Rosedale, which is roughly bounded by the CN tracks to the north, Yonge Street to the west, Rosedale Valley Road to the south, and Bayview Avenue to the east, is divided into a north and south portion by the Park Drive Ravine. 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, an all-boys boarding school (which has since moved to Aurora, Ontario) and the Rosedale Golf Club.
Although Rosedale has held the distinction of being Toronto's richest neighbourhood for over 100 years, its status has, in recent years, been challenged by Forest Hill and the Bridle Path.