Rosedale began when Sheriff William Botsford Jarvis and his wife Mary settled on a homestead in the neighbourhood during the 1820’s. It was Mary Jarvis who came up with the Rosedale name, as a tribute to the profusion of wild roses that graced the hillsides of the Jarvis estate.

Mary’s frequent walks and horseback rides through Rosedale blazed a trail for the meandering and winding streets that today, are a Rosedale trademark. The Jarvis family sold the Rosedale homestead in 1864, which led to the subdivision and development of South Rosedale.

North Rosedale’s development began in 1909, when a bridge was built over the Park Drive Ravine. Prior to its residential development, North Rosedale had been the original home of St. Andrews College and the Rosedale Golf Club. It was also the site of the former lacrosse grounds, where the Canadian Football League’s first Grey Cup game was played.