CHICAGO — In a city increasingly filled with modern gray open-concept apartments, a handful of historic condos still offer vintage layouts, original finishes, and enduring charm — and they’re currently on the market. From prewar flats in Edgewater and Hyde Park to a Gold Coast co-op designed by a renowned architect, these homes resist the bland conformity of today’s new construction.
If you’re someone who values separate rooms over open floor plans — and wouldn’t dream of painting original woodwork — these five properties might be exactly what you’re looking for.
Edgewater Gem With Five Bedrooms Near the Lakefront — $700,000
5863 N Kenmore Ave #2 offers a sprawling five-bedroom, three-bathroom layout in a 1917 building just a block from Lake Michigan. The unit retains its original floor plan, with bedrooms tucked down a hallway for added privacy.
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Vintage features include:
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Tiled fireplace
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Stained glass windows
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A classic butler’s pantry
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Unpainted woodwork that enhances the unit’s timeless appeal
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Gold Coast’s Venetian-Style Co-Op With Lake Shore Legacy — $415,000
At 1320 N State Pkwy #2A, you’ll find a 2,200-square-foot two-bedroom, two-bathroom co-op in a prestigious 1925–27 building designed by Robert S. De Golyer, an architect known for shaping Lake Shore Drive’s skyline.
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Standout features:
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Barrel-vaulted foyer
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Bold green-tiled vintage bathroom
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Monthly HOA: $4,237
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Amenities include: 24-hour door staff, fitness center, shared terrace, and more
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Hyde Park Prairie-Style Treasure Built For UChicago Faculty — $697,000
This third-floor unit at 5712 S Dorchester Ave #3 resides in a brick Prairie School–inspired three-flat originally built in 1913 for University of Chicago professors.
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Features include:
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Roman brick fireplace with Sullivanesque ornamentation
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Pink-tiled vintage bathroom
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Custom wood built-ins and original wood floors
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A sunroom that overlooks the building’s private backyard
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East Lake View’s Lake Shore Towers — Gothic Revival With Scale — $625,000
Located at 3920 N Lake Shore Dr APT 3S, this massive 3,000-square-foot co-op unit is in Lake Shore Towers, a Gothic Revival building developed in 1927 by Roy France and Max Thorek.
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Interior highlights:
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Three-bedroom suites plus powder room
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Arched foyers and preserved charm
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Monthly assessments: $4,654 (covering taxes, parking, 24/7 door staff)
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Oakdale Towers in East Lake View — Where Historic Meets Modern — $525,000
Last sold in 2021 for $440,000, the two-bedroom, two-bathroom unit at 431 W Oakdale Ave APT 3A now lists for $525,000 — a 19% jump.
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Updated while preserving charm:
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Renovated kitchen and bathrooms
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Modern windows paired with vintage layout
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HOA of $1,146/month includes gym, rooftop deck with grills, and on-site engineer
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Historic properties remain a rare opportunity to live in a piece of Chicago’s architectural legacy. With soaring new towers redefining the city’s skyline, these five homes offer a throwback to a time of craftsmanship, classic layouts, and neighborhood character. Whether in Hyde Park or Edgewater, each of these condos reflects the city’s enduring commitment to style and substance.
Have you toured a historic condo in Chicago recently — or do you prefer modern design? Let us know in the comments at ChicagoSuburbanFamily.com.
