The Chaplin Estates neighbourhood began with a plan of subdivision, registered by William John Chaplin and his son James D. Chaplin, in 1913. The Chaplin family had been landowners in this area dating back to 1860, when this district was known simply as ‘Eglinton’.

Chaplin Estates was marketed as a high-class residential district. The developers included a long list of building restrictions and zoning bylaws, in the sale of each property. There were no semi-detached houses allowed, and stucco exteriors were not to cover more than half the house.

The marketing of the subdivision was handled by the Chaplin Realty Company. Prices ranged from $500 to $9,000 a lot. Most of the lots were sold between 1921 and 1925.

Chaplin Estates’ two and three storey detached houses are situated on premium wide lots with private driveways.

The houses in this neighbourhood were built in the 1920’s and 1930’s, and include many fine examples of Tudor, Georgian, and English Cottage style architecture. 

There have been a growing number of new builds in this neighbourhood. 

This distinguished neighbourhood has always been one of Toronto’s most exclusive addresses. Chaplin Estates homeowners enjoy convenient access to excellent public and private schools, shopping, parks and recreation, and transit service. 

Neighbourhood landmarks include the Belt Line recreational path, Oriole Park Junior public School, Eglinton Way shopping district and the Neshama Playground which has a progressive layout designed to accommodate children with disabilities as well as all children in the greater community.