Top 10 Most Expensive Streets in Winnetka, IL

Sheridan Road is the 1st most expensive street in Winnetka. It has single-family homes built from 1917 to 2021, ranging in price from $1,311,375 to $31,250,000. It is home to the East Winnetka subdivision.

Pine Lane is the 2nd most expensive street in Winnetka. It has single-family homes built in 2010, with an average sale price of $5,500,000.

Blackthorn Road is the 3rd most expensive street in Winnetka. It has single-family homes built in 2009, with an average sale price of $5,157,000.

Prospect Avenue is the 4th most expensive street in Winnetka. It has single-family homes built from 1898 to 1970, ranging in price from $1,725,000 to $8,500,000.

Church Road is the 5th most expensive street in Winnetka. It has single-family homes built in 1906, with an average sale price of $4,919,900.

Fox Lane is the 6th most expensive street in Winnetka. It has single-family homes built in 1926, with an average sale price of $4,625,000.

Lindenwood Drive is the 7th most expensive street in Winnetka. It has single-family homes built in 2012, with an average sale price of $4,450,000.

Kent Road is the 8th most expensive street in Winnetka. It has single-family homes built in 2005, with an average sale price of $4,300,000.

Starr Road is the 9th most expensive street in Winnetka. It has single-family homes built in 1921, with an average sale price of $4,125,000.

Heather Lane is the 10th most expensive street in Winnetka. It has single-family homes built in 1955, with an average sale price of $3,988,472.