While home sales in the Chicago area remain strong and are projected to rise, it should also be noted that affordability and a lack of homes are expected to define 2026. I’ve definitely noticed that whenever I scroll through newly listed condos on Zillow, they tend to be snapped up rather quickly, especially when they are in desirable locations. I’m not sure how long these condos will remain on the market, but one is already contingent. According to Crain’s, the number of condos for sale in the city was down 28 percent in January, and it’s estimated there are 10 to 15 buyers for every condo listed. A vintage condo is typically defined as a residential property constructed before World War II and they’re often full of architectural charm (and also tend to be elevator-free). I had to include one located in Marina City as well, which was completed in 1967. After all, can you get more vintage than a pink kitchen?
227 N. Grove Ave., APT. 3, Oak Park, $399,900
This 1,500-square-foot, three-bedroom, two-bathroom penthouse unit in the Villa Grove condominiums is only one block north of Scoville Park in the heart of Oak Park’s Frank Lloyd Wright Historic District. It was designed in 1928 by architects Dubin & Eisenberg, who created several brick and terra cotta-clad Art Deco designs like this one throughout the Chicago area, including in the neighboring Austin neighborhood. This listing stood out for its remarkable details: the arched doorways, living room niches, dining room barrel ceiling, a cedar closet, and original cabinets and built-ins in the kitchen. I should also mention it has in-unit laundry, rare for a vintage building.
300 N. State St., APT. 4625, Chicago, $230,000
The Marina City complex, overlooking the Chicago River, is one of the city’s most iconic structures. This west-facing, 500-square-foot studio with $538 monthly HOAs is worth sharing, primarily because its recent rehab (it last sold in late 2024) complements the building’s exterior design perfectly. The corncob shape is echoed inside with some of the interior design choices, like the curves in the kitchen and walls, as well as the circular motifs found in the bathroom with the mirror and shower glass door. I also like the original pink kitchen with metal cabinets and vintage-inspired appliances. The property might be small (and pie-shaped), but hey, you’re living downtown!
1329 W. Chicago Ave., APT. 3, Chicago, $515,000
In West Town, directly across from Eckhart Park, this full-floor, two-bedroom, two-bathroom condo has hit the market for the first time in almost 13 years. Spanning nearly 2,000 square feet, the interior appears bright and open, which is helped by all the natural light streaming through the 20 brand-new double-paned windows. The $352 monthly HOAs include access to a shared rooftop deck, an ideal place to enjoy the amazing views of the downtown skyline. You’re also within walking distance of everything the neighborhood has to offer, including public transport like the 66 bus and the Chicago Avenue Blue Line station.
480 Sheridan Rd., #3, Evanston, $549,500
Not every potential buyer will want to live on the bend of Sheridan Road, right as you enter the city of Evanston from Calvary Cemetery, but you can’t beat this property’s great location: right across from Lake Michigan and South Boulevard Beach. Known as the Lake Shore Apartments, the S-shaped courtyard building, with Georgian Revival and Classical Revival elements, was designed by architect Roy F. France in 1927. No surprise that this two-bedroom, two-bathroom condo with $911 monthly HOAs has great character inside, as evidenced by the tall windows, arches, textured plaster walls, and wood-burning fireplace.
4451 N. Beacon St., APT. 1, Chicago, $435,000
This classic two-bedroom, one-bathroom condo with $536 monthly HOAs is situated in a brick six-flat in Sheridan Park. Already contingent, it is a designer’s dream come true. Just scrolling through the photos made my heart skip a beat. With a typical floor plan for the era, I absolutely love both the wallpapered foyer and sun room, as well as the updated dark green kitchen with bead board and hand-painted checkerboard flooring. The property last sold in October 2020 for $275,000, so its current asking price reflects a 58.2 percent increase. But with its refurbished interior and sought-after location, I kind of get it.