Although some green housing elements have become more commonplace in residential renovations in Canada, the undertaking of complete green retrofits is relatively uncommon. This paper explores the barriers to green retrofits, such as affordability and bureaucracy, in the urban context of the City of Toronto. The research was informed by one main case study, one supplementary case study, and six interviews with sustainable housing experts. The research has yielded nine recommendations that are directed towards three levels of government and related public and private housing organizations. These recommendations have been made in the hopes of making sustainable housing more ubiquitous in Toronto.