Born in Winnipeg in 1909, Winter received his art training under LeMoine FitzGerald at the Winnipeg School of Art. He moved to Toronto in 1937 where he established the advertising firm of Wookie, Winter and Bush.

Living in Toronto from the 1940s onwards, Bill Winter became known in the 1950s for his lively city scenes, many depicting children in a modern realist style. His subjects also include portraits, figures and the prairie landscape. He painted in oil, acrylic, and watercolour, and drew with pencil and coloured chalk.

Paul Duval noted that some of Winter’s best work was produced from the 1940s to the early 50s, and included “penetrating studies of Toronto’s inner city.” Duval added that they captured the colour and conflict of downtown life, citing Winter’s painting, Midnight at Charlie’s, 1945, a social realist work depicting a man alone in a diner, which was exhibited with a Canadian Group of Painters exhibition in 1945. This work, now in the Vancouver Art Gallery’s (VAG) collection, was also included in the VAG’s 1982 exhibition, Canadian Pictures 1951, an historical recreation of their 1951 exhibit.

In 1955, Winter left his career in commercial art to work as an independent artist. He deposited his RCA diploma painting, Street Scene, depicting a lively group of children playing on a side walk, at the National Gallery of Canada the same year.

He exhibited his work widely, including 19 exhibitions at Roberts Gallery, Toronto beginning in 1959. He was a member of the Royal Canadian Academy and the Ontario Society of Artists. Today, classified as a Canadian post-war modernist, he is best known for his paintings of children. His work is housed in museum collections across Canada and abroad, including the National Gallery of Canada and the Art Gallery of Ontario. He died in England in 1996.