This study concerns the domain of community development and probes methods of preventing isolation and loneliness. In so doing, this fundamental investigation attempts to answer the research question, “Which types of remedies, social or spatial, are more effective in alleviating isolation and loneliness, and in which aspects are they useful?” The study purposed to essentially evidence a means of evaluating the effectiveness of such social and spatial prescriptions by inferring the associations between isolation/loneliness and social and spatial preferences. The present investigation adopted a method that holistically considered both loneliness and isolation and conducted a complex analysis of these states. It employed a stochastic choice model with discrete dependent variables to elucidate the relationship between isolation and loneliness and social and spatial prescriptions.