The old city and East York
The pre-amalgamation city and the borough beside it: Victorian and Edwardian stock, the subway under it, and the only wards where six units are permitted on a residential lot.
One guide in the part of Toronto that existed before 1998. This is the old City of Toronto plus East York, which was the last borough in Canada until amalgamation folded it in, and it is where almost all of the city's pre-war housing stock is. The street grid is tight, the lots are narrow, the subway runs under two of the main streets, and the result is the most expensive low-rise housing in the country.
Two things make this area different from the other three rather than just older. The first is that walking is the default: ground-floor retail under three storeys runs along most of the main streets, which is a form the rest of Toronto largely does not have. The second is legal. Since June 2025 five and six units are permitted as of right on a residential lot in these wards, against four everywhere else in the city, so the four community council areas no longer share a zoning permission. What has not changed is the age of the stock. Knob-and-tube wiring, galvanised supply lines and century-old sewers are the things to establish on a specific address, and they move an insurance quote further than the address does.
