This article examines the main spatial and morphological transformations of the Vynogradar housing estate in Kyiv, related to the adaptation of the Soviet urban housing formation to new market conditions after the collapse of the Soviet Union. In Ukraine, due to the rapid destruction caused by the Russian-Ukrainian war has become more acute. An important step for strategic decision-making is to inventory the existing post-Soviet urban heritage and identify those features and acquired characteristics that are valuable in terms of architectural and cultural heritage, planning solutions, comfort and health of the urban environment, ability to flexible transformation and the degree of adaptability to new conditions. This study aims to find the key spatial and morphological transformations of the Vynohradar residential area at the stages of creating a project idea, its implementation and further development. The research is based on the study of archival materials and professional periodicals of the time, descriptions of concepts and design solutions for the restoration of the ideas that were the basis of the project; conducting field research and analysis of the modern urban environment; finding and analyzing qualitative changes and their consequences. The next three stages were found: creation of the project idea, project implementation, and transformation of the object. It was found that, despite the idealistic concept and romanticization of this space by the author, the residential area was able to adapt and continue its development in the new conditions, as evidenced by the development of housing – both individual point houses and entire complexes, as well as an extensive network of trade and services. The functional filling of the residential area with a large number of buildings for public institutions was positively implemented in the times of adaptation and transformation – this gave impetus to the development of the service market in the area. It was determined that the main spatial transformations were related to the housing market and mass trade. Children's spaces lost their dominant influence in the residential area.