Rosedale, which has loomed large on Toronto’s mythic landscape for nearly 150 years as home to many wealthy and well-known people, occupies an impressive 620 acres near the centre of the city, and contains over 2,200 dwellings. Bounded on the west by Yonge Street, the CPR rail line on the north, the Don Valley on the east, and by Bloor Street and the Rosedale Valley on the south, Rosedale is split by the Silver Creek or Park Drive ravine into a northern and southern part.

South Rosedale had its origins in the 1854 subdivision of part of Sheriff William B. Jarvis’s estate on the edge of Yorkville Village to create 61 villa lots within a pattern of winding streets that responded to the adjacent ravines rather than a grid. This plan, highly unusual for the time, originated with Jarvis’s surveyor, J. Stoughton Dennis. Later, between 1877 and 1896, it was extended over three other adjacent but smaller estates. From these four estates only one great-house survives (5 Drumsnab Road, 1835; altered 1856). Villas dating from the first wave of building in Jarvis’s subdivision include 23 Rosedale Road (1857; altered 1911), 124 Park Road (1857), “Glen Hurst” (1866) on the grounds of Branksome Hall Girls School, 27 Rosedale Road (1871), and 3 Meredith Crescent (1876). When Rosedale, as part of Yorkville, was annexed to the City in 1883, a few new houses stood on Elm Avenue and South Drive, but not many elsewhere. Along the ravine that separated South Rosedale from the near-empty lands to the north, three large mansions had taken up sentry-like positions flanking Glen Road and Elm Avenue. Today only shady grounds and handsome gates (1903) of “Craigleigh” survive to recall that trio.

Between 1884 and 1904 development was slow and scattered. No more than three dozen houses were constructed then, of which 2 Dale Avenue (1887), 128 Park Road (1893), and a terrace at 141–147 Roxborough Street East (c.1890) are good examples. The great boom in South Rosedale, which accounts for much of its present architectural character, didn’t occur until 1904–14, when a couple of hundred dwellings were built. Streets like Chestnut Park were filled up then with big, brick houses, many in an Arts-and-Crafts style, by architects like Burke, Horwood and White (No. 1, 1915), A.E. Boultbee (No. 20, 1905–06), S.H. Townsend (No. 24, 1905), and E.J. Lennox (No. 48, 1903). What was for many years the area’s only apartment house was erected at 75 Crescent Road in 1912. At that time, too, more boulevard trees were planted that now contribute so much to Rosedale’s garden-suburb appearance.

Meanwhile, North Rosedale had begun to grow. An iron bridge erected in the early 1880s to carry Glen Road over to the Silver Creek ravine did little to stimulate building there until shortly before the First World War. Development was helped by the decision in 1911 to erect “Chorley Park,” the palatial and now-demolished official residence of Ontario’s Lieutenant Governor, on a 14-acre site overlooking the Don Valley between Roxborough Drive and Summerhill Avenue. About that time, a few large houses were erected on Binscarth Road, Highland Avenue and Beaumont Road, and several smaller ones on streets north of Summerhill Avenue to the CPR right-of-way. But there was no building on the lands between, where the Lacrosse Grounds (now Rosedale Park) and St Andrew’s College were located, until after the school removed to Aurora in the 1920s.

Thanks to redevelopment of the George Estate as Old George Place, and other smaller projects, North Rosedale boasts some excellent examples of modern-period architecture by Ron Thom (4 Old George, 1971), John B. Parkin (3 Old George, 1959), and Barton Myers (51 Roxborough Drive, 1972).

In some ways, Rosedale led a charmed life in the post-war period, only to suffer more recently with the architectural excesses of Big Money. When Mount Pleasant Road was extended through the area to link up with Jarvis Street, only two houses and a worn-out school were demolished. A spate of apartment building in the 1950s, taking advantage of large ravine lots, was brought under control before much damage was done to the area’s character. And the Crosstown Expressway, linking the Don Valley to Davenport Road, died on the drawing board. Whether Rosedale will emerge with its integrity intact from the current wave of redevelopment, characterized by a taste for neo-Georgian country houses squeezed onto city lots, remains to be seen.

Stephen A. Otto