A cross-section of modern evaluation scales of the spatial organization of regional and urban systems is presented, focused on ensuring sustainable, information technology, architectural and urban development of the living environment of people. Theoretical models of unified indexing of the territorial and spatial organization of regions are proposed, corresponding to the current regulatory framework and priority scientific research in the field of criteria of spatial development of regions and their parts, as well as a table of correlation of differences in the conditions of spatial development of regions. The task of "developing the scientific foundations and methodology of the human habitat quality assessment system", including at the regional level, is included in the List of priority areas for the development of applied sciences and exploratory research of the RAASN and the Ministry of Construction of Russia. The methodological basis of the research is the principles of a systematic approach to urban planning, corresponding to the laws of goal-setting, construction and development (implementation) of complex systems. The practical significance of the research lies in the use of the main results of the work in the urban planning support of the spatial development strategy of Russia in terms of the application of its provisions in the preparation of regulatory requirements for urban planning documentation in the field of spatial and territorial planning of the development of regions and agglomeration forms of settlement; in the educational process of preparation in the areas of "Architecture" and "Urban Planning".