The City of Toronto is undergoing a significant demographic shift as a result of the aging ‘Baby Boom’ generation, the first of whom turned 65 years old in 2011. By 2031, the seniors population in Toronto is expected to almost double, increasing to 22 percent of the total population (Hemson Consulting Ltd, 2012) from only 14 percent in 2011 (Statistics Canada, 2011). This will produce a number of housing related planning challenges for the City, as aging Boomers are expected to demand an increasing amount of housing. This estimate is used to approximate the potential housing limitations in 2021 and 2031. As the largest seniors demand is projected to be for ground-related private dwellings, whose supply is physically constrained, the report will investigate the benefits of developing retirement homes to meet the growing seniors housing demand. The two-fold challenge to increase the stock and capture rate of retirement homes in Toronto will be examined. Creative mechanisms will be proposed for the City to incentivize retirement homes development and for potential developers to attract Boomer seniors to retirement homes.