I grew up on the South Side. Here is how I help people buy a building here.

Who you work with

On the South Side, I am the one you deal with. I show the buildings, I walk them with you, and I stay on the file through closing. Behind me is the rest of the Dan Loves Houses team, so nothing sits and waits while I am out showing.

I know these blocks because I grew up on them. What changes between one street and the next down here is real, and it does not show up on a listing site.

If you are buying a building down here

1. Figure out what you can actually spend. Five percent down on a conventional loan gets you up to four units. FHA takes it to 3.5 percent down, and that program is for a two unit building, with stipulations.
2. Pick the blocks before you pick the building. We go look. I tell you what I would pay on that street and what I would not.
3. Run the real numbers. Not the rents in the listing, what the units next door actually signed for.
4. Write it, then hold the file together. Inspection, appraisal, lender, attorney, closing.

If you are selling

Two things move the price of a small building down here. What the units rent for and whether that is on paper. Then which sales the appraiser leans on, because a finished vintage building and a new construction building on the same block can be hundreds of thousands apart. Bring me the leases and the receipts for the work you did and we start from a strong position.

Questions I get

How do I find out how many units this building is legally?

You ask the city, and you do it before you write the offer. The Office of the Zoning Administrator is the only office that decides how many residential units a Chicago building legally has, and it works through three things in order. First, historical building permits, and a permit only counts if it carries a zoning approval stamp and states the number of existing units. Electrical, sign and express permits prove nothing. Second, if the permits do not settle it, the Water Annual Examination Books, which you find through the Chicago Zoning Map. The column marked Fam. is the number of families recorded on each floor, and that is what points to the unit count. Third, a rebuild letter, which is a written determination from the Zoning Administrator.

What most people do instead is look at the Cook County Assessor record, and the city says plainly that assessor characteristics are not reliable for this. It matters for money, not paperwork. If that third unit downstairs is not legal, your lender may not count the rent when you qualify and the appraiser may not count it in the value, which means you are paying a three unit price for a two unit building. I pull this before we write, not after.

Can I add a unit, a coach house or a basement apartment?

On a lot of two flats and three flats down here, yes. The municipal code now allows additional dwelling units by right in all multifamily and mixed use districts, and in certain business and commercial districts. If the building sits on a single family RS lot, which happens with older two flats, it only works inside an ADU Allowed RS Area, and those carry a cap on how many get approved on your block each year: one on RS-1, two on RS-2, three on RS-3. Some of those areas also require the owner to live there.

What you can actually add. With one to four existing units you get one conversion unit, meaning a basement or an attic, plus one coach house out back. So a two flat can end up at four. The building has to be at least twenty years old for a conversion unit, which almost everything down here is. A coach house has no age rule.

Now the part that decides whether it pencils. This is not permit free. There is a pre certification through the Department of Planning and Development before anything else happens. To build a coach house you have to commit your general contractor and every subcontractor to a Registered Apprenticeship Program approved by the US Department of Labor, and that narrows who can bid the job. No short term rentals either, no Airbnb in a conversion unit or in any coach house built after 2021. It is a real option and it is a construction project. We price it while you are still deciding on the building.

The building already has tenants. What happens to them, and to me?

The leases come with the building. You are buying their agreements along with the bricks, so a lease that runs another nine months runs another nine months for you, and that is what decides when you can move in. On an occupied building that is the first thing I check, before we talk about price.

Here is the part almost nobody tells a first time buyer down here. Chicago's Residential Landlord and Tenant Ordinance does not cover units in an owner occupied building of six units or less. That is the city's own language. So if you live in your two flat, your units sit outside the RLTO. That does not mean there are no rules. Security deposit interest is set by the city and has been 0.01% every year since 2015, and Cook County's Just Housing Ordinance controls how a criminal background can be used in screening. Your attorney handles the paperwork at closing. My job is making sure we know what you are inheriting before you sign anything.

How much cash do I actually need to buy one of these?

Less than most people think. Across the South Side neighborhoods I work, the median two unit building sold somewhere between about $210,000 and $340,000 over the last twelve months, depending on which neighborhood. Five percent of $300,000 is $15,000. Add closing costs, and hold something back for the first repair, because there is always a first repair.

The number that matters more than the loan math is what that money buys on which block, and that changes a lot inside of a mile down here. I would rather walk you through three buildings at the same price in three different neighborhoods than talk you through a loan program.

Should I buy one that needs work?

If you have the money for it and the patience for it, that is where the value is on the South Side. What you cannot do is guess. Price the work before you own the building, because a two to four unit building is appraised off what similar buildings sold for, not off what you plan to charge in rent. The renovation has to make sense against the sold comps on that street.

On old Chicago buildings there are four line items that decide whether a project is a deal or a hole. The back porch. The tuckpointing. The electrical, if it is still knob and tube. And whatever is going on under the basement floor. Those are the ones that come in at five figures. Kitchens and baths are the easy part. I walk it with you and we put numbers on it standing in the building.

How do you actually tell one South Side block from the next?

Every buyer down here gets told it is block by block and then gets told nothing else. Here is the actual method. Stand on the block and read four things, on that block and the two either side of it.

1. What sold on the block in the last year, and for how much. Not the neighborhood median. The street. Two sales on one block and none on the next is the whole story.
2. How many buildings are owner occupied. Look for one mailbox and one doorbell instead of four, a car that is always there, a yard somebody planted. Owner occupancy is what holds a block steady.
3. What is being fixed right now. Scaffolding, new windows, a dumpster, a permit sign stuck in a yard. Money going into a block today is the leading indicator. Money that stopped going in is the other kind.
4. What sits on the corner. A corner with a busy storefront and a corner with a boarded one are two different streets, and the difference does not show up in any listing photo.

Do that at two different times of day, once on a weekday and once on a weekend. Then call somebody who has watched the block for years, because the fifth thing is what it was doing before you got there, and that is the part you cannot see in an afternoon. I grew up here. That is the part I am for.

Unit count and coach house rules from the City of Chicago Office of the Zoning Administrator and the September 2025 additional dwelling unit ordinance. Tenant ordinance coverage and security deposit interest from the City of Chicago Department of Housing. Sale prices from Cook County records for buildings with exactly two apartments, last twelve months.

The neighborhoods

Every one of these has its own page with what a small building actually costs there, what the units rent for, and a table of what sold in the last year. Start wherever you are curious.

Bronzeville · Woodlawn · South Shore · Chatham · Englewood · Greater Grand Crossing · Auburn Gresham · Avalon Park

Or run a building you are looking at through the deal analyzer and see what the numbers do.