The community of Winding Cypress is found in Naples. Superbly situated for access to all of the Naples region amenities and comforts has to offer.

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16 listings match your search criteria.
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7259 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2500Sq Ft
  • 2016Year Built
$969,000

An opportunity to unlock value! Great opportunity for buyers looking to build equity through a little hard work and personal vision. This home offers solid potential for someone willing to invest time, effort and updates to make it their own. What has been done is new luxury vinyl flooring , painting ,…

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7383 Mockingbird Ct   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3696Sq Ft
  • 2016Year Built
$1,550,000

Situated on a private .29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended…

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6932 Cocoplum St   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2019Year Built
$1,575,000

Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and…

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7591 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$539,000

Western sunset views, peaceful pond vistas, and added privacy, this Winding Cypress villa offers a setting that’s truly special! Beautifully upgraded, this unfurnished 2 Bedroom + Den residence enjoys desirable western exposure overlooking a picturesque pond, complemented by private green space adjacent to the property, creating a serene and tranquil retreat. Inside, an inviting open…

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7775 Winding Cypress Dr   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 3206Sq Ft
  • 2019Year Built
$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 the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's…

Active
7098 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$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 community of Winding Cypress. Being offered turnkey furnished, this thoughtfully designed residence has three bedrooms, two baths, and an inviting open-concept design, while combining comfortable living with effortless indoor-outdoor…

Active
7235 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2300Sq Ft
  • 2015Year Built
$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, pavers on front and side with a refresh landscaping with sitting area, new epoxy garage flooring in extended garage to…

Active
7247 Clamshell Ln   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2016Year Built
$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 seen both back and front. This quiet, lush green street is just a short walk to the recreation center where several activities, amenities and social events can be enjoyed. Winding…

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7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$548,000

**Motivated sellers! This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversion to a third bedroom, two full bathrooms, and a two-car garage. An open floor plan, bright kitchen with stainless-steel Whirlpool appliances, granite counters and an in-residence laundry room with a newer washer and dryer make…

Active
7072 Live Oak Dr   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3350Sq Ft
  • 2015Year Built
$1,350,000

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 the community. Designed for effortless Florida living, the spacious interior features multiple living and dining areas, a private office, elegant architectural details and an impressive kitchen with white cabinetry, a large island…

Active
7230 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2500Sq Ft
  • 2016Year Built
$1,100,000

Beautiful home on a premium pie shaped lot with lots of privacy. Seller keeps his landscaping impeccable. This home features 3 generous size bedrooms, 3 full bath , 3 car garage . with 2500 sq ft of indoor living space. Beautiful Custom oversized salt water heated pool with stairs , sunshelf, 3…

Active
6825 Greenbriar Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 3036Sq Ft
  • 2022Year Built
$945,000

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 living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan…

Active
7700 Winding Cypress Dr   Naples
  • 5Bedrooms
  • 3Bathrooms
  • 2950Sq Ft
  • 2021Year Built
$1,125,000

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 NAPLES, MARCO ISLAND’S PRISTINE BEACHES AS WELL AS NEARBY SHOPPING AND RESTAURANTS, THIS SUMMERWOOD FLOORPLAN FEATURES A MASTER ON MAIN LIVING FLOOR WITH LARGE BATH AND WALK-IN CLOSET, A LARGE LOFT…

Active
6907 Cocoplum St   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2515Sq Ft
  • 2020Year Built
$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 peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this…

Active
7156 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$590,000

PRICE ALERT- Turnkey 3-BEDROOM complete with your own private POOL and outdoor summer kitchen located in the amenity rich community of Winding Cypress!!! The ultimate blend of comfort, and effortless living for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright,…

Active
7478 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2634Sq Ft
  • 2016Year Built
$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, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a…

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