This is a list of the tallest buildings in Windsor, Ontario, the second-largest city in Southwestern Ontario, Canada. Windsor lies directly across the border from Detroit, Michigan, a metropolitan area of over 4 million people. It the largest city in Canada that directly borders the United States. This partly explains the larger presence of tall buildings compared to Windsor's neighbours, St. Catherines and Kitchener; laxer gambling and drinking laws in Canada compared to the United States contributes to economic activity in the city.
Windsor has 7 buildings that stand taller than . The tallest building in the city is the 27-storey, Caesars Windsor Augustus Tower. The second-tallest building in the city is Victoria Park Place Condominium, standing at tall with 31 storeys.
Unlike many similar sized cities in Ontario and elsewhere in Canada, Windsor has not seen a boom in residential high-rise construction starting from the early 2010s. , the city has no structures under construction or proposed. The most recent development in Windsor is Caesars Windsor Augustus Tower at and 27 floors, completed in 2008.
This list ranks buildings in Windsor that stand at least 50 m (164 ft) tall, based on CTBUH height measurement standards. This includes spires and architectural details but does not include antenna masts.