Winding Creek Real Estate

2 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code

Welcome to your new home or vacation home in Clearwater, Florida. This community is not in a flood zone and is a non-evacuation zone too. This beautiful furnished 2 bedroom condo offers the perfect blend of comfort and convenience in a high desirable location in the Countryside area. Just five miles away from destination 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 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

$384,900

4 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 32825 Zip Code

This updated 4-bedroom, 2-bathroom single-story home delivers modern style and ultimate peace of mind! Key upgrades include a Brand-New Roof (2026), Brand-New HVAC (2026), and a Whole-House Plumbing Re-Pipe (2026). Inside, a Freshly Painted Interior frames tile flooring throughout. The kitchen boasts New Shaker Cabinets, New Quartz Countertops, and New Stainless Steel Appliances. Both full bathrooms feature New Shaker Vanities, Quartz Countertops, updated fixtures, and toilets. Outdoors, the Freshly Painted Exterior is surrounded by manicured landscaping and a fully fenced backyard. The attached 2-car garage features Refinished Garage Floors. Move-in ready with zero heavy lifting required!

989 Little Creek Road, Orlando

$145,700

2 Beds ⋅ 2 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code

Virtually Staged. FIRST-FLOOR CORNER CONDO • NON-EVACUATION ZONE • APPROX. 66' ABOVE SEA LEVEL • GREAT HOA WITH GOOD RESERVES • 2 REMODELED BATHROOMS • COVERED PARKING! Welcome to easy Florida living in this beautifully maintained 2-bedroom, 2-bath, 948 sq. ft. FIRST-FLOOR CORNER UNIT in desirable Winding Creek! This move-in-ready condo checks so many of the boxes buyers are looking for—including a GREAT HOA WITH GOOD RESERVES, a NON-EVACUATION ZONE location and an elevation of approximately 66 FEET ABOVE SEA LEVEL. Step inside to a fresh, inviting interior featuring ALL TILE FLOORING—NO CARPET, fresh paint, attractive 4¼-inch baseboards, updated interior doors, ceiling fans and light fixtures throughout. Both bathrooms have been BEAUTIFULLY REMODELED with updated vanities and finishes, giving the home a clean, modern feel. The comfortable 2-bedroom, 2-bath floor plan is ideal for a full-time residence, seasonal Florida retreat or low-maintenance second home. Enjoy your morning coffee or evening cocktail from the SCREENED LANAI, then step outside to the adjoining paver patio and enjoy Florida's beautiful weather. The FIRST-FLOOR CORNER LOCATION means no stairs and offers additional privacy, while COVERED PARKING adds another everyday convenience. Additional improvements include an HVAC SYSTEM INSTALLED IN 2017 and WATER HEATER INSTALLED IN 2019. Winding Creek offers an impressive collection of amenities including a HEATED COMMUNITY POOL, HOT TUB, STEAM ROOMS, TENNIS AND PICKLEBALL COURTS, SHUFFLEBOARD, WALKING PATHS, MATURE TREES, GRILLING AREA and CLUBHOUSE with a pool table and table tennis. The HOA fee includes water, sewer and trash service, lawn care, tree trimming, Spectrum TV with two boxes and internet, helping make everyday living simple and convenient.....And the LOCATION IS HARD TO BEAT! Enjoy easy access to Honeymoon Island State Park, Caladesi Island, Downtown Dunedin, Safety Harbor, shopping, restaurants, recreation and the beautiful Gulf Coast beaches. If you've been searching for a FIRST-FLOOR 2-bedroom, 2-bath condo with remodeled bathrooms, all-tile flooring, covered parking, a well-positioned HOA and fantastic community amenities, put this one at the top of your list. MOVE-IN READY. FIRST FLOOR. CORNER UNIT. NON-EVACUATION ZONE. GREAT HOA. FLORIDA LIVING MADE EASY!

2400 Winding Creek Boulevard Unit 18-105, Clearwater

$115,000

1 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code

Move-in-ready first-floor condo offering a spacious, comfortable layout and excellent convenience. The large living area provides plenty of room for entertaining, while abundant storage throughout adds everyday functionality. The generously sized primary bedroom includes ample closet space to accommodate a large wardrobe, plus additional private storage just off the bedroom. Enjoy the added versatility of a private, enclosed Florida room—perfect for a sitting area, home office, or extra living space. The unit also features an *in-home washer and dryer, designated front-row carport parking, and plenty of guest parking. All furnishings are included with the sale, as desired by the buyer, and are subject to the terms, conditions, and purchase price stated in the applicable contract. Located in a well-maintained community with a pool, tennis courts, and additional park-like areas. Pets are welcome with some restrictions. Conveniently situated near restaurants, entertainment, beaches, doctors, and hospitals. No flood zone. A great opportunity at a price designed to sell! Included: Cable TV, Community Pool, Escrow Reserves Fund, Internet, Maintenance Exterior, Maintenance Grounds, Manager, Pest Control, Pool Maintenance, Sewer, Trash, Water.

2400 Winding Creek Boulevard Unit 17-103, Clearwater

$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

$120,000

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

$149,900

2 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv. ⋅ 33761 Zip Code

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. ⋅ 33761 Zip Code

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

$2,250,000

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

$1,090,000

4 Beds ⋅ 3 Baths ⋅ Winding Creek SubDv. ⋅ 34251 Zip Code

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

$310,000

Winding Creek SubDv. ⋅ 34251 Zip Code

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

$310,000

Winding Creek SubDv. ⋅ 34251 Zip Code

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

Winding Creek Real Estate

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