Castillo de Cifuentes in Guadalajara was begun in 1324 on the foundations of an earlier Muslim fortress by the Infante Don Juan Manuel, a patron of literature and arts who composed his celebrated work 'El conde Lucanor' within its walls. The castle features a distinctive square ground plan with four towers—one round, two square, and a pentagonal tower of homage—surrounded originally by a moat and protective walkway. The fortress later became the domain of the Silva family, counts of Cifuentes, and served as a residence for notable figures including Fernando de Antequera and King Juan II of Castile. During the Spanish Succession and War of Independence, it played military roles in regional conflicts. Declared a National Monument in 1931, the castle's fortified architecture showcases the transition from medieval military stronghold to noble residence.