#10. Casa Loma

From Toronto Life

In Casa Loma, house pride extends beyond property lines. When a townhouse developer began to gut the Georgian Revival residence of the late magazine magnate John B. Maclean in 2009, members of the residents’ association rose up and got the city to award a heritage designation. A new developer then stepped in with a plan to preserve the building, originally designed by Union Station architect John Lyle, by sub­dividing it into three residences, restoring and preserving as many historical details as possible. The entire drama was just repeated in short form to save an Arts and Crafts home formerly occupied by chocolate tycoon Charles Neilson. Even back when Sir Henry Pellatt first started laying out plans for the medieval fantasy castle that would give the neighbourhood its name, it was the Millionaire’s Row of its time.

The estates there were occupied by other self-made families like the Eatons, who lived in a Georgian mansion named Ardwold, and the Austins, who built a miniature Downton Abbey on Davenport Hill called Spadina House. Today, streets like Lyndhurst and Wells Hill are still home to some of the city’s nicest Tudor- and Edwardian-style properties. Further east is the family-filled Republic of Rathnelly, which irreverantly declared independence from Canada in 1967 (last year, the city installed street signs recognizing the secession), and the winding roads of South Hill. Society power couple David and Kate Daniels keep a magnificently restored art deco mansion nearby. It’s not all barons, though. Just north of the castle is a block of well-maintained rental buildings, and St. Clair and Avenue are full of charming old apartment blocks. The whole neighbourhood comes together in the middle at Sir Winston Churchill Park: high school students convene pickup soccer games, dog walkers let their pups loose in the large off-leash area and, in winter, tobogganers steel themselves for one the city’s steepest—and most scenic—runs.