Kenwood was once one of the most elite neighborhoods in Chicago and contains some of the largest homes in the city. Burnham Park runs along Kenwood's lakefront.

Kenwood is bisected by 47th Street, which marks a dramatic sociocultural and architectural boundary. North Kenwood suffered significant depopulation and attendant decline of the housing stock and retail base, bottoming out around 1990, although the area has been gradually redeveloping since then. South Kenwood fared this period rather better, and did not experience the same middle-class flight in the 1970s. In the real estate boom of the mid-2000s, houses sold for in excess of two million dollars, and long-vacant lots were redeveloped with high-end luxury houses.