Few fossils have been described from the very rich localities of Kalimantsi in southwestern Bulgaria, and none from Hadjidimovo, in the same area. These deposits have produced one of the best collections of Chalicotheriidae from the late Miocene of Europe, increasing the diversity of the family, and providing the first definite evidence of the co-occurrence of both subfamilies, Chalicotheriinae and Schizotheriinae. The milk dentition of Ancylotherium is described for the first time; it confirms that this genus is close to, but different from, the American Tylocephalonyx. A chalicotheriine skull from Kalimantsi, with a characteristic tooth morphology, is referred to a new genus and species, Kalimantsia bulgarica. A revision of the taxonomy and systematics of European Chalicotheriinae leads us to discard “Macrotherium,” which is a junior synonym of Chalicotherium, to revive Anisodon Lartet for middle Miocene forms, and to suggest the extension of Kalimantsia into the latest Miocene of the Balkans.