Top 10 Most Expensive Streets in Winter Garden, FL

Hopetown Alley is the 1st most expensive street in Winter Garden. It has single-family homes built in 2025, with an average sale price of $2,468,640. It is home to the Oakland Park subdivision.

Farm Stand Court is the 2nd most expensive street in Winter Garden. It has single-family homes and land with an average sale price of $2,421,000. It is home to the Oakland Hills subdivision.

Great Blue Heron Court is the 3rd most expensive street in Winter Garden. It has single-family homes built from 2014 to 2015, ranging in price from $2,047,000 to $2,200,000.

Burch Island Court is the 4th most expensive street in Winter Garden. It has single-family homes built in 2018, ranging in price from $1,860,000 to $2,300,000.

Morgana Court is the 5th most expensive street in Winter Garden. It has single-family homes built from 2021 to 2022, ranging in price from $2,050,000 to $2,100,000. It is home to the Avalon Cove subdivision.

Isleview Drive is the 6th most expensive street in Winter Garden. It has single-family homes and land ranging in price from $1,150,000 to $2,600,000. It is home to the Isles of Lake Hancock subdivision.

Wild Blackberry Trail is the 7th most expensive street in Winter Garden. It has single-family homes built from 2011 to 2024, ranging in price from $1,450,000 to $2,392,500.

John Hancock Drive is the 8th most expensive street in Winter Garden. It has single-family homes built from 2017 to 2022, ranging in price from $559,000 to $2,575,000.

Turkey Island Circle is the 9th most expensive street in Winter Garden. It has single-family homes built in 2018, with an average sale price of $1,775,000.

Green Mountain Way is the 10th most expensive street in Winter Garden. It has single-family homes built from 2014 to 2021, ranging in price from $1,450,000 to $2,050,000.