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Winding Cypress Naples Real Estate Search

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Winding Cypress Homes for Sale

The Winding Cypress Naples is a resort style community of single family homes and attached villas in the heart ofSouth Naples real estate developments between Naples and Marco Island. Located just 20 mins to 5th Ave and local beaches, 15 mins to Marco Island and only 45 min to Ft Myers international airport, its a great location.The Winding Cypress by Divosta model homes are well decorated allowing you to "feel" what it would be like to live in them. The community has spacious club house, gym, tennis, pickle ball, bocce ball and wonder heated resort style pool and outdoor cafe serving meals and has a full bar. The food is excellent and after your lunch or dinner, you can relax with drinks around the fire pit or watch sports on the multiple TVs around the bar. The pool is maintained at a nice constant temperature year round. With plenty of available sun-loungers, tables and umbrellas to provide shade if you want it so you can enjoy the community pool any time. There is also a little man made "beach" area with cabanas if you prefer. 

The Winding Cypress HOA fees are very reasonable for a community with so much to offer, so Divosta has done a good job of keeping the costs down. Winding Cypress homes for sale come in all prices for all pocket. For 2018, the villas are approx $810, Classic series homes are $875 and the larger state homes are $909 per quarter. Like many communities in the area, Winding Cypress has an annual CDD charge of $1,000 for villas, $1,104 for the Classic homes and $1,208 per year for the larger estate homes. Everyone pays a $360 per year food and beverage minimum that helps to retain the bar staff though the year when its not busy too.

Click here to watch more Winding Cypress community short video's.

Newest Winding Cypress Homes for Sale

7682 Jacaranda Ln, Naples image
7682 Jacaranda Ln, Naples $720,000 ▼

V8905 Beautiful Cressida villa with two bedrooms, den with glass French doors, two bathrooms, kitchen with island and outdoor kitchen with built-in gas grill. The prima...

  • 2 Beds
  • 2 Baths
  • 223012831 MLS
  • Winding Cypress SubDv.
7263 Clamshell Ln, Naples image
7263 Clamshell Ln, Naples $1,445,000 ▼

H8665 - New to the market! Make this stunning 3-bedroom 3-bathroom home your "forever home" in the exclusive gated community called Winding Cypress. This one owner hom...

  • 3 Beds
  • 3 Baths
  • 223009227 MLS
  • Winding Cypress SubDv.
6762 Pennyroyal Dr, Naples image
6762 Pennyroyal Dr, Naples $949,000 ▼

LOWEST PRICE PER SQUARE FOOT IN WINDING CYPRESS. 2884 square feet under air. Stunning Summerwood POOL home with EXPANSIVE LOFT (1000 sqft) in Winding Cypress, a premier ...

  • 3 Beds
  • 3 Baths
  • 222068098 MLS
  • Winding Cypress SubDv.
7768 Winding Cypress Dr, Naples image
7768 Winding Cypress Dr, Naples $849,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 223002759 MLS
  • Winding Cypress SubDv.
7383 Mockingbird Ct, Naples image
7383 Mockingbird Ct, Naples — Winding Cypress $1,500,000

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...

  • 4 Beds
  • 4 Baths
  • 222090919 MLS
  • Winding Cypress SubDv.

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Recent Blog Posts

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  • Should a buyer avoid CDD communities?
  • Winding Cypress Prepares Ground for Phase 3
  • Which South Naples community has the most space?
  • Winding Cypress offers design incentive to buyers
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Birgit A. Wolf, P.A.

Broker Associate

ABR, CIPS, CRS, GRI, SRES, SRS, SFR, RSPS, AHWD and a few more…

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