In Mediterranean Europe, wood-pasture landscapes with oak woodlands as emblematic ecosystems are undergoing rapid land-use change, which may threaten their legacy as hotspots of biodiversity, ecosystem services, and cultural heritage. The objective of this study was to quantify land cover changes and transitions as well as the dynamics of oak woodland patterns and densities over 50 years in two municipalities at the center and edges of Quercus macrolepis distribution in Northern Lesvos (Greece). We used aerial photographs from 1960 and WorldView-2 satellite images from 2010 to process land cover maps and metrics, and to calculate oak canopy cover with a point-grid sampling approach. Spatiotemporal dynamics of land cover change were generally high—especially between oak woodlands and grass- and shrub-lands, resulting in a more heterogeneous and fragmented landscape in 2010. Surprisingly, oak woodland area remained stable with marginal losses in one study site and gains in the other one. Oak canopy cover increased by 8 and 9 %. Spatial hotspots of change were mountainous and peripheral phrygana areas with expanding oak stands, as well as river valleys and near urban areas with expanding olive groves and grass- and shrublands in former complex cultivation and oak stands. We conclude that the parallel processes of abandonment of crop cultivation and intensification of livestock grazing have been less detrimental to oak woodlands than supposed. To ensure long-term persistence of oak woodlands in the face of ongoing rural depopulation and land-use intensification, environmental and agricultural policies should better address their specificities as anthropogenic habitats.