Winding Cypress

Winding Cypress is a master-planned, gated community in Southeast Naples developed by Divosta Homes. The community features 766 beautifully designed homes nestled within over 800 acres of natural preserves and 80 acres of serene lakes. Located adjacent to the Picayune Strand Forest, Winding Cypress offers residents a tranquil lifestyle surrounded by nature while maintaining convenient access to modern amenities.

Community Features

The community seamlessly merges the elegance of modern living with the serene beauty of its natural surroundings. Residents enjoy access to a spacious Clubhouse, luxurious resort-style pool, and the Shady Palm Café for dining. The location provides easy access to popular destinations including Tamiami Crossing for shopping and Freedom Square featuring restaurants and additional retail stores.

Natural Setting

With over 800 acres of natural preserves and 80 acres of lakes throughout the community, Winding Cypress offers an exceptional natural environment. The community''s proximity to the Picayune Strand Forest further enhances the connection to Southwest Florida''s natural beauty, providing residents with a peaceful retreat while remaining close to urban conveniences.

Quick Facts

Gated
Yes, 24/7 manned gate
Residences
766 homes
Location
Southeast Naples, adjacent to Picayune Strand Forest
Lifestyle
Nature-focused with modern amenities

Properties for Sale

Market Snapshot

Pricing

Track how home values are trending in Winding Cypress. Median sale prices and price-per-square-foot data help buyers and sellers gauge current market positioning.

Median Closed Price

Inventory

See how many homes are available in Winding Cypress and how quickly inventory is moving. Months of supply indicates whether conditions favor buyers or sellers.

Homes For Sale

Activity

Monitor real estate transaction volume in Winding Cypress. Pending and closed sales reflect the pace of buyer demand and overall market momentum.

Pending Sales

Map (26.069, -81.682)

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The information provided on this page, including market data and statistics, is believed to be accurate but is not guaranteed. Data may contain errors, omissions, or delays. Bonnycastle Realty makes no representations or warranties of any kind regarding the completeness, accuracy, or reliability of this information. Use of this data is at your own risk. Bonnycastle Realty shall not be held liable for any loss or damage arising from reliance on the information presented.

Southwest Florida MLS

The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than Bonnycastle Realty are marked with the listing broker's name. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the M.L.S. of Naples, Inc. BR Program, or contained in the database compilation of the M.L.S. of Naples, Inc.

The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Copyright 2026 M.L.S. of Naples, Inc. 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.

Some properties that appear for sale on this website may no longer be available. For the most current information, contact Bonnycastle Realty at (239) 778-0254 or info@bonnycastlerealty.com.

Page last updated 5/4/2026