A couple of weeks ago, Governor JB Pritzker met with hundreds of realtors to help promote his Building Up Illinois Developments (BUILD) initiative that “is designed to eliminate barriers to housing development, streamline construction, and help close the housing gap in neighborhoods across the state.” According to the Illinois Policy Institute, the state is short 142,000 homes and needs around 227,000 new units over the next five years. This is one of the reasons housing prices are more expensive across the board. As of March 2026, the overall median home sale price in Chicago was $410,000, up 5.2% from the prior year, according to Redfin’s Chicago Housing Market Trends. Obviously it depends on the location, but condos generally fall below the median. All the following condos, except for the one in Rogers Park, are listed above the average asking price. They’re all located in vintage buildings and come with two bedrooms (the Hyde Park listing has an extra bedroom), and three out of the five properties are near or in close proximity to Lake Michigan. One condo is directly on the lake, featuring a private pier with water access for the building’s residents, and — believe it or not — it’s our most affordable option.
4300 N Marine Dr APT 1601, Chicago, $425,000
Near Uptown’s commercial district and lakefront stands a red brick and cream-colored high-rise with massive entry Doric columns, designed in the Colonial Revival style by architects Johnck & Ehmann in 1931. With stunning lake views, this 1,600-square-foot, two-bedroom, two-bathroom condo is on the market with an asking price 54% higher than when it last sold almost 10 years ago. I love the beautiful architectural details, such as the walnut hardwood flooring and crown molding. If you are seeking privacy, the boutique building offers only two units per floor and three separate elevator banks. The $1,291 monthly HOAs include 24-hour door staff and an on-site manager/engineer, both indoor and outdoor parking, bike racks and a patio, daily trash removal, and services like heat, water, gas, cable, and internet.
3042 N Clifton Ave APT 3, Chicago, $450,000
A 1,115-square-foot, top-floor “penthouse” in Lake View, complete with two bedrooms, one bathroom, and a rooftop terrace, is currently listed for sale (though it is contingent as of this writing). The property has lots of character, evident in its greystone exterior, original woodwork, and green-tiled decorative fireplace. A trend typical of our properties for sale, its current asking price reflects a nearly 33% increase since it last sold seven years ago. On the positive side, it has relatively low $218 monthly HOAs, which cover storage, water, insurance, waste services, maintenance, and snow removal. The property is less than a half-mile walk to the Wellington Brown Line stop.
7639 N Eastlake Ter APT 2B, Chicago, $265,000
Northgate Pier Condominiums is right on the waterfront in East Rogers Park. This two-bedroom, one-bathroom condo with $692 monthly HOAs is likely cheaper than other units that have sold in the same building because it does not face the lake. However, the private pier offers water access for grilling, sunbathing, or launching paddle boards. Plus, it’s conveniently located between Rogers and Howard beaches, if you’re into the outdoor lifestyle. The condo’s split bedroom layout provides privacy, while the kitchen has plenty of counters and cabinets. An in-unit laundry is also included.
5602 S Blackstone Ave APT 3, Chicago, $415,000
The Thomas R. Bishop Company were prolific in the early decades of the 20th century as they constructed numerous walk-up apartment buildings throughout Hyde Park, including this one, originally built in 1915. This 1,600-square-foot, three-bedroom, top-floor condo exudes character. The living room fireplace, framed by statement floral wallpaper, works beautifully with the Art Nouveau windows in the adjoining sunroom. I love all the extensive woodwork, including the barrel-vaulted ceiling in the dining room. Right off the galley kitchen is an outdoor deck, but there is also a shared backyard for the property, which comes with $641 monthly HOAs. The condo last sold almost 10 years ago for $312,500.
70 E Cedar St #14WS, Chicago, $475,000
In the Gold Coast, about a block from Oak Street Beach, stands an elegant 30-unit pre-war limestone and brick building, designed by the local architecture firm of McNally & Quinn in 1926-27 and converted into a cooperative in 1949. While the listing describes this two-bedroom, two-bathroom residence as “turnkey,” the kitchen and bathrooms appear to need some updating. I do like the in-unit laundry with a sink, a feature not always guaranteed in older condo buildings. For a low-priced vintage cooperative, remember there is always a catch: the HOAs are high. So what do you get for $2,306 per month? An on-site building engineer, 24-hour staff, and sundeck — just to name a few of the amenities and services.