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The basic document for regulation of the settlement urban development is the Master Plan [1]. The legislative and regulatory framework for regulating the composition, content, approval and approval of this document is very extensive and is based on a broad basis of scientific research and practical experience of domestic and foreign specialists in this field. The larger the city, the more difficult it is to predict its continued existence. In this article the results of the analysis of historical-geographical, socio-demographic and legislative-normative aspects influencing the regulation of the city development issues (on the example of the historical and current master plans of the city of Kyiv) are covered. Also are outlined the peculiarities of the formation of the spatial organization of the city territory as a part of the master plans of Kyiv at different historical stages – prior the planning, the period of joining the Russian Empire, the Soviet and the present period. The evolution of models of spatial organization of the city territory is characterized. The master plans development periodicity is analyzed as well as a conclusion is made about the fallibility of the statutory requirement regarding the indefinite validity of the master plan of the settlement as a basic urban planning document. Population size (both actual and predicted) acts as a key indicator of settlement development. The article analyzes the dynamics of the population of Kyiv, identifies patterns of influence of positive and negative factors on  this indicator, establishes  faults between the actual and predicted population of Kyiv. The conclusion is made about the extreme complexity of forecasting the prospects for the development of urban systems. The reasons (accuracy of demographic forecasts, counter intuitiveness of development of complex urban planning system, imperfection of legislative and regulatory base) of impossibility of full realization of master plans of settlements, in particular, of the city of Kyiv are considered. The recommendations on improvement of the legislative and normative base for development of settlements master plans are given. In particular, the return of the fixed term of the Master Plan, that does not exceed 20 years. The author's vision of promising directions of development and transformation of the spatial organization of the territory at the present evolutionary stage of its existence of the city of Kyiv is formulated. Namely – a cardinal complex reconstruction of the city.

City Master Plan: Forecasting Methodology Problems (on the example of the Master Plans of Kyiv)