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.

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
WINDING CYPRESS Naples FL
WINDING CYPRESS
1100Acres
766Homes
9Plans
Naples Collier County
Resale Homes
View WINDING CYPRESS Active Listings
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.


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Community News-Stay Informed

WINDING CYPRESS Latest News and Information

Friday 28th of August 2026
WINDING CYPRESS Weather Forecast
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 homeowners annual tax bill which makes the total tax bill higher. Many master planned communities in SW Florida do have a CDD. One of the main reasons for a CDD would be to make the new home prices lower since the infrastructure costs are not bundled in the new home price.

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
WINDING CYPRESS Site Map
WINDING CYPRESS site map Open Site Map
Friday 28th of August 2026
Naples
Median Price Trend

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Buying or Selling in WINDING CYPRESS
Feel free to send a message or call anytime.

Call Direct
239-229-9926
WINDING CYPRESS

More Information

WINDING CYPRESS

Photo Gallery

Winding Cypress - New Homes For Sale in Naples FL 34114
1 / 10
9 Floor Plans
WINDING CYPRESS Floor Plans

WINDING CYPRESS is sold out of new construction. These are the floor plans that were offered by the builder at the time of 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

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

Blog

Showing 1–3 of 12
WINDING CYPRESS Naples Florida COLLIER COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET REPORT...
Blog
2025 January 13
COLLIER COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET REPORT...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida LEE COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET UPDATE...
Blog
2025 January 13
LEE COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET UPDATE...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida LEE COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Blog
2024 November 29
LEE COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida COLLIER COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Blog
2024 November 29
COLLIER COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida GOOD NEWS FOR BUYERS, RESALE HOME INVENTORY AND NEW HOME INVENTORY CONTINUES TO RISE IN SOUTHWEST FLORIDA.  THE BUILDERS
Archived Blog
2022 August 16
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...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida MLS INVENTORY IN SW FLORIDA IS UP OVER 80% IN THE LAST 11 WEEKS!  SURE LOOKS LIKE MUCH BETTER PRICES ARE COMING.  CONTAC
Archived Blog
2022 May 13
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....
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida WINDING CYPRESS INVENTORY HOMES...
Archived Blog
2020 January 13
WINDING CYPRESS INVENTORY HOMES...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida SAVE UP TO $55,000, WHEN YOU ACT BY MARCH 24TH, TOWARD BUILDING YOUR NEW DREAM HOME AT WINDING CYPRESS, LOCATED IN NAPLE
Archived Blog
2019 March 13
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 ...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida SAVE UP TO $35,000 - RECEIVE A POOL AT NO ADDITIONAL COST AT WINDING CYPRESS*---ENJOY AN ENDLESS SUMMER WITH A POOL AT N
Archived Blog
2018 September 25
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...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida INVENTORY HOMES TODAY::MARTIN RAY
7554 GERANIUM WAY, NAPLES, FLORIDA 34114

$459,690


3
BEDROOMS
2
BATHROOMS
Archived Blog
2018 January 02
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...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida ACT BY JULY 12TH AT WINDING CYPRESS AND RECEIVE UP TO
$30,000 OFF DESIGN OPTIONS*
...
Archived Blog
2017 June 19
ACT BY JULY 12TH AT WINDING CYPRESS AND RECEIVE UP TO $30,000 OFF DESIGN OPTIONS* ...
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
WINDING CYPRESS Naples Florida NICE ENTRY WITH LOTS OF PRESERVE AREA....
Archived Blog
2015 June 30
NICE ENTRY WITH LOTS OF PRESERVE AREA....
Categories: Winding Cypress - Naples, FL
By Ken O'Brian
Read More
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