Where Most Chicago Investors Start
A four unit brick building from 1923. Corner lot, mature trees out front, two parking spaces, hardwood and crown molding through the units.
Not a conversion. Not a single family someone chopped into apartments. A purpose-built four flat that has been standing on the south side for a century — and the kind of building where most people in this city actually start investing.
Photographed for the buyer who's actually looking
The standard listing photo template assumes someone is moving in. Lead with the kitchen, stage the living room, twenty-five frames of interiors.
On a four flat that buyer doesn't exist. The person writing the offer is purchasing an income stream attached to a maintenance liability, and most of what they're pricing isn't inside a unit.
So this set leads differently.
The building envelope comes first. Brick, roofline, corner exposure, the condition of the masonry. On a hundred-year-old building that's where the condition story lives, and it's the biggest number in a buyer's head. A roof is not a decorating problem.
The aerial comes second, not last. On a single-family listing we'll often close a carousel with the drone shot as a payoff. Here it's a decision criterion — roof condition and corner position are things a buyer is underwriting, and burying them at frame twenty-five means the person who most needs that information never sees it.
Then the entrances and the parking. Investors count doors, and two spaces on a Chicago corner lot is income, not amenity.
Then the units, as representative rather than exhaustive. Hardwood, crown molding, big windows, a bay in the front unit. Solid and worth showing — just not the argument.
A note about access
On a tenant-occupied building you frequently cannot get into every unit. Tenants have rights, notice requirements are real, and some people simply say no.
That's normal, it isn't a failure of the shoot, and it shouldn't be treated as one. But it does mean the floor plan carries more weight on a multifamily listing than on almost anything else we shoot — it's the only way a buyer understands the units they're never going to walk.
We'd recommend a floor plan on every 2-4 unit for that reason alone.
Calumet Heights and the south side four flat
Calumet Heights sits on the far south side, and like much of the surrounding area the housing stock runs heavily to 1920s brick — bungalows, two flats, and purpose-built small apartment buildings on corner lots exactly like this one.
That inventory is a large share of what changes hands in this part of the city, and it's the entry point for a great many first-time investors. It's also, almost universally, photographed with a template designed for a completely different transaction.
There's a gap there worth closing.
What was delivered
This was our Base package:
25 MLS-ready photos, six drone photos and a floor plan, delivered within 24 to 48 hours of the shoot.
Listed by Stephne Pettitt-Gaines.
Multifamily photography across Chicago
We shoot 2-4 unit buildings, small apartment buildings and mixed-use throughout Chicago and the surrounding suburbs. Pricing on multi-unit properties is quoted based on unit count and access.
Frequently asked questions
How much does real estate photography cost in Chicago? Our Base package starts at $200 and includes 25 MLS photos, 6 drone photos and a floor plan. The Plus package at $300 adds a property walkthrough and basic cinematic video. Our Pro package at $450 includes a full cinematic video. Multi-unit buildings are quoted based on unit count and access.
Do you shoot investment and multifamily properties? Yes. Two to four unit buildings, small apartment buildings and mixed-use. We shoot for the buyer who's underwriting the building, not just the units.
How fast do you deliver photos and video? Standard turnaround is 24 to 48 hours for photos and 48 to 72 hours for video.
What areas do you serve? We work throughout Chicago and the surrounding suburbs, including Calumet Heights, South Shore, South Chicago, Berwyn, Cicero, Stickney, Schaumburg and Arlington Heights.
Book a shoot on your next multifamily
If you're listing a 2-4 unit and you want it photographed for the person actually buying it, that's what we do.
See packages and book a shoot →
Related: A Homebuyer Wants the Kitchen. An Investor Wants the Meters. — the full argument, with this building as the case study.

