This book explores how and why Tokyo has been divided over time in terms of living conditions. First, recent urban discourses that explain the transformation of Tokyo’s urban structure are examined, along with social changes and the expansion of unequal residential conditions within the metropolitan area. Chapter 1 reviews: 1) discussions on globalization, neo-liberalization, and changes in housing policies; 2) debates on the divided city; 3) debates on the shrinking city and the urban lifecycle; 4) discussion of the urban residential environment from a social justice perspective; and 5) family–housing relationships in the post-growth society. Based on the literature review, the rest of the book is structured as follows. Chapter 2 explains the changes in urban and housing policies, demography, and socio-economic conditions. In Chapters 3 to 5, the background and characteristics of the growth of condominium living in the city center are examined. The next three chapters analyze the reality of shrinking suburbs, using case studies to demonstrate the increase in vacant housing and local responses toward shrinkage. In Chapter 9, possible solutions are proposed for dealing with problems related to urban shrinkage and the expanding gap in terms of the availability of investments to stimulate urban development, the residential environment, and the population age structure in Japanese cities by comparing the author’s findings and the literature review. This book provides deep insights for urban and housing scholars, urban planners, policy decision-makers, and local communities that struggle with aging populations and urban shrinkage.