Winding Bay

Winding Bay is a community of single family homes, and townhomes in Winter Garden, Florida, with a range of options priced between $435,000 and $1,049,000. There are currently a total of 8 homes for sale in Winding Bay. The smallest Winding Bay home presently available is a three bedroom three bathroom residence that is 960 square feet (1,732SF Under Air living space), and the largest of the Winding Bay homes currently on the market has five beds and six baths and is a 5,140 square foot (4,025SF 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 $102 and $203 for a townhome. This fee includes common area maintenance, grounds maintenance, the community pool, real estate taxes for common areas, property insurance, trash removal, internet, 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 Orlando Sanford International (SFB), which is 36 miles away from Winding Bay.

Winding Bay real estate activity on the Winter Garden MLS during the past year (as of June 2026) reflects twenty homes changing hands, with an average asking price of $788,030 and an average selling price of $774,440. This represents a healthy list-to-sell price ratio of 98% and $198 per square foot. During this period, Winding Bay homes for sale have taken an average of 61 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 BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Winding Bay Homes For Sale

Reduced

$1,049,000

$1,075,000

MLS#MFRO6382263

10472 Petrillo Way
Winter Garden, FL 34787

5

6

3

5,140 SqFt

Pool

0.17 Acres

130 Days

Reduced

$799,000

$849,000

MLS#MFRO6364989

14931 Lebeau Loop
Winter Garden, FL 34787

4

4

2

3,729 SqFt

Pool

0.14 Acres

199 Days

Under Contract

$799,000

MLS#MFRO6399081

10693 Petrillo Way
Winter Garden, FL 34787

4

4

2

4,110 SqFt

0.17 Acres

68 Days

Reduced

$684,000

$719,999

MLS#MFRTB8472370

16012 Micelli Dr
Winter Garden, FL 34787

4

3

2

2,428 SqFt

0.09 Acres

134 Days

$590,000

MLS#MFRO6417175

15367 Gilligan Ct
Winter Garden, FL 34787

4

3

2

2,954 SqFt

0.09 Acres

8 Days

Reduced

$550,000

$674,000

MLS#MFRA4660262

15456 Gilligan Ct
Winter Garden, FL 34787

3

3

2

3,494 SqFt

0.15 Acres

327 Days

Reduced

$435,000

$445,000

MLS#MFRS5143684

15659 Jungle Aly
Winter Garden, FL 34787

3

3

2

960 SqFt

0.06 Acres

94 Days

$420,000

MLS#MFRS5152170

12042 Grandrose Aly
Winter Garden, FL 34787

3

3

2

1,818 SqFt

0.06 Acres

5 Days

8 Active Listings in Winding Bay