The present study focuses on the transformations of a typical Mediterranean agroforestry landscape of southern Italy (high Agri Valley – Basilicata region) that occurred over 24 years. In this period, the valuable agricultural and natural areas that compose such a landscape were subjected to intensive industry-related activities linked to the exploitation of the largest European onshore oil reservoir. Landsat imagery acquired in 1985 and 2009 were used to detect changes in forest areas and major land use trajectories. Landscape metrics indicators were adopted to characterize landscape structure and evolution of both the complex ecomosaic (14 land cover classes) and the forest/non-forest arrangement. Our results indicate a net increase of 11% of forest areas between 1985 and 2009. The major changes concern increase of all forest covers at the expense of pastures and grasses, enlargement of riparian vegetation, and expansion of artificial areas. The observed expansion of forests was accompanied by a decrease of the fragmentation levels likely due to the reduction of small glades that break forest homogeneity and to the recolonization of herbaceous areas. Overall, we observe an evolution towards a more stable configuration depicting a satisfactory picture of vegetation health.