Homes for sale in
Woodlawn.

Woodlawn began as a small settlement of Dutch farmers in the mid-nineteenth century, and before the 1890s its population never reached much beyond a thousand residents. Everything changed when the neighboring lakefront in Jackson Park was chosen as the site of the 1893 World's Columbian Exposition. The fair drew a flood of entrepreneurs, residents, and tourists, and hotels and apartment buildings went up rapidly, with tens of thousands of new residents moving into Woodlawn in the years that followed. Streetcar and elevated rail lines, including the elevated that terminated at 63rd and Cottage Grove and the Illinois Central commuter line, knit the district into the city and fueled its growth into a dense, lively residential and commercial neighborhood through the first half of the twentieth century.

Woodlawn's population peaked at 81,279 in 1960, by which point it had become a predominantly African American community. Disinvestment, demolition, and population loss followed over the next several decades, and by recent estimates the community area held roughly 23,956 residents. The University of Chicago, on Woodlawn's northern border, has had a long and sometimes fraught relationship with the neighborhood, and in recent years has been a significant investor in its redevelopment. The decision to build the Obama Presidential Center in adjacent Jackson Park triggered a new wave of attention and investment, and in September 2020 the Chicago City Council passed the Woodlawn Housing Preservation Ordinance, a set of affordable-housing measures, right-of-first-refusal protections, and homebuyer support programs intended to keep long-time residents in place as the area changes.