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Toronto offers a lot of great places to live in permanently or for extended periods of stay. For those who can afford upscale residences, Downtown Toronto has a couple of historically wealthy neighborhoods, such as Casa Loma, Forest Hill, Lawrence Park, Moore Park, Rosedale, The Annex, and Yorkville. Other affluent residential neighborhoods in the city include the Bridle Path (in North York) and the Kingsway (in Etobicoke).

Of the neighborhoods above, Forest Hill, Rosedale, and the Bridle Path are considered by many as Toronto's three wealthiest neighborhoods. Of the three, Rosedale has held the distinction of being the city's wealthiest neighborhood for over a century. However, in recent years other upscale residential enclaves have challenged this prestigious status.

The neighborhoods mentioned above are known for their multi-million estate homes, though they are also home to luxury condominiums and apartments. High-end retail shops and services also abound in these areas.

One neighborhood known for its residences is the Annex, which borders the University of Toronto. The Annex has traditionally been home to a lot of University faculty and students. Residents in the Annex range from University students to well-established families. The Annex boasts of Victorian homes and mansions as well as multi-tenant apartments.

Recent immigrants or non-Canadians who plan to live in Toronto might feel more at home in the Downtown neighborhoods of Parkdale, Regent Park, and St. Jamestown (or St. James Town). These areas possess a high proportion of recent immigrants, and both social housing and rental high-rises abound. Asians form the largest minority group in these residences.