| Official Name: | Winding Cypress, Florida |
| Settlement Type: | Census-designated place |
| Pushpin Map: | Florida#USA |
| Pushpin Label: | Winding Cypress |
| Coordinates: | 26.0642°N -81.6792°W |
| Subdivision Type: | Country |
| Subdivision Type1: | State |
| Subdivision Name1: | Florida |
| Subdivision Type2: | County |
| Subdivision Name2: | Collier |
| Area Footnotes: | [1] |
| Area Total Sq Mi: | 1.94 |
| Area Land Sq Mi: | 1.85 |
| Area Water Sq Mi: | 0.09 |
| Area Total Km2: | 5.03 |
| Area Land Km2: | 4.80 |
| Area Water Km2: | 0.23 |
| Population As Of: | 2020 |
| Population Density Km2: | 145.24 |
| Timezone: | Eastern (EST) |
| Utc Offset: | -5 |
| Timezone Dst: | EDT |
| Utc Offset Dst: | -4 |
| Elevation Ft: | 7 |
| Postal Code Type: | ZIP Code |
| Postal Code: | 34114 (Naples) |
| Area Code: | 239 |
| Blank Name: | FIPS code |
| Blank Info: | 12-78063 |
| Blank1 Name: | GNIS feature ID |
| Blank1 Info: | 2806009 |
| Population Total: | 697 |
| Unit Pref: | Imperial |
| Population Density Sq Mi: | 376.15 |
Winding Cypress is a census-designated place (CDP) in western Collier County, Florida, United States. It is 9miles 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.