Englewood

The community area runs roughly from 59th to 75th between Racine and the Dan Ryan. It has lost more population than almost anywhere in the city, and there is a great deal of vacant land, which is the first thing anyone notices.

What is also true: Kennedy-King College anchors 63rd Street, the Englewood Square development at 63rd and Halsted brought a Whole Foods and other retail in the last decade, and there is a large and active network of community organizations and urban agriculture on the vacant parcels.

County records put the median 2-to-4 unit sale at roughly $30,000 in 2013 and about $180,000 in 2025, up around 500%, or 16.1% a year, on 258 or more sales per window. So the market is real and it has moved a great deal in percentage terms while remaining the lowest absolute basis in the city.

Here is the part I will not soften. At $180,000, the building you buy is likely to need substantial work, the rents that support it are modest, and vacancy and management are genuinely harder here than in the neighborhoods further north in this batch. People lose money in Englewood, and they usually lose it by underestimating rehab and overestimating rent.

If you know what you are doing and you have a contractor you trust, there is real value here. If this would be your first building, I would put you somewhere else and tell you why.