Chaplin Estates


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.


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, ON Real EstateChaplin Estates’ two and three storey detached houses are situated on premium 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.


(P) Oriole Park Jr., 80 Braemar Avenue, (416) 393-5215
(PH) North Toronto Collegiate Institute, 730 Eglinton Avenue West, (416) 393-1860
(PR) Bishop Strachan School, 298 Lonsdale Road, (416) 483-4325
(PR) St. Clement’s School, 21 St. Clement’s Avenue, (416) 484-4835
(PR) Upper Canada College, Upper School, 200 Lonsdale Road, (416) 488-1125
(PR) Upper CanadaCollege Prep School, 220 Lonsdale Road, (416) 488-1125


(P) Public School (PH) Public High School (CA) Catholic School (PR) Private School (PC) Private Catholic School (PJ) Private Jewish School (C) College (U) University


Chaplin Estates residents are within walking distance of ïThe 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 ïEglinton’ 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-kind stores, and trendy restaurants that draw customers from all over the city.


map_48The Neshama Playground at Oriole Park, features a water play area, sensory musical features, Braille panels, an enclosed climbing merry-go-round and bounce pad, accessible swings and play structures, and colourful, springy surfacing. The playground was built with the generous support of donors across the city.

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 Beltline 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 – 201 Oriole Parkway Toronto, ON M5P 2H4

Oriole Park is special to the community in that it contains the first playground designed for children with disabilities.Neshama Playground has a water park, sensory musical features, Braille panels, an enclosed merry-go-round and accessible swings.

Eglinton Park


The park has two baseball diamonds, soccer fields, a splash pool, and a kids playground. Outdoor tennis courts are turned into skating rinks in the winter. Also located in the park is the North Toronto Community Memorial Centre with an indoor pool, outdoor pool, water slides, gymnasium, walking track, and exercise rooms. There is also an indoor skating rink. It has a cricket ground that has hosted ICC trophy games.

Moorevale Park – 175 Moore Avenue

A 1.5 hectare park near St.Clair Avenue East and Mount Pleasant Road that features five lighted outdoor tennis courts, a lighted lawn bowling green and club house, a wading pool, children’s playground, sport field and a baseball diamond. The park is home to the Moore Park Tennis Club and the Moore Park Lawn Bowling Club. Moorevale Park is a nicely shaded park with lots of beautiful trees. There are washroom facilities in the clubhouse and parking is available on the street.

Rosehill Reservoir –

Stretching roughly three kilometers and located in Toronto’s Rosehill neighbourhood, the Rosehill Reservoir provides one of the most beautiful walking excursions that you’ll likely find in the city. With three main entrances (at Mt. Pleasant Cemetery, at David A Balfour Park, and from St. Clair Ave. at the Avoca St. bridge) the reservoir is easily accessible for a person to go for a nice stroll or to walk their dog. The City of Toronto has built wooden staircases and walking trails on the west side of the reservoir for both convenience and to ensure that a little bad weather doesn’t stave off any potential wanderers.

The reservoir is home to beautiful woods and flowers and even the odd wild animal sighting (even in Toronto this is one spot that you could still happen across a deer or fox). Below the Avoca St. bridge, there’s also some incredible grafitti art to be found. Stretching forty feet from side to side and nearly five stories from the ground, the underside of the bridge is covered in expansive spray-painted murals and tags, demonstrating a gorgeous juxtaposition between the simple colours of nature and the wide variety used in the art world.


Find Your Way Around Chaplin Estates