Search All Winding Cypress Real Estate

Winding Cypress is a newer gated resort-style community in south Naples. You won't need a thing because it's all here in Winding Cypress including a heated pool & spa, tennis, pickleball, fitness center, bocce, bird overlook, boardwalk, dog park, fire pit, community garden, nature preserves & lakes, plus an outdoor bar & grill and poolside beach with cabanas! Contact us today to find out about any available resale opportunities in Winding Cypress.

Our website features the best Winding Cypress real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor® database every 15 minutes. You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

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Hot Winding Cypress Properties

7775 Winding Cypress DR, Naples $990,000

Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of th...

4 Beds
3 Baths
226037594 MLS

7098 Live Oak DR, Naples $520,000

Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich comm...

3 Beds
2 Baths
226038340 MLS

7235 Live Oak DR, Naples $925,000

This home has had a complete refresh with a lot of new improvements, new heat/ac units on both floors new pool pump and heater, new roof vents, new lanai screen, paver...

3 Beds
3 Baths
226036844 MLS

7247 Clamshell LN, Naples $1,549,000

A MUST-SEE HOME IN A MUST SEE COMMUNITY Extensive upgrades and designer elements elevate this home, based on an award winning model. Gorgeous water/preserve views are ...

4 Beds
4 Baths
226035902 MLS

7602 Jacaranda LN, Naples $564,900 ▼

**Motivated sellers!! Seller concession of $5k!!!This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversio...

2 Beds
2 Baths
226035971 MLS

7072 Live Oak DR, Naples $1,450,000

Welcome to this beautifully appointed 4-bedroom, 4-bath residence offering approximately 3,350 square feet and a custom, one-of-a-kind floor plan not found elsewhere in t...

4 Beds
4 Baths
226031553 MLS

7670 Jacaranda LN, Naples $615,000 ▼

Escape cookie-cutter living at 7670 Jacaranda, where custom millwork, extensive built-ins and thoughtful upgrades give this 2018-built home a character all its own. The o...

3 Beds
2 Baths
226034452 MLS

7230 Live Oak DR, Naples $1,100,000 ▼

Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom ov...

3 Beds
3 Baths
226034017 MLS

6825 Greenbriar CT, Naples $965,000

Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor livi...

4 Beds
3 Baths
226034030 MLS

7700 Winding Cypress DR, Naples $1,250,000

BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN ...

5 Beds
3 Baths
226032436 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.

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