At recent open houses in Winnetka I've talked to several young buyers who were looking in the $1 million price range in Winnetka - and in west suburban Hinsdale. They had as yet developed no strong preference for either location.
The only rivalry between Hinsdale and Winnetka that I'd previously aware of was when Hinsdale Central and New Trier High School met (as they've done repeatedly) in the finals of state championship sporting events.
The villages have many similarities, including great schools, a mix of older homes and newer homes in older architectural styles, strong traditions of civic involvement, and almost identical commutes downtown on the Metra lines. Winnetka has had its share of teardowns, and Hinsdale has been known for years as "teardown central."
Real estate agent Gaby Jury, who raised her family in Hinsdale and now lives on the North Shore, tells me it's fairly common for buyers to consider both Winnetka and what I call, with tongue in cheek, "Winnetka West." Join us, in the above video, for a mini-tour of downtown Hinsdale. Gaby's a client of ours.