Born in Boston, Massachusetts, to a U.S. Army officer, Winter spent most of his childhood traveling from base to base. While growing up, he attended ten different schools, including two in Germany, settling in Michigan when his father retired. There, Winter attended Western Michigan University, where he earned a Bachelor of Arts degree in theatre. He also studied with the British American Dramatic Academy in Oxford. Among his favorite roles while in college, were 'Alan Strang' in Equus, and 'Lee Harvey Oswald' in Assassins. Winter later moved to Chicago where he trained with the Second City and Improv Olympic Theatre groups before landing the role of 'Cody' on The Chris Isaak Show, marking his Television debut. Winter has since moved to Los Angeles.