Winding Cypress Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winding Cypress and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

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Newest Listings in Winding Cypress

7098 Live Oak Drive, 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 Drive, 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 Lane, 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 Lane, 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 Drive, 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 Lane, 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 Drive, 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 Court, 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 Drive, Naples image

7700 Winding Cypress Drive, 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

6907 Cocoplum Street, Naples $1,295,000

PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with pea...

3 Beds
3 Baths
226027501 MLS

7156 Live Oak Drive, Naples $590,000 ▼

PRICE ALERT- This is the LOWEST TRUE 3-BEDROOM complete with your own private pool located in the amenity rich community of Winding Cypress!!! The ultimate blend of luxu...

3 Beds
2 Baths
226024508 MLS

7478 Winding Cypress Drive, Naples image

7478 Winding Cypress Drive, Naples $1,349,500

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, ...

3 Beds
3 Baths
226021460 MLS