WINDING CYPRESS

Winding Cypress is a gated DiVosta Homes community in Southeast Naples, north of US 41 and east of Collier Boulevard, bordering Picayune Strand State Forest. The larger Winding Cypress plan also takes in the older VeronaWalk section; this newer phase opened in early 2015 with about 550 residences, set among more than 800 acres of preserve and 80 acres of lakes (Naples Condo Boutique). Homes on the market date from 2015 to 2022.
Homes and Prices
DiVosta built three product lines: attached villas of about 1,542 sq ft, Classic Series single-family homes of 1,659 to 3,016 sq ft, and Estate Series homes of 2,384 to 3,656 sq ft with up to five bedrooms. In late July 2026, seven listings asked $575,000 to $1,400,000 with a median of $940,000 and an average near $411 per sq ft. Summer 2026 closings ranged from $470,000 for a Jacaranda Lane villa to $1,025,000 for a four-bedroom on Winding Cypress Drive (Naples Condo Boutique, Jul 2026).
Amenities and Lifestyle
The amenity center has a resort pool and lap pool, a spa, a staffed fitness center and movement studio, a library, a restaurant and an outdoor barefoot bar. Outside are tennis, pickleball and bocce courts, a fire pit, a dog park, a community garden and a boardwalk nature trail into the preserve (Raveis, 2026). Many lots back onto lakes or preserve rather than other houses.
HOA and Fees
A 2018 home with 2,923 sq ft on Winding Cypress Drive listed HOA dues of $1,646 per quarter in 2026, with pets permitted subject to limits (Raveis, 2026). We could not find a public website for the association or a published lease policy, so ask for the budget, any capital contribution and rental rules before you make an offer.
Location
Brokers estimate about 10 minutes to I-75 and Marco Island, around 15 minutes to Fifth Avenue South and roughly 20 minutes to the Naples Pier and beaches (Naples Condo Boutique). Assigned schools have included Lely Elementary, Manatee Middle and Lely High.
For other newer gated choices off Collier Boulevard, read our Esplanade at Hacienda Lakes page or the Azure at Hacienda Lakes page. See current Naples homes for sale, and Winding Cypress owners can price a sale with the Naples flat fee listing. Sal DiBenedetto, Licensed Real Estate Broker, The DiBe Group, brokered by eXp Realty, can show Classic and Estate homes; call 239-256-5005.
The older section of the same plan is covered on our Verona Walk page.
Farther south on Collier Boulevard, past US 41, is the gated Artesia community.