Winding Creek Real Estate

Winding Creek Real Estate

Welcome to Winding Creek, a picturesque subdivision nestled in the heart of Florida, where the charm of suburban living meets the beauty of nature. This enchanting community is designed for those who appreciate a serene lifestyle without sacrificing convenience.

Winding Creek boasts beautifully landscaped streets lined with majestic oak trees and vibrant gardens, creating an inviting atmosphere that feels like home the moment you arrive. The homes here are thoughtfully designed, featuring modern amenities and spacious layouts that cater to families of all sizes. Whether you’re looking for a cozy single-story residence or a grand two-story home, Winding Creek offers a diverse range of architectural styles to suit your taste.

One of the standout features of Winding Creek is its commitment to outdoor living. Residents enjoy access to scenic walking trails, tranquil parks, and sparkling ponds, perfect for leisurely strolls or weekend picnics. The community also features a well-maintained playground, providing a safe and fun environment for children to play and make lifelong friends.

Conveniently located near major highways, Winding Creek offers easy access to nearby shopping, dining, and entertainment options. Whether you’re in the mood for a night out or a day of retail therapy, everything you need is just a short drive away.

Experience the perfect blend of comfort, community, and nature at Winding Creek. Come discover your dream home in this idyllic Florida subdivision, where every day feels like a vacation!

Newest Listings in Winding Creek

2400 Winding Creek Boulevard Unit 3-202, Clearwater
$140,000
2 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code
Easy, affordable Florida living in a welcoming 55+ Clearwater community! This 2-bedroom, 1-bath home offers 913 square feet of comfortable living space, ideal as a year-round residence or a low-maintenance seasonal retreat. Start your mornings with coffee in the bright Florida room, settle in with a good book, or host friends and family in this inviting extra living space. The second bedroom adapts easily to visiting guests, a home office, or a hobby room. Monthly budgeting is simple, too: the HOA fee covers water, sewer, trash, cable TV, and internet. Add your personal touches and make this Clearwater home your own. Schedule your private showing today!

2400 Winding Creek Boulevard Unit 3-202, Clearwater
2400 Winding Creek Boulevard Unit 24-203, Clearwater
$139,000
2 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code
This beautiful furnished 2 bedroom condo offers the perfect blend of comfort and convenience in a high desirable location in the Countryside area. Just minutes away to Honeymoon Island State Park and Dunedin Causeway with plenty of restaurants, shopping, fishing, boating and more. The large furnished condo offers plenty of room for dining and hosting gatherings in your condo. The kitchen is updated and designed with ample cabinet space and has a large window above the sink for natural lighting and a open bar space overlooking the dining area. The dining area has a built-in storage cabinet offering plenty of space for cooking appliances, dishes and your keepsakes. The first bedroom is large with access to the enclosed lanai and lots of space to just bring your personal items. The second bedroom is also large and is completely furnished and tastefully decorated. The bathroom is located between both bedrooms and was renovated with a clean, modern design. The lanai is enclosed with glass windows and has a large storage room. The roof was replaced in 2025 and the community has well maintained landscaping with beautiful trees and plants and lots of sidewalks around the community. Located just a few steps to the heated pool with hot tub, clubhouse, covered seating area, pickleball or tennis and a barbecue grill perfect for outdoor gatherings. Don't miss your chance to make this condo your new home or vacation designation. Move in ready. Just call today for more information.

2400 Winding Creek Boulevard Unit 24-203, Clearwater
970 Little Creek Road, Orlando
$379,000
3 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 32825 Zip Code
Buyer's financing fell through- Back on Market! This won't last long! Welcome to 970 Little Creek Road in the desirable Winding Creek community of East Orlando! This well-maintained 3-bedroom, 2-bath home offers a functional one-story floor plan with approximately 1,240 square feet of living space. Recent updates include HVAC replaced in 2023, new stainless steel appliances, fresh interior and exterior paint, new windows, new patio sliding door, new water heater, new shower and faucet, and replaced interior doors. The home also features vaulted ceilings, ceramic tile flooring, a kitchen with breakfast bar, inside garage laundry, walk-in closet, and an attached 2-car garage. Enjoy the private fenced backyard with no rear neighbors, plus a patio for outdoor entertaining and relaxation. Conveniently located near SR 408, SR 417, UCF, Waterford Lakes, shopping, dining, and major East Orlando destinations. Buyer to independently verify all measurements, HOA information, schools, and property details.

970 Little Creek Road, Orlando
40710 11th Avenue E, Myakka City
$250,000
Winding Creek SubDv. ⋅ 34251 Zip Code
Discover the rare opportunity to create your own private retreat on 5.72 beautiful acres of buildable land. With ample space to bring your vision to life, this expansive property offers the perfect blend of privacy, natural beauty, and future potential. Imagine designing a custom home surrounded by open space, lush Florida landscapes, and room to enjoy the outdoor lifestyle you’ve always wanted. Whether you envision a peaceful country estate, a spacious family homestead, or a thoughtfully designed private sanctuary, this lot provides a remarkable canvas to build something truly your own. Opportunities to secure this much land in a desirable Florida setting are increasingly rare—come explore the possibilities and make your vision a reality.

