site of Sunnybrook Health Sciences Centre), northeast of Toronto, built by his wealthy father, as well as the family's summer home at Lake Simcoe. Dunkelman later recalled about growing on Sunnybrook Farm that "it was a dreamland, a children's paradise". As a child, he met prominent Zionists who stayed at Sunnybrook Farm, including future Israeli President Chaim Weizmann.

He attended Upper Canada College