Auburn Gresham

The neighborhood runs roughly from 75th to 89th between Racine and the Dan Ryan. The housing is the South Side standard in the best sense: brick bungalows, two-flats and three-flats built in the 1920s, on blocks laid out to a consistent pattern.

It has one of the more active community-organization networks in the city, and there has been real reinvestment along 79th Street over the last decade. That is the kind of thing that shows up in property values five years later rather than immediately.

County records put the median two unit sale at $335,000 over the twelve months ending May 2026, across 42 arms length sales, with the middle half between $190,000 and $410,000. On three year medians the figure ran $171,000 for 2019 through 2021 and $286,000 for 2023 through 2025. The last three year medians moved hard: $230,000 to $247,000 to $286,000.

At that basis against South Side rents, the yield still works, which is increasingly rare. Auburn Gresham is one of the few places I can point an investor to where the arithmetic has not been erased by the run.

The caveat is the same as everywhere on this side of the city: block-level variation is wide, vacancy is real in places, and condition needs verifying in person. The median is a starting point, not an answer.