In the socialist times, large housing estates in the Central and East European (CEE) cities were praised for effectively resolving the housing crisis, providing good and homogenous housing conditions at reasonable costs and enabling rapid urbanization. Following the collapse of communism, they have met with various consequences of low-cost construction based on prefabrication, lack of repair and upgrading investments and neglected or deferred maintenance, and the Western experience drew attention to the socioeconomic outcomes of further physical downgrading. As the flats located in these estates make up almost half of the total urban housing stock in the CEE region, thus having a significant impact on the overall housing quality, this paper discusses the post-socialist context of development of these estates based on the existing literature and an interdisciplinary analytical approach, with an emphasis on their rehabilitation. The research questions relate to the problems they have been affected by, mechanisms and methods of interventions and multifaceted differences between the CEE and West European estates. The aim of the paper is to analyse the development and rehabilitation challenges that these estates have encountered during post-socialism and thus join the discussion on future prospects and feasible and sustainable upgrading related policies and programmes.