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Winding Cypress is a nature focused community that offers a peaceful retreat on 1,100 acres, with over 800 acres dedicated to natural preserves. The community emphasizes outdoor living, with resort-style amenities that include a clubhouse with a state of the art fitness center, a lagoon style pool and tennis and pickleball courts. Residents can explore the surroundings via the community’s extensive network of walking and biking trails. Winding Cypress offers a variety of single-family homes and villas, each designed to blend seamlessly with the natural environment. The community's location provides residents with easy access to both Marco Island and downtown Naples.
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FEATURED LISTINGS WINDING CYPRESS
- 1/36 36Open 1/18 1PM-4PM
$1,188,000
3 Beds2 Baths2,166 SqFt7457 Winding Cypress DR, Naples, FL 34114
Single Family Home
Listed by Gulf Coast International Prop
- 1/48 48Open Sun 1PM-4PM
$1,160,000
3 Beds3 Baths2,496 SqFt7520 Blackberry DR, Naples, FL 34114
Single Family Home
Listed by Premier Sotheby's Int'l Realty
- 1/50 50Active
$943,000
3 Beds3 Baths2,150 SqFt6698 Pennyroyal DR, Naples, FL 34114
Single Family Home
Listed by Premier Sotheby's Int'l Realty
- 1/45 45Active
$1,150,000
4 Beds3 Baths3,036 SqFt6825 Greenbriar CT, Naples, FL 34114
Single Family Home
Listed by William Raveis Real Estate
- 1/48 48Active
$600,000
3 Beds2 Baths1,554 SqFt7167 Live Oak DR, Naples, FL 34114
Single Family Home
Listed by Premier Sotheby's Int'l Realty
- 1/43 43Pending
$900,000
3 Beds2 Baths2,198 SqFt7355 Mockingbird CT, Naples, FL 34114
Single Family Home
Listed by Realty One Group MVP
- 1/49 49Active
$925,000
3 Beds2 Baths2,094 SqFt6699 Pennyroyal DR, Naples, FL 34114
Single Family Home
Listed by William Raveis Real Estate
- 1/43 43Active
$819,000
3 Beds2 Baths2,230 SqFt7057 Live Oak DR, Naples, FL 34114
Single Family Home
Listed by Premiere Plus Realty Company
- 1/37 37Price Dropped by $10K
$639,900
2 Beds2 Baths1,685 SqFt7248 Live Oak DR, Naples, FL 34114
Single Family Home
Listed by William Raveis Real Estate
- 1/49 49Active
$899,000
3 Beds2 Baths2,084 SqFt6856 Winding Cypress DR, Naples, FL 34114
Single Family Home
Listed by Berkshire Hathaway FL Realty
- 1/37 37Price Dropped by $100K
$1,595,000
4 Beds4 Baths3,656 SqFt7412 Winding Cypress DR, Naples, FL 34114
Single Family Home
Listed by Manuela Realty
- 1/45 45Pending
$599,900
2 Beds2 Baths1,544 SqFt7659 Jacaranda LN, Naples, FL 34114
Single Family Home
Listed by Premiere Plus Realty Company













