Winding Cypress Home Search
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Winding Cypress Home Search
Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater M...
- 4 Beds
- 4.5 Baths
- 226024563 MLS
BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, ...
- 3 Beds
- 3 Baths
- 226021460 MLS
Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 ,...
- 3 Beds
- 2 Baths
- 226005365 MLS
This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious cor...
- 3 Beds
- 2 Baths
- 226022635 MLS
Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedr...
- 4 Beds
- 3 Baths
- 225081501 MLS
Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the...
- 3 Beds
- 2 Baths
- 226024508 MLS
Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath...
- 2 Beds
- 2 Baths
- 226008768 MLS
The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.
Winding Cypress Homes for Sale in Naples, Florida
Winding Cypress is a beautiful gated community in Naples, Florida, known for its resort-style amenities, natural surroundings, and modern single-family homes and villas. Buyers searching for Winding Cypress homes for sale will find a thoughtfully planned neighborhood with preserve views, lakes, walking trails, and convenient access to downtown Naples, Marco Island, Gulf beaches, shopping, dining, and everyday services.
Resort-Style Amenities in Winding Cypress
Life in Winding Cypress is centered around recreation, wellness, and social connection. The community features a large clubhouse, state-of-the-art fitness center, resort-style pool with cabanas, restaurant and bar, tennis courts, pickleball courts, bocce courts, dog park, event spaces, and miles of scenic walking and biking paths. Residents enjoy an active lifestyle with clubs, gatherings, and year-round community events.
Homes Designed for Modern Naples Living
Winding Cypress real estate includes single-family homes and attached villas with open floor plans, spacious kitchens, screened lanais, lake views, preserve views, and low-maintenance design options. Many homes were built by DiVosta and feature energy-efficient construction, flexible living areas, and outdoor spaces designed for the Southwest Florida lifestyle.
Nature, Preserves, and Outdoor Enjoyment
One of the defining features of Winding Cypress is its natural setting. The community includes hundreds of acres of preserve land, scenic lakes, and nature areas that create a peaceful backdrop for residents. Walking trails, boardwalk-style areas, and quiet streets make the neighborhood appealing for buyers who want a gated Naples community with both privacy and activity.
Convenient Location Near Naples and Marco Island
Winding Cypress is located in southeast Naples with easy access to downtown Naples, 5th Avenue South, Naples beaches, Marco Island, shopping centers, restaurants, healthcare, and major roadways. This location makes the community attractive for seasonal residents, full-time homeowners, and buyers seeking a newer gated community close to both Naples and Marco Island.
Explore Winding Cypress Real Estate
Use the Winding Cypress homes search, map search, and market report links above to view current listings, recent sales activity, pricing trends, and available properties. Whether you are looking for a villa, single-family home, lakefront view, preserve setting, or low-maintenance Naples lifestyle, Winding Cypress offers a compelling option in the Southwest Florida market.
Work with Schulz Realty
Schulz Realty specializes in gated community, waterfront, golf resort, and coastal properties throughout Naples, Marco Island, Bonita Springs, and Estero. Our team provides direct MLS access, private showing assistance, valuation guidance, local market knowledge, and community insight to help you compare Winding Cypress with other premier Naples communities.
Discover Winding Cypress — where Naples gated community living, resort-style amenities, natural preserves, and modern homes come together.
Work with Schulz Realty
Schulz Realty specializes in Naples gated communities, luxury homes, waterfront properties, and coastal real estate throughout Southwest Florida. We tailor your search, provide direct MLS access and alerts, and guide you through valuations, HOA details, inspections, negotiations, and closing.
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Winding Cypress Homes and Villas for Sale
Winding Cypress is a gated resort-style community in Naples offering single-family homes and attached villas built by DiVosta Homes. Residences feature a variety of floor plans designed for seasonal or full-time living, with select properties offering lake, preserve, or landscaped views.
Winding Cypress Interactive Map The community combines newer residential construction with lakes, preserved natural areas, landscaped streets, and walking and biking paths. Its non-golf resort setting appeals to buyers who want extensive recreation without the expense or obligations associated with a private golf membership.
Winding Cypress Resort-Style Amenities
The clubhouse serves as the center of community recreation and social activity. Amenities may include a resort-style swimming pool, fitness center, tennis, pickleball, bocce, gathering rooms, outdoor recreation areas, and an organized calendar of classes, clubs, and resident events.
Residents may also enjoy walking and biking trails, scenic lakes, preserved green space, landscaped common areas, and opportunities to relax or exercise outdoors. The neighborhood’s gated entrance and community design provide a peaceful setting for both seasonal and full-time owners.
Convenient Naples Location
Winding Cypress is conveniently located near shopping, restaurants, healthcare, golf courses, boating, Marco Island, Downtown Naples, Fifth Avenue South, and Gulf beaches. Its location provides access to both Naples and Marco Island attractions while maintaining a quieter residential environment.
Winding Cypress homes for sale may feature open floor plans, private pools, screened lanais, outdoor kitchens, garages, lake or preserve views, and low-maintenance villa living. Association fees, community assessments, maintenance responsibilities, rental restrictions, pet policies, amenity access, and property-specific features should be verified before purchasing.
Work with Schulz Realty
Schulz Realty provides current Winding Cypress MLS listings, customized property alerts, private tours, comparable sales, neighborhood information, association research, and personalized guidance for buyers and sellers throughout Winding Cypress, Naples, and Southwest Florida.
Call David Schulz at (239) 682-5800.