In the wonderful book that came out last year, Chicago Homes: A Portrait of the City’s Everyday Architecture, there is a section that discusses the definition and history of the Chicago flat. A “flat” refers to a specific type of apartment building in which every floor is essentially the same as the floor below, and the number preceding the word “flat” represents the number of total units in the building. The city experienced an explosion of the building type between 1910 and 1930, with variations that popped up in almost every neighborhood. In fact, two- and three-flats make up more than a quarter of the city’s housing. The listings below are all located in six-flats, which typically means there are three stories with two units per floor. Six-flats are the double version of a three-flat with a central entrance and hallway and mirror-image units on each level. With the exception of our first property, they often have the classic Chicago-flat interior layout: Living room in front, bedrooms and sometimes a dining room in the middle, and a kitchen and back porch in the back, as rear porches came about thanks to a 1906 building code that required flats to have two means of emergency exit.
5756 S. Blackstone Ave. #3N, Chicago, $749,000
In Hyde Park, just steps from the University of Chicago, is a 2,274-square-foot, four-bedroom condo located in a historic 1905 Arts and Crafts six-flat. This top-floor unit was recently renovated by a local architect in 2026 who reimagined its classic flat layout by moving the kitchen to the front of the home where it now opens up to the living and dining areas, as well as the east-facing sunroom. The upgrades also included new plumbing, central air conditioning, and updated electrical systems. The $750 HOAs cover storage and a bike room, along with services like heat, water, gas, and snow removal.
823 W. Belle Plaine Ave., Unit 3, Chicago, $525,000
The architectural character of this next property, both inside and out, is a real selling point. This top-floor, three-bedroom, one-bathroom unit is located in a vintage brick six-flat in Buena Park. The brick and limestone exterior is designed in the Classical Revival style, while the inside boasts preserved vintage details such as a wood-burning fireplace, original picture rails, and hardwood floors throughout. I particularly love the enclosed rear sunporch, which would make a great reading nook or hangout space. The monthly HOAs are $300.
1455 W. Rascher Ave. #2W, Chicago, $599,000
This vintage 1915 property in Andersonville is in an ideal location, within walking distance of the shops and restaurants of Clark Street. The condo features dark wood trim and has a massive dining room, along with two bedrooms and one and a half baths (although the half has the potential to be converted into a full bathroom). The HOAs are low ($375 to be exact), and there’s an in-unit washer and dryer, central air conditioning, oversized basement storage, and a detached garage space.
5330 S. Hyde Park Blvd. Apt. 1S, Chicago, $375,000
Let’s return to Hyde Park, specifically the east side, where you are close to both the lakefront trail and Promontory Point. This first-floor condo — being sold “as-is” — spans nearly 2,400 square feet, with four bedrooms, two full bathrooms, and a galley kitchen. The living room has a large fireplace with built-in bookshelves that take up an entire wall. It includes one assigned parking space and $785 monthly HOAs.
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6342 N. Magnolia Ave., Unit 3N, Chicago, $409,000
This top-floor penthouse unit, renovated in 2024 with lots of natural light, is located in what is described as “an intimate six-unit building” in Edgewater. Originally built in 1925, the building itself is situated kitty corner from Loyola University’s main campus and the lakefront. The 1,500-square-foot, two-bedroom condo includes one full bathroom, a tandem space that could easily be turned into an office or exercise room, an in-unit washer and dryer, one detached garage space, and a private deck overlooking the shared common backyard. The property has $325 monthly HOAs.Private 8′ × 8′ deck overlooking the common backyard.
Rachel Freundt is a freelancer writer for Chicago magazine.