The Annex's first residents included such famous personages as Timothy Eaton, the noted patriarch of Eatons department store, who helped fund the building of Trinity Methodist Church in 1889 at 427 Bloor Street West. European settlement of the Annex area began in the 1790s when surveyors laid out York Township. The area east of Brunswick Avenue became part of the Village of Yorkville, while the region west of Brunswick was considered part of Seaton Village. In 1883, Yorkville agreed to annexation with the City of Toronto. In 1886, a merchant and land developer by the name of Simeon James, created a subdivision which he called the Toronto Annex. The lands had been annexed by the City in order to provide essential services such as water, sewers and paved roads. The City of Toronto continued to annex additional properties west to Bathurst Street and the Annex as it is known today, was born. Many of the homes in the Annex were built during this time and into the early 1900's, encouraging the emergence of one of Toronto's elite neighbourhoods.

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