South Kenwood

The blocks roughly between 47th and Hyde Park Boulevard, running east from Drexel toward the lake. This is the mansion district: enormous houses on oversized lots, many landmarked, with the University of Chicago immediately south supplying buyers who need serious space and want to walk to work.

What makes this market hard is how little of it trades. In a typical year only a handful of houses change hands, and the ones that do are so different from each other that comps are close to meaningless. Pricing here is judgment, not arithmetic, and an automated valuation on a South Kenwood mansion is a number with nothing behind it.

Kenwood houses overall ran a median near $775,000 in 2025, up about 62% since 2013. That figure includes North Kenwood and is best read as a floor rather than a guide to what a mansion block costs.

On buildings: there is essentially no small multifamily market here, about six sales a year across all of Kenwood. If a two-flat is what you are after, this page is telling you to look elsewhere, and I would rather tell you that than show you listings that do not exist.

My advice if you want one of these houses: the work is patience and relationships, not searching. They come up rarely and are often sold before they are widely marketed, which is the kind of thing I would rather help you with directly than have you watch a portal for.