Naples, FL · residential community

Winding Cypress homes for sale

As of October 15, 2026, 12 homes are for sale in Winding Cypress, Naples, FL, priced from $575K to $1.55M with a median asking price of $1.06M (about $424 per square foot).

7247 Clamshell Ln, Winding Cypress — Current listing in Winding Cypress: 7247 Clamshell Ln $1.55M · Listing courtesy of Real Broker, LLC

12Active homes

$575K – $1.55MList price range

$424Median list $ / sq ft

47Closed sales, 12 months

Live from the MLS and refreshed through the day.

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For sale

Homes for sale in Winding Cypress

All Naples homes $3M+ →

New · 6 days1 / 34

$1,549,000

7247 Clamshell LnWinding Cypress · Naples

4 bd4 ba3,656 sf

Listing courtesy of Real Broker, LLC

New · 14 days1 / 50

$1,450,000

7072 Live Oak DrWinding Cypress · Naples

4 bd4 ba3,350 sf

Listing courtesy of Harborview Realty Inc

Waterfront1 / 50

$1,349,500

7478 Winding Cypress DrWinding Cypress · Naples

3 bd3 ba2,634 sf

Listing courtesy of Coldwell Banker Realty

1 / 43

$1,295,000

6907 Cocoplum StWinding Cypress · Naples

3 bd3 ba2,515 sf

Listing courtesy of Compass Florida LLC

Waterfront1 / 42

$1,250,000

7700 Winding Cypress DrWinding Cypress · Naples

5 bd3 ba2,950 sf

Listing courtesy of Anchor Real Estate

1 / 43

$1,100,000

7230 Live Oak DrWinding Cypress · Naples

3 bd3 ba2,500 sf

Listing courtesy of Royal Shell Real Estate, Inc.

Waterfront1 / 55

$1,030,000

7564 Winding Cypress DrWinding Cypress · Naples

4 bd2 ba2,230 sf

Listing courtesy of Gordon Pass Realty LLC

1 / 50

$965,000

6825 Greenbriar CtWinding Cypress · Naples

4 bd3 ba3,036 sf

Listing courtesy of Premier Sotheby's Int'l Realty

1 / 34

$625,000

7670 Jacaranda LnWinding Cypress · Naples

3 bd2 ba1,594 sf

Listing courtesy of DomainRealty.com LLC

1 / 31

$590,000

7156 Live Oak DrWinding Cypress · Naples

3 bd2 ba1,554 sf

Listing courtesy of William Raveis Real Estate

New · 9 days1 / 39

$579,000

7602 Jacaranda LnWinding Cypress · Naples

2 bd2 ba1,554 sf

Listing courtesy of Florida Listing Experts LLC

$575,000

7666 Jacaranda LnWinding Cypress · Naples

2 bd2 ba1,574 sf

Listing courtesy of EXP Realty LLC

Listings are shown courtesy of the listing brokerages. Information is deemed reliable but not guaranteed.

Questions about Winding Cypress

How many homes over $3M are for sale in Winding Cypress?

There are no homes listed at $3M or more in Winding Cypress right now, and 12 active listings overall. Listings change daily.

What do luxury homes cost in Winding Cypress?

Current asking prices run $575K to $1.55M, with a median of $1.06M or roughly $424 per square foot. Floor, view, finish and, for single-family homes, lot and water frontage account for most of the spread.

What kinds of homes are in Winding Cypress?

Winding Cypress is a residential community in Naples, FL. Current listings include homes with 2 to 5 bedrooms, 1,554 sq ft to 3,656 sq ft, built 2015 to 2022.

Are homes in Winding Cypress on the water?

Of the 12 current listings, 5 are waterfront, 9 have a private pool, per MLS data. Water type and access vary by street and building, so confirm each home's details before relying on them.

What are the association fees in Winding Cypress?

Current listings report association fees of $1,441 to $1,662 per quarter. What a fee covers differs by building or community, so ask for the budget and the reserve and milestone-inspection documents before you buy.

How fast do homes sell in Winding Cypress?

47 sales closed in the past 12 months at a median of $800K, with a median of about 73 days on market and a median sale-to-list ratio of 95.8%. A small number of sales means these medians are only a guide.

Who can show me homes in Winding Cypress?

Mindy Dolle, a licensed Florida real estate sales associate with Domain Realty, can arrange showings, pull comparable sales and review association documents for homes in Winding Cypress. Call or text (239) 851-2556.