Winding Cypress Homes with Gated Community features

Welcome to Winding Cypress, a stunning gated community nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming subdivision is designed for those seeking a serene lifestyle while enjoying the best that Southwest Florida has to offer.

Winding Cypress boasts a collection of beautifully crafted single-family homes, each showcasing modern designs and luxurious finishes. With a variety of floor plans available, residents can find the perfect fit for their lifestyle, whether they’re looking for a cozy retreat or a spacious family abode. The community is thoughtfully planned to foster a sense of belonging, with lush landscaping and scenic views that make every day feel like a vacation.

One of the standout features of Winding Cypress is its robust amenities. Residents can enjoy a resort-style pool, state-of-the-art fitness center, and a vibrant clubhouse that serves as a hub for social gatherings and community events. Nature enthusiasts will appreciate the walking trails and serene lakes, perfect for morning strolls or evening relaxation. Additionally, the community’s gated entry provides peace of mind, ensuring a secure environment for families and individuals alike.

Winding Cypress is ideally located in Naples, where pristine beaches, world-class dining, and upscale shopping are just a short drive away. With its blend of luxury, comfort, and convenience, Winding Cypress is not just a place to live; it’s a lifestyle waiting to be embraced. Discover the joys of living in this exceptional community and make Winding Cypress your new home today!

Newest Winding Cypress Homes with Gated Community features

7591 Jacaranda Lane, Naples $549,000

Western sunset views, peaceful pond vistas, and added privacy, this Winding Cypress villa offers a setting that’s truly special! Beautifully upgraded, this unfurnished 2 ...

2 Beds
2 Baths
Winding Cypress SubDv.

7775 Winding Cypress Drive, Naples image

7775 Winding Cypress Drive, Naples $990,000

Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of th...

4 Beds
3 Baths
Winding Cypress SubDv.

7098 Live Oak Drive, Naples $520,000

Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich comm...

3 Beds
2 Baths
Winding Cypress SubDv.

7235 Live Oak Drive, Naples $925,000

This home has had a complete refresh with a lot of new improvements, new heat/ac units on both floors new pool pump and heater, new roof vents, new lanai screen, paver...

3 Beds
3 Baths
Winding Cypress SubDv.

7247 Clamshell Lane, Naples $1,549,000

A MUST-SEE HOME IN A MUST SEE COMMUNITY Extensive upgrades and designer elements elevate this home, based on an award winning model. Gorgeous water/preserve views are ...

4 Beds
4 Baths
Winding Cypress SubDv.

7602 Jacaranda Lane, Naples $564,900 ▼

**Motivated sellers!! Seller concession of $5k!!!This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversio...

2 Beds
2 Baths
Winding Cypress SubDv.

7072 Live Oak Drive, Naples $1,450,000

Welcome to this beautifully appointed 4-bedroom, 4-bath residence offering approximately 3,350 square feet and a custom, one-of-a-kind floor plan not found elsewhere in t...

4 Beds
4 Baths
Winding Cypress SubDv.

7230 Live Oak Drive, Naples $1,100,000 ▼

Beautiful home on a premium pie shaped lot with lots of privacy. Seller keeps his landscaping impeccable. This home features 3 generous size bedrooms, 3 full bath , 3 c...

3 Beds
3 Baths
Winding Cypress SubDv.

6825 Greenbriar Court, Naples $965,000

Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor livi...

4 Beds
3 Baths
Winding Cypress SubDv.

7700 Winding Cypress Drive, Naples image

7700 Winding Cypress Drive, Naples $1,250,000

BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN ...

5 Beds
3 Baths
Winding Cypress SubDv.

6907 Cocoplum Street, Naples $1,295,000

PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with pea...

3 Beds
3 Baths
Winding Cypress SubDv.

7156 Live Oak Drive, Naples $590,000 ▼

PRICE ALERT- This is the LOWEST TRUE 3-BEDROOM complete with your own private pool located in the amenity rich community of Winding Cypress!!! The ultimate blend of luxu...