Toronto’s housing system is in crisis. As we persist in maintaining this failing system, we are limiting ourselves to the possibility of creating transformational change. Toronto’s housing arena is a complex organism of competing interests and influences, reinforcing a stratification between those who benefit from it and those who do not. With limited housing choices, many Torontonians are left with few opportunities to invest in their communities and to generate personal financial wealth for their futures. Through foresight methods, systems analysis, and generative design research techniques, this project asserts that we can create change in Toronto’s housing system by transforming real estate investment into an inclusive community-building tool. Housing Horizons begins by describing the evolution of the housing arena in Canada and analyzing the dynamics at play in the current system. The research then proposes several design principles for innovation: shift the power in the development industry to smaller community-based players, create wealth-generating mechanisms suitable for renters, and foster collaboration across stakeholders in the system. A city where all citizens can thrive is only possible when the housing system contributes to the wellbeing of its entire population – this vision can be realized through strategies that level the playing field for all.