Winding Cypress Homes for Sale

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, Florida. This vibrant community offers a unique blend of luxury living and natural beauty, making it the perfect place to call home. Located in Collier County, Winding Cypress is known for its stunning landscapes, tranquil lakes, and lush greenery.

Homes for sale in Winding Cypress are truly something special. From spacious single-family homes to modern townhouses, there is something for everyone in this sought-after neighborhood. Whether you're looking for a cozy retreat or a spacious family home, Winding Cypress has it all. With top-of-the-line amenities, including a clubhouse, fitness center, and swimming pool, residents can enjoy a resort-style lifestyle right at their doorstep.

Living in Winding Cypress means being surrounded by nature while still being close to all the conveniences of city life. From shopping and dining to outdoor recreation and entertainment, everything you need is just a short drive away. Plus, with easy access to major highways and airports, commuting to work or traveling for leisure is a breeze.

If you're looking for a place to settle down and enjoy the best that Naples has to offer, look no further than Winding Cypress. Come explore the homes for sale in this charming community and find your dream home today.

Newest Winding Cypress Homes for Sale

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.

7383 Mockingbird Court, Naples $1,550,000

Situated on a private .29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. ...

4 Beds
4 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.

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 $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.

7072 Live Oak Drive, Naples $1,350,000 ▼

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 $945,000 ▼

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...