Post-socialist urban transformation constitutes an important segment of the contemporary urban studies. In this paper we focused on transformation processes in two typical post-Soviet residential neighbourhoods, built in the period of mass construction in the second half of XX century and located in the Ukrainian cities of Vinnytsia and Kherson. Our goals were to reveal the spatial and temporal transformation patterns, to identify the factors of transformation, and to delineate certain transformation mechanisms and models. The assessment of morphological and functional changes of urban objects was carried out via field observation according to a specially developed methodology with the further comparison of results with urban planning documents reflecting the reality in the beginning of 1990s. Our findings permitted to identify key transformation processes (deindustrialization, commercialization, revitalization, functional diversification), to list a set of factors promoting more intense transformations, and to explain mechanisms defining existing spatial pattern of transformations within the test neighbourhoods. Private commercial activity, including rapid development of retail sector, was the main source of transformation, thus defining its partial, fragmented and somewhere controversial nature. Since the probability of further transformation in each point of the territory is determined by the already existing pattern, the existing heterogeneities tend to enhance with a lapse of time, and therefore the initial stages of transformation are especially important for the further development of the neighbourhood. Despite the similar starting conditions, two neighbourhoods demonstrated different outcomes in terms of modernization, explained by the differences in the urban spatial structure, spatial and sectorial structure of industrial zones, position (importance) of the neighbourhood in the whole city, as well as the economic dynamics of the city. Based on detected factors and mechanisms, we proposed models for further transformation intended to maximize the level of modernization within the entire test neighbourhoods.