Winnetka, Illinois, has long been considered Chicago’s marquee suburb with hotel-size homes at the end of heated driveways and faux-French country houses overlooking Lake Michigan. Popular with big-brand CEOs and lawyers, and familiar to non-Winnetkans as the setting of Home Alone, Ferris Bueller’s Day Off, and nearly every John Hughes movie ever made, it is a place where titanic wealth meets Midwestern folksiness.
Four years ago, at the height of the pandemic, a mystery buyer began acquiring mansions along Winnetka’s waterfront and knocking them down. One of the mansions was less than a decade old and featured an indoor basketball court and a movie theater. Another, whose previous residents included a plastic surgeon and the inventor of the retractable seat belt, had a distinguished architectural pedigree. All three had sat next to each other overlooking a beach known for its fine white sand and would become part of a gaping construction zone.
