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These Four Beautiful and Historic Kenwood Mansions Are for Sale

Fine finishes and Old World charm in this South Side neighborhood

4924 S. Woodlawn Ave.   Photo: Urban Search Corp Of Chicago

While Kenwood may be best known to outsiders as the Chicago home of the Obamas, locals know the neighborhood for its inventory of historic mansions. Famous names from the early days of Chicago architecture left their mark on the neighborhood, and fortunately, a landmark district has helped protect the area’s architecturally significant houses.

These residences are filled with finely crafted finishes and Old World charm. Built for Chicago’s industrialists and ultra-wealthy over 100 years ago, these mansions remain austere (and quite pricey) today. Here’s a quick look at a handful of the best examples currently on the market in Kenwood.

4924 S. Woodlawn Avenue — $2.95 million

Architect Howard Van Doren Shaw is a well known name in the North Shore, but this large 10,000-square-foot mansion (pictured above) in Kenwood is a rare example of his work within Chicago proper. Built with the finest materials, this home boasts elaborate ornamentation both inside and out. There’s a lot to take in with this one—including the nearly $3 million asking price.

4950 S. Ellis Avenue — $1.425 million

Photo: Berkshire Hathaway HomeServices KoenigRubloff

Revered Chicago architects Benjamin Marshall and Horatio Wilson are the designers behind this limestone-clad mansion, according to the listing. The 5,000-square-foot mansion features five bedrooms, five and a half bathrooms, and many updated finishes and amenities. Despite a thorough renovation, original architectural details abound.

4908 S. Kimbark Avenue — $1.495 million

Photo: Berkshire Hathaway HomeServices KoenigRubloff

By no means an ostentatious house, this century-old mansion is rich in history and features. According to the listing notes, this mansion was built for a prominent industrialist and it certainly has a no-nonsense flair. Notable details include an original fireplace and mantle, original mahogany millwork, and a lovely Arts & Crafts-inspired stairwell.

5008 S. Greenwood Avenue — $1.995

Photo: Coldwell Banker Residential

Alfred Alschuler, the architect behind some of Chicago’s early skyscrapers such as the London Guaranty & Accident Building and the old Chicago Mercantile Exchange Building, is the designer of this masonry home on Greenwood Avenue. A true piece of Chicago architectural history, the 8,300-square-foot mansion has been updated and features many contemporary comforts. 

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