Winding Cypress Naples

Winding Cypress is a new community of homes in Naples, Southwest Florida. Nestled amongst 800 acres of natural preserves and 80 acres of pristine lakes, the 1,100 acre Winding Cypress is a stunning place to call home.

Winding Cypress is situated across from Lely Resort in South Naples, and less than 10 miles from 5th Avenue and the beaches. The amenities at Winding Cypress are more akin to a world class luxury resort, than this beautiful semi-urban setting. Tennis courts, bocce-ball, fitness center, swimming pools and miles of walking and jogging trails are designed to allow you to embrace the outdoor lifestyle which southwest Florida is famous for.

Winding Cypress is pet friendly and with extensive trails, a boardwalk and also has a special park area where you can exercise your companion.

For those who are less physically inclined, there is ample opportunity for bird-watching, sitting by the fire-pit watching stars or enjoying a drink in the barefoot bar at the ‘beach-entry swimming pool.

When you need a change of pace Naples’ 5th Avenue is just a short drive away and here you will find excellent shopping in the boutiques and galleries, plus have the opportunity to enjoy a meal in one of the many great restaurants.

Models at Winding Cypress in Naples

There is a good choice of floor plans available at Winding Cypress with prices starting from the mid $200,000’s in this first phase.


Serenity model at Winding Cypress NaplesSerenity

2 Bedrooms

2 Bathrooms

1,542 Square Feet

Starting from $275,990



Abbeyville model at Winding Cypress NaplesAbbeyville

2 Bedrooms

2 Bathrooms

1,659 Square Feet

Starting from $331,990



Summerwood model at Winding Cypress NaplesSummerwood

2 Bedrooms

2 Bathrooms

1,861+ Square Feet

Starting from $362,990


Martin Ray model at Winding Cypress NaplesMartin Ray

2 Bedrooms

2 Bathrooms

1,968+ Square Feet

Starting from $366,990



Infinity model at Winding Cypress NaplesInfinity

3 Bedrooms

3 Bathrooms

2,385+ Square Feet

Starting from $445,990



Pinnacle model at Winding Cypress NaplesPinnacle

3 Bedrooms

3 Bathrooms

2,488+ Square Feet

Starting from $431,990



Tangerly Oak model at Winding Cypress NaplesTangerly Oak

2 Bedrooms

2.5 Bathrooms

2,589+ Square Feet

Starting from $440,990



  • Resort Style Pool
  • State of the Art Fitness Center & Movement Studio
  • Outdoor Barefoot Bar
  • Bocce Ball Courts
  • Tennis Courts
  • Clubhouse with Community Room and Activity Rooms
  • Activity Director
  • Fire Pit
  • Dog Park
  • Boardwalk with Pavilion and Bird Wading Overlook
  • 20 Minutes to Marco Island
  • 20 Minutes to Naples Pier and magnificent area beaches
  • 15 Minutes to Fifth Avenue Shopping & Dining
  • 10 Minutes to I-75
  • 5 Minutes to US-41
  • 80 Acres of Lakes
  • 800+ Acres of Natural Preserves


Approximate Location

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