Top 10 Most Expensive Streets in Winnetka

Blackthorn Road is the 1st most expensive street in Winnetka, with single family homes built from 1917 to 2020, and averaging $5,157,000.

Sheridan Road is the 2nd most expensive street in Winnetka, with single family homes built from 1905 to 2022, and ranging in price from $1,311,375 to $12,500,000. It is home to the East Winnetka subdivision.

Prospect Avenue is the 3rd most expensive street in Winnetka, with single family homes built from 2014 to 2019, and ranging in price from $1,600,000 to $8,500,000. It is home to the East Winnetka subdivision.

Fox Lane is the 4th most expensive street in Winnetka, with single family homes built from 1926 to 1948, and averaging $4,625,000. It is home to the Indian Hill subdivision.

Lindenwood Drive is the 5th most expensive street in Winnetka, with single family homes built from 1953 to 2012, and averaging $4,450,000.

Kent Road is the 6th most expensive street in Winnetka, with single family homes built from 1917 to 2005, and averaging $4,300,000.

Starr Road is the 7th most expensive street in Winnetka, with single family homes built from 1927 to 2014, and averaging $4,125,000.

Meadow Lane is the 8th most expensive street in Winnetka, with single family homes built from 1926 to 2013, and averaging $4,000,000.

Heather Lane is the 9th most expensive street in Winnetka, with single family homes built from 1952 to 2026, and averaging $3,988,472.

Gordon Terrace is the 10th most expensive street in Winnetka, with single family homes built from 1878 to 2017, and averaging $3,900,000.