Chaplin Estates lies west of Yonge Street andsouth of Eglinton. The southern boundary is Chaplin Crescent which itself runs parallel to the former Beltline Railway line, now a scenic walking and biking trail known as the Kay Gardner Beltline Trail. A portion of the Toronto Transit Commission's Yonge-University-Spadina subway line runs aboveground in the eastern fringe of Chaplin Estates, and transit access is provided through Davisville station and Eglinton station.

Chaplin Estates 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. Housing lots feature generous setbacks.

arketing 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. The majority of its houses were built in the 1920s and 1930s, and include many fine examples of Tudor, Georgian, and English Cottage style architecture.

Subdivided and built in the 1920’s with many building restrictions. Mainly brick and stucco detached single family homes and some purpose built duplexes on wide tree lined streets. Many area parks include playgrounds and are a friendly meeting place for dog owners. The Beltline, considered a treasure by all. Families are fortunate to have The Oriole Park School which is recognized for its high standards. Bordered by The Eglinton Way featuring family and high end restaurants, shopping and services. Steps to transportation and a short walk to the subway, a wonderful community.

Schools

Oriole Park Junior Public School (JK - 6)
Address: 80 Braemar Ave, Toronto, ON
Phone: 416-393-9215, Website
Fraser Institute Rating

Bishop Strachan Private School (Girls Jr. - Sr.)
Address: 298 Lonsdale Road, Toronto, ON
Phone: 416-483-4325, Website
Fraser Institute Rating

Upper Canada College (Boys Prep - Upper)
Address: 200 Lonsdale Road, Toronto, ON
Phone: 416-488-1125, Website