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After the fall of the Iron Curtain, CEE cities (as well as other cities in the former Socialist Bloc) experienced dynamic development in many areas. The presented article deals with one of the key areas of the post-socialist transformation of the city, specifically the humanisation of mass housing in large housing estates. These housing estates from the central planning period still dominate the skyline of many CEE towns. At the beginning of the 1990s, housing estates suffered from a number of shortcomings that needed to be put right within the frame of their humanisation. The paper analyses a more than two decade-long process of housing estate humanisation which gradually led to the replacement of the monofunctional (strictly residential) model with a multifunctional model. This leads to improvement of civic amenities, implementation of new urban-architectural solutions and the creation of new job opportunities. As a result, these changes increase the quality of life in housing estates, both from an objective and subjective point of view. Changes in the spatial, social, economic and physical structure of housing estates after 1989 will be analysed using examples from hierarchically different locations in the Czech Republic. The synthesis of findings will be supplemented with the results of empirical studies that were carried out by geographers, sociologists and urban planners.