John Macdonald, a major dry goods wholesaler, built Oaklands in 1860. It was enlarged by Mary McCormick, daughter of Cyrus McCormick, in the early 20th century. It is now De La Salle “Oaklands College. It got its name from the Oak trees, quite a few of which are still standing on the grounds. Oak was used for much of he interior paneling and wood finish. From the octagonal tower, which was added in 1870, the owners could see Brock’s Monument at Queenston Heights. By 1860, John Macdonald had the largest dry goods wholesale firm in Canada. In 1863, he turned to politics and became a member of the Legislative Assembly. Prime Minister John A. Macdonald appointed him to the Senate in November 1880. The two Macdonalds were friends, but not related.

The house was was sold in 1906. Mary McCormick added a stone porte-cochere, bay windows and a bowling alley. In 1931, the estate was sold to the Christian Brothers, who ran De La Salle College, then housed in two locations. De La Salle College “Oaklands” is now a private co-educational school. (For more about Oaklands and its owners see “Historical Walking Tour of Deer Park” by Joan C. Kinsella and “The Estatesof Old Toronto” by Liz Lundell). For a history of the school check this site