Winding Cypress, Southeast Naples · Naples, Florida
Sold, property tax rate, homes built and primary residence are from county records.
Listed in: Gated Naples Communities with Lower Fees
Type, amenities & maintenance
Amenities
What your fees pay for in Winding Cypress — the amenities available here, and the maintenance and services behind them.
Dining carries its own charges.
Maintenance
Fees in Winding Cypress typically cover lawn and grounds maintenance, a property manager, street lighting, irrigation water, and street maintenance.
Building types, pets & leasing
Building types
Pets
Pets are allowed in Winding Cypress. The terms, such as how many pets and what size, can differ from home to home.
Homes here allow pets with limits. Where limits are stated they run to 3 pets.
Leasing
The minimum lease is 30 days, and up to 3 leases are allowed each year.
Restrictions
Homes here are deed restricted. Deed restrictions are recorded against the property and pass with it, so they apply to every owner. They typically cover exterior changes and how a home is used, and the community's recorded documents set out the detail.
Homes for sale in Winding Cypress
Looking for something specific in Winding Cypress? Refine these homes by type, beds, price, fees, and more.
Refine your search · 16 homesDestinations & driving times from Winding Cypress
Winding Cypress is 10.4 miles from downtown at Fifth Avenue South, about 20 minutes by car. The nearest beach access is Naples Beach at 8th Ave. S., 11.3 miles, about 23 minutes by car. It is 23 minutes to Third Street South for dining and shopping, 20 minutes to Gulfshore Playhouse for the performing arts, and 15 minutes to Sugden Regional Park for parks and recreation. The drive to Southwest Florida International Airport (RSW) is about 52 minutes.
Every destination named here is described in the Destinations chapter of the 2027 Naples Buyer’s Guide.
Driving times are estimated from the community’s mapped center or primary access point, using OpenStreetMap road data.
| Name | Miles | ETA |
|---|---|---|
| Fifth Avenue South | 10.4 mi | 20 min |
| Third Street South | 11.5 mi | 23 min |
| Coastland Center | 12.5 mi | 25 min |
| Venetian Village | 14.6 mi | 29 min |
| Waterside Shops | 16.7 mi | 28 min |
| Galleria Shoppes at Vanderbilt | 16.9 mi | 28 min |
| Mercato | 19.1 mi | 32 min |
| Miromar Outlets | 28.8 mi | 39 min |
| Coconut Point | 29.6 mi | 42 min |
| Gulf Coast Town Center | 33.2 mi | 43 min |
| Name | Miles | ETA |
|---|---|---|
| Nearest beach access: Naples Beach at 8th Ave. S. | 11.3 mi | 23 min |
| Naples Municipal Beach and Pier | 11.6 mi | 23 min |
| Tigertail Beach Park | 12 mi | 25 min |
| Lowdermilk Park | 12.5 mi | 25 min |
| Via Miramar Beach | 14.1 mi | 28 min |
| Clam Pass Park | 17.2 mi | 29 min |
| Vanderbilt Beach Park | 20 mi | 34 min |
| Delnor-Wiggins Pass State Park | 21.9 mi | 34 min |
| Barefoot Beach Preserve | 26.6 mi | 38 min |
| Bonita Beach | 26.8 mi | 39 min |
| Lovers Key State Park | 31.5 mi | 49 min |
| Name | Miles | ETA |
|---|---|---|
| Gulfshore Playhouse | 10.4 mi | 20 min |
| Sugden Community Theatre | 10.5 mi | 21 min |
| Artis—Naples | 17 mi | 28 min |
| Music & Arts Community Center | 38.1 mi | 49 min |
| Barbara B. Mann Performing Arts Hall | 42.4 mi | 57 min |
| Name | Miles | ETA |
|---|---|---|
| Sugden Regional Park | 7.6 mi | 15 min |
| Paradise Coast Sports Complex | 8 mi | 17 min |
| Naples Botanical Garden | 8.3 mi | 17 min |
| Baker Park | 10.6 mi | 20 min |
| Cambier Park | 10.7 mi | 21 min |
| Gordon River Greenway Park | 11.7 mi | 22 min |
| Naples Zoo | 12 mi | 24 min |
| Fred W. Coyle Freedom Park | 13.2 mi | 23 min |
| North Collier Regional Park | 19.1 mi | 31 min |
| Big Corkscrew Island Regional Park | 22.4 mi | 39 min |
| Corkscrew Swamp Sanctuary | 28 mi | 48 min |
| Name | Miles | ETA |
|---|---|---|
| Physicians Regional Collier Blvd. | 2.7 mi | 7 min |
| NCH Baker Downtown | 11.3 mi | 23 min |
| Physicians Regional Pine Ridge Rd. | 12.9 mi | 22 min |
| NCH North Naples Hospital | 19.6 mi | 30 min |
| Name | Miles | ETA |
|---|---|---|
| Marco Island Executive Airport (MKY) | 8.5 mi | 19 min |
| Naples Airport (APF) | 10.3 mi | 20 min |
| Southwest Florida International Airport (RSW) | 39.4 mi | 52 min |
Sales history · 18 months
Over the past 18 months the county recorded 67 single-family sales at a median of $830,000 in Winding Cypress.
Types follow county records, which classify by how a home is owned rather than how it is built. Attached villas and townhouses appear within them according to how each home is deeded.
Source: Collier County Property Appraiser · 18 months to September 2026 · October 2026 from closed sales reported to M.L.S. of Naples, Inc.; county records for those months are still being finalized.
Flood zones & evacuation
100% of homes in Winding Cypress sit on a lot mostly inside a FEMA Special Flood Hazard Area, chiefly zone AE, where a federally backed mortgage requires flood insurance — measured across 766 mapped homes, and it varies from home to home. For hurricane evacuation Winding Cypress is in Collier Zone D.
Two different things, measured by two different agencies. Evacuation zones are about storm surge and who leaves first. Flood zones are FEMA’s insurance rating, and they vary from home to home.
Zone D Collier
Called in the fourth wave, for stronger storms.
FEMA flood maps and Collier County Emergency Management. A revised Collier County flood map is in preparation and may change these zones.
Flood zone varies by home — each home’s page shows its own.Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.
Jeffrey Waldman
REALTOR® and Owner, Naples Abodes
Call (239) 450-3763 Text (239) 450-3763
Florida License SL3295589
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