The development of information and computer technologies, starting from the second half of the twentieth century and rapidly continuing in the twenty-first century, is closely related to their penetration into the world of human living space. This rapid invasion leads to the complication of the volumetric-spatial organization of the urban environment, changes in the visual appearance of the city, and transformations in architectural activity. The purpose of the study was to identify the problems of implementing the “smart city” concept and the features of the formation of “smart spaces” in a number of Russian cities in the Volga region—Samara, Volzhsky, Volgograd. The article reveals various aspects of the developed projects of smart urban spaces. The authors identified difficulties in the spread of new urban spaces, including the commercial focus of digitalization of cities, unpreparedness for the introduction of new technologies of the historically established urban structure and development, the unpreparedness of part of the urban community for widespread digitalization.