Castlewood Terrace

Castlewood Terrace is a residential block in Uptown comprising 26 single-family homes with spacious lots and front driveways, surrounded by high-rise buildings. The street forms a cohesive architectural group of two to three-story structures that contrasts with the tall apartment buildings neighboring the area.

The homes were built between 1897 and 1927 as a residential enclave in an area of rapidly changing development. The ensemble was added to the National Register of Historic Places in 2009, recognizing its importance for preserving this residential architecture.

The district displays various architectural styles including Tudor Revival, Renaissance Revival, Foursquare, Colonial Revival, and Queen Anne across its residential structures. Visitors can observe the different details and facades that show how various periods and tastes were expressed in the architecture of these homes.

The dead-end street experiences minimal traffic, making it a quiet place to walk and explore at your own pace. Proximity to Chicago public transit options provides easy access for visitors arriving from other neighborhoods.

Contrary to Uptown overall, residents successfully resisted high-rise development throughout the 20th century. This created a rare pocket of low-rise brick homes in an area otherwise dominated by tall apartment complexes.

Location: Chicago

Address: 819-959 West Castlewood Terrace

GPS coordinates: 41.97056,-87.65167

Latest update: December 14, 2025 11:00