This paper investigates residents living experience in the common courtyards of cooperative housing and cohousing in Canada, and their sense of happiness associated with it. Cooperative housing as a form of social housing established in Toronto, Ontario, Canada as early as the 1910s. Cohousing as its subsequent name has evolved into a global movement since the 1960s, to promote residents sharing and caring for one another through active participation in community lives and cooperative management. A key feature of this housing is the inclusion of shared spaces, such as common courtyards. This research explored what make residents happy and/or unhappy in the common courtyards, and how to improve their living experience in the common courtyards. Semi-structured interviews were conducted with 20 residents in three cooperative housing in Toronto and three cohousing across Canada. The findings suggest that the Courtyard is a central component to promote social happiness of residents. The paper contributes to the topic of Housing and Happiness that is rarely studied. It finally proposes a courtyard garden housing system that can be a template for universal application. The main conclusion is that there is a need for more courtyard configuration in contemporary Canadian urban planning and architectural design to promote community development.