Father Arnold Damen helped establish the Jesuit presence in Chicago by founding one of the city’s oldest Catholic parishes, Holy Family Church, as well as its next door neighbor, St. Ignatius College Prep, in the 1860s. The priest was also responsible for the institution that would later become Loyola University. In 1927, the Chicago City Council voted to change the name of Robey Street to Damen Avenue in honor of Father Damen. It was specifically chosen because Robey crossed the Chicago River at the exact spot where explorer and Jesuit missionary Pere Jacques Marquette landed and spent the winter of 1674-75. An Art Deco bronze monument completed in 1930 near the northeast corner of the South Damen Avenue bridge honors Marquette’s meeting with the Native Americans. Damen is one of the city’s longest streets, stretching from the West Ridge neighborhood all the way south to Beverly. So let’s take a look at current real estate listings for sale that are located near this major city thoroughfare. 

2028 W Walton St, $1,000,000

The charm of this four-bedroom, three-bathroom workers cottage in Ukrainian Village totally called out to me. First of all, it’s always great to see intact elements left inside, specifically at that lovely woodwork. Yet it’s a great mix of old and new with the updated kitchen and some of the bathrooms. If the kitchen isn’t big enough for you, get rid of the office so the space opens up. An addition to the rear of the home contains a large family room with vaulted ceilings. Plus there’s a finished basement as well as a nice deck and paved patio.

1813 W 19th St, $699,000

What’s for sale around the Pilsen/Heart of Chicago Area? Even though the exterior of this three-bedroom, two-bathroom house’s front porch and colonnade might look “old” (it was built in 1889), the inside was entirely rehabbed in 2016. All new plumbing, HVAC, electricity, roof, and gutters were installed. The gray wood flooring and walls feel trendy, but it does freshen up the space. The house is directly across the street from Harrison Park and the National Museum of Mexican Art. And it’s just a short walk away from the 18th Street Pink Line L stop. 

2000 W Haddon Ave APT 210, $500,000

Located only a block away from the intersection of Damen and Division, this two-bedroom, two-bathroom duplex loft recently got a price cut, bringing the sale price down to $500,000. Converted into condos 30 years ago, the 14-unit building originally built in the 1920s comes with a heated parking garage and common rooftop deck. The primary en-suite bedroom looks over the main living space with western-facing windows and 15-foot-high ceilings. The second bedroom has a built-in Murphy bed and expansive closets, making this the perfect “flux” room. A truly stunning space with all its high-end finishes and custom design work.

9856 S Seeley Ave, $459,900

A block or so from where Damen Avenue undisputedly comes to an end is where you’ll find this beautifully restored 1920 bungalow listed at $459,900. With four bedrooms and two full bathrooms, the historic home has some cool details like the Motawi tile fireplace and the built-in butler’s pantry hutch. The upstairs attic has been completely renovated into a bright, white office space and the primary bedroom suite includes a large bathroom with a walk-in shower. 

1934 W Grace St, $1,385,000

Here’s an opportunity to purchase a historic three-flat that’s only had three owners since it was constructed in 1910. Located in the Alexander Graham Bell school district in North Center, the multi-unit building is a mix of vintage charm and tasteful modern updates. Not only is there a three-bedroom, two-bathroom owner’s unit duplex that currently rents at about $4,000 a month, but the second and third floors feature three bedrooms and one bathroom with a market rental value of $2,400 per month. Each flat comes with its own outdoor deck that looks over a lovely backyard and patio.