Windsor attended Queen Mary's Grammar School, Walsall, and studied speech training and drama at the Central School of Speech and Drama, then based at the Royal Albert Hall, London.
From 1987 to 1989, Windsor starred in the comedy drama Flying Lady written by Brian Finch.
Windsor had regular roles in the BBC drama Casualty; the ITV drama Peak Practice; he played Major Charlie Grace in EastEnders (1992); appeared twice in Doctor Who; had various stage roles, and in his later years appeared in television commercials advertising life-assurance policies for people over 50.
He was the subject of This Is Your Life on 3 December 1975 when he was surprised by Eamonn Andrews at the Metropolitan Police Sports Club in East Molesey.
[citation needed] Windsor was married to Mary Corbett from October 1959 until his death.