In 1897, Walter Massey, President of Massey-Harris Company, purchased about 100 ha of land to establish an experimental farm. Walter named the farm "Dentonia Park" after his wife, Susan Marie Denton. The farm produced eggs and poultry as well as trout. Dentonia was also the home of a prized dairy herd that sparked the formation of the City Dairy Company. The City Dairy produced the first pasteurized milk in Canada, which helped to combat tuberculosis and typhoid fever among Toronto children. In 1901, Walter Massey passed away after contracting typhoid fever, but Susan continued to operate Dentonia Park Farm well after his death. Walter's brother, Chester (and his children Vincent and Raymond) and Susan's children (Ruth, Madeline, Dorothy and Denton) also lived at Dentonia. The Goulding Estate was built in 1921 for Dorothy Massey Goulding.
In the benevolent tradition of the Massey family, Susan donated 25 ha of Dentonia, in memory of her husband, to the City of Toronto around 1926, for use as a public park to be named "Dentonia Park". Susan generously donated her home (built in 1914) along with 16 ha of Dentonia, to Crescent School (an independent school for boys) in 1933. Until Susan's death in 1938, she continued to live at Dentonia with her daughter Madeline.
Crescent School operated at Dentonia until 1969 when it moved and the property was developed into the Crescent Town neighbourhood. Prior to 1900, the neighbourhood south of the Massey Farm developed, a portion of which became part of East York Township in 1924. Many other residential and recreational areas were created out of the Dentonia Park Farm, including the City of Toronto's Dentonia Park Golf Course and part of Taylor Creek Park. The Dentonia Athletic Field continues to serve the community with a soccer field, baseball diamond, basketball court, cricket pitch, splash pad and playground.