Do you ever come across a home that catches your eye and wonder what it looks like inside? These five residences all have distinct exteriors that may not appeal to everyone’s taste, but never judge a book by its cover. Our first two listings are examples of historic buildings located in Lincoln Park and West Town, both of which have maximized their floor space by adding more stories. And I couldn’t resist also sharing a house designed by Conrad Schneider in the western suburbs. A local stone mason and building contractor, Schneider created nearly 30 “boulder” homes for himself and others in Brookfield and surrounding communities. Another unique feature these properties share, especially for single-family homes, are their roof decks. 

1934 N Bissell St, Chicago, $1,895,000

Let’s begin with this reactivated listing for a historic workers’ cottage with a massive mansard roof that is located in Lincoln Park’s Ranch Triangle. Originally built around 1876, just five years after the Great Chicago Fire, the four-bedroom, four-bathroom home was fully renovated inside from top to bottom in 2021. Spanning 4,000 square feet, the interior now features an open-concept design with a “showstopper” kitchen and “luxurious” primary ensuite bedroom on the third floor. But what truly stands out is the top-floor roof deck that comes with a kitchen, built-in grill, gas fireplace, wraparound bar, and stunning city views. 

1445 W Huron St APT 1, Chicago, $749,999

In West Town, on the edge of Noble Square, is another example of an older building featuring a large addition. This 2,700-square-foot, three-bedroom duplex down sold just over a year ago for $589,000. If this was a flipper situation, I have to admit they did a good job as the updated space is well designed. The home has a chef-inspired kitchen with new appliances, quartz countertops, and a built-in banquette, along with a custom mudroom and reading nook. The $515 monthly HOAs cover storage and a private garage deck. 

535 N Ashland Avenue, La Grange Park, $895,000

Local builder Conrad Schneider collected fieldstones found in local prairies and incorporated them into what became his speciality “boulder homes,” like this unique four-bedroom residence in the Harding Woods section of La Grange Park. Spanning nearly 2,700 square feet, the house was featured in the May 1917 issue of Motor Age, which noted that it was constructed with fireproof concrete roofs and also included built-in garages. The main level has vintage millwork, oak wood flooring, leaded glass windows, and a brick fireplace. 

1608 S Throop St, Chicago, $799,900

What appears to be a multi-unit building from the outside is actually a single-family residence. This nearly 1,700-square-foot, three-bedroom home is situated directly across from the two-mile embankment featuring public art and murals that runs along 16th Street in Pilsen. With its two-story living room and corner windows, the interior is filled with lots of natural light. The multi-level home features four floors, plus a partially finished basement. The primary bedroom suite on the top level opens directly onto a rooftop deck, which can also be accessed via an exterior spiral staircase.

400 N Racine Ave APT 204, Chicago, $440,000

Behind the gates of an unassuming concrete-block multi-unit complex at Racine and Kinzie lies a shared courtyard, with all the condos opening onto it. Although it is situated on the border between Fulton Market District and West Town, the building, which includes $352 monthly HOAs, is known as River West Village Lofts. This property was originally built in 1990 when this area was more industrial than it is today. Open and bright, this 1,257-square-foot, one-bed, one-bath loft has a staircase that leads up to a private rooftop deck.