In the last decades, several studies have revealed how critical the urban heat island (UHI) effect can be in cities located in cold climates, such as the Canadian one. Meanwhile, many researchers have looked at the impact of the city design over the urban microclimate, and have raised concerns about the development of too dense cities. Under the effect of the “Places to Growth” plan, the city of Toronto is experiencing one of the highest rates of building development in North America. Over 48,000 and 33,000 new home permits were issued in 2012 and 2013 respectively, and at the beginning of 2015, almost 500 high-rise proposals across the Greater Toronto Area were released. In this context, it is important to investigate how new constructions will affect the urban microclimate, and to propose strategies to mitigate possible UHI effects. Using the software ENVI-met, microclimate simulations for the Church-Yonge corridor both in the current situation and with the new constructions are reported in this paper. The outdoor air temperature and the wind speed are the parameters used to assess the outdoor microclimate changes. The results show that the new constructions could increase the wind speed around the buildings. However, high-rise buildings will somewhat reduce the air temperature during day-time, as they will create large shadow areas, with lower average mean radiant temperature.