Winbush was born in Culver City, California. Her credits include a role in Ghost Dog: The Way of the Samurai and an appearance in Eraser. Additionally, she had a recurring role on 7th Heaven and roles on Criminal Minds, That's Life, The Norm Show, NYPD Blue and Any Day Now. She also guest starred in Disney's musical production of Geppetto.
She got her big break playing the role of Vanessa "Nessa" Thomkins on The Bernie Mac Show. During her run on the show Winbush earned numerous award nominations for her role, winning three NAACP Image Awards for Outstanding Supporting Actress in a Comedy Series and a Young Artist Award for Best Performance in a TV Series (Comedy or Drama) - Leading Young Actress. In 2007, she appeared in an episode of Grey's Anatomy.
As of 2008, Winbush can be seen playing Lauren Treacy, a recurring character in The Secret Life of the American Teenager.
In 2002, she recorded "One Small Voice" featuring singers Myra & Taylor Momsen and "The Night Before Christmas Song" for the compilation album School's Out! Christmas. She also sang on the soundtrack of the Disney musical production of Geppetto.