Lochleven was probably a small stone-built keep by the end of the 13th century. Loch Leven was a royal castle from 1257. The English besieged the castle in 1301, but it was saved by John Comyn before it could be captured. The castle held again against Edward Balliol and the English in 1335. By 1335, Alan de Cipont defended the castle against the English. Robert III was said to have resided here for awhile. By the end of the 14th century, Lochleven had passed to the Douglases of Lochleven.
Archibald, 5th Earl, was imprisoned and died here in 1439, as did Patrick Graham, Archibishop of St. Andrew, in 1477. Mary, Queen of Scots was also held here from 1567-8, when she escaped, during which time she signed her abdication. She was a prisoner in the Glassine Tower, and miscarried twins by her 3rd husband, Francis, Earl of Bothwell, in the castle before her escape with the aid of the Douglas family.
Lochleven consisted of a small 15th century keep of 5 stories, and stands at one corner of a 14th century courtyard. A corbelled out parapet, with three open rounds, crowns the keep. Today, the entrance to the castle is on the ground level, through a converted window. At one time, the island was much smaller, but the water level of the loch has been lowered, previously the castle occupied nearly all of the island.
The 5 story tower house was added in the late 14th or 15th century. The fourth story formed a suite for the lord and there were bedrooms above. The wall of the polygonal barmkin was completed during several periods, with one thick section going back to the late 13th century. The courtyard has a small round tower, with gunloops, at one corner and several ranges of buildings, including a hall and kitchen, but these are very ruined. The original entrance was one the second-floor level, from an external stair, and leads to the hall. A turnpike stair leads down to the kichen on the first floor. The vaulted basement has a modern entrance.
The ghost of Mary, Queen of Scots supposedly haunts the castle. She reputed haunts a lot of castles. She must be busy.