Winding Cypress
Fast Facts
Location
Southeast Naples
Community Type
Gated, Resort
Building Types
Attached Villas, Houses
Properties Built
2015 – 2023
Pets Allowed
Yes
Community Rating
Amenities
| Level: | High |
| Onsite: | Community Pool Food & Beverage Golf Gym Pickleball Spa Tennis |
Listings
Currently Available
23
Past Year Sold
36
Average Days on Market
144
Financials
Current Pricing
$529k – $1.7m
Total Annual Fees
$2k – $9k
Total One-Time Fees
$75 – $1k
Past 6 Months – Sold Price Range
$453k – $1.3m
Past 6 Months – Sold Price / Sq. Ft. Range
$288 – $503
Past 18 Months – Sold
All Currently Available Properties
in Winding Cypress
Updated: 10/26/2025 at 09:35 AM
$539,000
2 Bed
2 Bath
1,574 sq. ft.
Built: 2018
Days on Site: 4
Winding Cypress
Naples
$819,000
3 Bed
2 Bath
2,230 sq. ft.
Built: 2016
Days on Site: 9
Winding Cypress
Naples
$925,000
3 Bed
2 Bath
2,094 sq. ft.
Built: 2022
Days on Site: 9
Winding Cypress
Naples
$1,188,000
3 Bed
2 Bath
2,166 sq. ft.
Built: 2017
Days on Site: 16
Winding Cypress
Naples
$649,900
2 Bed
2 Bath
1,685 sq. ft.
Built: 2016
Days on Site: 25
Winding Cypress
Naples
$899,000
3 Bed
2 Bath
2,084 sq. ft.
Built: 2021
Days on Site: 33
Winding Cypress
Naples
$1,695,000
4 Bed
4 Bath
3,656 sq. ft.
Built: 2017
Days on Site: 42
Winding Cypress
Naples
$599,900
2 Bed
2 Bath
1,544 sq. ft.
Built: 2017
Days on Site: 48
Winding Cypress
Naples
$749,900
3 Bed
2 Bath
1,594 sq. ft.
Built: 2018
Days on Site: 55
Winding Cypress
Naples
$950,000
3 Bed
2 Bath
2,084 sq. ft.
Built: 2022
Days on Site: 76
Winding Cypress
Naples
$899,000
3 Bed
3 Bath
2,128 sq. ft.
Built: 2023
Days on Site: 86
Winding Cypress
Naples
$639,000
2 Bed
2 Bath
1,554 sq. ft.
Built: 2018
Days on Site: 131
Winding Cypress
Naples
$539,000
2 Bed
2 Bath
1,554 sq. ft.
Built: 2017
Days on Site: 138
Winding Cypress
Naples
$959,900
3 Bed
2 Bath
2,186 sq. ft.
Built: 2022
Days on Site: 149
Winding Cypress
Naples
$870,000
3 Bed
2 Bath
2,230 sq. ft.
Built: 2015
Days on Site: 155
Winding Cypress
Naples
$1,185,000
3 Bed
3 Bath
2,496 sq. ft.
Built: 2017
Days on Site: 195
Winding Cypress
Naples
$579,900
3 Bed
2 Bath
1,554 sq. ft.
Built: 2015
Days on Site: 216
Winding Cypress
Naples
$534,500
2 Bed
2 Bath
1,554 sq. ft.
Built: 2018
Days on Site: 235
Winding Cypress
Naples
$615,000
3 Bed
2 Bath
1,544 sq. ft.
Built: 2016
Days on Site: 242
Winding Cypress
Naples
$640,000
2 Bed
2 Bath
1,574 sq. ft.
Built: 2019
Days on Site: 242
Winding Cypress
Naples
$665,000
2 Bed
2 Bath
1,805 sq. ft.
Built: 2016
Days on Site: 295
Winding Cypress
Naples
$900,000
3 Bed
2 Bath
2,198 sq. ft.
Built: 2016
Days on Site: 310
Winding Cypress
Naples
$529,000
2 Bed
2 Bath
1,574 sq. ft.
Built: 2017
Days on Site: 388
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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