Have you ever walked by a building and wondered what it looks like inside? We are all guilty sometimes of being a little “house curious,” which is why people spend countless hours scrolling through Zillow. Well, in the case of the following properties for sale, you are in for a surprise. On a major street in Chicago stands a nondescript brick exterior that could be located anywhere in the city, but this isn’t just any old property. The inside has been turned into a beautiful urban retreat. It’s just one of the latest residential conversion projects by a well-known designer. There are some other examples of reimagining old non-residential structures, such as a school, church, and military hall. It’s always interesting to see what developers do, so let’s take a look at the unexpected interiors that lie behind these facades.

2733 N Pulaski Rd, Chicago, $3,500,000

Alison Victoria, the designer behind HGTV’s Windy City Rehab and other television shows, transformed this 1920s historic bow truss factory building in Logan Square neighborhood into a European-inspired live-work space. Underneath the 80-foot-long skylight is a stylish central courtyard anchored by a water feature and surrounded by olive trees. The 7,000-square-foot residence with four bedrooms has black and white marble flooring throughout its interior. According to Crain’s, Victoria purchased the property for $500,000 in 2017. So you can see that the asking price is quite high, which explains why it has been on the market for a month and a half. 

2210 W North Ave, Chicago, $2,500,000

In Wicker Park, there is a building that you might not notice at first or even second glance. This award-winning Wheeler Kearns design is now on the market for the first time since it was built nearly 30 years ago in 1995. Behind the simple exterior is a unique live-work space with large MDF pivot doors dividing the creative offices from the residential area. The 4,560-square-foot property is currently zoned B3-2, so it can continue as-is or be fully converted into either a commercial spot or a single-family home. 

240 Whistler Rd APT 1E, Highland Park, $2,500,000

Almost 25 years ago, non-military residents first moved into the decommissioned Fort Sheridan, originally designed by architects Holabird & Roche in 1893. What functioned as an infantry drill hall before being reused as a gymnasium is now an eleven-unit condo building. Right next to the prominent water tower, this particular end unit comes with five bedrooms, six-and-a-half bathrooms, and three different exposures. The rounded arch entrance on the eastern facade is now a large window, flooding the 7,000-square-foot interior with lots of natural light. The $1,810 monthly HOA fees cover services like water, lawn care, and snow removal.

154 School St APT 205, Libertyville, $495,000

The Central School in Libertyville was in use between 1939 and 1984, but today it has been repurposed as an industrial-style loft building. The classic exterior contrasts with the sleek living space. This 1,520-square-foot unit, once a fourth-grade classroom, has raw exposed ceilings and large east- and west-facing windows that bring in natural light. Location and walkability are the selling points for the three-bedroom, two-bathroom property, located only a block away from the downtown area.

2411 W Walton St APT 2B, Chicago, $969,999

Right on the border between Ukrainian Village and Humboldt Park sits the former Our Lady of Good Counsel, established by Bohemian immigrants in 1898. Now known as the Sanctuary, the church, rectory, and school were converted into condos just over 15 years ago. This penthouse duplex, which just received a price cut, lacks historic character beyond its exposed brick walls, but there is still plenty to appreciate. The property features three bedrooms, two full bathrooms, two balconies, and its own private rooftop space with a wet bar, gas fire pit, and observation deck.