Most grazing lands in Mediterranean ecosystems that support extensive sheep farming systems are characterized by unfavorable edapho-climatic conditions, especially in semi-arid areas. Often, though, their use is far from sustainable, causing erosion and ecosystem degradation impacts. In this paper, we explore the use, productivity, and flora diversity of typical Mediterranean grazing lands in four farms at the Agra locality in the western part of Lesvos Island, Greece. For a period of two consecutive growing seasons (September to June), we recorded herbage biomass on 16 plots of grazing lands with three measurements per season of land cover and plant productivity (biomass) inside small exclosures (cages) protected from grazing. We recorded the species richness of herbaceous plant communities within and outside the cages at the end of every growing season, the period of maximum growth of herbaceous species. We also chemically analyzed the biomass for crude protein at the end of each season. Results show sizable productivity differences among pasture plots as well as seasons and an overall medium to high degree of productivity and species richness considering the relatively intensive grazing, with little differences over the different cages and the degree of grazing intensity. These results suggest that the “history” of the fields is important, as grazing lands that had been used for arable crops in the past, as well as those leveled and in favorable locations, were the most productive and diverse ones, while shallower soils and inclined grazing lands showed signs of overuse and degradation. Overall, though, these ecosystems showed a high degree of resilience despite their intensive use.