Howard Van Doren Shaw was pretty prolific in his day, and designed the homes for many of Chicago's wealthiest residents back in the early decades of the 20th century. Take for instance this stoic Georgian mansion built in 1907. The listing states that the eight bedroom home was once owned by Quaker Oats founder James Douglas. Once you get inside things brighten up, and although it has been updated over the years, the historic home still looks and feels like a historic home (well, besides the purple-walled bedroom). In true wealthy old school fashion, the manse sports seven fireplaces, large windows, a walnut-clad library and an elaborately ornamented dining room area. The manse also includes a very large backyard area, including a very old fire pit. New to the market, this South Side Van Doren Shaw can be had for $2.595 million.