According to a study by Construction Coverage, Chicago ranks “dead last” among the 10 largest metropolitan areas in the country when it comes to new home construction. It’s no secret that Chicago needs more multi-unit housing. Between 2013 and 2021, the city lost more than 4,800 two- and four-unit buildings to demolition or deconversion, which is 11,775 housing units or 4.2% of the total housing stock, per a report from DePaul University’s Institute for Housing Studies. In early September, I wrote about properties with income potential, so consider this next real estate roundup to be its sequel. All five properties for sale are multifamily-zoned buildings scattered around the city, each with two or more units intended for rental use.
6909 S Chappel Ave, Chicago, $1,674,900
Since this multi-unit property in Chicago’s South Shore hit the market at the end of July, I’ve been paying close attention to see how quickly it would sell. The $1.6 million asking price, which is a 260% price increase since it last sold in 2011, might be why it’s taking a while. But what a beauty! The architecturally significant three flat, designed by Edward McClellan in 1925, has almost 9,000 square feet of living space, featuring a total of eight bedrooms and six full bathrooms. It boasts many vintage details, including original doors and hardware, built-in cabinets, beautiful woodwork, and original tiling in one of the kitchens and three of the bathrooms. I also love the top-floor unit, originally the maid’s quarters, which comes with a large skylight and a private balcony.
1224 W Lunt Ave, Chicago, $850,000
Calling all investors: A fully rented two-flat, located just one block from the CTA Red Line, Loyola Park, and the beach, is now for sale. For anyone who has struggled to find a place to park in the city, especially in a neighborhood like Rogers Park, this property includes eight high-demand, income-generating parking spaces. The first unit features two bedrooms, two full bathrooms, and an in-unit laundry, while the second unit comes with two bedrooms and one bathroom. Both units have large, south-facing sunrooms that allow plenty of natural light to enter the interior. There have been upgrades to the electrical, plumbing, and roof.
1100 W Wellington Ave, Chicago, $1,199,900
A three-unit building with a historic Victorian facade, located on a corner lot in Lake View, is now for sale after being owned by the same person for over 40 years. The owner’s “duplex-up” unit is like a single-family home with four beds, two full baths, an enclosed sunroom, in-unit laundry, and a private deck. The front first-floor unit is a studio, while the rear unit has two bedrooms, one bathroom, and an updated kitchen. The backyard features a large communal deck and a two-and-a-half car garage with storage.
6447 N Glenwood Ave, Chicago, $850,000
Let’s return to Rogers Park to check out this historic brick three-flat, which last sold five years ago for $517,500. Its current asking price is a 64% increase, reflective of the present condition of Chicago real estate. In addition to a two-bed, one-bath garden unit, the building also includes four-bed, one-bath units on the first and second floors. All units are currently leased and occupied through May/June 2026. The property is within walking distance of the Loyola Red Line stop and the Loyola University campus.
815 S Bell Ave, Chicago, $925,000
Located on a quiet cul-de-sac in the Tri-Taylor/Illinois Medical District, this greystone features four fully rented units, including a rear brick coach house. All four units, last remodeled in 2018, come with their own laundry facilities. Additionally, there is a large rooftop deck with a spiral staircase that goes down to the backyard and the coach house. One of the units, likely the largest, has an open-concept layout and appears bright and airy, while the other three units seem quite small. I do like some of the details, such as exposed brick walls and historic fireplace mantels. The listing says this investment is for cash-only buyers.