While there were a number of settlers who moved into the area now known as Streetsville, the village's growth was stimulated by Timothy Street--for whom the village is named--and his family, who settled there in 1825. As payment for completing the New Survey, the government gave Street 4,451.7 hectares (11,000 acres) of land, the equivalent of 28,187 hockey rinks.
On this land, Street built his family home, a sawmill, a gristmill and a tannery. These businesses helped the settlement. By 1824, Streetsville already had two taverns, two stores, two shoemakers, a cabinet maker, a church and school house, as well as the original gristmill and sawmill. By 1851, a newspaper, "The Streetsville Review," and the Toronto Township's first high school had been added. The Street Family house is believed to have been the first brick building in the area. This house still stands at 41 Mill Street.
Streetsville was incorporated as a village in 1858, with John Street as the first Reeve. In January 1962, Streetsville was incorporated as a town; at that point, the town's population had exceeded 5,000. The Town of Mississauga was incorporated in 1968, joining together the settlements of Dixie, Clarkson, Meadowvale Village, and Erindale. While Port Credit and Streetsville were excluded from this, they were merged into the new City of Mississauga, when it was incorporated in 1974.