The article considers the sustainable development of the city public spaces and the penitentiary complexes problems from the Synergetics and Socionics standpoint. These approaches provide consideration of the opposite processes of public spaces socialization and correctional complexes resocialization, sustainability, and dynamism its organization, and self-organization. The regularities of sustainable development are present in the cyclical nature of historical changes in public spaces and the penitentiary system. Cycles unfold in the alternation order of pairwise polarized processes, on the one hand, dispersion and concentration, and, on the other, – self-organization and adaptation. We have found that the interaction of universal processes and the natural change of cycles stimulates, on the one hand, growth and stabilization, and, on the other, – transformation and metamorphosis, which lead to the emergence of new forms and structures of public spaces and penitentiary complexes. We have proposed to use Socionical methods for increasing tolerance and democracy in the architectural environment of settlements. We have described the methodological tools to achieve the harmonization of the architectural environment of settlements.