The postagrogenic transformation of landscapes is one of the key problems leading to a decrease in soil fertility in the territory of Northwest Russia. In order to assess the degree of land degradation, field studies of soils from fallow lands in the Leningrad Region were carried out. Different evolutionary trends of ontogenesis of soils with types of soil parent materials were revealed. At morphological and micromorphological levels, degradation processes of old-arable horizons were noted, including secondary podzolization and decreasing Ap horizon thickness. Using a CHN analyzer, the stock levels of soil organic carbon and nitrogen of the studied chronoseries were estimated. The data obtained show that the carbon stocks of old-arable soils are lower than the benchmark ones due to the weak development of the Oi horizon. Carbon dynamics varied substantially by parent materials: soils on silt–clay materials showed a low 7.1% carbon decrease, while soils on sandy and bottom sediments increased by 139% and 163%, respectively, in old-arable horizons by the accumulation of coarse forms of carbon. For nitrogen, it was revealed that the highest stocks are observed in old-ploughed soils, which is due to the input of a large amount of plant residues from small-leaved forests. The content of biogenic elements in the soil showed separate evolutionary direction depending on parent materials: soils on silt–clay materials showed 7.6% phosphorus depletion and 15% potassium loss over 15–30 years, while soils on sandy materials demonstrated 18% phosphorus loss and 114% potassium increase during 30–86 years of fallow state. On the contrary, the content of nitrate and ammonium forms of nitrogen was higher than in the benchmark zonal soils, with nitrate nitrogen increasing by 150 times on sandy parent materials and ammonium nitrogen increasing by 102% in soils formed on bottom sediments over 35–70 years, which is due to the transformation of grass and forest plant residues. The duration of transformation and regradation of soils of fallow land depends on geogenic and bioclimatic conditions that determine the direction and speed of changes.