An iconic sight in the heart of the old town, the Flatiron is impossible to miss. Built in 1892, it's a five-story iron-shaped building with a steep copper roof and turret; in the background, Toronto's skyscrapers provide a beautiful contrast. Be sure to check out the mural on the building's western side; created by Canadian artist Derek Michael Besant, it integrates with the existing structure to make it appear that a curtain of windows has not been properly tacked up.
A long-time office building, the Flatiron was originally built for the Gooderham and Worts Distillery's administrative offices (notably, its repurposed factory serves as the central building of the Distillery District).