Dwellers facing one housing problem typically face multiple risky housing circumstances that threaten an array of their outcomes. Experiencing multiple unfavorable housing issues can intensify the negative effects that such conditions have on the whole person’s physical, psychological, emotional, and cognitive development. This paper is a survey study, and it discusses the effect of some housing issues and conditions on dwellers’ psychological and emotional well-being. The purpose is to understand the effect of such problems, such as housing price, safety and security, housing quality, transportation, schools, and economic development on dwellers’ stress levels and emotional well-being. Simple random sampling was assigned to a large number of middle-income residents in Malaysia. The accumulated data were then analyzed, and descriptive statistics were used to interpret and evaluate the prevalence of housing issues and housing stress. The findings of this study indicated that there is housing stress among middle-income groups caused by transportation, housing quality, and economic development that force dwellers to stay far from their workplace and be unable to afford the moving cost. Hence, it is highly advisable for the governments and stakeholders to look comprehensively at these issues and tackle their consequences by emphasizing people’s need for an affordable, liveable home standard.