Winding Cypress - Naples

winding cypress - naples fl

Winding Cypress is a master-planned gated community located in Southeast Naples that was developed by Divosta Homes.  The community features over 800 acres of natural preserves and 80 acres of lakes and is positioned adjacent to the Picayune Strand Forest.  At full build-out, Winding Cypress is targeted for over 2,000 homes.  Read more about Winding Cypress real estate.

Winding Cypress Homes For Sale

Winding Cypress Homes For Sale February 6, 2023
12
Listed
25
Avg. DOM
$467.85
Avg. $ / Sq.Ft.
$994,450
Med. List Price
12 Properties
$1,595,000
Neighborhood: WINDING CYPRESS
3
Beds
3F11/2
Baths
2,911
Sq.Ft.
2018
Year Built
25
Days on Site
223002560
MLS
Wow! This beautifully designed and meticulously maintained home is spectacular. Featuring the highly desirable and rarely available Stonewater floor plan, you are welcomed through a double-door...
$1,595,000
Neighborhood: WINDING CYPRESS
3
Beds
3
Baths
2,619
Sq.Ft.
2016
Year Built
3
Days on Site
223009227
MLS
H8665 - New to the market! (Professional photos are on their way) Make this stunning 3-bedroom 3-bathroom home your "forever home" in the exclusive gated community called Winding Cypress. This one...
$1,500,000
Neighborhood: Winding Cypress
4
Beds
4
Baths
3,696
Sq.Ft.
2016
Year Built
36
Days on Site
222090919
MLS
This is your Next Home 4bed/4 bath + den. Gorgeous Pulte/DeVosta expanded, Pinnacle, two-story model with many upgrades. This is the largest home on the street built w/ a lot upgrades, no neighbors...
$1,200,000
Neighborhood: WINDING CYPRESS
3
Beds
3
Baths
2,496
Sq.Ft.
2016
Year Built
33
Days on Site
222089855
MLS
Combining the unique privacy of a long lake view with the unparalleled value offered in Winding Cypress, this Pinnacle model is everything you are seeking in your new Naples home! Enjoy relaxing or...
$1,125,000
Neighborhood: WINDING CYPRESS
3
Beds
3
Baths
2,668
Sq.Ft.
2015
Year Built
68
Days on Site
222084256
MLS
Pristine 3+den pool home with lake views in highly sought-after Winding Cypress. They spared no expense with upgrades everywhere to include custom saltwater pool, walk-in pantry, oversized two car...
$998,900
Neighborhood: WINDING CYPRESS
3
Beds
3
Baths
2,158
Sq.Ft.
2021
Year Built
18
Days on Site
223004832
MLS
NICER THAN A MODEL HOME!!! Spacious 3 bedroom + den, 3 FULL bathroom house with FULL impact glass doors and windows. $138,000 in builder upgrades PLUS over $110,000 in CUSTOM upgrades that were done...
$990,000
Neighborhood: WINDING CYPRESS
3
Beds
2
Baths
2,230
Sq.Ft.
2015
Year Built
25
Days on Site
223003084
MLS
The ultimate waterfront home site in the resort community of Winding Cypress in Naples. This Summerwood model has every option and add-on imaginable. From impact windows to a whole-house generator...
$989,000
Neighborhood: WINDING CYPRESS
3
Beds
2
Baths
2,188
Sq.Ft.
2018
Year Built
49
Days on Site
222086983
MLS
Beautifully appointed Summerwood floorplan, with over $150,000.00 in builder design option upgrades, heated pool and spa, raised ceilings, and more. The owners have added over $45,000.00 in...
$979,000
Neighborhood: WINDING CYPRESS
3
Beds
3
Baths
2,577
Sq.Ft.
2021
Year Built
14
Days on Site
222068098
MLS
Stunning Summerwood POOL home with expansive LOFT in Winding Cypress, a premier Naples Location. Better than new, barely lived in 3 Bedroom plus DEN, 3 FULL BATH home. Live Naples at its best....
$975,000
Neighborhood: WINDING CYPRESS
4
Beds
3
Baths
2,078
Sq.Ft.
2015
Year Built
19
Days on Site
223004315
MLS
Just water and trees. This ultra-premium home and lot has waterfront, preserve, and sunset western views set in the ultimate Naples resort community of Winding Cypress. This Abbeyville home features...
$879,000
Neighborhood: WINDING CYPRESS
2
Beds
2
Baths
1,893
Sq.Ft.
2021
Year Built
19
Days on Site
223002759
MLS
H8344. Desirable 2021 built Summerwood within the gated natural gas community of Winding Cypress. Wood plank laminate floor throughout common living spaces and den. Brown/grey shaker cabinets and...
$736,000
Neighborhood: WINDING CYPRESS
2
Beds
2
Baths
1,544
Sq.Ft.
2016
Year Built
6
Days on Site
223004659
MLS
Presenting the rare opportunity to own a luxury villa Serenity model with saltwater pool and hot tub spa set on a breathtaking view over water and sunset. This highly sought-after Winding Cypress...

More About Winding Cypress Real Estate

Winding Cypress Amenities

Amenities at Winding Cypress include a resort-style pool, outdoor barefoot bar, fitness center and movement center, amenity center,  tennis courts, Bocce and a fire pit.

Winding Cypress Location

Winding Cypress is located in Southeast Naples off Collier Boulevard, south of Interstate 75 at exit 101.  This location is directly east of Lely Resort and south of Verona Walk.   Winding Cypress is served by the Lely Elementary School, Manatee Middle School and Lely High School

Explore Winding Cypress

Winding Cypress New Model Gallery

Abbeyville

  • 1,659 Square Feet
  • 2 Bedrooms / 2 Bathrooms
  • 1 Story Home

Infinity

  •  2,385+ Square Feet
  • 3 Bedrooms / 3 Bathrooms
  • 1 Story Home

 Martin Ray

  • 1,968+ Square Feet
  • 2 Bedrooms / 2 Bathrooms
  • 1 Story Home

Pinnacle

  • 2,488+ Square Feet
  • 3 Bedrooms / 3 Bathrooms
  • 1 Story Home

 Serenity

  • 1,542 Square Feet
  • 2 Bedrooms / 2 Bathrooms
  • 1 Story Home

Tangerly Oak

  • 2,589+ Square Feet
  • 2 Bedrooms / 2.5 Bathrooms
  • 1 Story Home
From Our Blog - Winding Cypress
Winding Cypress Offers All the Amenities for Today’s Buyer

From tennis courts to swimming, Winding Cypress offers all the shared and private amenities for today’s buyer, also including outdoor living, flex spaces, and generous closets. This active ... Read more about Winding Cypress Offers All the Amenities for Today’s Buyer

Winding Cypress Offers a Resort Lifestyle

For new resort-like homes designed how you want to live, it’s time to explore the many different options of a Winding Cypress lifestyle. This new construction community in Naples offers ... Read more about Winding Cypress Offers a Resort Lifestyle

Winding Cypress: At Home with Nature

  While praised for its amenities and its home designs, Winding Cypress also holds the distinction of being at home with nature. The 1,100-acre community offers a true dedication to the ... Read more about Winding Cypress: At Home with Nature

Winding Cypress: New Homesites Released

Another 200 home sites have now been released to mark the third phase of Winding Cypress. The just released properties in this Naples community include both water and preserve views, with classic ... Read more about Winding Cypress: New Homesites Released

Winding Cypress Offers Affordability in Naples

Winding Cypress has everything you could want from a home in Naples at a great value and affordable price.  An Activities Director on-site plans community events, and an amenity-rich Clubhouse ... Read more about Winding Cypress Offers Affordability in Naples