Someone once told me on Twitter that “Nostalgia is poison for cities.” While it’s important that cities grow and move forward, I’m not sure Rome, Venice, and pretty much the entire world would have survived if it wasn’t for the power of tourism. That’s also true for Chicago, a city that loves to sell its history to tourists with various boat and walking tours. But let’s not forget about the people who actually live here, who love to learn about the Windy City’s past. While new construction is taking place all the time across the city, the best way to appreciate our architectural heritage is to take a look around at what’s existed here for decades. And if you’re lucky, maybe you can own a piece of that past. The following properties for sale are ideal for the home buyer looking for historic elegance in the city. 

6721 S Bennett Ave, Chicago, $885,000

Located in Jackson Park Highlands, this French Provincial residence by architect J.A. Carlson was possibly inspired by the 1927 home design competition held by the Chicago Tribune. Considering it was built for the owner of Nelson Cut Stone Works, the home has a limestone exterior and retains much of its original character, from the slate roof and decorative copper gutters to the mahogany beamed ceilings and wood paneled dining room. The four-bedroom, three-bathroom single-family house had quite a price increase since it was last on the market a decade ago, from $342,500 to $885,000. It’s just steps away from Jackson Park and all its wonderful features like Wooded Island and the 18-hole golf course.

3857 N Kedvale Ave, Chicago, $775,000

The historic Richard Mates home, originally built between 1870 and 1880, is located on a prime corner lot in Chicago’s Old Irving neighborhood. While completely renovated in 2013, the four-bedroom, three-bathroom home still has the feel of the 19th century with its wraparound porch, grand staircase, vintage light fixtures, mahogany millwork, and hardwood floors. Behind its white picket fence, the oversized property comes with a vegetable garden and a former horse stable that’s now a two-car garage. It’s right near the CTA and Metra stops, as well as Interstate 90/94.

9341 S Hoyne Ave, Chicago, $499,000

If you’re familiar with Beverly, then you’ve probably heard of the Hetherington family, three generations of architects who are responsible for creating a hundred buildings in the community. This three-bedroom, two-bathroom home built in 1934 last sold ten years ago. With its 20-foot-high vaulted ceilings and leaded glass windows, Murray Hetherington’s whimsical design is a play on an English countryside cottage (he lived in his own version a few blocks away). While the craftsmanship has a feel of another century, the residence has undergone recent improvements over the last five years, from its exterior trim and chimney to a new air conditioner and furnace. 

2114 W 112th St, Chicago, $389,900

Staying in the Beverly/Morgan Park area to share with you this truly handsome house that fits in perfectly with its neighboring 19th century residences, all located on wide lots and curving streets. Laid out with small parks and roundabouts in the 1870s by Englishman Thomas F. Nichols, Morgan Park has an almost suburban feel. Not a surprise knowing the village wasn’t annexed to Chicago until 1914. The five-bedroom, two-bathroom “Federal Blue” home is close to the 111th Street Metra Station and Morgan Park Academy.

6627 S Woodlawn Ave, Chicago, $499,000

It’s difficult to imagine Woodlawn as a small farming community, but that is exactly what this neighborhood was like before its annexation into Chicago in 1889. This lovely Shingle style residence was constructed for German immigrant Henry E. Scholle, the owner of a furniture company that largely manufactured upholstered items and folding beds. It dates from the time of the 1893 World’s Columbian Exposition, which led to an explosion of development in the surrounding area. Notice the great details on the exterior, like stylized foliage in the pediment. The inside of this three-bedroom, two-bathroom home has absolutely dazzling woodwork, including the coffered ceiling and intricate staircase.