Welcome to Winding Cypress - Naples FL
Winding Cypress is a gated, master-planned community in Southeast Naples developed by DiVosta Homes. Its 766 single-family homes and attached villas are surrounded by more than 800 acres of natural preserves and approximately 80 acres of lakes, creating a nature-focused alternative to a golf-course community.
The community clubhouse is located at 7180 Winding Cypress Drive, Naples, FL 34114. Residents enjoy an extensive amenity campus, on-site dining and direct access to walking paths, lakes and preserve scenery near Picayune Strand State Forest.
Winding Cypress was developed primarily from approximately 2015 through 2022 and is now largely a resale community. One-story DiVosta plans include attached villas and detached single-family homes, generally ranging from roughly 1,500 square feet to more than 3,000 square feet.
Homes vary in lot position, preserve or lake outlook, private-pool design, lanai exposure, storm protection and interior upgrades. Lawn maintenance is commonly included, but buyers should confirm the services, fees and CDD assessment attached to a specific property.
- Guarded, gated community entrance
- Resort-style swimming pool and spa
- Shady Palm Café, poolside bar and resident dining
- Fitness center and movement studio
- Tennis, bocce and Pickleballl facilities
- Nature boardwalk, bird-watching overlooks and picnic pavilion
- Walking and biking paths with exercise stations
- Dog parks, community garden and fire-pit gathering area
Clubhouse phone: 239-732-7171
Office hours: Monday-Friday, 8:00 a.m.-4:00 p.m.; closed 11:30 a.m.-12:30 p.m.
Winding Cypress sits off U.S. 41 East near Collier Boulevard, approximately nine miles southeast of downtown Naples. Shopping and restaurants at Tamiami Crossing and nearby retail centers are convenient, while Marco Island, downtown Naples and Gulf beaches are accessible by car.
The community does not have a golf course or mandatory golf membership. Its lifestyle instead centers on the clubhouse, social programming, outdoor recreation and its extensive natural-preserve setting.
Compare the villa or single-family floor plan, preserve or lake view, lanai privacy, pool exposure, storm protection and renovation level. Review current HOA fees, CDD assessments, reserves, insurance, maintenance coverage, leasing restrictions and pet rules before purchasing.
Mike Shoaff, REALTOR® with RE/MAX Hallmark Realty, is a Winding Cypress Real Estate Agent who helps buyers and sellers compare floor plans, views, community costs, recent sales and competing Southeast Naples properties.
Call 239-298-9903 or connect with a Naples FL Realtor.
