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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

6962 Winding Cypress Dr, Naples image
6962 Winding Cypress Dr, Naples $1,865,000

Presenting the exclusive Stonewater model in Winding Cypress. This impeccably maintained home is nearly new, offering three bedrooms, a versatile den, and three baths, pl...

  • 3 Beds
  • 3.5 Baths
  • 223069971 MLS
7441 Winding Cypress Dr, Naples image
7441 Winding Cypress Dr, Naples $759,900 ▼

This rarely available Abbeyville with a Premium Waterfront location has been meticulously maintained. The open concept will astound while walking into the light kitchen f...

  • 2 Beds
  • 2 Baths
  • 223069455 MLS
7097 Live Oak Dr, Naples image
7097 Live Oak Dr, Naples — Winding Cypress $594,095 ▼

Special Financing available.  Contact a Sales Consultant for more information. Your final opportunity to own a new home at Winding Cypress is here! This serenity villa ho...

  • 2 Beds
  • 2 Baths
  • 222037701 MLS
  • Winding Cypress Bldg.
7634 Arrowhead Way, Naples image
7634 Arrowhead Way, Naples $1,200,000

Discover Your Dream Home Nestled W/in The Prestigious Community Of Winding Cypress. This Exquisite Residence Epitomizes Luxury Living W/ Its Open-Concept Design Seamlessl...

  • 3 Beds
  • 2 Baths
  • 223065392 MLS
7175 Live Oak Dr, Naples image
7175 Live Oak Dr, Naples $699,000

V11010 Beautifully updated 3 bedroom in Winding Cypress. This Serenity floorplan features granite kitchen with under cabinet lighting, pantry plus a hands-free faucet. Op...

  • 3 Beds
  • 2 Baths
  • 223051149 MLS
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New Construction Communities

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Popular Communities

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New Home Construction

  • Marco Island
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Area Attractions

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The Ultimate Guide To Selling Your Home

  • The Ultimate Guide To Selling Your Home
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1079 Bald Eagle Dr. Unit #1004 Marco Island, FL

239-682-7600

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