Winchester graduated from Belgrade High School in Belgrade, Montana in 1999. He then lived and worked in London, England (his mother's native country), attending the London Academy of Music and Dramatic Art.
Working consistently since 2010 he has played the role of Frank Stanton, parallel universe fiance of Olivia Dunham, in the Fox series Fringe. From 2011, he has appeared as Leontes in the Starz series Camelot. Other credits include the second, third, fourth and fifth seasons of Strike Back, which aired on Sky1 in the UK and Cinemax in the US. The series follows the adventures of two Section 20 agents, Sgt. Michael Stonebridge (Winchester) and American former Delta Force officer Damien Scott (Sullivan Stapleton). He currently stars with Wesley Snipes and Charity Wakefield in the NBC drama The Player.
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