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 by-laws 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.


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.


Chaplin Estates two and three-storey detached houses are situated on premium lots.

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


Chaplin Estates residents are within walking distance of "The Eglinton Way" shopping district along Eglinton Avenue West.  This ritzy shopping area includes high-end fashion boutiques, gourmet food shops, professional offices, restaurants, and the Eglinton movie theatre.

The Yonge street shopping district is also within walking distance of Chaplin Estates.  This highly visible shopping area includes many one-of-a-king stores, and trendy restaurants.


The ultra-modern North Toronto Community Centre has an indoor and outdoor pool, water slides, a gymnasium, a walking track and exercise rooms.

Eglinton Park is adjacent to the community centre.  Its facilities include:  a baseball diamond, tennis courts, a wading pool and an artificial ice hockey rink.

The historic Belt Line Trail walking and cycling path is easily accessed from Oriole Park, at the south end of the neighbourhood.

The Northern District branch of the Toronto Public Library is located on Orchard View Boulevard.  This branch offers programs for seniors, adults and children.



Oriole Park Jr.

80 Braemar Avenue

(416) 393-5215


North Toronto Collegiate Institute

730 Eglinton Avenue West

(416) 393-1860


Bishop Strachan School

298 Lonsdale Road

(416) 484-4835


St. Clement's School

21 St. Clement's Avenue

(416) 488-1125


Upper Canada College, Upper School

200 Lonsdale Road

(416) 488-1125


Upper Canada College Prep School

220 Lonsdale Road

(416) 488-1125



Chaplin Estates residents can walk to the bus stops on Yonge Street, Eglinton Avenue, Oriole Parkway and Chaplin Crescent.  The Davisville and the Eglinton subway stations are also within walking distance of this neighbourhood.

The main east-west arterial roadway is Eglinton Avenue.  Residents are approximately 15 minutes from the Allen expressway and the Don Valley Parkway.

Motorists can be downtown in 15 minutes via Yonge Street or Avenue Road.

Chaplin Estates

Dunkelman, David, Your Guide to Toronto Neighbourhoods, Copyright © 1997 by David Dunkelman