Top 10 Most Expensive Streets in Winter Park, FL

Bett Mar Lane is the 1st most expensive street in Winter Park. It has single-family homes built in 1995, with an average sale price of $8,900,000.

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.

Howell Point is the 3rd most expensive street in Winter Park. It has single-family homes built in 1989, with an average sale price of $6,300,000.

Golfview Terrace Terrace is the 4th 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 5th 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 6th most expensive street in Winter Park. It has single-family homes built from 1919 to 2024, ranging in price from $1,600,000 to $9,250,000.

Chelton Circle is the 7th most expensive street in Winter Park. It has single-family homes built in 2024, with an average sale price of $5,250,000.

Venetian Way is the 8th most expensive street in Winter Park. It has single-family homes built from 1953 to 2008, ranging in price from $1,089,000 to $9,140,000.

Tom Gurney Drive is the 9th most expensive street in Winter Park. It has single-family homes built in 1997, with an average sale price of $4,330,000.

College Point is the 10th most expensive street in Winter Park. It has single-family homes built from 1926 to 2005, with an average sale price of $3,900,000. It is home to the Virginia Heights subdivision.