The housing landscape of Tokyo has shifted dramatically from a housing shortage immediately after World War II, to an urban sprawl driven by the ‘salaried men's dream’ of a single-family home, to the more recent popularity of high-rise living. Tokyo as a global megacity provides a distinctive picture given its density, culture and changing economic fortunes in the postwar period. This article draws on qualitative research conducted in Tokyo among home-owning families over three generations, exploring the links between housing and family relations in the context of changing housing and labour markets. The article provides two housing ‘narratives’ highlighting different experiences and strategies of families over generations. These narratives not only capture key elements of socio-economic change in Japan since the end of the War, but also illustrate the contrasting experiences of different families, particularly in relation to the interaction between housing and employment.