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Winding Cypress is a gated community in Naples, Florida known for its natural beauty, modern homes, and resort-style amenities. Developed by DiVosta, the community offers beautifully designed single-family homes ranging from approximately 1,542 to over 2,589 square feet, with floor plans typically featuring 2 to 3 bedrooms, 2 to 3 bathrooms, and spacious open living areas designed for comfortable Southwest Florida living.
One of the most appealing aspects of Winding Cypress is the surrounding landscape. The community is thoughtfully designed around more than 80 acres of scenic lakes and over 800 acres of protected natural preserves, creating a peaceful environment filled with nature views, walking trails, and wildlife. Many homes enjoy beautiful water or preserve views, offering residents a quiet and private setting while still being close to everything Naples has to offer.
Residents of Winding Cypress enjoy a wide range of amenities centered around an impressive clubhouse and lifestyle center. Community features include a resort-style pool and spa, fitness center, tennis courts, pickleball courts, bocce ball courts, and miles of walking and biking trails. Social gatherings, events, and activities are frequently held at the clubhouse, giving residents plenty of opportunities to stay active and connect with neighbors.
The location is another major advantage of Winding Cypress. The community is conveniently located just off Collier Boulevard (County Road 951) in Naples, providing easy access to downtown Naples, Marco Island, shopping centers, golf courses, restaurants, and the beautiful Gulf beaches that make Southwest Florida famous.
Winding Cypress is ideally positioned between several well-known Naples communities. It is bordered by Naples Reserve to the east, Lely Resort to the west, and Verona Walk to the north, placing residents in the heart of one of the most desirable areas of South Naples.
With its combination of modern homes, extensive preserve land, scenic lakes, and resort-style amenities, Winding Cypress offers a lifestyle that blends comfort, nature, and convenience. The community continues to be a popular choice for buyers looking for newer homes in Naples with strong amenities and a peaceful setting.
Be sure to read the Southwest Florida monthly real estate market report to gain insights on the local market.
Go to Real Estate Market ReportView currently active MLS listings in WINDING CYPRESS, Naples.
WINDING CYPRESS is located within a Community Development District (CDD). A CDD is essentially a tax-free municipal bond that the homeowners pay off over time. The bond is structured to pay for the infrastructure and/or maintenance of the community.
The CDD annual debt service is listed as a non-ad valorem tax on the homeowner's annual tax bill, which makes the total tax bill higher. Many master-planned communities in Southwest Florida have a CDD.
One reason for a CDD is to help keep initial new-home prices lower because certain infrastructure costs are not bundled into the new-home purchase price.
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