Winding Cypress market snapshot
Homes, condos and townhomes. Source: Naples MLS listing data, updated October 27, 2026. Information deemed reliable but not guaranteed.
About Winding Cypress
Winding Cypress is an established gated community in Southeast Naples, located off Collier Boulevard near the U.S. 41 corridor. Developed by DiVosta Homes, the community includes 766 single-family homes and villas surrounded by more than 800 acres of natural preserves and approximately 80 acres of lakes. The extensive preserved land is one of Winding Cypress’ defining characteristics, creating a lower-density setting where nature, water and native vegetation are integrated throughout the residential neighborhoods. Homes offer a variety of lake, preserve and landscaped settings, while the community’s proximity to Picayune Strand State Forest further contributes to its natural surroundings.
Winding Cypress combines this preserve-focused setting with a well-rounded collection of recreational and social amenities. Residents have access to a clubhouse, resort-style pool and spa, fitness center and movement room, on-site dining, tennis, pickleball, bocce, a community garden, dog park and a distinctive boardwalk extending into the preserved landscape. Clubs, fitness programs, organized sports and social activities provide opportunities for residents who want an active community lifestyle, while the extensive natural areas create a quieter backdrop for those who simply value space and scenery. There is no golf course or mandatory country club membership, allowing Winding Cypress to offer a resort-style lifestyle without requiring residents to support a private golf club.
Why People Like the Winding Cypress Community
- Extensive Natural Preserves: More than 800 acres of preserved land surround the residential neighborhoods, giving Winding Cypress a particularly spacious and natural character.
- Only 766 Homes: The combination of a relatively limited number of residences and extensive preserve acreage helps distinguish Winding Cypress from more densely developed master-planned communities.
- Single-Family Homes and Villas: Buyers can choose between detached single-family residences and villa-style living with different sizes, settings and maintenance considerations.
- Resort-Style Amenities: Swimming, fitness, racquet sports, bocce, dining and social spaces provide a comprehensive recreational lifestyle within the community.
- On-Site Dining: The Shady Palm Café provides residents with a casual poolside restaurant and gathering place without leaving the neighborhood.
- Nature Boardwalk: A wooden boardwalk winds through preserved areas and leads to a sheltered overlook, providing opportunities for walking, birdwatching and enjoying the natural environment.
- Active Racquet Sports: Five clay tennis courts and four pickleball courts support both recreational and organized play.
- No Mandatory Golf Membership: Winding Cypress provides extensive amenities without requiring residents to maintain a private golf or country club membership.
What You Need to Know About Living in Winding Cypress
- Winding Cypress Is Gated: The community has controlled access and is governed through a mandatory homeowners association.
- There Are 766 Homes: Winding Cypress is an established community rather than an active new-construction development, so buyers will primarily be comparing resale properties.
- There Is a Mandatory HOA: Buyers should review current assessments, reserves, included services and governing documents before purchasing.
- Housing Types Differ: Single-family homes and villas can have different maintenance responsibilities and ownership considerations, making it important to understand exactly what applies to the individual property.
- Preserve and Lake Locations Vary: Some residences offer direct preserve or lake views, while others have landscaped or neighborhood settings. Homesite orientation can significantly affect the outdoor experience.
- Homes Are Established Rather Than New Construction: Buyers should compare hurricane protection, HVAC systems, water heaters, appliances, pools, outdoor living improvements and other property-specific upgrades when evaluating individual residences.
- There Is No Golf Course: Winding Cypress is centered around nature, recreation, fitness and social amenities rather than golf, and there is no mandatory private golf membership.
- Current Costs and Rules Should Be Verified: HOA assessments, included services, leasing policies, pet restrictions, application requirements and other community provisions can change and should be confirmed through current documents.
Current listings
Winding Cypress Homes for Sale
See the newest homes for sale in Winding Cypress, updated throughout the day from the Naples MLS. Want a private showing or an honest read on value? Call Renee Hahn at (239) 287-2576.
