The design and assessment of the spatial environment are widely used in management and regulated by statutory instruments at the national and regional levels. However, regional territorial and spatial development lacks generally accepted assessment criteria because of its multi-sectoral nature and the absence of a unified classification system of indexed objects in the regulation. This paper proposes theoretical models for the unified indexing of regional territorial and urban spatial organization and a system of the differences in the conditions of their development, which comply with regulations and research into indicators of spatial regional development. These consider the types of use established in the federal classifier for spatial planning objects as the object of indexing. This methodology does not define the territory of the region as an urban planning system and cannot represent the interests of its spatial organization. Therefore, a second system of indicators indicators is proposed, where urban planning complexes and frameworks are the objects for the assessment of the current spatial environment state. This approach justifies the object and the subject of indexing regional spatial organization. The study is practically significant as its basic findings can be used for the urban planning support of the Russian spatial development strategy. The work can be used to prepare regulatory requirements for urban planning documentation on the spatial and territorial planning for the development of regions and settlements and in the training of architects and urban planners.