During the 13th, 14th and 15th centuries, this land was in a progression towards the noble scheme, and it begins to feel the shame of servitude in a monarchical decomposition, strengthened nobility, peasant resistance, religious conflict, plague and livelihood crisis. Guadamur entered medieval history under the hand of Pedro López Ayala, son of the royal chancellor and mayor of Toledo, whose family disputes control to the Silva. He intervened in the war that pitted Juan II and favorite Álvaro with infants of Aragon, Don Enrique and Don Juan, and ended up giving Toledo in 1440. Lost ground, Juan II forgave Pedro in 1444; in 1446 won Guadamur, among other possessions, as a royal granting. This date marks the beginning of four centuries of manorial system in the town: the town became a possession of an absolute landlord that judges, punishes, fines, legislates, chooses the authorities and subjects the villains to taxes and benefits. The son of Don Pedro was the first Count of Fuensalida (1470); two years before he had obtained permission from the king to build a castle in Guadamur, probably on a previous moose Arabic watchtower. It holds the shields of the Ayala and the Silva families, rivals in medieval Toledo. The 15th century also dates the nearby shrine of Our Lady of the Nativity, influenced by the Toledo Mudéjar style.