Winchester graduated from Belgrade High School in Belgrade, Montana in 1999. He then lived and worked in London, United Kingdom (his mother\'s native country), attending the London Academy of Music and Dramatic Art (LAMDA).\n', '

Winchester\'s acting career started with a small role in the 1998 film The Patriot, which was filmed in and around the towns of Bozeman and Ennis, Montana. After graduating from high school, he began to take roles in plays, including that of Edmund in King Lear opposite Ian McKellen in the 2007 Royal Shakespeare Company production.\n', '

In 2003, he starred in the independent film The Telephone, which was filmed in Bristol and produced by Robert Finlay. In 2008, he was cast as Robinson Crusoe in the NBC action TV series Crusoe. In 2009, he was cast in Maneater, a two-part Lifetime miniseries starring Sarah Chalke.\n', '

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