor plan with 2 full bathrooms offers a charming, airy vibe with a mixture of modern touches. Have your morning coffee or evening happy hour in this cozy enclosed lanai overlooking the courtyard and close to the pool. Inside you will find gorgeous wood vinyl flooring throughout and a custom modern kitchen with a custom built buffet area with granite, pull out drawers, and storage. There is a convenient pass-through breakfast bar that is open to the dining area. The spacious bedroom include a walk-in closet and an updated en-suite bath with shower and bathtub. This Floorplan is designed with split-bedrooms and offers private bathrooms for privacy. The second bedroom has two closets with ensuite bathroom featuring a walk-in shower updated vanity and fixtures. You will love the furnishings that are included and are tastefully decorated with the Florida vibe of style and comfort. There is a Laundry Room in the unit that has newer washer and dryer with storage shelves and space for brooms, mops and other items. There is a covered carport and is included with this unit and you will enjoy an beautiful sparkling heated pool, pickleball courts, hot tub and clubhouse. The condo fees include cable, internet, water, sewer, trash and the roof. The Roof was recently replaced in 2025. Plus, you're just minutes away from everything that makes living here ideal for convenience. Honeymoon Island State Park is only five miles away, and close by is Clearwater Beach, Caladesi State Park and other coastal towns like Dunedin, and TD Ballpark are local fun spots. Also, the Westfield Countryside Mall has a theatre and ice skating rink and are down the street and so much more. The St. Pete/Clearwater airport is located just minutes away and Tampa Airport is just across the bridge. Whether your looking for your forever home, a sunny seasonal getaway, or a fresh start in one of Florida's most beloved coastal towns, this condo is the perfect blend of style, comfort and location. Lastly, the images of furniture, mirrors, artwork, furnishings and more are actual and not virtually staged.

2400 Winding Creek Boulevard Unit 9-202, Clearwater
$249,000
Winding Creek SubDv.
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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