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Some of the best housing stock in the city lies along a narrow swath of the South Side — namely the Prairie Avenue Historic District. The pocket of land between 16th and 20th Street quickly grew into the city’s Millionaires’ Row after the Great Chicago Fire, with buildings by Daniel Burnham, Henry Ives Cobb (architect of the Newberry Library and much of the original University of Chicago), and Richard Morris Hunt (architect of the Biltmore House).

There’s not a lot of stock left in the Prairie District, the encroachment of industry having sent the industrialists north, but you can still buy a house there. And if you want more options, you can keep heading south. It’s no longer Millionaires’ Row or a Historic District, but there are still gorgeous, huge old houses all the way down to Kenwood in the corridor surrounding Prairie Avenue.

1900 South Prairie Avenue, $2.625 million


Photo: Redfin

Here’s your opportunity to live like a turn-of-the-century master of finance: this eight bedroom, eight bath house was built for banker Elbridge Keith in 1870, former president of title monopolists Chicago Title and Trust. If you need an income stream for the $2.625 million price, you can keep the first floor as an events space and live in one of the apartments above, or use it for anything that fits with in its light-commercial zoning—which in the past has included publishing offices, an art gallery, and an architectural bookstore. The coach house was used as an actual coach house as recently as the late 20th century, sheltering actual horses and coachmen, but it’s since been turned into a full residential unit.

3326 South Calumet Avenue, $800,000


Photo: Redfin

On the outside, it looks like it might have when it was built in 1890. On the inside, it’s been gut renovated, and this four-bed, 3.1-bath house looks the six days it’s been on the market. There’s lots of white paint, plentiful quartz and marble, and a subway-tile shower, plus a heated floor and high-end appliances in the open-concept kitchen — a big party space for the way we entertain now.

3348 South Prairie Avenue, $799,000


Photo: Redfin

Similar in approach is this 4,500-square-foot rowhouse nearby, with a classic brick and graystone facade outside and a very white contemporary look inside. This one’s a bit wilder than its near neighbor, with multicolored lighting in the master suite, which also features a fireplace and three walk-in closets. The living room also has a fireplace, as well as bold frosted-glass accents. It’s got five beds and five baths — including a basement that can serve as a small garden apartment — but is comparably priced at $799,000.

4541 South Forrestville Avenue, $599,000


Photo: Redfin

For a bargain of sorts, check out this 1890 Grand Boulevard mansion. It’s a fixer-upper, as you can see in some of the photos. But some of its period details are in outstanding shape: the built-ins and windows in the large, handsome living room, the arched windows in the sunroom, and the woodwork on the charming stairwell window nook. Expect to put in a lot of renovation, but at $599,000 for nine beds and six bedrooms, it starts at a comparatively low price.

4943 South Vincennes, $373,500


Photo: Redfin

No contempo gut-rehab here. There are benefits to buying a home from a family that’s been there 63 years, like the hardwood staircase that greets you when you come in, or the built-in cabinet in the dining room. The downside is that some of the rooms are dated to the period they were renovated: you may not be into the stuccoed ceiling in the parlor, or the brick paneling in the maid’s kitchen, or the transition from red to blue carpet on the staircase. But $373,500 for a 1905 graystone with six bedrooms gives you room to work.

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