Caherconlish, just off the old road between Limerick and Clonmel, carries its past almost entirely in its name and its street plan, an L-shaped arrangement hugging the western bank of a small stream called the Groodie. Not a single building in the village predates 1700, and of four castles that were recorded as standing within the settlement, not one has left so much as a foundation course above ground.

The place enters the documentary record only with the Anglo-Norman conquest, when the lands of Owney were granted to Theobald Walter, ancestor of the Butler family. It is largely because of that Butler connection that a detailed extent of the manor, drawn up in 1300, has survived. The document confirms that Caherconlish was a functioning borough, home to free tenants, cotters, and betaghs, the last being a class of unfree tenant tied to the land under Gaelic and later Anglo-Norman custom. The settlement was defended, though probably by earthen ramparts rather than stone walls, and in 1358 a murage grant gave the provost, bailiff, and commonalty of the town of Catherkenlyshe the right to collect a tax on goods entering the town in order to fund those defences over a period of twenty years. Murage was a standard medieval mechanism for financing town walls. A gatehouse is said to have survived into the early nineteenth century. The four castles recorded here appear to have been fortified town houses of the type still recognisable at Fethard in County Tipperary and at Ardee and Carlingford in County Louth, urban tower houses built for defence within a settled commercial context. The settlement suffered repeated attacks, notably by the O'Briens, and the Wars of Turlough record the burning and capture of the castle in the 1280s. There are also passing references to a college, and to the south-west of the village, in an area known as College Field, reports from the late nineteenth century mention finds of stone axeheads, pottery, and house foundations.

Ordnance Survey maps mark two castle sites, one to the south-east of the churchyard and another to the north of the village, though nothing survives at either location. A third may have occupied the site of Caherconlish House. Visitors familiar with reading landscapes will find the L-shaped street plan itself the most legible remnant of the medieval town, its geometry still oriented around the Groodie stream to the west. The village is easily reached from the main Limerick to Clonmel road, and the OS maps, compared against the present streetscape, remain the most useful tool for tracing what was once a walled and garrisoned borough.