Monasterio de San Juan was founded in 1091, when the kings Alfonso VI and Constance of Burgundy donated a small land to monk Lesmes, who came from the Chaise-Dieu abbey. In 1537 a fire destroyed practically the whole monastery. The reconstruction lasted until the confiscation. During the first half of the 19th century, several confiscations destroyed the heritage of the monastery and the hospital of San Juan. The monks were expelled from the monastery. The buildings were used as a prison.
Kakesbeck is one of the largest medieval fortifications in Münsterland and the oldest castle in Lüdinghausen. The imposingly grown complex originated in 1120 as a motte, a small hilltop tower castle. After numerous changes of ownership, the castle was extended onto two islands, but it was not until the 14th century that it underwent significant alterations and extensions under the von Oer family. The estate experienced its heyday in the middle of the 18th century, when it covered an area of almost one square kilometre and consisted of five further outer castles in addition to the core castle, which were secured by ramparts and moats.
The well-maintained condition of the castle today is thanks to the late Wilfried Grewing, the former lord of the castle. The foundation named after him has been particularly committed to preserving the property since 2020.