Global change threatens alpine biodiversity and its effects vary across habitat types and biogeographic regions. We explored vegetation changes over the last 20 years on two Mediterranean alpine calcareous grasslands in central Apennines (Italy): stripped grasslands (EUNIS code E4.436) with Sesleria juncifolia growing on steep slopes, and wind edge swards (EUNIS code E4.42) with Carex myosuroides. Based on a re-visitation of 25 vegetation plots of 4 × 4 m, we assessed changes in overall and endemic plant species cover and richness by nonparametric Kruskal–Wallis test. We explored changes in structure and ecology using growth forms and Landolt indicators for temperatures. We identified species’ contribution to temporal changes using the similarity percentage procedure (SIMPER). The results evidenced a significant decline in all species cover and richness on both plant communities with a significant decline in alpine and endemic species and in hemicryptophytes with rosette and scapose ones on stripped grasslands, as well as a decline in subalpine and suffruticose chamaephytes species on wind edge swards. Such biodiversity loss, so far observed only in the warmest and Southern Mediterranean summits of Europe, is likely attributable to the combined effect of higher temperatures; the increase in the vegetative period; and the decrease in water availability, which is particularly severe in calcareous regions. Our study suggested the vulnerability of the analyzed alpine ecosystems to global change and the importance of monitoring activities to better understand vegetation trends and adaptation strategies in subalpine, alpine, and nival ecosystems.