Due to legume-based systems improving several aspects of soil fertility, the diversification of agrosystems using legumes in crop succession is gaining increasing interest. The benefits of legumes aroused the interest of farmers in the association of the Economic and Environmental Interest Group (EEIG), who introduced the idea of using the winter pea instead of rapeseed in their crop succession. The aim of this study is to evaluate the effects of the winter pea compared to those of rapeseed, as a head crop of the rotation, on soil microbial communities, enzyme activities, nitrogen (N) balance and yields. The field experiment involved two farmer plots that were selected within the EEIG. In each plot, two crop successions, including winter pea–wheat and rapeseed–wheat with fertilized and unfertilized strips, were examined for two years. Three times a year, under the wheat crop, composite soil samples were collected at depths of 0–20 cm, for microbial abundance and enzyme activity analyses, and twice a year at a depth of 0–60 cm, for the measuring of the mineral N. The results showed that the rapeseed–wheat succession maintained or enhanced soil bacterial and fungal biomasses and their enzyme activities. The winter pea–wheat succession enriched the soil’s mineral N content more consistently than the rapeseed–wheat succession. The mineral N enhancement’s effect was maintained under the wheat crop. Overall, the impact of the winter pea was positive on the soil’s N dynamics, but wheat yields were equivalent regardless of the previous crop (winter pea or rapeseed with and without fertilization). In the Normandy region, as rapeseed requires a large amount of N fertilizer and pesticide to maintain the yield and quality of crop products, it is suitable to favor the introduction of the winter pea as the head crop of the rotation, which indirectly allows for a reduction in the costs of input production and use, the working time of farmers and environmental pollution