The Annex is so called because it was one of the first districts north of Toronto as it existed in the mid-19th century to be added (“annexed”) to the city. In 1886, Simeon Janes, a land speculator, purchased an area spanning from Bedford Road to approximately Spadina Road, and from Bloor Street up to Dupont Street from James Austin (founder of the Dominion Bank) who had previously acquired the land from the Baldwin family (of the famous Reform leader of Upper Canada, Robert Baldwin). The streets of the area and beyond had for the most part already been laid out and many named by the Baldwins.
One year after Janes made his purchase, Toronto City Council accepted his petition to extend the city limits to include this area, and Toronto's gentry rushed to build large houses in the new neighbourhood. Notable among others were the mansions of Timothy Eaton at the corner of Spadina Road and Lowther Avenue, of Senator Sir Allen Aylesworth at 21 Walmer Road, and of the Masseys at Madison, Walmer, and Lowther avenues.
Houses in the eastern part of the Annex were generally smaller and attracted businesspeople and professionals in the service sector. Working class homes were few and far between, though some of the small houses on streets east of Bedford Road (now among the most expensive real estate in Toronto) were designed as housing for servants. Later the “Annex” designation was extended to its current boundaries of Bloor Street north to the railway tracks, and Avenue Road west to Bathurst Street.
The most famous architect of the grand houses was Edward James Lennox, who, as in the case of Old City Hall (which he also designed) largely appropriated a Romanesque style lightened with the addition of Queen Anne Revival features. This innovative new style, coined “Annex Style” by architectural historian Patricia McHugh, is evident in buildings such as those at 37 and 69 Madison Avenue. Other prominent architects followed suit.
Early in the 20th century when the wealthiest families began moving farther north in the city, some of these larger houses were divided into multi-tenanted dwellings. After World War II many estates were converted into rooming houses to accommodate returning veterans and new immigrants including a number of Eastern European refugees who settled in the Annex after fleeing the repression of the 1956 revolt in Hungary. In 1966 a group of individuals dedicated to an idiosyncratic version of psychotherapy through communal living purchased 55 Admiral Road. Branding its movement as “Therafields,” the organization subsequently purchased more than 30 houses in the Annex for this purpose.
Not all the large houses were converted to multi-tenant living. During the 1950s and 1960s several of the original houses, primarily on St. George Street and Walmer Road, were torn down to be replaced by apartment buildings. For the most part these were low rise, reflecting the simple mid-century moderne aesthetic. However, a cluster of these reflected unique design, such as those of the Estonian-Canadian architect Uno Prii whose sweeping-walled high-rise apartments include the Vincennes at 34 Walmer Road and the Prince Arthur Towers at 20 Prince Arthur Avenue.
More recently the Annex has undergone a period of gentrification, especially in the eastern portions, and many of the erstwhile rooming houses are being restored to single-family dwellings. Nevertheless, as of this writing (2023), a full 70% of Annex residents are renters rather than property owners. By contrast to its beginnings when the population was largely white Anglo-Saxon Protestant, the area now also reflects Toronto’s multicultural diversity. It includes a mix of residence types and income levels that differentiates it from, for example, Rosedale, which was built contemporaneously to the Annex, or Forest Hill, which started development later beginning around the 1920s.
Original by Frank Cunningham [Revised by Sandra Shaul 2023]
For a personal account, see Jack Batten’s The Annex: The Story of a Toronto Neighbourhood (Boston Mills Press, 2004), which includes references to several other pertinent histories.
For a more formal study, refer to James Lemon's pamphlet The Annex: A Brief Historical Geography.