Oakville Country Estate

Many illustrious Rosedale neighbours of W.G. MacKendrick belonged to the Toronto Horticultural Society.

toronto archives 1244, 4021


As ardent gardeners they took great interest in the landscape design of their country estate grounds along with their city gardens.

Canadian Architect and Builder Vol.22 (1908) issue 1


Among these Rosedale neighbours was J.H. Ryrie, owner of Birks’ Jewellers and resident of the landscaped subdivision of Chestnut Park, whose celebrated Arts and Crafts villa, Edgemere, was located several lots east of Mackendrick’s property on the prestigious Lakeshore Road estate area near Oakville.



toronto archives 1244, 9051


From 1909 to 1922, when he took up residence there, MacKendrick accumulated 400 acres of farm property. His plan was to retire to a home that offered continuity from his pre-war days.



The Oakville home was an almost exact replica of the one in Rosedale and he landscaped his grounds to echo the ravine setting of his former garden. In ‘Chestnut Point’ he was in surroundings that evoked his rural youth and offered scope for his landscaping projects.



The property was an address worthy of his accumulated wealth; a sure investment that would escalate in value as industry and suburban settlement radiated westward along the lake from Toronto.



In investing in a country property with the profits of the pre-war boom years he was not alone. At the same time that the fate of the English gentry plunged due to land reform, would-be country squires began to appear near large North American cities. Bankers, captains of industry, financiers, all wanted to pursue rural pastimes associated with the English aristocracy. Working farms with scenic views and within easy travelling distance of Toronto were bought-up to be converted to estates with extensive landscaped grounds.



A quintessential example of the appropriation of the English rural ideal was the Oakville Hunt Club. It met in Ennisclare, the estate of the Cox family, owners of Canada Life Insurance Company, on the other side of the fence from MacKendrick’s Chestnut Point property. The baying of the hounds would have regularly announced to lakeshore estate residents that the Ennisclare Hunt Club was gathering.



toronto archives 1244, 1324


In June of 1946 Mackendrick sold an adjoining field to a developer. A decade later, the private wooded lane-way leading to the lakeshore estate, Ennisclare, became the spine of another subdivision. The three resident groups that arrived in sequence, the farmers, the estate owners and the suburbanites were now living side by side, marking a century of  transposition of one landscape upon another and investment in a life just beyond the city.

To read more go to Menu: “Paving the Way to Paradise…” Chapter 4.

1. city of toronto archives fonds 1244 item 9051 Oakville (James Ryrie’s) 1919
2. Canadian Architect and Builder Vol.22 (1908) issue
3. map detail, Illustrated Atlas of Halton County 1877
4. city of toronto archives fonds 1244 item 9050 Oakville (Herb Cox residence) 1920?
5. MacKendrick family collection Chestnut Point 1926
6. centerfold illustration, 1913 Marketing Booklet For The Brantwood Survey, Town of Oakville by the Cumberland Land Co. Ltd. Oakville Historical Society
7. Advertisement, City and Country Life magazine
8. Ennisclare, courtesy Oakville Historical Society
9. Oakville Hunt Club, courtesy Oakville Historical Society
10. city of toronto archives fonds 1244 item 132 Oakville Fall fair 1914?