Oriole Park Association


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HISTORY AND HERITAGE HOMES – IN CHAPLIN ESTATES

Chaplin Estates originated in 1860 when the Chaplin family owned the land in the neighbourhood. William Chaplin and his son James decided to develop the land and a plan of the subdivision was filed in 1913 at the City of Toronto’s registry office. There existed a long list of building restrictions and zoning bylaws, in the sale of each property: Semi-detached houses were forbidden and stucco exteriors were not to cover more than 50% of the house. Many of the homes were later built in the 1920’s and 30’s by Douglas Kertland, a prominent Toronto architect at the time, who was known for his award-winning design of the CNE Automotive Building . The original architectural drawings can still be found in the Ontario Archives. Other prominent architects who designed homes in the Chaplin estates neighbourhood include E. R. Hoare, William Somerville, Dyce Saunders and Mathers & Haldenby.

Our research has uncovered some very interesting historical information. For example, did you know that the house at 287 Oriole Parkway incorporates bricks from the Ontario Parliament Buildings which had burned down in 1909?

Chaplin Estates has been and continues to be  home to many prominent Canadians, including Lawren Harris from the Group of Seven, architects Ernest Annau and William Somerville to name a few.

If you have any information about the history of your home or would like to volunteer your time researching alongside us, we would love to hear from you.


133 Imperial Street - Ann MacIntosh Duff 

Ann MacIntosh Duff, an accomplished Canadian artist, has resided in the neighbourhood since 1954. Ann and her mother used to live on Cluny Drive in Rosedale until her father John MacIntosh Duff’s unexpected passing at an early age in 1952. The house on Cluny Drive was designed by the architect Douglas Kertland, a close family friend who is best known for his award winning design of the CNE automotive building. When the family decided to build a new home they selected Chaplin Estates, an area in ‘North Toronto’.

They purchased the only remaining lot on Imperial Street from family friends. It was a double lot and functioned as a rose garden at the time. They commissioned Douglas Kertland to design the house on Imperial Street and they wouldn’t have considered another architect since Doug and his wife Gladys were special family friends. In fact in the 1920’s Mr. Kertland designed many of the houses in the neighbourhood including almost every house on Imperial Street.

Ann was a promising young artist at this time and it was imperative that the new house have an artist’s studio. Ann was keen on having a “modern” design for the new custom house but Mr. Kertland influenced them to have something more in keeping with the existing architectural style of the neighbourhood. The house is a unique 1 ½ story Georgian style structure. The second story is an artist’s loft that features a skylight and lots of south facing windows for natural light. The existing door knocker and exterior light were from the original house on Cluny Drive. Ann has resided in her home since 1954 and enjoys working in her studio and relaxing in the garden.

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