This project seeks to uncover how the urban real estate development industry might transform, and how to best shape its change to better benefit people and communities. The investigation considers Canadian cities, with a focus on Toronto. The project first uncovers the system of urban real estate development by examining how these cities grew over the past century. An analysis of the system’s actors is performed, with deeper inquiry into the business models of organizations that build space. To explore how the future of the industry might unfold, four future scenarios were created using the system analysis and findings from a horizon scan. A holistic assessment framework was created to evaluate the scenarios. From the results, common themes were identified, along with risks, opportunities and final recommendations. These findings highlight how different capital structures and organizational models can influence urban residents, as well as the potential implications of new technology, changes in capital structures, and innovations in architecture and construction.