Numerous achievements in science and technology have a significant impact on the living environment and the life activity of the population, providing broad opportunities for communication, development and improvement: the Internet, social networks, distance learning, etc., thereby increasing the comfort of our existence. At the same time, this urban environment, including buildings, constructions, engineering and network infrastructure, road communications, is a quite conservative and inert environment, which usually lags behind the demands of a modern man. Thus, the need for reconstruction of the compact built-up development areas is one of the primary urban planning tasks. In this research, the authors, based on the principles of system analysis, developed the methodological approach to planning and making decisions on the complex reconstruction of the compact built-up development areas. The book can be useful to a wide range of readers: architects, design and civil engineers,managerial, municipal and regional employees, and everyone interested in the problems of improving the comfort and living conditions in the urban environment.