Top 10 Most Expensive Streets in Winter Park, FL

Isle Of Sicily is the 1st most expensive street in Winter Park. It has single-family homes built in 2014, with an average sale price of $9,700,000.

Anchorage Court is the 2nd most expensive street in Winter Park. It has single-family homes built in 2021, with an average sale price of $6,600,000.

Golfview Terrace Terrace is the 3rd most expensive street in Winter Park. It has single-family homes built in 2023, with an average sale price of $6,300,000. It is home to the Golfview Terrace subdivision.

Virginia Drive is the 4th most expensive street in Winter Park. It has single-family homes built from 1969 to 2021, ranging in price from $3,250,000 to $10,900,000.

Via Tuscany is the 5th most expensive street in Winter Park. It has single-family homes built from 1919 to 2024, ranging in price from $3,500,000 to $9,250,000.

Laurel Road is the 6th most expensive street in Winter Park. It has single-family homes built in 1994, with an average sale price of $4,500,000.

Tom Gurney Drive is the 7th most expensive street in Winter Park. It has single-family homes built in 1997, with an average sale price of $4,330,000.

Via Palermo is the 8th most expensive street in Winter Park. It has single-family homes built in 2018, with an average sale price of $3,850,000.

Via Lugano is the 9th most expensive street in Winter Park. It has single-family homes built from 1990 to 2007, ranging in price from $3,800,000 to $3,850,000. It is home to the Lugano Terrace subdivision.

Via Del Mar is the 10th most expensive street in Winter Park. It has single-family homes built from 2020 to 2024, ranging in price from $3,550,000 to $3,850,000.