Winding Cypress is a census-designated place in western Collier County, Florida, United States. It is 9 miles southeast of Naples and is bordered to the southwest by U.S. Route 41 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.