Winokur will play Amy, a series regular in the upcoming season. Amy, a quick-witted successful saleswoman, is the sister of David, who is played by Johnathan McClain.
"Retired at 35," according to TV Land, focuses on "successful young businessman David (McClain), [who] decides to leave the rat race of New York City behind and move into his parents' (George Segal and Jessica Walter) Florida retirement home."
Winokur won the Tony Award in 2003 for her performance as Tracy Turnblad in Hairspray, which she reprised in the recent Hollywood Bowl production. She has also been seen on Broadway in Grease.
"Retired at 35" will return to TV Land for its second season in March 2012.