Investing on Chicago's West and South Side, Done Right

The opportunity is real, and so is the responsibility

On the West Side and the South Side, you can still buy a brick two-flat or a greystone for a price that would be a rounding error in Lincoln Park. Redfin recently showed Englewood's median sale price near 148,000 dollars and East Garfield Park around 218,000 dollars (see Redfin's Englewood page and Redfin's East Garfield Park page; these numbers swing month to month, so verify before you underwrite).

We invest in these neighborhoods on purpose. The building stock is good, the location is unbeatable, and the demand for a clean, fairly priced home is real. But we hold a strong opinion about how it should be done, because the same affordability that draws investors is fragile, and careless money can break it. Our area pages on Austin, Garfield Park, and Englewood go deeper on each market.

Value-add is good, displacement is not

Value-add investing has a bad reputation in some circles, and sometimes it earns it. But taking a vacant or beat-up greystone and turning it back into safe, occupied housing is one of the most useful things anyone can do on these blocks. The problem is never renovation itself. The problem is when renovation becomes a tool to push out the people who held the neighborhood together through the hard years.

We draw the line clearly. Improving a building so a local family can live in it with pride is value-add. Pricing that same family off their own block, or flipping to the highest churn regardless of who it hurts, is extraction wearing a tool belt. Both can show a profit. We are only interested in the first kind, and we think the city is better off when more investors choose it too. You can see how we approach this on our sellers page.

The tax warning every owner here needs to hear

There is a quiet crisis on the West and South Side that owners must understand before they buy or sell. Recent reporting found that more than 37,000 residential properties on the South and West sides saw their assessments more than double between 2023 and 2024, with parts of Englewood, Roseland, and North Lawndale seeing median valuation jumps between roughly 119 and 160 percent (per Block Club Chicago and WTTW News).

Translated into bills, the median Englewood homeowner reportedly saw a residential tax increase around 82 percent, and parts of West Garfield Park saw bills rise by nearly 2,000 dollars (per Illinois Answers Project). Ironically, that pressure is partly driven by investors crowding into the few affordable corners left. If you are going to invest here, you have to know this number, plan for it, and never use it as a lever to squeeze a longtime owner who is already underwater on taxes.

The new ADU rule is a tool worth using well

There is a genuinely good piece of news for owners on these blocks. Chicago's expanded Additional Dwelling Unit ordinance took effect April 1, 2026, legalizing coach houses, basement units, and attic conversions across far more of the city than the old 2021 pilot, with the eligible area growing by roughly 135 percent (per Block Club Chicago and the city's ADU program page).

We see this as a quiet wealth-building tool for the very owners who have been squeezed by taxes. A legal coach house behind a two-flat, or a properly converted basement, can throw off rent that helps an owner stay put rather than sell under pressure. That is the opposite of displacement: it is helping a family keep the building and add income. The catch is that single-family blocks still depend on the local alderperson opting the ward in, so check your address against the city's eligibility map before you plan anything.

• Allowed by right in most multi-unit and many commercial districts outside downtown.
• Conditional on single-family blocks, where your ward must have opted in.
• A path to legalize an existing basement or attic unit if it meets code on ceiling height, exits, and ventilation.
• Not usable as a short-term rental under the ordinance.

Partner with local owners instead of around them

The best work on the West and South Side does not happen to a neighborhood. It happens with it. Plenty of owners here hold a building with real equity, real history, and a rehab bill they cannot cover alone. A fast cash offer takes the upside away from them. A partnership lets them keep a piece of it.

We will sometimes bring renovation capital and project management to an owner who brings the property, then share the result rather than buying them out at the bottom. That keeps ownership and wealth in the community, which is exactly where it should stay. If you own a building in Austin, Garfield Park, Englewood, Roseland, or Auburn Gresham and that resonates, our joint ventures page explains how we structure those deals.

Our bottom line for the West and South Side

We are bullish on these neighborhoods, and we are unapologetic about being investors in them. What we reject is the idea that you have to choose between making money and doing right by a community. On the West and South Side, the investors who add housing, pay fairly, plan around the tax reality, and partner with local owners are the ones who will still be welcome here in ten years.

If you own a home or a building on these blocks and are weighing your options, talk to people who understand both the numbers and the neighborhood. We are glad to be one of them, whether you want to sell, partner, or just get an honest read on what your property is worth and what the new ADU rule could do for it.