Winding Cypress is a census-designated place (CDP) in western Collier County, Florida, United States. It is 9 miles (14 km) southeast of Naples and is bordered to the southwest by U.S. Route 41 (Tamiami Trail) and to the north by the community of Verona Walk.

Winding Cypress was first listed as a CDP prior to the 2020 census. The population was 697 at the 2020 census. It is part of the Naples-Marco Island, Florida Metropolitan Statistical Area.

Demographics

Historical population

Census	Pop.	Note	%±
2020	697		—
U.S. Decennial Census