In modern science, the study of digitalization and digital transformation in spatial socio-economic systems, among which urban and regional agglomerations are the most complex ones, plays a special role. The paper considers scientific publications devoted to the problems of smart city development. Russian practices of smart city development are investigated in comparison with the world leaders in urban space digitalization. Based on the analysis of the achieved level of digital transformation of urban space and development of “smart city” technologies in the cities-leaders in the development of “smart” technologies in the subjects of the Russian Federation in 2021, the issue of scaling promising technologies and successful practices from urban to the level of regional space is being considered. The prospects of integrating the smart city as a point of digital development of regional space into the system of inter-regional interactions of digital regions are disclosed.