On its age, its old homes and the National Register, Winding Cypress is more historic than 6% of U.S. towns. Its National Register listings hold the grade up; its share of homes from before 1940 pulls it down.
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HistoryA character grade: shown, never part of Winding Cypress’ overall grade.
Few Florida towns list much on the Register (a typical Florida town has 0.0 per 10,000 residents, the U.S. 2.4), so Winding Cypress’ 0.0 sits below most of its state (33% of Florida towns have fewer) while its 0 listings outnumber those of 23% of U.S. towns.
How sure. Graded on two of the three inputs, so a change in either one moves the letter more than it would with three. The pre-1940 share (±2.6 points) is firm at this size.
Founding year: our sources. Homes: Census ACS 2020–24. National Register: National Park Service, May 2026 list; each listing counted once (boundary changes and added documentation belong to their listing), and a historic district counts its contributing buildings. How TownRatings grades history →
What stands out about Winding Cypress’ past
Read from the archive, the National Register and the record. The page puts what stands out first.
Wikipedia doesn’t have a history of Winding Cypress yet. The photos, dates and memories neighbors add here are how it gets written.
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.
Intro from Wikipedia. Population: U.S. Census Bureau.
By decade
No old photos in the archives yet
Weddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Be the first to add onePhotograph a print flat, in daylight, no flash.
Every edition of the U.S. Geological Survey’s map of Winding Cypress. Tap a year, or press play to watch the town change.
1958Belle Meade sheet · 1:24,000
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Winding Cypress.
Famous people
Famous people close to Winding Cypress
Nobody well known was born in Winding Cypress itself, so here are the best known from just nearby.
Winding Cypress is more historic than 6% of U.S. towns. The History grade combines the town’s founding era, the share of homes built before 1940 and its National Register listings. It’s a character grade, so it isn’t part of the overall grade. How it works.
How old are the homes in Winding Cypress?
0.0% of Winding Cypress’ homes were built before 1940 (Census estimate, ±2.6 points), against a typical 0.6% for a Florida town; the median home was built in 2017.
Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021).
From U.S. Geological Survey historical maps and the USGS Geographic Names Information System. Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.
