Winter has won four Emmys, an Edgar, three Norman Felton Awards for Outstanding Producer of Episodic Television Drama, a Golden Globe, a PEN USA, and four WGA Awards during his time on both The Sopranos and Boardwalk Empire.
In 2014, he received his first Oscar nomination for Best Adapted Screenplay for The Wolf of Wall Street.
Winter wrote or co-wrote 25 episodes of The Sopranos. He also directed "Walk Like a Man". In 2001, together with Tim Van Patten, Winter won both the Writers Guild Award and the Edgar Award for his episode "Pine Barrens," directed by Steve Buscemi. In 2004, Winter won two Emmys, one as Executive Producer for The Sopranos for Outstanding Drama Series, and one for Best Writing in a Drama Series for the episode "Long Term Parking." He won another writing Emmy in 2006 for his episode "Members Only." Also in 2006, Winter wrote and directed an episode, "Walk Like a Man," for the show's final season. Winter won his second Writers Guild Award and his fourth Emmy when The Sopranos won Outstanding Drama Series. He won his third Writers Guild Award and the Pen USA award for his episode "The Second Coming," in 2008.The Sopranos also won The Norman Felton Award for Outstanding Producer of Episodic Television Drama in 2005 and 2008.
Winter and Boardwalk Empire won a Writers Guild of America Award for Best Writing in a New Series and he was nominated for Best Writing in a Dramatic Series 2011 - 2013.Boardwalk Empire won the Golden Globe Award for Best Television Series Drama in 2011 and was nominated in 2012 and 2013. In addition, Steve Buscemi won for Best Actor in a Dramatic Series and Kelly MacDonald was nominated for Best Supporting Actress in a Series, Miniseries or Motion Picture Made for Television.Boardwalk Empire was in The American Film Institute's Top Ten List for TV in 2010 and 2011. The Cast of Boardwalk Empire won the Screen Actor's Guild Award for Best Ensemble in a Drama Series, while Steve Buscemi won the Screen Actor's Guild Award for Outstanding Performance by a Male Actor in a Drama Series and Martin Scorsese won the Directors Guild Award for Outstanding Directorial Achievement in Dramatic Series. Boardwalk Empire was nominated for the Emmy for Outstanding Drama series in both 2011 and 2012. In addition, Boardwalk Empire won The Norman Felton Award for Outstanding Producer of Episodic Television Drama in 2012 and was nominated for BAFTA Best International Television in 2011.