The repopulation activity of the Montes de Toledo and places from the end of San Pablo, began in the last third of! 11th century, as in most of the municipalities in this area.
With the subsequent segregation of this territory in favor of the Valladolid Knight Téllez de Meneses and the Archbishop Jiménez de Rada, repopulation action will head South looking for new paths to the Guadiana basin. With this repopulation is conducive to settlements in the areas most filled with mountains and the first foothills of the cordillera.
In this repopulation process and due to the rugged terrain, the mountains become refuge of brigands, documented from the 13th century, known as golfines.
The golfines came from different parts of the Peninsula and were nomadic groups which were dedicated to the assault and to plunder, creating instability in many areas as for example in the port you Marches de San Pablo, since that crossed an important channel of communication to the South of the mountains by that port.
With repopulation action began frequent clashes between settlers and the golfines. Settlers to defend themselves, decided to organize into a brotherhood, which was recognized by Toledo in 1300 as a form of popular justice based on the medieval right to defensión.
The population of San Pablo is definitely formed in the first half of the 15th century, influenced decisively by the Foundation of the Augustinian monastery. At the end of this century, Paul takes Charter of nature as a place of the Town Hall of Toledo's Municipal Lordship together with the localities of Las Ventas con Peña Aguilera, Los Yébenes, Marjaliza, El Molinillo, Navahermosa,... that was linked to Toledo until the 19th century.