Healthy living is always a significant part of community well-being. The quality of human living spaces plays an important role in promoting health and wellbeing. Increasingly, there are many mental and physical health concerns in multicultural, complex urban living environments. Living environments, which include dwellings and community areas, become important examples when considering potential leveraging points to improve the quality of healthy urban living. Considering the current rapid technological development and cultural shifts, there are many significant changes in people’s lifestyles that will affect their living space needs. This project begins by describing the current development of residential living space in urban cities, such as Toronto, and analyzing the dynamics at play and their patterns of social support. Utilizing foresight methods, systemic analysis, and generative research methodology, this project will research urban ecologies to understand the relationship between humans and their living spaces and how space could shape their wellbeing, highlighting the physical and mental issues that impact people today in urban city living spaces. Through an investigation of various aspects of current urban development patterns, possible future directions and solutions for the living environment may be proposed. This research will focus on intervention strategies and key design principles for future residential design innovations as a guide, catalyst, and opportunity for future residential design inspiration.