Winding Cypress

Winding Cypress is a gated community of single family homes, and townhomes in Naples, Florida, with a range of options priced between $649,900 and $1,595,000. There are currently a total of 21 homes for sale in Winding Cypress. The smallest Winding Cypress home presently available is a two bedroom two bathroom residence that is 1,574 square feet, and the largest of the Winding Cypress homes currently on the market has four beds and four baths and is a 4,415 square foot (3,656SF Under Air) residence.

The Winding Cypress community offers a plethora of amenities for its residents to enjoy, including a clubhouse, swimming pool, spa / hot tub, cabana, a state-of-the-art fitness center, billiards room, hobby room, business center, vehicle wash area, and a library. Sports facilities include tennis courts, pickleball courts, Bocce ball, basketball court, and shuffleboard. Onsite dining venues consist of a restaurant, picnic area, and a barbecue area. There is also a community park, a playground, a dog park, walking or jogging trails, as well as guest suites for visitors.

Pets are allowed in Winding Cypress. Dogs and cats are allowed.

There are two commercial airports that serve Winding Cypress - Southwest Florida International Airport (RSW), which is 33 miles away, and Page Field (FMY), which is 38 miles away.

Winding Cypress real estate activity on the Naples MLS during the past year (as of November 2025) reflects 39 homes changing hands, with an average asking price of $861,138 and an average selling price of $815,038. This represents a healthy list-to-sell price ratio of 95% and $294 per square foot. During this period, Winding Cypress homes for sale have taken an average of 157 days to sell.

In addition, there are numerous other communities in Naples to choose from, or you may browse all available Naples Real Estate, including some new construction opportunities. Homes for sale in Winding Cypress are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winding Cypress hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Gulf Coast real estate needs.

Winding Cypress Homes For Sale

Reduced

$1.595 Million

$1,695,000

MLS#225067265

7412 Winding Cypress Dr
Naples, FL 34114

4

4

3

4,415 SqFt

Pool

Water Front

0.202 Acres

70 Days

$1,188,000

MLS#225067825

7457 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,470 SqFt

Pool

0.19 Acres

44 Days

Reduced

$1,160,000

$1,299,000

MLS#225038123

7520 Blackberry Dr
Naples, FL 34114

3

3

3

3,061 SqFt

Pool

0.2 Acres

223 Days

Reduced

$959,900

$999,000

MLS#225050485

6787 Pennyroyal Dr
Naples, FL 34114

3

2

2

2,300 SqFt

Pool

Water Front

0.16 Acres

177 Days

$950,000

MLS#225065830

6902 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,557 SqFt

Pool

0.2 Acres

104 Days

$925,000

MLS#225075399

6699 Pennyroyal Dr
Naples, FL 34114

3

2

2

2,505 SqFt

Pool

Water Front

0.21 Acres

37 Days

Under Contract

$900,000

MLS#225078259

7355 Mockingbird Ct
Naples, FL 34114

3

2

2

2,640 SqFt

Pool

Water Front

0.17 Acres

337 Days

$899,000

MLS#225071664

6856 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,557 SqFt

Pool

61 Days

Reduced

$825,000

$899,000

MLS#225065477

6770 Pennyroyal Dr
Naples, FL 34114

3

3

2

2,602 SqFt

0.17 Acres

114 Days

$819,000

MLS#225074768

7057 Live Oak Dr
Naples, FL 34114

3

2

2

2,690 SqFt

0.16 Acres

37 Days

Reduced

$749,900

$760,000

MLS#225068781

7670 Jacaranda Ln
Naples, FL 34114

3

2

2

Pool

83 Days

Under Contract

$665,000

$795,900

MLS#224103914

7370 Mockingbird Ct
Naples, FL 34114

2

2

2

2,222 SqFt

Water Front

0.19 Acres

323 Days

21 Active Listings in Winding Cypress