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Winding Cypress Properties for Sale

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Welcome to Winding Cypress | Naples Florida 

From the moment you arrive at the stunning entry, Winding Cypress invites you in. Remaining almost 2/3 natural preserve, this natural gas, resort-style community welcomes you with a streetscape of superb views and homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own backyard, including a grand clubhouse, resort pool, sports courts, dog park, community garden, and more. Resort-style living and a welcoming community await you at Winding Cypress. Relax by the resort pool and spa, play a pick-up game at the sports courts, or pick fresh produce from the community garden. Headed into town?

Enjoy easy access to upscale shopping and dining in Downtown Naples, or when plans call for escaping to the sugar-white sand beaches, breeze over to Marco Island just minutes away. 

Newly Listed Properties in Winding Cypress

7097 Live Oak Dr, Naples image
7097 Live Oak Dr, Naples $574,592

Don't miss one of your last chances to live at Winding Cypress! This serenity floorplan villa home features 2 bedrooms, 2 baths, a den, and a covered lanai on a preserve...

  • 2 Beds
  • 2 Baths
  • 222037701 MLS
7060 Live Oak Dr, Naples image
7060 Live Oak Dr, Naples $1,399,000

H5960 Beautiful Pinnacle model. Lots of upgrades. Full impact doors and windows throughout. Upgraded Kitchen Cabinets with quartz countertops, gas range. Walk in pantry....

  • 4 Beds
  • 3 Baths
  • 222036902 MLS
7666 Jacaranda  Lane, Naples image
7666 Jacaranda Lane, Naples $699,000

The Finest in Resort Style Living! You do not want to miss this opportunity to own a find like this in the Community of Winding Cypress. This Beautifully updated 2+Den/2 ...

  • 2 Beds
  • 2 Baths
  • SWFL-222036835 MLS
7156 Live Oak Dr, Naples image
7156 Live Oak Dr, Naples $699,000

Rare 3 bedroom, 2 bath, 2 car garage pool villa available for sale in Winding Cypress. This home is being offered turnkey furnished and features tile floor throughout, st...

  • 3 Beds
  • 2 Baths
  • 222036657 MLS
7163 Live Oak Dr, Naples image
7163 Live Oak Dr, Naples $609,000

This meticulously maintained Serenity villa boasts 2 bedroom plus den, 2 bathrooms, and a 2 car garage! The villa is tastefully decorated and being offered Turnkey furnis...

  • 2 Beds
  • 2 Baths
  • 222030785 MLS
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Popular Communities

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New Home Construction

  • Marco Island
  • Naples

Area Attractions

  • Naples Zoo
  • Naples Botanical Gardens
  • Naples Princess
  • Marco Island Princess
  • Key West Express
  • Rookery Bay
  • Golf Courses
  • Beaches
  • 5th Ave Naples
  • 3rd St. Naples
  • Marco Farmers Market
  • Naples Farmers Market
  • Marco Walk Plaza
  • Tin City Naples

The Ultimate Guide To Selling Your Home

  • The Ultimate Guide To Selling Your Home
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Livin The Dream Team

Keller Williams Marco Island/Naples Realty

830 Bald Eagle Drive

Marco Island, FL 34145

239-682-7600

  • Marco Island
  • Fiddler's Creek
  • Treviso Bay
  • The Isles
  • Hammock Bay
  • Lely Resort
  • Winding Cypress
  • Naples Reserve
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