Top 10 Most Expensive Streets in Bucktown, Chicago, IL

The following are the Top 10 most expensive streets in Bucktown. The average price for homes on these streets range from $1,563,500 to $2,650,000.

1. Castlewood Terrace

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.

Average Price: $2,650,000
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2. Fern Court

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.

Average Price: $2,325,000
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3. Race Street

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.

Average Price: $2,210,000
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4. Wacker Drive

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.

Average Price: $2,173,890
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5. Marion Court

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.

Average Price: $1,962,500
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6. Oak Street

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.

Average Price: $1,839,583
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7. Howe Street

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 and 1964 N. Howe subdivisions.

Average Price: $1,728,293
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8. Dayton Street

Dayton Street is the 8th most expensive street in Chicago. It has condos, single-family homes, townhouses, and land built from 1890 to 2025, ranging in price from $505,000 to $4,000,000. It is home to the 1651 N. Dayton, 4324 N. Dayton, and 1911 N. Dayton subdivisions.

Average Price: $1,669,455
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9. Maud Avenue

Maud Avenue is the 9th 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.

Average Price: $1,571,000
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10. Ainslie Avenue

Ainslie Avenue is the 10th most expensive street in Chicago. It has single-family homes and multi-units ranging in price from $827,000 to $2,300,000.

Average Price: $1,563,500
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