Winding Cypress Homes for Sale

Welcome to Winding Cypress, a stunning community nestled in the heart of Naples, Florida, within the picturesque Collier County. This enchanting development offers a perfect blend of luxury, comfort, and natural beauty, making it an ideal destination for those seeking their dream home in a vibrant and serene environment.

Winding Cypress features an array of beautifully designed homes for sale, each showcasing modern architecture and high-end finishes. With various floor plans available, prospective buyers can choose from spacious single-family homes that cater to diverse lifestyles and preferences. From open-concept layouts to private outdoor spaces, these residences are thoughtfully crafted to enhance your living experience.

One of the standout features of Winding Cypress is its commitment to preserving the natural landscape. The community is enveloped by lush greenery, tranquil lakes, and scenic walking trails, providing residents with an idyllic backdrop for outdoor activities and leisurely strolls. The amenity-rich lifestyle here includes a resort-style pool, state-of-the-art fitness center, and a vibrant clubhouse, perfect for social gatherings and community events.

Located just minutes away from Naples' stunning beaches, world-class shopping, and exquisite dining options, Winding Cypress offers the best of both relaxation and recreation. Whether you’re looking to enjoy a day on the golf course or indulge in the local arts scene, this community places you at the center of it all.

Explore the homes for sale in Winding Cypress today and discover the perfect haven where luxury meets nature in the heart of Naples! Your dream home awaits!

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
226040604 MLS

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
226038449 MLS

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
226033394 MLS

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
226038979 MLS

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
226037594 MLS

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
226038340 MLS

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
226036844 MLS

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
226035902 MLS

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
226035971 MLS

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
226031553 MLS

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
226034017 MLS

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...

4 Beds
3 Baths
226034030 MLS