40710 11th Avenue E, Myakka City
2400 Winding Creek Boulevard Unit 17-203, Clearwater
$117,000
1 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code
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
40916 11th Avenue East, Myakka City
$2,250,000
5 Beds ⋅ 4 Baths ⋅ Winding Creek SubDv. ⋅ 34251 Zip Code
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
1210 408th Court E, Myakka City
$1,090,000
4 Beds ⋅ 3 Baths ⋅ Winding Creek SubDv. ⋅ 34251 Zip Code
HOME & INTERIOR: Custom-built Mark Cahill home | 4 bedrooms | 3 bathrooms | Dedicated office | Formal living room | Formal dining room | Oversized kitchen | Breakfast bar | Center island | Granite countertops | Vaulted ceilings | 8-foot interior doors | Crown molding with accent lighting | Double tray ceilings | Built-in shelving | Aquarium window overlooking pool | Kitchen and dining room chandeliers | Tile flooring throughout | Plantation shutters | Pocket doors PRIMARY SUITE: Sitting area | Jetted garden tub | Walk-through shower | Dual vanities | Private water closets GUEST ACCOMMODATIONS: Guest suite with private ensuite pool bath | Additional guest bedrooms OUTDOOR LIVING: Nearly 6 fully fenced acres | Private coded motorized entry gate | Private pond | Saltwater PebbleTec pool | Separate solar pool heating system | Resistance swim system | Winter safety cover | Cool deck pool surface | Retractable motorized awning | Sunshade | Outdoor shower | Pool bath access | Separate fenced dog run adjacent to pool enclosure WORKSHOP, GARAGE & STORAGE: Approx. 900 SF workshop | Water and electric | Approximately half of workshop air-conditioned | Pass-through overhead doors at both ends | Attached covered parking for boats, trailers and equipment | 3-car garage PROPERTY FEATURES: Horse-friendly acreage | Chicken coop | Open space for recreation, gardening and hobbies | Mature landscaping CONSTRUCTION & INFRASTRUCTURE: Hurricane-impact windows | Hurricane-impact sliding glass doors | Hurricane-impact garage doors | Icynene insulation | Barrel tile roof | Generac backup generator | Buried 250-gallon propane tank | Security system with door and window sensors | New well system (2026) | Sulfur filtration system | Chlorinated water lines | No history of flooding | No history of hurricane damage ENERGY EFFICIENCY: Owned 9.5 kW grid-tied solar energy system | No solar lease to assume | Low utility costs COMMUNITY AMENITIES: Community equestrian park | Riding trails | Lakefront picnic areas | Planned community events | HOA $800 annually NEARBY RECREATION: Myakka River State Park | Myakka Elephant Ranch | Sporting clays and shooting facilities | Horseback riding | Fishing | Kayaking | Hiking | Wildlife viewing | Access to Lakewood Ranch, Sarasota and Gulf beaches

1210 408th Court E, Myakka City
Sr-64 E, Myakka City
$299,900
Winding Creek SubDv. ⋅ 34251 Zip Code
Motivated Seller! PRIME 5+ ACRE PARCEL IN WINDING CREEK — BUILD YOUR FLORIDA DREAM! Discover the freedom and tranquility of country living on this beautiful 5+ acre parcel in the desirable Winding Creek community of Myakka City. Surrounded by natural beauty and offering a peaceful, low-density setting, this property provides plenty of space to create your custom home, private estate, or peaceful Florida retreat. Enjoy the privacy and wide-open space of acreage living while remaining conveniently located just a short drive from Lakewood Ranch and Sarasota, providing easy access to shopping, dining, entertainment, medical facilities, and everyday conveniences. Opportunity to expand: An adjoining 5+ acre parcel, also owned by the seller, is available separately. Purchase both properties and create an impressive approximately 10+ acre homesite or private family compound — a rare opportunity to secure this much land in the area. The property is not located in a flood zone, adding another attractive feature for future development. Winding Creek residents also have access to an impressive 148-acre community preserve, offering opportunities for horseback riding, hiking, and bow hunting, plus a covered equestrian arena within the community. Whether you're ready to build your dream home or looking for a long-term land investment, this exceptional property offers privacy, space, natural beauty, and the opportunity to create something truly your own.

Sr-64 E, Myakka City
41155 State Rd 64 East, Myakka City
$299,900
Winding Creek SubDv. ⋅ 34251 Zip Code
Motivated Seller! PRIME 5+ ACRE PARCEL IN WINDING CREEK — BUILD YOUR FLORIDA DREAM! Discover the freedom and tranquility of country living on this beautiful 5+ acre parcel in the desirable Winding Creek community of Myakka City. Surrounded by natural beauty and offering a peaceful, low-density setting, this property provides plenty of space to create your custom home, private estate, or peaceful Florida retreat. Enjoy the privacy and wide-open space of acreage living while remaining conveniently located just a short drive from Lakewood Ranch and Sarasota, providing easy access to shopping, dining, entertainment, medical facilities, and everyday conveniences. Opportunity to expand: An adjoining 5+ acre parcel, also owned by the seller, is available separately. Purchase both properties and create an impressive approximately 10+ acre homesite or private family compound — a rare opportunity to secure this much land in the area. The property is not located in a flood zone, adding another attractive feature for future development. Winding Creek residents also have access to an impressive 148-acre community preserve, offering opportunities for horseback riding, hiking, and bow hunting, plus a covered equestrian arena within the community. Whether you're ready to build your dream home or looking for a long-term land investment, this exceptional property offers privacy, space, natural beauty, and the opportunity to create something truly your own.

41155 State Rd 64 East, Myakka City
41025 E 20th Place, Myakka City
$249,000
Winding Creek SubDv. ⋅ 34251 Zip Code
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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