In early December, Edward McClelland wrote a post about famous people who have lived in the Chicago area over the years, from Mr. T in Lake Forest to Oak Park’s own Ernest Hemingway. But would you consider purchasing a property where a famous person once lived? Consider the Sheridan-Aldine Apartments in Chicago’s East Lakeview, an Italian Renaissance Revival design created by architects Maurice B. Rissman and Leo S. Hirschfeld. The lakefront building was developed and inhabited by Chicago’s grande dame Edith Rockefeller McCormick in 1926. Local newspaper columnist Mike Royko, who dubbed himself “High-Rise Man” bought a unit in the building between 1981 and 1985 as an experiment to study yuppies by living among them. Royko’s condo is now for sale, along with other properties that also have notable connections. 

1239 N Dearborn St, $2,000,000

For the first time in over half a century, a property in the Gold Coast linked to Ernest Hemingway has hit the market. Originally built as a single-family residence in the 1890s, the building was divided into several units in 1910, including a rear coach house. Just over a decade later, Hemingway and his new wife, Hadley, rented the top-floor apartment for a short time when the neighborhood was still rough, before moving abroad to Paris. This is a perfect opportunity for rehabbers to restore the building to its original glory or maintain it as a rental property, which now includes a five-bedroom unit spread over three floors and two street-level studios.

999 N Lake Shore Dr UNIT 4C, $1,150,000

A decade ago, a book was published about the renowned residents of one of architect Benjamin Marshall’s most notable designs: a Beaux-Arts high-rise that stands 10 stories above Lake Shore Drive. This particular unit, with absolutely stunning lake views, was home at different times to gangster Terry Druggan and Eloise ReQua, who founded the Library of International Relations. The nearly 3,000-square-foot property boasts its own private hallway entrance, three bedrooms, two full bathrooms, a tiger mahogany wood-paneled library, and a charming sunroom. Plus there is a wonderful rooftop with a garden.

3300 N Lake Shore Dr APT 6AB, $1,400,000

Once the home of local newspaper columnist Mike Royko, this four-bedroom, four-bathroom condo has been recently restored to its original 1920s appearance. With views of Belmont Harbor and Lake Michigan, the property features its own private elevator foyer, wood-paneled library with a secret closet, and eat-in kitchen. The electrical system was updated and all 28 windows have been replaced. The HOA fees are over $3,000 per month and cover services such as heating, water, and cable. The unit includes two extra downstairs storage spaces and a deeded parking spot. 

829 E 88th St, $265,000

Just over two years ago, the residence that belonged to Muddy Waters, known as “the father of modern Chicago blues,” officially became a historic landmark. Fellow legendary blues musician Howlin’ Wolf temporarily stayed there as he resettled in Chicago after moving from the South. He later constructed his own home in Chicago’s Chatham neighborhood in 1964, where he resided with his wife, Lillie, and their two daughters. The 1,300-square-foot raised ranch, which has been fully remodeled with an HGTV-inspired interior, comes with four bedrooms and two bathrooms. 

403 N Grove Ave, Oak Park, $1,100,000

If you’re at all familiar with the history of the Mayflower, then you’ve probably heard of Myles Standish. According to an article in the Wednesday Journal, the long-time owners of this six-bedroom, three-bathroom house in Oak Park discovered that it was originally built by members of the Standish family. Constructed in 1887 as a single-family residence and later converted into a three-flat in the 1920s, the home has been restored and features vintage details such as pocket doors and an original fireplace with tilework displaying the initials of Albert H. Standish. The third floor is still a legal apartment with separate utilities, so new owners can rent it out for additional income.