For the new year, let’s check out some condos around Chicago that have recently hit or returned to the market over the past month. And the best part? For the city, they’re all decently priced at less than $500,000 (although the HOA dues will get you in the end). If anyone’s noticed, real estate in general has been pretty stale lately. I feel like I keep seeing the same listings over and over again; a number of properties just aren’t selling. It’s time for a fresh start as we begin 2023. Browsing through Zillow, I came across five interesting and surprisingly affordable units that have been for sale only a week or two. From a classic highrise on Lake Shore Drive to a South Loop conversion, I think you’ll enjoy looking through this sample of condo buildings in Chicago. 

3520 N Lake Shore Dr APT 9F, $275,000

For $275,000, you can buy a one-bedroom, one-bathroom condo in the 1924 prewar Sheridan-Brompton apartment building in East Lake View. The architects Maurice Rissman and Leo Hirschfeld were responsible for a number of the early highrises built on Lake Shore Drive. With an older unit like this one, there is a small galley kitchen while nearly 20% of its entire square footage is devoted to a large dining room. The bathroom looks vintage, and the southeast-facing windows have great views of the lake and harbor. The HOA fees may be high, but that’s expected with the maintenance of any historic property and it includes on-site management.

5842 S Stony Island Ave APT 16G, $390,000

Listed right before the Christmas holiday weekend and already contingent, this 1,800-square-foot, three-bedroom, two-bathroom condo is priced at $390,000. One of the tallest courtyard buildings in the city, Vista Homes was designed by Paul F. Olsen, an architect who specialized in speculative co-ops during the 1920s. With views of Jackson Park and Lake Michigan, this unit comes with one parking space in the attached garage, but it’s also next to numerous bus lines and a Metra stop. Because it’s a cooperative, the $1,600 monthly HOA fees include 24-hour door staff, utilities, and property taxes.

237 E Delaware Pl #6B, $399,000

Live right in the middle of everything with this three-bedroom, two-bathroom condo that has recently returned to the market after a sale fell through last summer. Located a block away from the John Hancock Center, this 1922 vintage yet stylish building was designed by Fugard & Knapp, the architects behind a number of Streeterville’s classic cooperatives. This particular unit last sold for $812,500, so the current price tag of $399,000 seems like a bargain. But don’t be scared by the high monthly HOA fees ($3,658 to be exact), as it covers a plethora of utilities and services, including taxes.

1516 S Wabash Ave #902, $485,000

This northeast corner unit in a vintage South Loop building hit the market right before Christmas. On sale for $485,000, the two-bedroom, two-bathroom condo has 11-foot floor-to-ceiling windows with views of the city, including Soldier Field. Now known as Landmark Lofts, the 1920 building was once home to a wholesale furniture company and other businesses. Open and airy inside, the unit comes with a 70-square-foot deck with gas hook-up, a parking space, and the lower end of HOA fees at $731 per month.

3950 N Lake Shore Dr APT 420D, $249,000

Back in Lake View to share this three-bedroom, two-bathroom condo that was put on the market right before the new year. While the 23-story structure itself dates from 1956, this particular unit has been freshened up. Listed at $249,000, there are a lot of trendy updates throughout the interior, including newer floors and bathrooms. The $887 monthly HOA fees cover all utilities, the outdoor space on the roof, and more. The building also has a bike storage room, perfect for residents who want to take advantage of the lakefront trail right outside your door.