Winding Cypress Naples FL Homes for Sale | Resort-Style Villas & Single-Family Homes

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Winding Cypress in Naples, Florida, is a beautifully designed, resort-style, natural-gas-gated community offering a mix of single-family homes and attached villas. With nearly two-thirds of the neighborhood preserved as natural conservation land, Winding Cypress stands out as one of the most scenic and tranquil communities in South Naples.

Residents enjoy an impressive lineup of amenities centered around the community’s Grand Clubhouse, including an outdoor bar, state-of-the-art fitness center, and a resort-style swimming pool with lap lanes. Outdoor living is a highlight, with four pickleball courts, five tennis courts, and two bocce courts available for year-round enjoyment.

Its prime location—close to both Marco Island and Downtown Naples—makes Winding Cypress an excellent choice for those seeking natural beauty, luxury amenities, and convenient coastal living.

📞 Contact Us for more information or to schedule a private showing of homes for sale in Winding Cypress, Naples, FL.

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Winding Cypress - Homes For Sale

6820 Winding Cypress DR, Naples $799,900

Nothing to do but move in to this beautiful upgraded Mystique model home. ( Interior photos forthcoming) built in 2021 in Phase 3 in the sought after community of Winding...

3 Beds
2 Baths
226027255 MLS

7759 Winding Cypress DR, Naples $1,400,000

Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater M...

4 Beds
4.5 Baths
226024563 MLS

7156 Live Oak DR, Naples $599,900

Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the...

3 Beds
2 Baths
226024508 MLS

6727 Pennyroyal DR, Naples $940,000 ▼

This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious cor...

3 Beds
2 Baths
226022635 MLS

7478 Winding Cypress DR, Naples $1,349,500

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, ...

3 Beds
3 Baths
226021460 MLS

7666 Jacaranda Ln, Naples — Winding Cypress $575,000

Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath...

2 Beds
2 Baths
226008768 MLS
Winding Cypress Bldg.

6844 Winding Cypress DR, Naples $949,900

Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 ,...

3 Beds
2 Baths
226005365 MLS

6825 Greenbriar CT, Naples $940,000 ▼

Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedr...

4 Beds
3 Baths
225081501 MLS