Winding CypressFL
A town of 1,160.
Is Winding Cypress a good place to live?
The best of Winding Cypress’ subject grades is an A− for schools; the weakest is a D− for hazard risk. Winding Cypress’ mean commuting time is 37 minutes, above both the Florida town median (27 minutes) and the median of U.S. towns (25 minutes). Only 25 of Florida’s 776 towns score lower on walkability. The typical home is worth about $991K, 11 years of the Naples metro’s $90K median household income. The biggest park or preserve is Rookery Bay Reserve Lands, at 66 acres. Winding Cypress has fewer than 2,500 residents, so it gets subject grades but no overall grade.
1,160 people, and everyone knows the way
In a town this size, neighbors are the best guide. Ask them anything.
How Winding Cypress grades
Each subject compared with towns across the country (schools within Florida), ordered by how far Winding Cypress is from typical.
How TownRatings grades towns →
Moving to Winding Cypress: who provides what
Winding Cypress is unincorporated, so Collier County and regional agencies provide most services.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Nov 17, 2025.
The data
Ordered by what stands out in Winding Cypress.
Very high risk in Winding Cypress, with hurricanes at the top
Winding Cypress’ risk rating from FEMA stands at 93 of 100, where Florida’s towns sit at 73 of 100 and U.S. towns at 44 of 100. Of the losses FEMA expects here, 57% come from hurricanes and 31% from inland flooding.
FEMA National Risk Index · OpenFEMA
Most of Winding Cypress’ workers head elsewhere: there are 0.1 jobs for each of them
The median commute is under 13 miles. For Winding Cypress, the income of the median household is $138,000. The top destinations are Marco Island (13%), Naples (9%) and Fort Myers (3%). Among residents locally, 19% live below the poverty line.
| Winding Cypress | Florida towns | U.S. towns | |
|---|---|---|---|
| Median household income | $138,000 | $73,000 | $80,000 |
| Below the poverty line | 19% | 11% | 9.6% |
Where working residents work
Census LEHD 2023 · ACS
In Winding Cypress, expect mild winters and hot summers
The July high in Winding Cypress is 92°F.
Typical low → high °F
NOAA U.S. Climate Normals, 1991–2020
Fewer of Winding Cypress’ adults binge drink than in the typical Florida or U.S. town
Just over a tenth of Winding Cypress adults report frequent mental distress. Only 7 of the 637 Florida towns we compare have a lower share of adults who sleep under 7 hours than Winding Cypress. CDC measures, 31 in all: Winding Cypress beats Florida on 15 and trails on 8.
| Winding Cypress | Florida towns | U.S. towns | |
|---|---|---|---|
| Binge drink (CDC PLACES) | 8.7% | 15% | 16% |
| Sleep under 7 hours (CDC PLACES) | 25% | 37% | 36% |
| High blood pressure (CDC PLACES) | 48% | 37% | 35% |
| Yearly checkup (CDC PLACES) | 86% | 79% | 79% |
| What stands out | Winding Cypress | FL |
|---|---|---|
| Fewer adults facing housing insecurity | 5.8% | 13.9% |
| Fewer adults facing a utility shut-off | 3.9% | 8.6% |
| More adults who have had cancer | 18.3% | 9.1% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
In Winding Cypress, 6% of the land is conserved
Trails run 0.2 miles in 2 parks and preserves. The trail network density for Winding Cypress comes to 0.1 miles per square mile. Parks and preserves locally: 2, covering 74 acres.
| Winding Cypress | Florida towns | U.S. towns | |
|---|---|---|---|
| Miles of trail per square mile | 0.1 miles per square mile | 0.4 | 0.4 |
| Conserved land | 6% | 3% | 4.3% |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Rookery Bay Reserve Lands | — | 66 |
| 2. Picayune Strand State Forest | — | 8 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Winding Cypress stands out in Florida and nationally: a larger share of its households own their home
The median sale price was $818,000 in May 2026. A home in Winding Cypress typically sold within 70 days of listing. Homes in Winding Cypress sold for 93.4% of their list price on average.
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Everglades National Park and 9 more within 40 miles
Museums, parks, gardens and other places to visit around Winding Cypress. Close and well known come first.
18 mi National ParkEverglades National Park778K visitors a year
21 mi National PreserveBig Cypress National Preserve2.3M visitors a year
27 mi Stadium & arenaHertz Arena28 mi State parkMound Key Archeological State Park
27 mi State parkKoreshan State Historic Site
10 mi Zoo & aquariumNaples ZooPhoto credits
Everglades National Park: Everglades NPS from Homestead, Florida, United States, Public domain · Big Cypress National Preserve: Gzzz, CC BY-SA 4.0 · Hertz Arena: Tthaas, CC BY-SA 3.0 · Koreshan State Historic Site: Ebyabe, CC BY-SA 3.0 · Naples Zoo: Exupery67, CC BY 4.0
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Everything we know about Winding Cypress
Colleges nearby
1 within 15 miles of the center of Winding Cypress
About 2 of every 100 Winding Cypress residents are enrolled in college, against 6 across Florida.
100% of working residents leave Winding Cypress for work
Where Winding Cypress’s working residents go each day. Line width shows the share.
Census LEHD 2023
About Winding Cypress
Census-designated place in Florida, United States
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.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
- Elevation
- 7 ft
Questions about Winding Cypress
Short answers, built from the data on this page.
Is Winding Cypress, FL expensive?
Yes. The typical home is worth about $991,000, 164% above the Florida typical home. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades D.