The beginnings of Streetsville are interwoven with the history of its founder, Timothy Street. Street was born in 1778 to a British Loyalist family in what became the United States. At the age of 23, he moved with his family from New York to St. David's, a settlement off of the Niagara River in Upper Canada (now known as Ontario).

In 1818, the British offered up 648,000 acres (2,620 km²) of land to be surveyed, from their second purchase from the indigenous Mississauga peoples. Along with Richard Bristol, a qualified surveyor, Street applied for a contract to survey parts of the newly available land, which would enable him to eventually own parts of that same land as a sort of payment for his services. The two men were granted the contract and quickly Street began to realize the immense potential for settlement along the Credit River, making plans to erect both a saw and grist mill.

The first settler in the area now known as Streetsville was James Glendinning in April of 1819, who settled just along Mullet Creek. It was with the stones from his settlement that the grist and saw mill were constructed. Timothy Street acquired 1,000 acres here and proceeded to establish industries vital to a pioneer community. The village was named Streetsville by 1824.

In 1821, Streetsville's first general store, otherwise known as the Montreal House, was built and still stands to this day. Another landmark, Timothy Street's house, was built in 1825 and is one of the oldest brick houses in Peel Region.

The backbone of Streetsville's importance was its five major mill sites along a three-mile stretch of the fast-flowing Credit River. By 1850, it was the "Queen of the County".

In 1855, William Graydon and Peter Douglass built the Franklin House. Graydon and Douglass sold it in 1859 to Bennet Franklin, a partner in Barber Brothers Toronto Woollen Mills. In 1910, under new ownership, the name was changed to the Queen's Hotel. It ceased to operate as a hotel with the enforcement of the Canada Temperance Act, but continued to be used for commercial purposes. Designated under the terms of the Ontario Heritage Act and protected by a heritage easement. It is now home to Sundance Saloon & Grill, Micheal J. Fisher Law Office, Interstrata, Dr. Ted Blackmore and Streetsville Florist.

In 1858, Streetsville was incorporated as a village, with John Street as its first reeve.

In January 1962, Streetsville was incorporated as a town when at that point, the town's population had exceeded 5,000. The first Mayor was Frank Dowling.

The Town of Mississauga was incorporated in 1968, joining together the settlements of Cooksville, Dixie, Erindale and Malton. While Port Credit and Streetsville were excluded from this amalgamation, they were annexed, along with Clarkson, Erin Mills and Meadowvale Village, when Mississauga became a city in 1974. Since that time, Streetsville's community comes together every June to celebrate the founding of the village with the Streetsville Founders' Bread & Honey.

The Bread & Honey Festival originated through the Promo tion Committee of the Town of Streetsville in 1973. The first Festival, under the auspices of the Streetsville and District Chamber of Commerce, was such an outstanding success; it became an annual event, held the first Saturday in June. In 1974, it was incorporated, with Sam McCallion as Charter President.

Hazel McCallion, who had been the mayor of Streetsville from 1970 to 1973, became the mayor of Mississauga in 1978, only the third in the city's history, and is still serving as of 2007.

The members of the popular Billy Talent band: singer Ben Kowalewicz, guitarist Ian D'sa, bassist Jon Gallant and drummer Aaron Solowoniuk, met in Streetsville High School and performed in many school talent shows. At that time the band was known as Pezz.