Winding Cypress Homes with Ranch Style

Welcome to Winding Cypress, a charming subdivision nestled in the heart of Naples, Florida. This vibrant community is located in Collier County and offers a unique blend of natural beauty and modern convenience.

Winding Cypress is known for its stunning homes with Ranch-style architecture, perfect for those seeking a cozy and inviting living space. These homes exude a sense of warmth and comfort, with spacious layouts and beautiful design elements that create a welcoming atmosphere for residents and guests alike.

Living in Winding Cypress means enjoying a relaxed lifestyle surrounded by lush landscapes and serene lakes. Residents can take advantage of the community amenities, including a clubhouse, fitness center, swimming pool, and walking trails. Whether you're looking to socialize with neighbors or simply unwind in nature, Winding Cypress has something for everyone.

With its convenient location in Naples, residents of Winding Cypress have easy access to shopping, dining, entertainment, and outdoor activities. Explore the nearby beaches, golf courses, and parks, or take a short drive to downtown Naples for a day of exploration.

Experience the best of Florida living at Winding Cypress, where Ranch-style homes and a close-knit community come together to create the perfect place to call home.

Newest Winding Cypress Homes with Ranch Style

7259 Live Oak Drive, Naples $969,000

An opportunity to unlock value! Great opportunity for buyers looking to build equity through a little hard work and personal vision. This home offers solid potential fo...

3 Beds
3 Baths
Winding Cypress SubDv.

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- Turnkey 3-BEDROOM complete with your own private POOL and outdoor summer kitchen located in the amenity rich community of Winding Cypress!!! The ultimate ble...

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, ...