Rosedale is a neighbourhood in Toronto, Ontario, Canada. It is located north of Downtown Toronto and is one of its oldest suburbs. It is also one of the wealthiest and highly priced neighbourhoods in Canada. It is known as the area where the city's 'Old Money' lives, and is home to some of Canada's richest and most famous citizens, including Ken Thomson who was the richest man in Canada at the time of his death.

Rosedale's boundaries consist of the CPR railway tracks to the north, Yonge Street to the west, Bloor Street to the south, and Bayview Avenue to the east. The neighbourhood is within the City of Toronto's Rosedale-Moore Park neighbourhood. The neighbourhood is divided into a north and south portion by the Park Drive Ravine.

 History

South Rosedale was first settled by Sheriff William Jarvis and his wife, Mary, in the 1820s. Mary Jarvis, whose frequent walks and horseback rides blazed the trails for Rosedale's meandering streets (which are one of the area's trademarks), named Rosedale as a tribute to the abundance of wild roses that graced the hillsides of the Jarvis estate. The Jarvis Family sold the Rosedale homestead in 1864, which led to the residential development of the area soon after.

North Rosedale's development began after the construction of a bridge across the Park Drive Ravine, in 1909. Prior to its development, North Rosedale was the home of St. Andrew's College (1899-1924), an all-boys boarding school (which has since moved to Aurora, Ontario) and the Rosedale Golf Club. The golf club was also home to a lacrosse field (Rosedale Field) and site of the first Grey Cup game.

Real Estate in Rosedale

The Bridle Path’s houses are bigger, and Forest Hill's and Lawrence Park's ’s lots are more grand, but Rosedale and its northern neighbour, Moore Park, remain tops in Toronto for their class. The massive houses appear to take up all the available air space within their property lines. There’s a long history of the city’s notables making their homes here at one point or another, with everyone from Tom Thomson (on Severn Creek) to Ken Thomson (8 Castle Frank Road). Laid out on streets that follow the natural topography rather than a grid, Rosedale is a maze to outsiders, and a protective labyrinth to residents who value the low traffic produced by all the dead ends and roads that turn back on themselves. Though it has earned a reputation as one of the city’s most exclusive neighbourhoods, it’s been quietly diversifying, with dozens of grand old homes replaced in the 1950s with apartment buildings, about half of which are now condos. On Crescent Road, one of the two streets colonized by Heather Reisman and Jerry Schwartz’s massive compound, for instance, there are three buildings with units accessible to thrifty Indigo branch managers. As you head north toward Moore Park, houses become more modern. Development in the area was first planned in the 1880s, but was waylaid till the early 1900s. Bordered by one of the most interesting commercial strips of Yonge, with some of the most attractive houses and charming parks in the city (not to mention Rosedale Ravine), this neighbourhood is hard to beat.

HOUSING STOCK: Though most houses in Rosedale and southern Moore Park—a mix of early-20th-century Tudor, Georgian and Edwardian—are impressive, there’s a great deal of variety. Homes by Old City Hall architect E. J. Lennox (89 Elm Street) and Arts and Crafts master Eden Smith (2 Cluny Drive) rub shoulders with brick-arched designs (44–46 Castle Frank Crescent) that wouldn’t be out of place in any 1970s suburb. There is even a smattering of row houses on Tacoma in north Moore Park.

BARGAIN ZONES: Streets such as Standish and Astley, as well as the upper numbers of Summerhill Gardens all present relatively good deals, as do the row houses on Tacoma and the slightly larger ones on Ottawa.

THE VERDICT: Rosedale has long served as the shining Camelot upon which generations of hopeful Bay Streeters have pinned their hopes. A house in this ’hood signifies the owner’s arrival like no other in the city.

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Schools in Rosedale