Imagine buying and living in a home that boasts special “connections”: an intriguing history, or perhaps a place where a notable person once lived. In November, former congressman Bobby Rush put his house on the market. The property, which he has owned for over 30 years, is located in historic Bronzeville, once dubbed the “Black Metropolis” due to it being the center of African American culture and business starting in the 1920s (along with the Grand Boulevard neighborhood to the south). Formerly known as Douglas, it has been experiencing a comeback in recent years, thanks to increased development and a plan to revitalize the 100-plus acre lakefront site of the former Michael Reese Hospital. I was curious to find out what other properties are currently for sale in this significant area of the South Side and discovered that the childhood home of Harold Washington, Chicago’s first Black mayor, is also available for purchase. While the property needs work, this historic greystone is loaded with vintage charm and has significant potential. As described in the listing, here is a “chance to bring this iconic beauty back to life.”  

3534 S Calumet Ave, Chicago, $795,000

Photos courtesy of Redfin

Less than two weeks after hitting the market, politician Bobby Rush’s restored 1880s row house is already contingent. After a quick glance at the real estate listing’s photos, you can see why the property is described as “a true masterpiece of architecture.” The nearly 3,500-square-foot interior spans three levels, including a finished basement, and boasts great vintage details such as intricate woodwork, elegant fireplaces, and a stunning staircase. The exterior of the five-bedroom residence, featuring a combination of red stone and greenish bay windows, complements the neighboring walled courtyard, which includes a two-and-a-half-car garage with a rooftop terrace and brick pavers (so plenty of space for more vehicles). It’s close to the lakefront trail, 31st Street Beach/Harbor, and Guaranteed Rate Field.

3936 S King Dr, Chicago, $685,000

In addition to its connection to Mayor Harold Washington, who lived here for five years as a child, this 1890s greystone is located on what was once Grand Boulevard, originally developed by the South Parks Commission in 1874. The street, also known as South Park Way, was renamed in 1968 after Martin Luther King Jr., making Chicago the first city in the world to do so. The seven-bedroom residence will require a costly large-scale rehab. However, if you see beyond its current state, the original elements that remain throughout the 5,100-square-foot interior are truly remarkable and worth preserving. There is a grand staircase, original built-ins, marble and inlaid wood flooring, numerous fireplaces with historic tile, and a mural of trees on the dining room walls. 

765 E 41st St #1A, Chicago, $425,000

This ground-floor unit in a historic 1870s corner building at 41st and Cottage Grove comes with loads of character, featuring exposed brick walls and vents, wooden beams and columns, and floor-to-ceiling windows. The 3,600-square-foot interior appears to be quite spacious, likely due to the open-concept design of the main living area. Additionally, as a four-bedroom, three-bathroom duplex, the living room seamlessly connects to the family room located directly below. It also would be a great place to entertain friends and family. The property comes with multiple balconies, one parking space, and $626 HOA monthly fees.

4757 S Langley Ave, Chicago, $549,900

This 2,520-square-foot residence, an example of infill urban housing built around 2002, features four bedrooms and two full bathrooms. It boasts nice hardwood and ceramic floors, a finished basement, and a new hot water tank, electrical system, and sump pump. I particularly like the outdoor space, not always a given in the city, which includes a pergola and a double deck. Having been on and off the market since the summer, the asking price for this listing has been reduced by nearly $50,000.

4240 S Champlain Ave, Chicago, $890,000

Even though Bronzeville has a rich history, the neighborhood has experienced a surge of new construction, as you can see with this 3,475-square-foot, five-bedroom house. Compared to the median of $270,000 (as of October 2024), the asking price is quite high for the area. The contemporary design features an open-concept interior that includes a gas fireplace with built-in shelving on either side, detailed wall molding, and a chef’s kitchen. The stylish mudroom, the oversized walk-in shower in one of the three full bathrooms, and the convenience of having the family room adjacent to the kitchen are all ideal for modern living.