People around Chicagoland are all familiar with the bungalow belt or suburban tract housing where everything pretty much looks the same. But what about one-of-a-kind homes that got a second chance at life? I’ve shared some properties that fall under the category of adaptive reuse or repurposed buildings before in the real estate section. Instead of demolition, an owner takes a structure that no longer fits its original function and converts it for residential use. Like historic schools, 19th century bakeries, old train cars, or the contributing properties at the Fort Sheridan Historic District. these dwellings are great examples of historic preservation and environmental sustainability. They’re not too bad to look at, either. 

96 Ronan Rd, Highwood, $2,275,000

Photo courtesy of Redfin

Let’s start with the priciest listing: A former artillery storehouse at Fort Sheridan that dates from the late 19th century was transformed into a stunning 6,000-square-foot single-family residence when the military base was decommissioned 30 years ago. Once featured in an Architectural Digest article, the home comes with three bedrooms and two-and-a-half bathrooms and is situated on a beautifully landscaped half-acre site. The interior is defined by a sequence of 16 10-ft-high arches with a catwalk above that crosses the main living space. Just outside are a forest preserve, scenic walking paths, ravines, the lakefront, and the Robert McClory Bike path.

2655 W Huron St, Chicago, $599,900

Photo courtesy of Redfin

The family-owned and operated C&C Bakery specialized in handmade breadsticks called “grissini,” which were baked daily for local restaurants and hotels. Two years ago, the building on the western edge of Chicago’s West Town was converted into a sleek  and modern four-bedroom, two-bathroom single-family residence. The historic brick facade was painted black while the inside is completely new with high quality finishes. The architect-owned property recently got a price cut less than a month after it hit the market in early July. 

301 East Townline Road Unit 30 E, Lake Geneva, WI, $130,000

Photo courtesy of Redfin

Would you live at the “End of the Line”? In 1984, Dave and Pat Hanley purchased a bunch of 1930s shiny red cabooses from the Chicago & North Western Railway, setting them up together into one long train on a mile-long stretch of the abandoned right-of-way tracks near Lake Geneva, Wisconsin. Some of the remodeled cabooses form suites, like this 960-square-foot three-car condo with a deck, one of the largest units available in this unique development that operates seasonally from May through October. Its current cash-only price is $125,000 with $550 in monthly HOA fees covering a clubhouse and pool. 

915 N Hoyne Ave #9, Chicago, $1,350,000

Photo courtesy of Redfin and VHT Studios

In the early 1900s, architect Henry Worthmann, a member of St. John Evangelical Lutheran Church’s congregation, was chosen to design a new church, school building, and parsonage in Chicago’s Ukrainian Village. Notice the German name of the school engraved above the entrance door of what’s now a nine-unit condo building. Completed in 2018, this 3,000-square-foot condo with downtown skyline views has exposed brick walls, incredible finishes, and two outdoor terraces. Considering this listing is for the penthouse, it is hardly surprising that we have a price tag of $1.3 million.

832 Stables Court West #832, Highwood, $675,000

Photo courtesy of Redfin

Returning to Fort Sheridan in Highwood to share another adaptive reuse project that is currently on the market for $625,000. This two-bedroom, two-bathroom townhouse was originally built as one of the five horse stables found at the closed army post. With a cream-colored brick facade designed by Holabird and Roche in the 1890s, the interior features 24-foot-high ceilings with exposed wood beams that really opens up the nearly 1,700-square-foot space. The property also has a patio and attached two-car garage.