Winding Cypress Real Estate

About Winding Cypress

Winding Cypress is a Southwest Florida community in Naples where the NABOR MLS currently shows 8 active listings, asking $575,000 to $1,400,000, averaging 97 days on market, with 4 closed sales recorded here in the last 90 days. Waterfront Realty Group, Inc. has worked this market as an independent, Realtor-owned brokerage since 1986, and pairs every customer with a Sales Associate who knows these streets, waterways, and price trends firsthand.

Figures reflect the active Winding Cypress inventory shown on this page, drawn live from the Naples Area Board of REALTORS® (NABOR) MLS. Closed-sale counts cover the trailing 90 days.

$1,400,000

7759 Winding Cypress DR

4 bd · 4.5 ba · 3,464 sf

Listing courtesy of William Raveis Real Estate

$1,349,500

7478 Winding Cypress DR

3 bd · 3 ba · 2,634 sf

Listing courtesy of Coldwell Banker Realty

$1,295,000

6907 Cocoplum ST

3 bd · 3 ba · 2,515 sf

Listing courtesy of Compass Florida LLC

$1,250,000

7700 Winding Cypress DR

5 bd · 3 ba · 2,950 sf

Listing courtesy of Anchor Real Estate

$949,900

6844 Winding Cypress DR

3 bd · 2 ba · 2,100 sf

Listing courtesy of Royal Shell Real Estate, Inc.

$940,000

6727 Pennyroyal DR

3 bd · 2 ba · 2,076 sf

Listing courtesy of Realty One Group MVP

$599,900

7156 Live Oak DR

3 bd · 2 ba · 1,554 sf

Listing courtesy of William Raveis Real Estate

$575,000

7666 Jacaranda LN

2 bd · 2 ba · 1,574 sf

Listing courtesy of EXP Realty LLC

Listing data provided via the Naples Area Board of REALTORS® (NABOR) MLS. Information deemed reliable but not guaranteed. Equal Housing Opportunity. © 2026 Waterfront Realty Group, Inc. License CQ257718. All rights reserved.