Crescent Town can trace its roots back to 1887 when Walter Massey' - the son of Hart Massey, Canada's first major industrialist - purchased a 240 acre (1 km²) country property centered around Dawes Road and Victoria Park Avenue. The Massey farm was named Detonia after Mrs. Massey's family whose surname was Denton. The Massey farm sold fresh eggs and poultry as well as fresh trout which was caught in the many streams and rivulets that criss-crossed the farm. The Massey farm was also the home of the City Dairy Company which produced the first pasteurized milk in Canada.
In 1933, Susan Massey generously gave 40 acres (160,000 m²) of Detonia to Crescent School where her grandsons were educated. Crescent School operated at Detonia until 1969 when this property was sold to the developers who built the present day Crescent Town neighbourhood.
Hollywood actor Kiefer Sutherland from the hit fox television show 24 was among the first Crescent Town residents. He spent part of his childhood in Crescent Town and attended the Crescent Town Elementary School.