Article focuses on the method of digital analysis of the land survey materials. They provide highly detailed data, characterizing the settlement structure and land use at the local (М 1 : 8400) and regional (М 1 : 42 000) levels. These materials are used for the analysis of structure of land use at the end of the XVIII century for two regions, differentiated in terms of climatic, geological, geomorphological, soil and socio-economic conditions but situated in one district of the Ryazan region. The proposed method consists of six basic steps: 1) creation of dachas’ outlines; 2) combining of individual plans into a single coat; 3) binding the resulting images to the geographic coordinates of solid reference points, taking into account local features of the landscape; 4) reconstruction of landuse with the creation of unified land type legend; 5) binding the county plan; 6) reconstruction of socio-economic infrastructure of the entire county. We estimate the accuracy of spatial data, so it concludes that there is a need to incorporate information about the landscape structure of the territory to increase the quality of the land use reconstruction.