The shift in the urban paradigm during the 20th century led to a significant reconsideration of the living space of city residents. The principles of the modernist worldview, which acquired the nature of a universal urban design strategy in the Athens Charter of 1931, initiated a negative attitude towards the block development that had prevailed before. The courtyard spaces inherent in it started to be perceived as insufficient, and their original concept as places of recreation and social interaction was redefined. As a result, the internal environments of blocks were spontaneously used by residents for various purposes, leading to their degradation and chaos. This was particularly relevant to Ukrainian cities, where the population of historic centres was densifying, with an increased impact on all types of spaces. The crisis of modernist urban design and the expansion of postmodern values have returned attention to historical heritage as an auxiliary source of shaping and removed the intensity of the confrontation between the ‘contemporary’ modernist worldview and the ‘historical’ one. Subsequently, urban concepts have absorbed many ideas related to the environmental discourse, inclusiveness, barrier-free accessibility, pedestrian accessibility, and density. All of this has significantly changed the understanding of approaches and principles of interpretation of historic urban spaces, including residential courtyards. The article considers promising urban design strategies that can be used for the contemporary interpretation of courtyard environments, primarily focused on design and social aspects. This is due to the methodological structure, which is based on a dual understanding of the priorities of this process. On the one hand, courtyard spaces are perceived as places of recreation and greening, and on the other hand, as environments for socialising and community bonding. In this regard, four urban design strategies have been identified that may form the basis of certain areas of urban design in the future: a) functional universalisation; b) spatial diversification; c) communicative adaptability; d) variable accessibility. The first strategy refers to the integration of courtyard spaces into measures to introduce walkability and optimal density. In this case, we are dealing with introducing a number of functions into courtyard spaces that were typical of external street areas, but aimed at the nearest residents. The second strategy is aimed at returning to the ideology of green oases and recreational areas, with further expansion of spatial elements through vertical development. The strategy of communicative adaptability is related to the development of courtyards as places of gathering and solidarity of the resident’s community. The last strategy is related to the proposal to provide access to the courtyards to external visitors at certain times.