This paper analyses the regulatory and legislative tools for affordable housing in Toronto. Through a review of relevant literature and interviews with key informants, key trends in affordable housing in Toronto have been identified. An analysis of affordable housing in Vancouver and Montreal is provided to show divergences and similarities in other Canadian cities. Key findings of this research reveal several trends. Firstly, past funding of housing was often rationalized as an economic imperative, rather than as a social policy issue. Secondly, federal retrenchment and Ontario government offloading have placed responsibility for housing on Toronto, which has neither the financial nor regulatory tools to adequately fund housing. Thirdly, this lack of capacity has led Toronto to adopt a more entrepreneurial approach to housing, using public-private partnerships, social mix revitalization initiatives, and other market influenced development mechanisms. These findings highlight difficulties on the part of Toronto to develop new affordable housing at a time when the city continues to grow and demand for housing is increasing.