Winding Cypress

Winding Cypress is a gated community of single family homes, and townhomes in Naples, Florida, with a range of options priced between $639,900 and $1,599,900. There are currently a total of 24 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 January 2026) reflects 40 homes changing hands, with an average asking price of $858,760 and an average selling price of $813,038. 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 168 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

$1,599,900

MLS#225084091

7072 Live Oak Dr
Naples, FL 34114

4

4

2

3,714 SqFt

Pool

Water Front

0.2 Acres

5 Days

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

115 Days

Under Contract

$1,200,000

MLS#225083620

7716 Winding Cypress Dr
Naples, FL 34114

3

4

3

3,997 SqFt

Pool

Water Front

0.23 Acres

14 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

268 Days

Reduced

$1,155,000

$1,188,000

MLS#225067825

7457 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,470 SqFt

Pool

0.19 Acres

89 Days

$1,150,000

MLS#225081501

6825 Greenbriar Ct
Naples, FL 34114

4

3

2

3,166 SqFt

Pool

0.18 Acres

37 Days

Reduced

$949,900

$999,000

MLS#225050485

6787 Pennyroyal Dr
Naples, FL 34114

3

2

2

2,300 SqFt

Pool

Water Front

0.16 Acres

222 Days

$949,000

MLS#226000491

7679 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,591 SqFt

Water Front

0.17 Acres

1 Days

$943,000

MLS#225082316

6698 Pennyroyal Dr
Naples, FL 34114

3

3

2

2,624 SqFt

Pool

0.16 Acres

33 Days

Reduced

$925,000

$950,000

MLS#225065830

6902 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,557 SqFt

Pool

0.2 Acres

149 Days

$925,000

MLS#226000187

6779 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,497 SqFt

Pool

Water Front

0.17 Acres

5 Days

Under Contract

$899,000

MLS#225071664

6856 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,557 SqFt

Pool

106 Days

24 Active Listings in Winding Cypress