We had a Trappist Cistercian monastery in Orangeville. Over the course of about fifteen years, there were no vocations; this meant the monks had to return to Oka, Quebec. One young man who lived in Markham, and who did have a monastic vocation, entered the Abbey of the Genesee in Piffard, New York, about an hour and a half drive over the border from Toronto.
The Trappists’ buildings were taken over by a Ukrainian Catholic monastery of Studites; I believe Father Terry of EWTN fame belongs to this group. They moved out, and sold the property to an Orthodox monastic group. The Studites still have a monastery in Woodstock, Ontario, next to the prayer tower/lighthouse, visible from highway 401(just drive west from Toronto, you can’t miss it).
The Augustinian friars have a monastery at Marylake, but theirs is a mendicant, rather than a monastic, order.
There are monasteries of contemplative nuns in Ontario-Redemptoristines (1); Poor Clares (1); Discalced Carmelites (2); Visitandines (1). There are also convents of contemplative sisters.
I think there are benedictines somewhere in there too. Try