A young couple with two toddlers sell their home, and newlyweds move in. A tech bro puts his bachelor pad on the market, and a crypto king snags it. When properties change hands, the newcomers are often similar to those who just left. But when the house at 1352 North La Salle Drive sold over a century ago, seller and buyer couldn’t have been more different.

A sitting area with a fireplace inside 1352 North La Salle Drive

Built in 1886 and now on the market at $3.95 million, this five-bedroom residence once belonged to John F. Jelke, an oleomargarine magnate who successfully sued Wisconsin over the right to sell his product in the Dairy State. When Jelke moved out in 1921, Mabel Sykes bought it for $80,000. Born in Homewood in 1883, Sykes learned photography from her first husband and opened her own studio in the Loop after the couple divorced. Portraits were her specialty (movie star Rudolph Valentino was a favorite subject), and her work appeared regularly in the local papers. When she moved in, a news item indicated that she had plans to turn the billiard room into a studio “to be used exclusively for registering the charms of the Gold Coast beauties.”

The furnished rooftop deck at 1352 North La Salle Drive

The residence has had plenty of TLC over the years, most recently in 2024, with a stylish refresh by Brianne Bishop Design. Handsome historic details — eight-foot-high pocket doors, substantial cased openings, and five fireplaces — combine with upgrades to the kitchen and baths. There’s no telling which space was Sykes’s studio, but the public areas are all amply scaled. Standing four stories, plus basement, the house is equipped, luckily, with an elevator. The 9,200 square feet include a two-bedroom guest apartment and a two-bedroom in-law suite. There’s also a five-car garage — plenty of room for photo shoots of your own.