Top 10 Most Expensive Streets in Bucktown, Chicago, IL

Castlewood Terrace is the 1st most expensive street in Chicago. It has single-family homes built from 1909 to 1990, with an average sale price of $2,650,000.

Fern Court is the 2nd most expensive street in Chicago. It has single-family homes built in 1903, with an average sale price of $2,325,000.

Race Street is the 3rd most expensive street in Chicago. It has single-family homes built in 2020, with an average sale price of $2,210,000.

Wacker Drive is the 4th most expensive street in Chicago. It has condos built from 2020 to 2021, ranging in price from $930,000 to $6,475,000. It is home to the Vista Residences subdivision.

Marion Court is the 5th most expensive street in Chicago. It has single-family homes built from 1999 to 2024, ranging in price from $1,550,000 to $2,375,000.

Oak Street is the 6th most expensive street in Chicago. It has condos and townhouses built from 1995 to 2015, ranging in price from $435,000 to $5,250,000. It is home to the 30 W. Oak, Oak Club Condos, and Oak Street Terrace subdivisions.

Howe Street is the 7th most expensive street in Chicago. It has condos and single-family homes built from 1904 to 2025, ranging in price from $250,100 to $4,400,000. It is home to the 2020 N. Howe subdivision.

Maud Avenue is the 8th most expensive street in Chicago. It has townhouses, single-family homes, and condos built from 1989 to 2025, ranging in price from $630,000 to $2,650,000. It is home to the 1920 N. Maud Ave. and Maud Court subdivisions.

Ainslie Avenue is the 9th most expensive street in Chicago. It has single-family homes and multi-units ranging in price from $827,000 to $2,300,000.

Dayton Street is the 10th most expensive street in Chicago. It has condos, single-family homes, townhouses, and land ranging in price from $505,000 to $3,100,000. It is home to the 1651 N. Dayton, 4324 N. Dayton, and 1911 N. Dayton subdivisions.