The site, whose name derives from the Irish “Cathair-cind-lioss” meaning “rampart guarded, solid stone,” was held by Theodore Walter le Botiller in 1214. The castle, complete with vaulted towers and a drawbridge, met its first major catastrophe between 1285 and 1287 when Torlough O’Brien, Prince of Thomond, stormed and burned it. Despite this setback, the settlement’s strategic importance on the marches, surrounded by Irish rebels, led Edward III to grant permission in 1338 for the provost and bailiffs to construct a stone wall around the town. The castle received a royal charter in 1358, cementing its significance in the region.

Throughout the centuries, the castle changed hands amongst various notable families. The Bourkes held it in the late 16th and early 17th centuries, with William Bourke in possession in 1583 and Theodore Bourke leasing it from Lord Caher in 1605. A monument to Theodore and his wife, Slany Brien, was erected in the church in 1641. The castle played a role in the Williamite War, being occupied by King William himself in 1690 and by General Ginckell the following year during his advance to besiege Limerick. By 1680, the antiquarian Dyneley sketched the church and peel tower, showing a four-storey structure with a bartizan at one corner.

The site underwent dramatic transformation in the 19th century when Major William Wilson erected Caherconlish House, described in 1837 as “a handsome modern residence” built near the original family mansion’s location, surrounded by fine plantations and ornamental grounds. The old mansion, perched on a rock and identified as one of the castle structures, met a peculiar end; despite showing no signs of decay, it suddenly split from top to bottom, with half collapsing into ruins whilst the other half remained standing. The gateway bearing the Wilson family arms survived this collapse. By 1827, Fitzgerald noted four castle structures and a fortified gate, though little remained by the time of Westropp’s early 20th century survey.