The original castle here was built on a large farm owned by the Cistercian Monks of St Mary’s Abbey in Dublin between the 14th and 15th centuries. This area was on the border of the ‘Pale’ and was frequently raided by Gaelic tribesmen such as the O’Tooles and the O’Byrnes of Wicklow. After King Henry VIII dissolved the monasteries in 1539 Monkstown passed in and out of ownership of the some of the most prominent characters and families in Irish history including the Cheevers family (a French Norman family who also owned Dalkey Castle), General Edmund Ludlow (Cromwell’s Master of the Horse in Ireland) and Michael Boyle the Lord Chancellor of Ireland. In its day, the castle complex had many outbuildings and was regarded as one of Dublin’s finest residences. Today, however, all that remains is the gatehouse and the 3 story tower, which once formed one side of a large hall.