[9] Mary Jarvis, the granddaughter of chief justice and loyalist William Drummer Powell frequently walked and rode on horseback around the trails for that formed Rosedale's meandering streets (which are one of the area's trademarks).

[11] The Jarvis Family sold the Rosedale homestead in 1864, which led to the residential development of the area soon after, including the extension of Cluny Drive.

[15] One of Canada's foremost fiction writers both pre- and post-World War II, Morley Callaghan lived in the southern part of Rosedale at 20 Dale Avenue from 1951 until his death in 1990;[16] a historic plaque at the nearby Glen Road footbridge summarizes Callaghan's noteworthy writing career and his best-known literary contemporaries, including Ernest Hemingway and F. Scott Fitzgerald.

Rosedale is full of cul de sacs and convoluted routes through the neighbourhood, which coupled with other physical boundaries (such as the ravines and bridges) lead to low levels of vehicular traffic.

Even though Rosedale is located in the middle of Toronto, virtually no vehicular traffic can be heard with the abundance of trees and foliage that surround the community.

[23] Additionally, Rosedale possesses a large population of people of English, Scottish, and Irish ethnic origin.

In Provincial Parliament, Rosedale is also a part of the University-Rosedale electoral district, and is represented by Jessica Bell.