As I was scrolling through real estate listings this past week, a property for sale in Barrington caught my eye. What looks like a brand-new home actually began life as an upholsterer’s barn. It has now been updated inside and out, along with a three-story addition attached to the original structure. Who doesn’t like the idea of owning a property with some interesting history, but that has been reimagined for modern living? Whether it was previously a ComEd substation in Chicago or a former dairy farm in Oswego, these five properties boast major design appeal for potential buyers. These old buildings have been given new life as residences. 

21318 N IL Route 59, Barrington, $725,000

Photos courtesy of Redfin

This vintage barn and upholstery shop was transformed into 2,400-square-foot, four-bedroom single-family residence by ALA Architects & Planners in 2019. Located on nearly two acres of land along Route 59, part of the original barn’s outline is still visible on the home’s exterior. This thoughtfully redesigned, modern industrial farmhouse features many great details, like an oversized island and floating shelves in the kitchen, as well as a pull-out countertop in the laundry/mudroom that also includes a pet shower. The property offers a country-like atmosphere but it is conveniently close to downtown Barrington for everyday needs.

1128 W Ardmore Ave APT 1, Chicago, $600,000

Would you live in a historic Commonwealth Edison substation? Located right next to the elevated tracks in Chicago’s Edgewater, this structure was originally constructed in 1925 and converted into sixteen lofts between 2006-07. (Thank goodness for those soundproof windows!) This 1,800-square-foot, two-bedroom condo has an industrial look throughout its interior with exposed brick walls, vaulted concrete ceilings, and original substation railings that lead down to the lower level. There is a private, ivy-covered walled outdoor space, which is perfect for grilling and hanging out (if you don’t mind the noise from the el train).

3760 Gilgare Ln, Highland Park, $1,149,500

It’s always interesting to see what is currently available in the Fort Sheridan Historic District, a U.S. Army post designed by architects Holabird & Roche in 1889 and closed in 1993. Most of the original structures, including housing, barracks, stables,the water tower, and the 54-acre parade ground, have all been preserved. This six-bedroom duplex, spanning just over 5,000 square feet, once served as a residence for lieutenant colonels who stationed at Fort Sheridan. I particularly love all the outdoor spaces, including the gazebo on one of the three decks, where you can enjoy lake breezes and ravine views. The property has been on and off the market since June, with a contingency that fell through, and its asking price was recently reduced.

531 S Plymouth Ct APT 602, Chicago, $535,000

The Mergenthaler Building was originally constructed in 1886, with an addition and remodeling completed in 1917. It once housed the linotype machine, known as the “second Gutenberg” because it revolutionized the printing industry. One of the first structures on Printers Row to be converted into lofts in 1979 by architect Ken Schroeder, this southwest-facing penthouse features two beds, one full bath, two half baths, and 2,400 square feet of interior space spread over multiple levels. The clever design features numerous internal windows, including circles, to allow extra light into the kitchen and bedrooms, as well as nooks that maximize the use of space. 

51 Chippewa Dr, Oswego, $1,200,000

Originally a working dairy farm built in 1917, this sprawling 1.3-acre property in Oswego featuring stunning outdoor areas has been on and off the market for over a year. Now a single-family residence with six bedrooms, including two primary suites, the home retains reminders of its past with a prominent grain silo, an original pulley hanging in the living room, and a large sundial overlooking the large open-concept interior. During the 1990s conversion, K. Peterson Associates Architects skillfully re-used the barn’s original materials, including flooring, ceiling, beams, and stairwell. An elevator shaft connects all three levels. What an amazing place!