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This paper describes and analyses the imageability and the perceptual portraits of the (post-) socialist largescale housing estates in Kyiv in the eyes of young people (university students). The research is based on the analysis of Lynch-type mental maps focusing on urban vernacular districts among the other their principal elements. The results show that mass housing areas still constitute an important part of the city’s image. However, apparently similar neighbourhoods differ significantly in terms of their imageability and likeability depending on their location in the city and the trajectory of the post-socialist development. Consequently, individual approaches to positive image change based on the complex evaluation of development factors are needed to response the challenges faced by the different types of the (post-) socialist mass housing.