In spite of the fact that almost everywhere in the territories of historic cities, under the influence of the shortcomings of landscaping, there is a progressive technogenesis of the geological environment and groundwater, which can lead to the destruction of architectural monuments and historically valuable buildings, this problem remains poorly studied. Given the enormous scale of work on the improvement of the historical territories, which is planned to perform under the national projects and municipal programs, the study of this direction to improve the design methodology and engineering surveys as an objective basis for the development of design decisions, is very relevant. For the historical territories of cities that include architectural monuments and valuable buildings, specialized methods of design and engineering and environmental surveys, geoecological monitoring, including measures to ensure the preservation of cultural heritage, are necessary. The article provides a review of literary sources, analysis of examples, and actual data confirming the impact of landscaping factors on the state of cultural heritage sites (CHS). The most significant in terms of the impact on the geological environment and, accordingly, on the preservation of monuments of architecture are the shortcomings of vertical planning and drainage. In the conditions of high-density housing development, the unsatisfactory improvement can stimulate the processes of underflooding, suffosion, and karst, as well as the general technogenesis of soils, and loss of the bearing capacity of the bases and foundations. Underflooding of basements, “soaking” of walls, and formation of cracks on facades can be observed in architectural monuments and historical buildings. The study summarizes the observations and results obtained by the authors – representatives of various specialties (engineers, geologist, architect-restorer) at various stages of their creative work and takes into account the long experience of OOO “IGBI” on the design of improvement on the historical territories of Moscow.