Prior to its settlement, the site of Montesclaros was a pasture called Anadinos in Higueruela de las Dueñas. Montesclaros was not populated until February 1491 when it acquired the title of Villa thanks to María de Luna, the daughter and rich heir of the Constable of Castile, Álvaro de Luna. María de Luna wanted to suppress the robberies and deaths that occurred in the nearby mountains. Fifteen residents of Navamorcuende were given the rights to relocate to Montesclaros.
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