Winding Cypress is an alluring gated community nestled in the scenic landscape of Naples, Florida. This thoughtfully designed neighborhood features elegant homes, exceptional amenities, and lush natural surroundings, providing a truly remarkable living experience for its esteemed residents. Discover your dream home by exploring Homes For Sale In Winding Cypress Naples FL.

Latest Homes For Sale In Winding Cypress Naples FL

28 Results

Refine Search

Min. Price

$

Max. Price

$

Beds Any1+2+3+4+5+

Baths Any1+2+3+4+5+

Update

Sort

• Price (High to Low)
• Price (Low to High)
• Status
• City
• Listing Date
• Type / Price Descending
• Listing Number
• Open Home Date Asc

$544,000

7602 Jacaranda LN
NAPLES, FL 34114

2
Beds

2
Baths

1,554
SqFt

(16)

Close

Open House: Jun 15, 2025, 1:00 PM - 4:00 PM

 

#225051042 | House

Listing Courtesy of: Coldwell Banker Realty

$900,000

6848 Winding Cypress DR
NAPLES, FL 34114

2
Beds

2
Baths

1,901
SqFt

(47)

Close

Virtual Tour

 

 

#225053774 | House

Listing Courtesy of: Realty One Group MVP

$999,000

6787 Pennyroyal DR
NAPLES, FL 34114

3
Beds

2
Baths

2,100
SqFt

(34)

Close

Open House: Jun 15, 2025, 1:00 PM - 3:00 PM

 

#225050485 | House

Listing Courtesy of: Royal Shell Real Estate, Inc.

• «
• 1 of 10
• »

The data relating to real estate for sale on this limited electronic display come in part from the Broker Reciprocity Program (BR Program) of the Bonita Springs-Estero Association of REALTORS®, Florida Gulf Coast Multiple Listing Service, Inc., and the M.L.S. of Naples, Inc. Properties listed with brokerage firms other than EXP Realty are marked with the BR Icon and detailed information about them includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties available through the BR Program.
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2025 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

Southwest Florida data last updated at June 12, 2025, 9:17 AM ET

Real Estate in Winding Cypress

Discover Winding Cypress homes for sale, featuring a diverse selection of properties that cater to various lifestyles and tastes. From charming villas to elegant single-family homes, there’s something for everyone. Begin your search for the perfect Homes For Sale In Winding Cypress Naples FL today.

Community Highlights

• Gated community with 24-hour security
• Resort-style pool and spa
• State-of-the-art fitness center
• Lighted tennis courts and pickleball courts
• Outdoor barefoot bar and grill
• Miles of walking and biking trails
• Nearly 800 acres of natural preserves and 80 acres of lakes
• Pet-friendly community

Nearby Attractions and Amenities

• Winding Cypress is conveniently located near numerous local attractions and amenities, including:
• Pristine beaches along the Gulf of Mexico
• Top-rated golf courses in the area
• Upscale shopping and dining at Mercato and Waterside Shops
• Downtown Naples and Fifth Avenue South
• Naples Botanical Garden
• Naples Zoo at Caribbean Gardens
• Rookery Bay Environmental Learning Center

Schedule a Tour

Ready to explore Winding Cypress homes for sale? [Contact us] (contact-us.html) to schedule a personalized tour and experience the serene lifestyle that awaits you in this beautiful community.