Over the last several years, an increasing number of scholarly contributions have questioned the usefulness of the concept of gentrification for cases outside of the context in which the term was originally developed. The paper builds on this debate and explores the unfolding of gentrification in two contrasting environments undergoing post-socialist transformations. It analyzes the course of urban upgrading in Prenzlauer Berg in East Berlin as well as in the central city of Saint Petersburg, arguing that while the transformation from a planned economy to a market system generally made gentrification possible, the specific conditions of property transfer, the transformation of inherited social rights, as well as the different setup of planning institutions have produced very different patterns of neighborhood change. In sum, it is suggested that "gentrification" is in fact an umbrella term for fairly disparate socio-spatial formations which result in different dynamics of regeneration and population change.