Top 10 Most Expensive Streets in Winter Park, FL
The following are the Top 10 most expensive streets in Winter Park. The average price for homes on these streets range from $3,818,750 to $8,900,000.
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1. Bett Mar Lane
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.
2. Anchorage Court
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.
3. Venetian Way
Venetian Way is the 3rd most expensive street in Winter Park. It has single-family homes built from 1953 to 2008, ranging in price from $3,845,000 to $9,140,000.
4. Howell Point
Howell Point is the 4th most expensive street in Winter Park. It has single-family homes built in 1989, with an average sale price of $6,300,000.
5. Virginia Drive
Virginia Drive is the 5th most expensive street in Winter Park. It has single-family homes built from 1966 to 2021, ranging in price from $3,250,000 to $10,900,000.
6. Chelton Circle
Chelton Circle is the 6th most expensive street in Winter Park. It has single-family homes built in 2024, with an average sale price of $5,250,000.
7. Tom Gurney Drive
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.
8. College Point
College Point is the 8th most expensive street in Winter Park. It has single-family homes built from 1926 to 2005, ranging in price from $3,900,000 to $4,273,211. It is home to the Virginia Heights subdivision.
9. Via Del Mar
Via Del Mar is the 9th most expensive street in Winter Park. It has single-family homes built in 2024, with an average sale price of $3,850,000.
10. Lakewood Drive
Lakewood Drive is the 10th most expensive street in Winter Park. It has single-family homes built from 1954 to 2000, ranging in price from $3,550,000 to $4,087,500.
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