About

WINDING CYPRESS
Naples, FL CDD

🏓 Pickleball • 4 Courts🎾 Tennis • 4 Courts🐕 Dog Park

Winding Cypress in Naples Florida is a gated single family home community in Naples.
Additional WINDING CYPRESS Information:

Winding Cypress in Naples, Florida

Winding Cypress is a gated community in Naples, Florida known for its natural beauty, modern homes, and resort-style amenities. Developed by DiVosta, the community offers beautifully designed single-family homes ranging from approximately 1,542 to over 2,589 square feet, with floor plans typically featuring 2 to 3 bedrooms, 2 to 3 bathrooms, and spacious open living areas designed for comfortable Southwest Florida living.

One of the most appealing aspects of Winding Cypress is the surrounding landscape. The community is thoughtfully designed around more than 80 acres of scenic lakes and over 800 acres of protected natural preserves, creating a peaceful environment filled with nature views, walking trails, and wildlife. Many homes enjoy beautiful water or preserve views, offering residents a quiet and private setting while still being close to everything Naples has to offer.

Residents of Winding Cypress enjoy a wide range of amenities centered around an impressive clubhouse and lifestyle center. Community features include a resort-style pool and spa, fitness center, tennis courts, pickleball courts, bocce ball courts, and miles of walking and biking trails. Social gatherings, events, and activities are frequently held at the clubhouse, giving residents plenty of opportunities to stay active and connect with neighbors.

The location is another major advantage of Winding Cypress. The community is conveniently located just off Collier Boulevard (County Road 951) in Naples, providing easy access to downtown Naples, Marco Island, shopping centers, golf courses, restaurants, and the beautiful Gulf beaches that make Southwest Florida famous.

Winding Cypress is ideally positioned between several well-known Naples communities. It is bordered by Naples Reserve to the east, Lely Resort to the west, and Verona Walk to the north, placing residents in the heart of one of the most desirable areas of South Naples.

With its combination of modern homes, extensive preserve land, scenic lakes, and resort-style amenities, Winding Cypress offers a lifestyle that blends comfort, nature, and convenience. The community continues to be a popular choice for buyers looking for newer homes in Naples with strong amenities and a peaceful setting.

We are not affiliated with the HOA or management of WINDING CYPRESS, and we do not handle rentals within the community.
Our role is as a real estate brokerage, assisting buyers and sellers with their real estate needs within WINDING CYPRESS.
WINDING CYPRESS Naples FL
WINDING CYPRESS
1100Acres
766Homes
9Plans
Naples Collier County
Community Street Names
ARROWHEAD WAY, BLACKBERRY DR, BLACKBERRY WAY, CHENILLE CT, CLAMSHELL LN, COCOPLUM ST, GERANIUM WAY, JACARANDA LN, LILY WAY, LIVE OAK DR, MOCKINGBIRD CT, PENNYROYAL DR, and WINDING CYPRESS DR.
Naples Attractions
Historic Palm Cottage, 5th Ave South, 3rd Street, Naples Train Museum, Barefoot Beach Preserve, Tin City, Naples Winter Wine Festival, Naples Botanical Garden, Corkscrew Swamp Sanctuary, Naples Pier and Beaches, Lowdermilk Beach, Revs Institute, Big Cypress, Greenway, The Bird Rookery Swamp, Rookery Bay Environmental Learning Center, and Air Boat Rides.

Be sure to read the Southwest Florida monthly real estate market report to gain insights on the local market.

Go to Real Estate Market Report
Current Resale Inventory

Homes for Sale in WINDING CYPRESS

View currently active MLS listings in WINDING CYPRESS, Naples.

12 Active Listings
Community News • Stay Informed

WINDING CYPRESS Latest News and Information

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Local Weather
Thursday 22nd of October 2026

WINDING CYPRESS Weather Forecast

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Community Information

WINDING CYPRESS CDD

WINDING CYPRESS is located within a Community Development District (CDD). A CDD is essentially a tax-free municipal bond that the homeowners pay off over time. The bond is structured to pay for the infrastructure and/or maintenance of the community.

The CDD annual debt service is listed as a non-ad valorem tax on the homeowner's annual tax bill, which makes the total tax bill higher. Many master-planned communities in Southwest Florida have a CDD.

One reason for a CDD is to help keep initial new-home prices lower because certain infrastructure costs are not bundled into the new-home purchase price.

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Community Features

WINDING CYPRESS Amenities & Info

Gated
Community pool
Tennis
CDD community
24 hour guard gated
Dog Park
Bocce ball
20 min from beach
Clubhouse
Pickleball
Natural Gas
Irrigation water included in fees
Lawn care included in fees
No age restrictions
Boardwalk
Community garden
Spa
40 min from airport
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Local Market
Thursday 22nd of October 2026

Naples Median Price Trend

Southwest Coast Realty

Interested in WINDING CYPRESS?

Buying or Selling in WINDING CYPRESS

Send us a message or call directly to learn more about this community and available real estate opportunities.

