Top 10 Most Expensive Streets in Winter Park, FL

Fosgate Drive is the 1st most expensive street in Winter Park. It has single-family homes built from 1956 to 1957, ranging in price from $999,999 to $1,186,200. It is home to the Timberlane subdivision.

Woodland Avenue is the 2nd most expensive street in Winter Park. It has single-family homes built in 1953, with an average sale price of $750,000. It is home to the Comstock Park subdivision.

Mckean Circle is the 3rd most expensive street in Winter Park. It has single-family homes built in 1955, with an average sale price of $1,430,000. It is home to the Palmer Park subdivision.

Lazy Oaks Drive is the 4th most expensive street in Winter Park. It has condos built from 1982 to 1984, ranging in price from $260,000 to $285,000. It is home to the Lazy Oaks subdivision.

Tom Gurney Drive is the 5th most expensive street in Winter Park. It has single-family homes built in 1997, with an average sale price of $4,330,000. It is home to the Tuscania subdivision.

Woodcrest Drive is the 6th most expensive street in Winter Park. It has single-family homes and condos built from 1961 to 2020, ranging in price from $195,900 to $1,170,000. It is home to the Woodcrest subdivision.

Lake Howell Lane is the 7th most expensive street in Winter Park. It has land and single-family homes built from 1954 to 1996, ranging in price from $1,099,000 to $3,400,000.

Pine Avenue is the 8th most expensive street in Winter Park. It has single-family homes built from 1951 to 2022, ranging in price from $1,102,000 to $2,371,600. It is home to the Lake Knowles Terrace and Conwill Estates subdivisions.

Overlook Road is the 9th most expensive street in Winter Park. It has single-family homes built from 1925 to 1936, with an average sale price of $1,000,000. It is home to the Sylvan Lake Shores subdivision.

Soaring Oak Way is the 10th most expensive street in Winter Park. It has single-family homes built in 2021, ranging in price from $899,000 to $1,080,000. It is home to the Waters Edge at Hawks Crest subdivision.