Winding Cypress Homes with One Story Style

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, FL, in Collier County. This charming community offers a serene and luxurious lifestyle for residents looking to embrace the beauty of Southwest Florida.

One of the standout features of Winding Cypress is its collection of stunning one-story homes. True to their style, these homes offer a seamless blend of elegance and functionality, perfect for those seeking a comfortable and convenient living space.

Living in Winding Cypress means enjoying the best of both worlds - the tranquility of a peaceful neighborhood and the excitement of Naples city life just a short drive away. Residents can take advantage of the community's top-notch amenities, including a clubhouse, fitness center, swimming pool, and more.

Whether you're looking to relax in a beautifully designed home or explore the vibrant surroundings, Winding Cypress has something for everyone. Come and discover the allure of one-story living in this exceptional Naples community.

Newest Winding Cypress Homes with One Story Style

6932 Cocoplum Street, Naples $1,575,000

Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pi...

3 Beds
3 Baths
Winding Cypress SubDv.

7591 Jacaranda Lane, Naples $539,000 ▼

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.

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.

7602 Jacaranda Lane, Naples $548,000 ▼

**Motivated sellers! This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversion to a third bedroom, two fu...

2 Beds
2 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.

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...

3 Beds
2 Baths
Winding Cypress SubDv.

7478 Winding Cypress Drive, Naples image

7478 Winding Cypress Drive, 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, ...