This research article focuses on the evolution of a Mediterranean landscapes and the intricate interplay between natural and human-induced processes in the context of the Italian Anti-Apennine mountains. The study employs a multi-temporal approach to analyze changes in land use and landscape ecology, livestock activities, and agro-pastoral practices over seven decades. We noted a 18% decrease in animal units, particularly in goat and pig farming, accompanied by a 10% reduction in horse populations. Farmers’ adaptation strategies involve increasing animals per farm, aligning with broader agricultural trends toward intensification and specialization. In parallel, we observed a 22% reduction in grassland surfaces juxtaposed with an overall 15% increase in woodlands and shrublands, a 13% decreasing trend in habitat edge, and an overall 18% increase in patches aggregation at the landscape scale. The decline in anthropogenic pressures linked to depopulation triggered secondary successions, resulting in a 25% increase in homogeneous closed woodlands. These landscape alterations contribute to a 19% decrease in ecosystem heterogeneity and complexity, favoring ecological connectivity for forest-linked species but posing challenges for open meadow species. This, coupled with the loss of biocultural heritage, including traditional settlements dating back to the Bronze Age and Roman times, as well as pastoral traditions and knowledge, underscores the need to rethink future development strategies with a focus on retaining younger generations and preventing the loss of crucial ecosystem services.