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Accuracy of this information is not warranted or guaranteed. Information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Winding Cypress Amenities
The Winding Cypress clubhouse and amenity center serve as the recreational and social heart of the community. Residents have access to a resort-style swimming pool and spa, fitness center and dedicated movement room used for exercise and group activities. The Shady Palm Café provides casual poolside dining and a bar, creating a convenient gathering place for meals, drinks and socializing. The clubhouse also provides spaces for community events, activities and informal gatherings, while organized clubs and programs offer additional opportunities for residents who want to participate in community life.
Outdoor recreation includes five clay tennis courts, four pickleball courts and bocce, along with a community garden, dog park, fire pit and outdoor gathering areas. The community’s amenities support both organized and independent recreation, with resident clubs centered around activities such as tennis, pickleball, gardening, water aerobics, books, crafts, cards and games. This variety gives residents opportunities to be socially active without making organized programming the only way to enjoy the community.
One of Winding Cypress’ most distinctive amenities is its nature boardwalk, which extends through preserved wetlands and wooded areas to a sheltered overlook. Rather than treating the community’s extensive preserves simply as undeveloped land surrounding the homes, the boardwalk provides residents with a way to experience the natural setting through walking, birdwatching and wildlife observation. Combined with more than 800 acres of preserve and approximately 80 acres of lakes, this connection to nature gives Winding Cypress a character that is noticeably different from communities where recreational facilities are the primary focus.
Winding Cypress’ Southeast Naples location near Collier Boulevard and U.S. 41 provides access to shopping, dining and everyday services while positioning residents between Naples and Marco Island. Tamiami Crossing and other nearby commercial areas provide convenient everyday shopping and restaurants, while downtown Naples, Fifth Avenue South, Gulf beaches, Marco Island and the outdoor recreational areas of southern Collier County are accessible by car. For buyers seeking an established gated Naples community with single-family homes and villas, extensive preserved land, resort-style amenities, on-site dining and a strong connection to the natural environment without mandatory golf membership, Winding Cypress offers a distinctive combination.
What Is Near Winding Cypress?
Downtown Naples (5th Avenue South): 9.3 miles
Closest beach: Naples Pier, 9.6 miles
RSW Airport: 32.9 miles
Notable shopping & dining nearby: Naples Lakes Village Center, 3.5 miles
Closest park: Donna Fiala Eagle Lakes Community Park, 2.7 miles
(Distances are approximate straight-line distances.)
Winding Cypress Floor Plans
Floor plans are provided as a complimentary resource to help you understand the layouts available in Winding Cypress. Plans and specifications can change, so confirm details for any specific home.
View Winding Cypress floor plans (PDF)
Where Is Winding Cypress?
Winding Cypress FAQ
Where is Winding Cypress located?
Winding Cypress is in Southeast Naples off Collier Boulevard near the U.S. 41 corridor, between Naples and Marco Island. Tamiami Crossing is nearby for everyday shopping, and Picayune Strand State Forest adds to the natural surroundings.
What types of homes are in Winding Cypress?
Winding Cypress, developed by DiVosta Homes, has 766 single-family homes and villas set among lakes, preserves and landscaped homesites. It is an established community, so buyers will mostly be comparing resale homes.
Is Winding Cypress gated, and is there an HOA?
Yes, Winding Cypress is gated and governed by a mandatory homeowners association. There is no golf course and no mandatory country club membership.
What amenities does Winding Cypress offer?
Residents have a clubhouse, resort-style pool and spa, fitness center, movement room and the Shady Palm Cafe for poolside dining. Outdoors there are five clay tennis courts, four pickleball courts, bocce, a community garden, dog park, fire pit and a nature boardwalk.
What makes the natural setting at Winding Cypress special?
More than 800 acres of preserves and about 80 acres of lakes surround the homes, giving the community a spacious, lower-density feel. A wooden boardwalk winds through preserved wetlands and woods to a sheltered overlook, a favorite spot for walking and birdwatching.
Last updated October 2026 by Renee Hahn, Your Naples Expert. Community details, fees and amenities can change, so confirm specifics for any home you are considering.
