Winding Cypress
Fast Facts
Location
Southeast Naples
Community Type
Gated, Resort
Building Types
Attached Villas, Houses
Properties Built
2015 – 2022
Pets Allowed
Yes
Community Rating
Amenities
| Level: | High |
| Onsite: | Community Pool Food & Beverage Golf Gym Pickleball Spa Tennis |
Listings
Currently Available
8
Past Year Sold
51
Average Days on Market
152
Financials
Current Pricing
$575k – $1.3m
Total Annual Fees
$5k – $7k
Total One-Time Fees
$1k
Past 6 Months – Sold Price Range
$460k – $1.5m
Past 6 Months – Sold Price / Sq. Ft. Range
$280 – $505
Past 18 Months – Sold
All Currently Available Properties
in Winding Cypress
Updated: 06/20/2026 at 07:05 PM
$960,000
3 Bed
2 Bath
2,076 sq. ft.
Built: 2021
Days on Site: 10
Winding Cypress
Naples
$1,349,500
3 Bed
3 Bath
2,634 sq. ft.
Built: 2016
Days on Site: 17
Winding Cypress
Naples
$935,000
3 Bed
2 Bath
2,076 sq. ft.
Built: 2022
Days on Site: 50
Winding Cypress
Naples
$750,000
3 Bed
2 Bath
2,078 sq. ft.
Built: 2016
Days on Site: 75
Winding Cypress
Naples
$575,000
2 Bed
2 Bath
1,574 sq. ft.
Built: 2018
Days on Site: 116
Winding Cypress
Naples
$949,900
3 Bed
2 Bath
2,100 sq. ft.
Built: 2021
Days on Site: 133
Winding Cypress
Naples
$940,000
4 Bed
3 Bath
3,036 sq. ft.
Built: 2022
Days on Site: 201
Winding Cypress
Naples
$698,500
3 Bed
2 Bath
1,594 sq. ft.
Built: 2018
Days on Site: 292
Winding Cypress
Naples
The data relating to real estate for sale displayed on this Website comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc., under License No. SL3295589. Properties listed with brokerage firms other than Premiere Plus Realty Company are marked with the “BR House” logo. Detailed information about such properties includes the name of the listing broker. The properties displayed may not be all the properties listed with brokerage firms participating in the M.L.S. of Naples, Inc. BR Program, or contained in the database compilation of the M.L.S. of Naples, Inc.
Some properties that appear for sale on this limited electronic display may no longer be available. For the most current information, contact Jeffrey Waldman, Premiere Plus Realty Company here.
Destinations, Distances & ETAs
| Name | Miles | ETA |
|---|---|---|
| Tigertail Beach Park | 11.9 mi | 26 min |
| Naples Municipal Beach and Pier | 12.6 mi | 31 min |
| Lowdermilk Park | 15.7 mi | 33 min |
| Via Miramar Beach | 16.1 mi | 34 min |
| Clam Pass Park | 17.3 mi | 37 min |
| Vanderbilt Beach Park | 20.1 mi | 38 min |
| Pelican Bay Beach (Private) | 21.6 mi | 46 min |
| Delnor-Wiggins Pass State Park | 21.9 mi | 38 min |
| Barefoot Beach Preserve | 26.6 mi | 43 min |
| Bonita Beach | 26.8 mi | 43 min |
| Name | Miles | ETA |
|---|---|---|
| 5th Avenue South | 11.2 mi | 25 min |
| Third Street South | 12.4 mi | 32 min |
| Coastland Mall | 13.9 mi | 29 min |
| Venetian Village | 16.1 mi | 34 min |
| Waterside Shops | 16.8 mi | 35 min |
| Galleria Shoppes at Vanderbilt | 16.9 mi | 31 min |
| Mercato | 19.1 mi | 36 min |
| Miromar Outlets | 28.8 mi | 42 min |
| Coconut Point | 32 mi | 44 min |
| Gulf Coast Town Center | 32.9 mi | 43 min |
| Name | Miles | ETA |
|---|---|---|
| Gulfshore Playhouse | 11.3 mi | 25 min |
| Sugden Community Theatre | 11.4 mi | 29 min |
| Artis-Naples | 17.1 mi | 35 min |
| Music & Arts Community Center | 38 mi | 51 min |
| Barbara B. Mann Performing Arts Hall | 42.3 mi | 64 min |
| Name | Miles | ETA |
|---|---|---|
| Physicians Regional (Collier Blvd.) | 2.9 mi | 8 min |
| Naples Comprehensive Health (NCH Baker Downtown) | 12 mi | 29 min |
| Physicians Regional (Pine Ridge Rd.) | 12.9 mi | 25 min |
| Naples Comprehensive Health (North Naples Hospital) | 19.6 mi | 33 min |
| Name | Miles | ETA |
|---|---|---|
| Marco Island Executive Airport (MKY) | 8.5 mi | 19 min |
| Naples Airport (APF) | 11.3 mi | 26 min |
| SW Florida Int'l (RSW) | 39.4 mi | 49 min |
| Name | Miles | ETA |
|---|---|---|
| Sugden Regional Park | 7.6 mi | 17 min |
| Paradise Coast Sports Complex | 8 mi | 19 min |
| Naples Botanical Garden | 8.2 mi | 18 min |
| Baker Park | 11.5 mi | 26 min |
| Cambier Park | 11.7 mi | 28 min |
| Fred W. Coyle Freedom Park | 13.2 mi | 26 min |
| Gordon River Greenway | 14.1 mi | 28 min |
| Naples Zoo | 14.4 mi | 32 min |
| North Collier Regional Park | 18.9 mi | 32 min |
| Big Corkscrew Island Regional Park | 28.1 mi | 46 min |
Please flip your mobile to landscape view or use a device with a larger screen to see these destinations mapped.
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