Toronto is the largest city in Canada, with a metropolitan area population of over 6.2 million. Many of Toronto's tallest buildings are also the tallest in all of Canada. Toronto has one of the largest skylines in the world, with 108 completed skyscrapers taller than 150 m (492 ft) as of 2026, 31 of which have a height greater than 200 m (656 ft). It is the third largest skyline in North America, after New York City and Chicago. The city's tallest building since 1975 has been First Canadian Place, which rises 298 metres (978 ft) tall. It is also the tallest building in Canada. However, the tallest free-standing structure in the city is the 553.3 m (1,815 ft) CN Tower, which was the tallest free-standing structure in the world from 1975 until 2007, and remains the most prominent landmark on Toronto's skyline.
The history of skyscrapers in Toronto began in 1894 with the construction of the Beard Building, which is often regarded as the first skyscraper in the city. Toronto went through its first building boom in the late 1920s and early 1930s, increasing the number of tall buildings in the city. Following the Great Depression, there was a great lull in high-rise construction for over 30 years. A second, larger building boom began in the 1960s, which saw the construction of many recognizable commercial skyscrapers, such as the TD Bank Tower and Commerce Court West in 1973, the aforementioned First Canadian Place, and the postmodernist skyscrapers of Scotia Plaza and TD Canada Trust Tower towards the end of the boom.
A third, much larger high-rise construction boom emerged in the mid-2000s and has continued to the present, dramatically expanding and reshaping Toronto's skyline; of the skyscrapers taller than 150 m (492 ft), only 11—less than one ninth—were built before the 21st century. Unlike the previous two booms, most of Toronto's recent high-rise development has been in residential and mixed-use buildings. The rate of construction accelerated further in the 2010s and 2020s, with the completion of Toronto's tallest mixed-use building, The St. Regis Toronto, in 2012, and its tallest fully residential building, Aura, in 2014. The boom's extent has led it to be described as an example of Manhattanization. As of 2026, there are over 15 further skyscrapers under construction, three of which being supertall skyscrapers that will overtake First Canadian Place in height. The tallest is SkyTower at Pinnacle One Yonge, which will rise to 351.4 m (1,153 ft), followed by The One at 308.6 m (1,012 ft), and Concord Sky at 300.2 m (985 ft).
While most of Toronto's skyscrapers are located in Downtown Toronto, there are significant skyscraper clusters in Yonge–Eglinton as well as in North York City Centre to the north of downtown, Scarborough City Centre to the east, and in Humber Bay to the west. Downtown, Yonge–Eglinton, and North York all sit along Yonge Street, a major arterial. Smaller clusters of high-rises, such as in Yonge-St.Clair and Islington-City Centre West, can be found across the city. In the Greater Toronto Area, large skyscraper clusters are developing in Mississauga and Vaughan. The Toronto skyline, especially the CN Tower, can be spotted by the naked eye during clear daylight skies from locations as far as Newmarket from the north, Clarington from the east, several points along the Niagara Escarpment from the west, and Fort Niagara State Park in the south across Lake Ontario in the U.S. state of New York.
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