The dissertation is devoted to the solution of the scientific and applied problem to increase the efficiency of organization and management of the process of complex reconstruction of urban development by developing the concept, methods of organizational and technological designing of reconstruction of industrial buildings with a change in their functional purpose on the basis of further development of the toolkit for evaluation, analysis, substantiation and selection of rational organizational and technological decisions that provide improvement in the quality of reconstruction of buildings and structures in the effective use of resources and reduce adverse environmental impacts, due to the consideration of systematic influences of determining organizational and technological, technical and managerial factors. It is proposed to solve a formulated problem based on the search for rational decisions that meet the desired (specified) technical and economic characteristics (indicators), based on the application of statistical modeling of projects as managed processes. Together with this, it is advisable to take into account the influence of determining organizational and technological, technical and managerial factors. To evaluate the decisions relative to these factors it is necessary to find a rational value of the efficiency criterion. From the position of the customer (investor) as such criteria, it is expedient to consider a minimum cost and duration of reconstruction of industrial buildings with a change in functional purpose. It is proposed to take into account the influence of factors of technical condition, constraintness, saturation of the territory of an industrial enterprise by engineering networks and conditions of their operation, saturation of the territory of an industrial enterprise by engineering structures and conditions of their exploitation, quality, safety, energy efficiency, environmental friendliness. The adequacy and significantness of the influence of these factors on the performance indicators of organizational and technological decisions of the reconstruction of industrial buildings with a change in functional purpose is substantiated by the results of an expert survey. To realize the possibility of obtaining quantitative values of the decisive organizational and technological, technical and management factors, their formalization was carried out. Mathematical models that are based on taking into account the systematic influence of decisive factors are obtained. The application of the developed approach allows to achieve the rational values of predicted indicators in specific conditions of construction works and within the specified resource constraints. Operating projected estimates of expected results, investors have the opportunity to adjust their goals and choose the most rational version of the investment project. When additional information is received, in particular regarding the conditions for the reconstruction of industrial buildings and resource restrictions, in the subsequent stages of reconstruction, the expected value can be clarified. The assessment of established dependencies of the duration and value of the reconstruction of industrial buildings with a change in functional purpose from the decisive factors on the Fisher’s criterion, as well as practical testing in the design and building organizations confirmed their adequacy of the process under study. Keywords: organizational and technological decisions, reconstruction, industrial building, functional purpose, duration, cost, efficient use of resources, organizational and technological, technical and managerial factors, technical condition, constraintness, quality, energy efficiency, safety, environmental friendliness.