The houses in Chaplin Estates are all detached, and feature two or three storeys and private driveways – a huge plus in the centre of the city, where a private drive is a luxury. Constructed in the 1920s and 1930s, these homes exhibit Tudor, Georgian, and English cottage-style architecture. Many have been renovated over the years, and some have been replaced by modern houses.

The history of this pretty, midtown neighbourhood dates back to 1913, when William John Chaplin and his son, James, whose family had been landowners in the area for half a century, registered a plan of subdivision for a high-class residential district. The neighbourhood is fairly small, bounded by Eglinton Avenue to the north and Chaplin Crescent to the south, between Yonge Street and Avenue Road. Midtown itself is a thriving business and retail district and Chaplin Estates is also ideally situated for easy access to the subway and downtown.

All that the city has to offer can be had in walking distance from a home in Chaplin Estates. Eglinton Ave. and Yonge St. provide every manner of business, service, shop, and restaurant, as well as movie theatres. For recreation, there is the Belt Line Trail, for walking and cycling, at the southern boundary of the neighbourhood, and the North Toronto Community Centre, on Eglinton Ave., with indoor and outdoor pools, a gym, a walking track and exercise rooms. Adjacent to the community centre, Eglinton Park provides tennis courts, a baseball diamond, and a hockey rink.

 With material from Your Guide to Toronto Neighbourhoods, by David Dunkelman

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