While modern heritage is often discussed as a critical resource for sustainable urban and social development, the future of such housing is often limited not by technical but rather by cultural, historical, or socio-economic constraints. In cities with a socialist past, mass housing provided individual apartments for a number of Soviet families and tended to create particular spatial qualities. However, with the collapse of the socialist system, attitudes towards such housing began to transform. This paper is a reflection on the range of perceptions of this heritage, attitudes towards it, and difficulties in shaping contextually informed renewal policy approaches. To what extent do traumatic experiences of the past and the rational use of resources in the present mutually influence each other? This article introduces the controversial debate based on the cases of three former socialist countries: Moldova, Armenia, and Uzbekistan. On the one hand, the ubiquity of mass housing in post-socialist countries fostered tolerance for such a typology. On the other hand, large housing estates are a constant reminder of the traumatic experience of the socialist experiment. This essay discusses the present and the future of large residential estates based on reports, policies, media, and collected expert interviews on approaches to working with mass housing areas. Together, the three contributions and joint reflections attempt to add to the debate about the past, present, and future of middle-class mass housing in various social, cultural, and political conditions.