While Chicago is a city of bungalows and three-flats, it is also home to hundreds of historic prewar apartment buildings constructed close to the lakefront from Edgewater and Uptown down to Hyde Park and South Shore. The term “prewar apartment” refers to multi-unit residential buildings constructed before World War II, usually between 1900 and 1939. Many were designed in historic revival styles like Beaux Arts, Tudor, and Georgian, but some were also part of the modern new Art Deco movement of the 1920s. While smaller in scale than the later steel and glass high-rises that followed them, prewar apartments overall tend to have more space (although they’re divided into lots of rooms) with a variety of floor plans. They’re also quieter due to the solid masonry materials used in construction, like terra cotta, limestone, and brick. Here are some prewar beauties currently for sale on the Chicago market.

1320 N State St #2B, $649,900

Completed between 1925-27, this prestigious Venetian style building in the Gold Coast is the work of architect Robert S. De Golyer, whose prewar designs are located up and down the shore. A cooperative since day one, it comes with everything you’d expect with such a price point, such as a 24-hour doorman and your own private elevator lobby. This particular unit’s large living room with high ceilings and built-ins overlooks State Parkway, while the three en-suite bedrooms all have updated marble bathrooms. It comes with a full-sized gym, party room, outdoor patio, and three storage units in the basement. 

5000 S East End Ave APT 23C, $459,900

Here is another co-op by Robert S. De Golyer, the terra cotta and brick “Tudor Gothic” design with a five-story stone base was once the tallest structure south of the Loop. The two-bedroom, three-bathroom corner unit with lake views was a full gut rehab, remodeled by expatriate owners who never lived in it. The condo mixes the original 1920s craftsmanship with contemporary upgrades. The materials used in the renovation are sleek and lavish from the high-end Italian porcelain flooring in the kitchen to the free-standing South African volcanic stone soaking tub in the bathroom. The HOA fees are almost $2,500 per month, but that includes 24/7 on-site staff and management, concierge, library, gym, laundry, and private garden/yard with gas grill.

1640 E 50th St APT 17B, $175,000

In the Kenwood neighborhood you can also find the Narragansett, a 22-story Art Deco building designed by architects Peter M. Leichenko and Curt A. Esser in 1928. The exterior’s facade is covered in terra cotta decorations of zodiac animals and Native American faces that were created by Charles Morgan, an artist who once worked with Frank Lloyd Wright. Inside past the gorgeous lobby is a three-bedroom, three-bathroom unit with soaring ceilings, original parquet floors, plaster molding, a formal dining room, and en-suite bedrooms. Although the price tag is only $175,000, it comes with high HOA fees, which cover maintenance costs (facade repair and elevator repair) of the vintage building, but also includes utilities and full-time door staff. 

421 W Melrose St APT 1D, $320,000

The Eddystone, just steps away from the Lakefront Trail and Belmont Harbor, is a marvelous 1928 prewar building by Holabird & Root, best known for the Palmolive and Board of Trade Buildings. With only two units per floor, this condo comes with both east and west exposures, making it bright and airy. There are great vintage details like a barrel vaulted foyer, herringbone floors, and crown molding while the open, updated kitchen has granite countertops and brand new stove and dishwasher. Although it is an older structure, the windows are only five years old while the roof membrane was just replaced and a new roof deck with grill area is currently being completed in time for summer. 

5555 N Sheridan Rd APT 238, $159,900

Once part of the larger complex that included the long-demolished Edgewater Beach Hotel, this twenty-story neoclassical building stands out in the city skyline for its pink-colored stucco facade. With an ingenious X-shaped design by architect Benjamin Marshall in 1928 to guarantee light and views for residents, this two-room studio takes you back to a time when people lived small but well. The co-op building’s monthly expenses include property taxes, heat, cable, internet, cooking gas, water, contribution to the reserve fund, and use of all amenities such as an indoor pool, fitness center, small reading room and library, and private park with gazebo and grills.