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Winding Cypress Real Estate Search

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Winding Cypress Homes and Condos for Sale

Winding Cypress is a gorgeous gated community in Naples, Florida. Homeowners in Winding Cypress have an assortment of entertaining activities and amenities available to them. Between the heated, resort-style pool and the spa where massages and facials are a must, relaxation never seemed so accessible. Residents can head to the outdoor barefoot bar or to the fantastic clubhouse which is home to an activity room, a library, and a kitchen. Families love the playgrounds, walking trails, and the dog park where kids and pups can run wild. Homeowners can meet friends and neighbors for lunch at the Shady Palm Cafe, or they can train together in the stocked fitness center.

Living in the safe, guarded community is a treat for future homebuyers who crave privacy. Those buyers who are more active can participate in a game of bocce ball or tennis before driving to the Fifth Avenue and Third Street shopping centers where they can shop until they drop and have a delectable meal afterward. Winding Cypress is twenty minutes away from Marco Island as well as Naples Pier and beaches. Precious moments can be captured on the boardwalk, and days can be spent admiring the 800-acres of Nature Preserves, and 80-acres of glistening, flowing lakes. Prospective homebuyers looking for single-family homes for sale in Winding Cypress can look forward to well-built houses with four bedrooms, 2,000 square feet, and vast 8,000 square foot properties. If you are interested in buying a home for sale in Winding Cypress, Florida, please contact us today.

Newest Winding Cypress Homes and Condos for Sale

7263 Clamshell Ln, Naples image
7263 Clamshell Ln, Naples $1,595,000

New to the market! (Professional photos are on their way) Make this stunning 3-bedroom 3-bathroom home your "forever home" in the exclusive gated community called Windin...

  • 3 Beds
  • 3 Baths
  • 223009227 MLS
7611 Jacaranda Ln, Naples image
7611 Jacaranda Ln, Naples $736,000

Presenting the rare opportunity to own a luxury villa Serenity model with saltwater pool and hot tub spa set on a breathtaking view over water and sunset. This highly sou...

  • 2 Beds
  • 2 Baths
  • 223004659 MLS
6762 Pennyroyal Dr, Naples image
6762 Pennyroyal Dr, Naples $979,000

Stunning Summerwood POOL home with expansive LOFT in Winding Cypress, a premier Naples Location. Better than new, barely lived in 3 Bedroom plus DEN, 3 FULL BATH home. ...

  • 3 Beds
  • 3 Baths
  • 222068098 MLS
6754 Pennyroyal Dr, Naples image
6754 Pennyroyal Dr, Naples $998,900

NICER THAN A MODEL HOME!!! Spacious 3 bedroom + den, 3 FULL bathroom house with FULL impact glass doors and windows. $138,000 in builder upgrades PLUS over $110,000 in CU...

  • 3 Beds
  • 3 Baths
  • 223004832 MLS
7021 Live Oak Dr, Naples image
7021 Live Oak Dr, Naples $975,000

Just water and trees. This ultra-premium home and lot has waterfront, preserve, and sunset western views set in the ultimate Naples resort community of Winding Cypress. T...

  • 4 Beds
  • 3 Baths
  • 223004315 MLS
7768 Winding Cypress Dr, Naples image
7768 Winding Cypress Dr, Naples $879,000

H8344. Desirable 2021 built Summerwood within the gated natural gas community of Winding Cypress. Wood plank laminate floor throughout common living spaces and den. Brown...

  • 2 Beds
  • 2 Baths
  • 223002759 MLS
7211 Live Oak Dr, Naples image
7211 Live Oak Dr, Naples $990,000 ▼

The ultimate waterfront home site in the resort community of Winding Cypress in Naples. This Summerwood model has every option and add-on imaginable. From impact windows ...

  • 3 Beds
  • 2 Baths
  • 223003084 MLS
7483 Blackberry Dr, Naples image
7483 Blackberry Dr, Naples $1,595,000

Wow! This beautifully designed and meticulously maintained home is spectacular. Featuring the highly desirable and rarely available Stonewater floor plan, you are welcome...

  • 3 Beds
  • 3.5 Baths
  • 223002560 MLS
7453 Winding Cypress Dr, Naples image
7453 Winding Cypress Dr, Naples $1,250,000 ▼

Combining the unique privacy of a long lake view with the unparalleled value offered in Winding Cypress, this Pinnacle model is everything you are seeking in your new Nap...

  • 3 Beds
  • 3 Baths
  • 222089855 MLS
7546 Blackberry Dr, Naples image
7546 Blackberry Dr, Naples $989,000 ▼

Beautifully appointed Summerwood floorplan, with over $150,000.00 in builder design option upgrades, heated pool and spa, raised ceilings, and more. The owners have added...

  • 3 Beds
  • 2 Baths
  • 222086983 MLS
7235 Live Oak Dr, Naples image
7235 Live Oak Dr, Naples $1,125,000 ▼

Pristine 3+den pool home with lake views in highly sought-after Winding Cypress. They spared no expense with upgrades everywhere to include custom saltwater pool, walk-in...

  • 3 Beds
  • 3 Baths
  • 222084256 MLS

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

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Leah Paige ~ Realtor®

2020-2021 Florida Realtors® Director
GRI, CHLMS, RSPS, ABR, SRS, e-PRO, CNE, PSA, AWD
Naples Five Star Professional Agent - 2018, 2019, 2020, 2021

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