Hi Robert, Chester Village was the western most of a series of small villages that sprouted along the Danforth starting around the 1850s, just outside the city limits of Toronto. At the western end, before the Township of Scarborough at Victoria Park Avenue was Little York, located in the vicinity of Dawes Road and Danforth.

Chester Village, which was never incorporated legally as a municipality comprised the area generally east of the Don River valley, just north of the Danforth, east to around Donlands Avenue and north perhaps up to O'Connor Drive.

In the 1860s the Playter family, which owned about 200 acres of land in the area which became known as Chester Village started to sell building lots, bringing people to the area.

Around 1858, James Beaven the first rector of St John's Norway Church is credited with naming the area Chester after the old Roman town in north west England called Cheshire. Sometimes Chester Village was referred to as Doncaster.

Chester was made up mostly of market gardens. In 1891 the Chester Public School opened. In 1959 the school closed and today its the Estonian Centre.

Chester remained part of York Township until 1909 when some the land just north of the Danforth was annexed to the City of Toronto.

Hope this helps.