He has appeared in the television roles of Tim Bradford on the ABC show The Rookie (2018-present), Rex Brady on the NBC soap opera Days of Our Lives, FBI Special Agent Craig O'Laughlin on the CBS drama series The Mentalist (2010–2012), and Dash Gardiner on the Lifetime fantasy-drama series Witches of East End (2013–2014).

[1][2] Initially he began modeling and auditioning for small roles in soap opera with the intention of only earning extra money for college tuition.

From 2010 to 2012, Winter appeared in the CBS crime drama The Mentalist as FBI agent Craig O'Laughlin, the boyfriend and later fiancé of Amanda Righetti's character Grace Van Pelt.

[6] In 2013, Winter began starring in the Lifetime television series Witches of East End as Dash Gardiner.

He then dated actress Roselyn Sánchez for two years prior to their engagement in December, 2007, during a holiday vacation on Vieques, an island just east of mainland Puerto Rico.