Tag Archives: Oaklands


Sunday, April 9, 2023

Oaklands was built in 1860 as the private home of Senator John Macdonald. John, who was born in Perth, Scotland in 1824 is not to be confused with Sir John A Macdonald. The two Macdonalds would later fight over Confederation. He came to Canada in 1837 with his family and in 1849 opened a dry goods store. He switched to wholesaling in 1853 and by 1870 his annual sales had reached $1,000,000. In 1860 he had purchased a plot of land on the top of the old Lake Iroquois shoreline where the richest men in the city were building their mansions. Many of these have been demolished but Spadina House and Casa Loma are two examples that still exist.

The property on which John built his home was originally a 200 acre grant given to Chief Justice John Elmsley in 1798. The family gave the property to St. James Anglican Church in 1836 and they sold 35 acres to John Macdonald in 1858. Macdonald named his property Oaklands because he admired the large oak trees that grew on the property. The image below shows the home and Avenue Road in 1860 and was taken from the De La Salle College website.

John Macdonald opposed the confederation of the British colonies and went against John A Macdonald in doing so. After Confederation in 1867 he served in the House of Commons as an Independent Liberal. Prime Minister John A Macdonald appointed him to the Senate in 1887 and he served there until his death in 1890.

The building is now in use as a school with its own history which dates back to 1651, the year in which St. John Baptiste De La Salle was born in Reims, France. He had an opportunity to enter the priesthood but in 1678 he elected to form a Christian education group called Les Freres des Ecoles Cheretiennes. In the image below the front door can be seen with its side lights and glass transom window. The entrance is protected from the elements by the porte cochere. John Macdonald would have arrived home in the porte cochere in his horse drawn carriage and later there would have been early automobiles such as the Model T passing through here.

The Brothers De La Salle arrived in North America in 1837 and set up a school in Montreal. Fourteen years later they came to Toronto and had their first Christian School at Lombard and Jarvis Streets.

In 1871 they moved to the old Bank of Upper Canada building at George and Adelaide Streets and also occupied the building that had served as Toronto’s first post office. After completing a building in between the two they stayed there until 1914 when they moved to 67 Bond Street.

In 1931 De La Salle College made the move to Avenue Road and occupied the Oaklands estate. Since then they have added other buildings including the main school building in 1949. They also have a sports field on their property below the escarpment. As I was photographing the building I noticed the artwork below. There’s a ship with wings but above that is a hand with a knife that is held in a stabbing motion. This is an unusual emblem to put on the side of your estate.

Oaklands is considered to be the best example of Gothic Architecture in a residence, as apposed to a church building, in the city.

Related articles: Spadina House, Casa Loma, Inside Casa Loma, Toronto’s First Post Office, Toronto’s Model T Factory

Google Maps Link: Oaklands (De La Salle College)

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