Winding Bay

Winding Bay is a community of single family homes, and townhomes in Winter Garden, Florida, with a range of options priced between $403,990 and $1,200,000. There are currently a total of 15 homes for sale in Winding Bay. The smallest Winding Bay home presently available is a three bedroom two bathroom residence that is 2,172 square feet (1,944SF Under Air living space), and the largest of the Winding Bay homes currently on the market has five beds and four baths and is a 4,634 square foot (3,672SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Winding Bay range from $101 to $105. This fee includes common area maintenance, grounds maintenance, the community pool, real estate taxes for common areas, property insurance, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Winding Bay home.

Winding Bay amenities include a clubhouse, and swimming pool. Sports facilities include tennis courts, and basketball court. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Winding Bay HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

There are four commercial airports that serve Winding Bay - Kissimmee Gateway (ISM), which is fourteen miles away; Orlando International (MCO), which is twenty miles away; Orlando Executive (ORL), which is twenty one miles away, and Lakeland Linder International (LAL), which is 36 miles away from Winding Bay.

Winding Bay real estate activity on the Winter Garden MLS during the past year (as of February 2026) reflects nine homes changing hands, with an average asking price of $762,756 and an average selling price of $756,111. This represents a healthy list-to-sell price ratio of 99% and $197 per square foot. During this period, Winding Bay homes for sale have taken an average of 60 days to sell.

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

Winding Bay Homes For Sale

$1,200,000

MLS#MFRO6372954

15312 Gilligan Ct
Winter Garden, FL 34787

5

5

2

4,582 SqFt

Pool

Water Front

0.15 Acres

21 Days

$975,000

MLS#MFRO6375228

15391 Lebeau Loop
Winter Garden, FL 34787

4

4

2

3,986 SqFt

Pool

0.15 Acres

23 Days

$950,000

MLS#MFRO6362955

14955 Lebeau Loop
Winter Garden, FL 34787

5

4

2

4,343 SqFt

Pool

0.14 Acres

79 Days

Reduced

$919,999

$960,000

MLS#MFRO6368778

10551 Petrillo Way
Winter Garden, FL 34787

5

5

2

4,634 SqFt

0.21 Acres

51 Days

Under Contract

$899,000

$1,100,000

MLS#MFRO6301935

10699 Petrillo Way
Winter Garden, FL 34787

5

5

2

4,575 SqFt

Pool

0.18 Acres

292 Days

$884,500

MLS#MFRO6367059

15372 Gilligan Ct
Winter Garden, FL 34787

4

4

2

3,480 SqFt

Pool

0.15 Acres

59 Days

Under Contract

$874,500

$924,900

MLS#MFRO6355206

15378 Gilligan Ct
Winter Garden, FL 34787

5

5

2

4,577 SqFt

Pool

0.18 Acres

111 Days

Reduced

$834,000

$849,000

MLS#MFRO6364989

14931 Lebeau Loop
Winter Garden, FL 34787

4

4

2

3,729 SqFt

Pool

0.14 Acres

68 Days

Under Contract

$799,500

$830,000

MLS#MFRO6371897

10759 Petrillo Way
Winter Garden, FL 34787

5

4

2

4,278 SqFt

0.17 Acres

35 Days

$719,999

MLS#MFRTB8472370

16012 Micelli Dr
Winter Garden, FL 34787

4

3

2

2,428 SqFt

0.09 Acres

3 Days

$699,000

MLS#MFRO6365269

15399 Gilligan Ct
Winter Garden, FL 34787

4

4

2

3,658 SqFt

0.09 Acres

70 Days

Reduced

$665,000

$685,000

MLS#MFRO6309092

14925 Lebeau Loop
Winter Garden, FL 34787

4

3

2

2,638 SqFt

0.14 Acres

269 Days

15 Active Listings in Winding Bay