Winding Cypress - Naples, FL

Quick Facts

Price Range
High $400s - Mid $1Ms
Home Types
Attached, Single-Family
Number of Homes
New / Resale
Resale Homes Only
Age Restrictions
Construction Dates
2014 - 2022
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Winding Cypress Overview

Winding Cypress is an active lifestyle community in Naples, Florida. Set amid 800 acres of natural preserves and 80 scenic lakes, homeowners in Winding Cypress will enjoy beautiful views in an amenity-rich setting. Residents will have a luxurious clubhouse, low-maintenance homes, and easy access to major highways and attractions.

Winding Cypress Amenities

Residents of Winding Cypress have access to a clubhouse, which has plenty of space for social gatherings so neighbors can interact with each other and build community bonds. Additional amenities include a state-of-the-art fitness center, catering kitchen, community room, and activity room.

The outdoor amenities are sure to please buyers with an active lifestyle. Homeowners have access to a resort-style pool, lap pool, spa, outdoor movement studio, outdoor barefoot bar, bocce ball courts, tennis courts, a fire pit, dog park, boardwalk with pavilion, and bird watching overlook.

Winding Cypress Homes & Real Estate

DiVosta began construction in Winding Cypress in 2014 and has now built 774 residences total. These homes include elegant single-family and attached homes that offer one-story living with a few models offering optional second floors. All homes feature covered lanais, granite countertops, tile flooring, wood kitchen cabinets, gourmet kitchens, decorative fixtures, walk-in closets, and spacious master suites.

The Serenity model is an attached home that offers 1,542 square feet of living space, which is perfect for the downsizing homebuyer. It has two bedrooms, two bathrooms, a flex room, and an attached two-car garage.

Homebuyers can choose from six single-family floor plans. They offer 1,659 to 2,589 square feet of living space with two or three bedrooms, two or three bathrooms, and an attached two to three-car garage.

Winding Cypress Lifestyle

As the community continues to grow, homeowners have a variety of clubs, activities, and events to keep them busy throughout the year. An activities director is on hand to assist residents in planning social functions in Winding Cypress.

Another great reason to live in Winding Cypress is the maintenance-free lifestyle. Residents can leave the lawn mowing and exterior home chores to the homeowners association (HOA). The HOA allows residents to have more free time so they can enjoy their activities at the clubhouse or create a fun club with other neighbors.


Naples, known as the crown jewel of Southwest Florida, offers residents plenty of recreational attractions and easy access to major highways. Interstate 75 and U.S. Highway 41 are less than ten minutes away. Residents can take a 15-minute drive to well-known Fifth Avenue South for shopping, dining, and entertainment options. The Esplanade Shoppes of Marco Island is also a great nearby shopping destination. For fun in the sun and sand, homeowners can visit the beautiful Naples Pier and beaches that are only 20 minutes away. Whatever your preference, Winding Cypress in Naples has everything to satisfy your active lifestyle.

Winding Cypress Homes for Sale

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    Winding Cypress Models


    Showing 5 Models with area.floorplan.default_home_size_filter_label for All Collections

    Serenity - Attached Homes

    Abbeyville - Single Family Homes

    Summerwood - Single Family Homes

    Martin Ray - Single Family Homes

    Tangerly Oak - Single Family Homes

    Winding Cypress Amenities

    Tentative plans include the following amenities:

    • Clubhouse - (Coming Soon!)
    • State-of-the-Art Fitness Center
    • Catering Kitchen
    • Activity Rooms
    • Community Room
    • Outdoor Movement Studio
    • Resort-Style Outdoor Pool & Spa
    • Lap Pool
    • Outdoor Patio
    • Fire Pit
    • Outdoor Barefoot Bar
    • 6 Tennis Courts
    • Bocce Ball Courts
    • Dog Park
    • Boardwalk with Pavilion
    • Bird Wading Overlook
    • Walking & Biking Trails
    • Scenic Lakes
    • Parks & Natural Space

    Winding Cypress Clubs, Groups, Activities & Classes

    Check back soon for more information on the lifestyle in Winding Cypress.

    Winding Cypress Reviews (1)

    Average Rating for this Community
    Date (Recent first)
    Buyer beware. Divosta sold out to Pulte builders. We lived in Village Walk a "Divosta" development. By the time our home was completed they had sold to Pulte. Pulte is a much lower line builder by reputation and quality. We got burned. When selling a few years later, our home was not worth near what we expected under the Divosta name. The same could happen to you. Beware!
    January 24, 2018

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