Kharkiv is a great post-socialist industrial city with a population of over 1 million. Owning large objects with different functional components (both industrial and social infrastructure, other municipal institutions), the big city in the early 90’s faced with the fact that there was no resource for their maintenance and development. Variable and unstable economic situation drowned in demand for many services. A situation of paralysis of the public space of the city has been created. Only with the beginning of privatization and commercialization processes, we can talk about the gradual filling of the created emptiness. Individual investors become the subjects of assessment and planning of the territory. And the urban space is the object of commercial activity. The new conditions have created opportunities for dialogue between the authorities, the city community and business. Disorder of these relationships has given the poor results of spatial transformations and modernization of territory in Ukrainian cities. An investor, focusing on profit, determined the place, form and function of a new object at its discretion, often changing the face of the city and the role of the territory. Our research is caused by the need in the study of spatial transformations and modernization processes in the great post-socialist city, which may be a prerequisite for further changes. Perhaps, Kharkiv is the best example of a post-socialist city for the study of spatial-functional transformations. The purpose of the paper is to analyze the processes of spatial transformation and modernization, as the prerequisites for further spatial-functional transformations in a big city of Kharkiv, based on discovered transformation elements and a core of modernization on the territory. Analysis of the objects we were investigated, allowed for us to see directions of the transformation of the urban territory, outline the spatial structure of the sites, identify possible functional changes in the space and his contemporary role in the urban environment. Investigation of two test sites in Kharkiv – “old centre” and social centre, revealed the difference in the processes of spatial transformation and modernization of urban objects in these parts of the city. It is not always possible to fix a completed transformation. It is important here to see the beginning of the change, to “snatch” the very tendency for a possible change, then to be able to predict the direction and its dynamics.