The contemporary globalized world characterizes the rapid population growth, its significant concentration in cities, and an increase in the urban population. Currently, many socio-cultural, economic, environmental, and other challenges are arising in modern cities, negatively affecting the state of the urban environment, health, and quality of life. There is a need to study these problems in order to solve them. Urban Green Areas (UGAs) are a part of the social space and a vital part of the urban landscape. They act as an environmental framework of the territory and a factor ensuring a more comfortable environment of human life. This study aims at substantiating the importance of the UGAs, identifying the spatiotemporal dynamics of their functioning, and transforming changes in their infrastructure given the expansion of their functions. This research was carried out as a case study of the second city in Ukraine, Kharkiv. The authors developed and used an original integrated approach using urban remote sensing (URS) and GIS for changes detection to evaluate the current state and monitor spatial transformations of the UGAs. We used several GIS platforms and online resources to overcome the lack of digital cadastre of the thematic municipal area of Kharkiv. This resulted in the present original study. The study analyses the dynamics of the spatial and functional organization of the UGAs according to the Master Plans, plans, maps, and functional zoning of the city for the period from 1867 to 2019. The peripheral green areas became important after the large-scale development of the extensive residential areas during the rapid industrial development in remote districts of the city. They provide opportunities for population recreation near living places. Central UGAs are modern, comprehensively developed clusters with multidisciplinary infrastructure, while the peripheral UGAs are currently being developed. The use of URS/GIS tools in the analysis of the satellite images covering 2000–2020 allowed identifying the factors of the UGAs losses in Kharkiv and finding that UGAs were not expanding and partially shrinking during the study period. It is caused by the intensive construction of the residential neighborhoods, primarily peripheral areas, infrastructure development, and expansion of the city transport network. Nonetheless, some sustainable trends of UGA functioning without more or less significant decrease could be proved as existing in a long-term perspective. The authors analyzed and evaluated changes and expansion of the UGAs functions according to modern social demand. The research value of this is the usage of different approaches, scientific sources, URS/GIS tools to determine the UGAs transformation in the second-largest city in Ukraine (Kharkiv), to expand and update the main functions of UGAs and their role in the population’s recreation. The obtained scientific results can be used to update the following strategies, programs, and development plans of Kharkiv.