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239-229-9926
WINDING CYPRESS

More Information

Your information will only be used to respond to your real estate inquiry.
9 Floor Plans

WINDING CYPRESS Floor Plans

Historical Floor Plans: WINDING CYPRESS is sold out of new construction. These are floor plans that were offered by the builder during construction.
Showing 1–3 of 9
Serenity  floor plan at WINDING CYPRESS, Naples, Florida
Serenity Sold Out
Villa Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 1,542 sqft
  • ✓ 2 car garage
Cressida floor plan at WINDING CYPRESS, Naples, Florida
Cressida Sold Out
Villa Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 1,579 sqft
  • ✓ 2 car garage
Abbeyville  floor plan at WINDING CYPRESS, Naples, Florida
Abbeyville
Classic Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 1,671 sqft
  • ✓ 2 car garage
Summerwood  floor plan at WINDING CYPRESS, Naples, Florida
Summerwood
Classic Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 1,861 sqft
  • ✓ 2 car garage
  • ✓ 1 floor
Martin Ray  floor plan at WINDING CYPRESS, Naples, Florida
Martin Ray
Classic Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 1,968 sqft
  • ✓ 2 car garage
Pinnacle  floor plan at WINDING CYPRESS, Naples, Florida
Pinnacle
Estate Series
  • ✓ 3 bed
  • ✓ 3 bath
  • ✓ 2,488 sqft
  • ✓ 3 car garage
Tangerly Oak floor plan at WINDING CYPRESS, Naples, Florida
Tangerly Oak
Estate Series
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 2,589 sqft
  • ✓ 2 car garage
Infinity  floor plan at WINDING CYPRESS, Naples, Florida
Infinity
Estate Series
  • ✓ 3 bed
  • ✓ 3 bath
  • ✓ 2,634 sqft
  • ✓ 3 car garage
Stonewater  floor plan at WINDING CYPRESS, Naples, Florida
Stonewater
Estate Series
  • ✓ 3 bed
  • ✓ 3 bath
  • ✓ 2,852 sqft
  • ✓ 3 car garage
WINDING CYPRESS

Builder Features

Historical Builder Features WINDING CYPRESS is sold out of new construction. These are the features that were offered by the builder at the time of construction.
INCLUDED FEATURES- Winding Cypress

CUSTOM INTERIOR FEATURES:

• Tile floors in foyer, kitchen, breakfast nook, baths, gathering room , and laundry
• Frame down coffered ceiling in owner's suite
• Decorative baseboard trim
• Upgraded raised-panel interior doors
• Walk-in owner's closet
• Decorative chrome door hardware
• 9'4" standard ceiling heights on first floor

EXTERIOR FEATURES:

• Tile roof
• Whole House Gutter wrap
• Easy to maintain decorative stucco exterior
• Ventilated aluminum soffits
• High-grade Sherwin-Williams latex paint
• Decorative brick paver driveway
• Large, private screened lanai
• Galvanized steel hurricane shutters
• Professionally landscaped home site with full sod coverage and automatic sprinkler system

KITCHEN FEATURES:

• Wood kitchen cabinets with 36" upper wall cabinets
• Granite countertops
• Whirlpool® refrigerator
• Whirlpool® microwave
• Whirlpool® multiple-cycle dishwasher
• Whirlpool® gas range with self-cleaning ove
WINDING CYPRESS

Latest News & Updates

9 Articles
Showing 1–3 of 9
WINDING CYPRESS Naples Florida real estate news
Blog
October 21, 2026
Collier County Florida September 2026 Real Estate Market Update in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
October 21, 2026
Lee County Florida Real Estate Market Update September 2026 in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
October 5, 2026
Walking 5th Ave South in Naples Florida in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
October 5, 2026
Lee County Florida Real Estate Market Report August 2026
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
October 5, 2026
Collier County Florida Real Estate Market Update August 2026
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
January 13, 2025
Collier County Florida November 2024 Real Estate Market Report
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
January 13, 2025
Lee County Florida November 2024 Real Estate Market Update
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
November 29, 2024
Lee County Florida October 2024 Real Estate Statistics in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Blog
November 29, 2024
Collier County Florida October 2024 Real Estate Statistics in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDING CYPRESS Archives

Archived Community Posts

8 Articles
Showing 1–3 of 8
WINDING CYPRESS Naples Florida real estate news
Archived Blog
August 16, 2022
Good news for Buyers, resale home inventory and new home inventory continues to rise in Southwest Florida. The builders are reducing prices and giving Buyer incentives. Sellers on MLS are cutting pr...
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
May 13, 2022
MLS Inventory in SW Florida is up over 80% in the last 11 weeks! Sure looks like much better prices are coming. Contact me now to get more info.
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
March 13, 2019
Save up to $55,000, when you act by March 24th, toward building your new dream home at Winding Cypress, located in Naples. Offer available on Classic and Estate Series homes.* Personalize the perfect ...
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
September 25, 2018
Save up to $35,000 - Receive a Pool at No Additional Cost at Winding Cypress*---Enjoy an endless Summer with a pool at no additional cost at Winding Cypress in Naples, select homesites only. Now exten...
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
January 2, 2018
Inventory Homes Today::Martin Ray 7554 Geranium Way, Naples, Florida 34114 $459,690 3 Bedrooms 2 Bathrooms 2,107 Sq. Ft. 2 Car Garage 10901 Lot # Stainless gas appliances & 42...
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
June 19, 2017
Act by July 12th at Winding Cypress and receive up to $30,000 Off Design Options*
Winding Cypress - Naples, FL By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida real estate news
Archived Blog
June 30, 2015
Nice entry with lots of preserve area.
Winding Cypress - Naples, FL By Ken O'Brian
Read More