Despite rising demand for agricultural products, agricultural land abandonment is increasing, especially in developed countries, leading to recolonization by natural vegetation. This phenomenon impacts ecosystem services, biodiversity, and the economy, causing, for example, the loss of agrobiodiversity, soil erosion, and increased frequency and intensity of fires. Monitoring and understanding the drivers of agricultural abandonment are crucial for protecting historic landscapes. The aim of the study was to assess land use in the 1950s in areas of the Latium region that are currently classified as natural and semi-natural (about 736,000 hectares), and analyze the dynamics of renaturalized agroforestry landscapes. The diachronic land use analysis highlighted that approximately 76,700 hectares of today's wilderness areas were used for agriculture in the 1950s, with 70% consisting of arable land and 17% comprising complex cropping and farming systems. Grasslands covered more than 136,000 hectares, 57% of which are still preserved, while 40% have transitioned to forest or shrubland. Forest land use class increased from 25.59% in 1954 to 31.39% in 2006. The loss of agricultural land has significant implications for the economic sustainability of extensive livestock farming, the self-sufficiency of the food system, and also the proliferation of ungulates, a phenomenon that has become increasingly difficult to manage in Italy. At the same time, the loss of grasslands leads to the simplification of the landscape with a consequent loss of biodiversity. This phenomenon has also been observed in Natura 2000 sites, where around 30% of grasslands, including habitats of priority importance, have been lost. This decline highlights the critical challenges that must be addressed to achieve the goals of the “Nature Restoration Law”, which sets habitat restoration targets of 20% by 2030 and 100% by 2050, and the reduced capacity of these new simplified landscapes to provide ecosystem services.