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The article examines trends and consequences of the urban space transformations in Holosiivskyi district of Kyiv caused by social transformations in the post-Soviet period. The authors focused attention on mapping the key changes that taken place at major historic-geographical sections characterizing formation and development of the territory comprising now a part of the urban district. The authors highlight the fact that changing of predominant spatial functions within the district was connected with the context of main functional (contextual) and spatial vectors of Kyiv development and by the corresponding change of spatial functions in the conditions of industrial and post-industrial periods. The authors developed a technique to determine the qualitative and quantitative parameters of the spatial transformation of the studied territory. Also, they determined the peculiarities of territorial functional changes in one of the centers of spatial development within the district–Lybidska square. There were determined the features and the quantitative and qualitative territorial differences in transformations of the functional structure of urban center under the influence of the core: shopping center “Ocean Plaza”. The authors determined the number of key factors that have influenced and continue to influence the spatial transformations within this city center and function of territory belonging to the most and the least flexible in the context of the transformation of urban space.