Top 10 Most Expensive Streets in Highland Park, IL

Lakewood Place is the 1st most expensive street in Highland Park. It has single-family homes built from 1929 to 1999, ranging in price from $1,440,000 to $2,300,000.

Sheridan Road is the 2nd most expensive street in Highland Park. It has single-family homes and condos built from 1900 to 2025, ranging in price from $190,000 to $5,750,000. It is home to the Braeside subdivision.

Woodbine Road is the 3rd most expensive street in Highland Park. It has single-family homes built from 1971 to 1977, ranging in price from $600,000 to $1,380,000.

Scott Loop is the 4th most expensive street in Highland Park. It has single-family homes built from 1888 to 1902, ranging in price from $1,236,800 to $1,665,000. It is home to the Fort Sheridan subdivision.

Ridge Road is the 5th most expensive street in Highland Park. It has single-family homes built from 1941 to 2008, ranging in price from $303,500 to $1,805,000. It is home to the Sherwood Forest subdivision.

Winthrop Road is the 6th most expensive street in Highland Park. It has single-family homes built from 1961 to 1963, ranging in price from $350,000 to $705,000. It is home to the Heatherdale subdivision.

Pleasant Avenue is the 7th most expensive street in Highland Park. It has single-family homes built from 1924 to 2003, ranging in price from $265,000 to $803,000.

Burton Avenue is the 8th most expensive street in Highland Park. It has single-family homes built from 1928 to 1961, ranging in price from $515,000 to $711,000. It is home to the Ravinia subdivision.

Green Bay Road is the 9th most expensive street in Highland Park. It has single-family homes, condos, and multi-units built from 1912 to 2012, ranging in price from $400,000 to $1,500,000. It is home to the Ravinia, 1600 Green Bay, and Laurel Hill subdivisions.

Flora Place is the 10th most expensive street in Highland Park. It has single-family homes built from 1948 to 1954, ranging in price from $582,500 to $880,000. It is home to the Ravinia subdivision.