There are varied accounts as to when exactly the main tower/keep was constructed; ranging anywhere from the 13th century to the late 15th century, but most likely around 1250 AD. It was built by the O'Bannon clan and was originally called "Léim Uí Bhanáin" (as was the fertile land around the castle which was associated with the Bannon clan), or "Leap of the O'Bannons". The O'Bannons were the "secondary chieftains" of the territory and were subject to the ruling O'Carroll clan. There is evidence that it was constructed on the same site as another ancient stone structure perhaps ceremonial in nature, and that that area has been occupied consistently since at least the Iron Age (500 BC) and possibly since Neolithic times.
The Annals of the Four Masters record that the Earl of Kildare, Gerald FitzGerald, tried unsuccessfully to seize the castle in 1513. Three years later, he attacked the castle again and managed to partially demolish it. However, by 1557 the O'Carrolls had regained possession.
Following the death of Mulrooney O'Carroll in 1532, family struggles plagued the O'Carroll clan. A fierce rivalry for the leadership erupted within the family. The bitter fight for power turned brother against brother. One of the brothers was a priest. While he was holding mass for a group of his family (in what is now called the "Bloody Chapel"), his rival brother burst into the chapel, plunged his sword into him and fatally wounded him. The butchered priest fell across the altar and died in front of his family.
In 1659, the castle passed by marriage into the ownership of the Darby family, notable members of which included Vice-Admiral George Darby, Admiral Sir Henry D'Esterre Darby and John Nelson Darby. The central keep was later expanded with significant extensions. However, in order to pay for these extensions, rents were raised and much of the land accompanying the castle was sold. This is one theorised motivation for the burning of the castle during the Irish Civil War in 1922.
In 1974 the castle was bought by Australian historian Peter Bartlett, whose mother had been a Banon. Bartlett, together with builder Joe Sullivan, did extensive restoration work on the castle up to the time of his death in 1989.
Since 1991, the castle has been privately owned by musician Seán Ryan, who is undertaking restoration work.
There is a popular legend which states that Leap Castle is haunted by a supernatural entity known as an Elemental. The alleged entity is known as "It".
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- Description, history and pictures of Leap Castle