According local sources the first castle in Montessoro was built in the 13th century. It was acquired by Spinola family in 1330 and the rebuilt the new castle in the early 15th century. The castle was used until 1797 when it was destroyed and abandoned in wars between French and local armies.
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.