Top 10 Most Expensive Streets in Oakland, Chicago, IL

Clifton Street is the 1st most expensive street in Chicago. It has single-family homes built in 2008, with an average sale price of $3,275,000.

Wacker Drive is the 2nd most expensive street in Chicago. It has condos ranging in price from $800,000 to $7,000,000. It is home to the Vista Residences subdivision.

Castlewood Terrace is the 3rd most expensive street in Chicago. It has single-family homes built from 1909 to 1990, ranging in price from $1,399,000 to $2,775,000.

Caton Street is the 4th most expensive street in Chicago. It has single-family homes built from 1888 to 1906, ranging in price from $1,575,000 to $2,370,000.

Draper Street is the 5th most expensive street in Chicago. It has condos and single-family homes built from 1900 to 2016, ranging in price from $565,000 to $4,150,000.

Saint James Place is the 6th most expensive street in Chicago. It has condos and single-family homes built from 1893 to 2024, ranging in price from $153,000 to $4,395,000.

Marion Court is the 7th most expensive street in Chicago. It has single-family homes and townhouses built from 1878 to 2024, ranging in price from $1,380,000 to $2,375,000.

Bell Street is the 8th most expensive street in Chicago. It has single-family homes built in 2008, with an average sale price of $1,740,000.

Howe Street is the 9th most expensive street in Chicago. It has single-family homes, condos, and townhouses built from 1905 to 2025, ranging in price from $325,000 to $4,400,000. It is home to the 2020 N. Howe, Old Town Village, and 1964 N. Howe subdivisions.

Maud Avenue is the 10th most expensive street in Chicago. It has single-family homes, condos, and townhouses ranging in price from $685,000 to $2,650,000. It is home to the 1920 N. Maud Ave., 1916 N. Maud, and Maud Court subdivisions.