As the name suggests, Earlscourt was first developed by British immigrant workers, largely in an unplanned way between 1900-1920. Until it was annexed by the City of Toronto in 1910, there were no building regulations. Many people built their own homes often starting with shacks that they later improved or replaced. After annexation, owner-builders moved north beyond Rogers Road, then the city limits, into York Township.
At first Earlscourt had no municipal services: a city-run streetcar line (1913), and then water and sewer lines were constructed after the area was partly settled. Then, stores sprang up along the streetcar line.
In the late 1950s, a wave of Italian immigrants moved into the area making improvements in homes and small businesses. They built extensions and cantinas on their homes, while transforming porches with Romanesque arches and ironwork.