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 $960,000. There are currently a total of 10 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 five baths and is a 5,140 square foot (4,014SF 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 $104. 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 September 2025) reflects seven homes changing hands, with an average asking price of $819,971 and an average selling price of $812,143. This represents a healthy list-to-sell price ratio of 99% and $216 per square foot. During this period, Winding Bay homes for sale have taken an average of 57 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

$960,000

MLS#MFRG5099434

10732 Petrillo Way
Winter Garden, FL 34787

5

6

3

5,140 SqFt

Pool

0.15 Acres

80 Days

Reduced

$959,000

$1,100,000

MLS#MFRO6301935

10699 Petrillo Way
Winter Garden, FL 34787

5

5

2

4,575 SqFt

Pool

0.18 Acres

155 Days

Reduced

$958,000

$1,100,000

MLS#MFRO6308169

15378 Gilligan Ct
Winter Garden, FL 34787

5

5

2

4,577 SqFt

Pool

0.18 Acres

138 Days

$925,000

MLS#MFRO6325190

15113 Mayberry Dr
Winter Garden, FL 34787

5

3

2

4,641 SqFt

Pool

Water Front

0.14 Acres

79 Days

Under Contract

$820,000

MLS#MFRO6342743

15457 Lebeau Loop
Winter Garden, FL 34787

5

4

2

4,337 SqFt

0.15 Acres

13 Days

Reduced

$775,000

$825,000

MLS#MFRO6293366

15313 Lebeau Loop
Winter Garden, FL 34787

4

4

2

3,487 SqFt

Pool

0.15 Acres

178 Days

$744,900

MLS#MFRS5135292

14978 Lebeau Loop
Winter Garden, FL 34787

5

4

2

3,679 SqFt

0.09 Acres

5 Days

$674,000

MLS#MFRA4660262

15456 Gilligan Ct
Winter Garden, FL 34787

3

3

2

3,494 SqFt

0.15 Acres

59 Days

Reduced

$665,000

$685,000

MLS#MFRO6309092

14925 Lebeau Loop
Winter Garden, FL 34787

4

3

2

2,638 SqFt

0.14 Acres

132 Days

Reduced

$615,000

$670,000

MLS#MFRO6308900

15408 Lebeau Loop
Winter Garden, FL 34787

4

3

2

3,261 SqFt

0.09 Acres

129 Days

10 Active Listings in Winding Bay