Whether an individual landmark or part of a local historic landmark district, the following properties for sale in Chicago are all legally protected from demolition. The mayor and City Council approve these historic sites after the nine-member Commission on Chicago Landmarks presents its recommendations that must meet a minimum of two criteria: site of a significant event, critical part of the city’s heritage, association with a significant person, important piece of architecture, important architect, distinctive theme as a district, or unique visual feature. While not every homeowner is interested in taking on the stewardship of such buildings, there are preservation-minded people out there who want to protect a piece of the past. Tourists from all over the world come to visit the city, which is renowned for its influential architecture, having been the birthplace of the skyscraper and the hometown of numerous prominent architects. Let’s review five landmark properties currently on the market, including an architectural masterpiece that is one of the best examples of prairie style in the city that once was home to two important political figures. 

1354 E 49th St, Chicago, $795,000

Our first property for sale is a five-bedroom, two-bathroom brick residence located in the picturesque Kenwood Historic Landmark District. This 2,800-square-foot home with formal rooms and a screened porch off the kitchen was originally built for Clara Turner in 1893. According to Chicago’s Historic Hyde Park, architect Charles H. Dornbusch, who taught at the Illinois Institute of Technology, resided here starting in 1953 and undertook renovations of the structure. On the market for the first time since 1987, this property is directly across from the seven-acre Kenwood Community Park, which features sports fields and tennis courts. It is also conveniently located near Metra Electric, University of Chicago bus routes, and the lakefront trail.

3234 W Washington Blvd, Chicago, $485,000

Located in Chicago’s East Garfield Park, George W. Maher’s King-Nash House is an official city landmark for a number of reasons. Originally built in 1901, the limestone residence is a great blend of architectural styles: Prairie School, Sullivanesque, and Colonial Revival. Its second occupant from 1925 until his death in 1943 was political boss Patrick Nash. The 5,832-square-foot historic mansion with six bedrooms and three and a half bathrooms needs work but would be an absolute stunner under the right owner who sees its potential. I mean, look at all those fireplaces! (Although a few of them have been taken out and are now part of museum collections, like the LACMA.) Just 10 days after being listed on the market for the first time in ages, the “sold as-is” property is already contingent.

727 S Dearborn St APT 911, Chicago, $725,000

Right in the middle of the city’s historic Printing House Row District stands the Donohue Building and Annex, the first large factory in the city to be repurposed into residential use back in 1979. Designed by architect Julius B. Speyer and built in 1883 for a children’s book publisher, the structure is full of original details including a vintage iron cage elevator that takes you to this top floor unit. Although the property has high monthly HOA fees of $1,709, there is much to appreciate about this 2,345-square-foot, three-bedroom, two-bathroom condo. It comes with numerous built-in bookcases (fitting, considering its history) as well as a deck right off the kitchen, a perfect space for taking in views of the city. 

300 N State St Unit 4432-4433, Chicago, $499,900

When it comes to the iconic Marina City, only parts of the complex were designated as a Chicago Landmark in 2016. The recognition was long overdue, considering that this unique design began construction in 1960 and has since come to define our skyline. This condo is located in the highly sought-after 32nd and 33rd tiers, giving it fantastic eastern and southern views of downtown and the Chicago River. The 1,450-square-foot two-bedroom, two-bathroom condo feels brighter and more open, likely because it combines two separate smaller units — and I suspect that the second kitchen has been turned into a laundry area. But I do like that the property features three, pie-shaped private balconies.

2303 S Michigan Ave #317, Chicago, $299,000

Last but not least, we have a one-bedroom, one-bathroom loft for sale that is located in the historic Motor Row District. In the early age of the automobile, this is where people went to visit showrooms and repair their vehicles. In its heyday, 116 different types of cars were sold here. This particular structure was originally designed by architects Holabird & Roche for the Cadillac Motor Car Company in 1911. Even though this unit is less than 1,000 square feet, the interior feels bright and open due to the floor-to-ceiling windows and 15-foot timber ceilings. It comes with its own balcony (on the non-Michigan Avenue side of the building) and rooftop deck access. It has a decent asking price and low HOA fee of $535 per month.