Winding Cypress single-family homes: market snapshot
Source: Naples MLS listing data, updated October 27, 2026. Information deemed reliable but not guaranteed.
Current listings
Winding Cypress Single-Family Homes for Sale
These single-family homes in Winding Cypress update throughout the day from the Naples MLS, newest first. Want a private showing or an honest read on value? Call Renee Hahn at (239) 287-2576.
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.
Read our full community guide to Winding Cypress
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Winding Cypress Single-Family Homes FAQ
How many single-family homes are for sale in Winding Cypress?
As of October 27, 2026, 11 single-family homes are listed for sale in Winding Cypress on the Naples MLS, including 1 that came on the market in the last 7 days.
What do single-family homes cost in Winding Cypress?
Current list prices for single-family homes in Winding Cypress range from $920K to $1.55M, with a median list price of $1.25M and an average of $418 per square foot. Over the last 12 months, 33 sold at a median price of $890K.
Who can help me buy single-family homes in Winding Cypress?
Renee Hahn of Alfred Robbins Realty Group is a Naples Realtor, Certified Negotiation Expert (CNE) and Certified Luxury Home Marketing Specialist (CLHMS), consistently ranked in the top 0.5% to 1.5% of real estate professionals nationwide. Call (239) 287-2576 for showings, pricing guidance or an honest read on value in Winding Cypress.
Listing information is from the Naples MLS and is deemed reliable but not guaranteed. Counts and prices reflect active listings on October 27, 2026.