Winding Cypress

Winding Cypress is a gated community of single family homes, and townhomes in Naples, Florida, with a range of options priced between $630,000 and $1,595,000. There are currently a total of 28 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 February 2026) reflects 41 homes changing hands, with an average asking price of $852,132 and an average selling price of $804,878. This represents a healthy list-to-sell price ratio of 94% and $293 per square foot. During this period, Winding Cypress homes for sale have taken an average of 163 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

Under Contract

$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

163 Days

Reduced

$1,499,900

$1,599,900

MLS#225084091

7072 Live Oak Dr
Naples, FL 34114

4

4

2

3,714 SqFt

Pool

Water Front

0.2 Acres

53 Days

Under Contract

$1,160,000

$1,299,000

MLS#225038123

7520 Blackberry Dr
Naples, FL 34114

3

3

3

3,061 SqFt

Pool

0.2 Acres

316 Days

Reduced

$1,098,000

$1,188,000

MLS#225067825

7457 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,470 SqFt

Pool

0.19 Acres

137 Days

Reduced

$1,050,000

$1,150,000

MLS#225081501

6825 Greenbriar Ct
Naples, FL 34114

4

3

2

3,166 SqFt

Pool

0.18 Acres

85 Days

$949,900

MLS#226005365

6844 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,400 SqFt

Pool

0.165 Acres

17 Days

$949,000

MLS#226000491

7679 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,591 SqFt

Water Front

0.17 Acres

49 Days

$943,000

MLS#225082316

6698 Pennyroyal Dr
Naples, FL 34114

3

3

2

2,624 SqFt

Pool

0.16 Acres

81 Days

Under Contract

$925,000

MLS#226000187

6779 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,497 SqFt

Pool

Water Front

0.17 Acres

53 Days

Reduced

$919,000

$999,000

MLS#225050485

6787 Pennyroyal Dr
Naples, FL 34114

3

2

2

2,300 SqFt

Pool

Water Front

0.16 Acres

270 Days

Reduced

$899,000

$950,000

MLS#225065830

6902 Winding Cypress Dr
Naples, FL 34114

3

2

2

2,557 SqFt

Pool

0.2 Acres

197 Days

$899,000

MLS#226007913

7460 Blackberry Dr
Naples, FL 34114

3

2

2

2,990 SqFt

Water Front

0.18 Acres

4 Days

28 Active Listings in Winding Cypress