Top 10 Most Expensive Streets in Oakland Park, Winter Garden, FL

Isleview Drive is the 1st most expensive street in Winter Garden. It has single-family homes and land built in 2010, ranging in price from $1,150,000 to $4,560,000. It is home to the Isles of Lake Hancock subdivision.

Hopetown Alley is the 2nd 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.

Phil C Peters Road is the 3rd most expensive street in Winter Garden. It has land and single-family homes built in 2004, with an average sale price of $2,250,000. It is home to the Lake Avalon Groves subdivision.

Great Blue Heron Court is the 4th 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.

Crown Point Road is the 5th most expensive street in Winter Garden. It has land with an average sale price of $2,100,000.

Roberson Road is the 6th most expensive street in Winter Garden. It has land with an average sale price of $2,100,000.

Morgana Court is the 7th most expensive street in Winter Garden. It has single-family homes built from 2021 to 2022, ranging in price from $1,875,000 to $2,100,000. It is home to the Avalon Cove subdivision.

Agnes Street is the 8th most expensive street in Winter Garden. It has single-family homes built from 1924 to 2023, with an average sale price of $1,950,000.

Burch Island Court is the 9th most expensive street in Winter Garden. It has single-family homes built in 2018, with an average sale price of $1,860,000.

John Hancock Drive is the 10th 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.