The village of Kiltinan, known in medieval documents as Kiltevenan or Kyltewnan, once occupied a north-to-south ridge above the Clashawley River, which runs through a deep valley along the eastern edge of the settlement. Aerial photographs taken in the 1960s and 1970s showed it with unusual clarity: a hollow-way, essentially a sunken lane worn down by centuries of foot and animal traffic, running through the centre of the village, with six long linear plots stretching eastward and smaller paddocks to the west. That evidence was ploughed out in the 1980s, and the earthworks that had survived into living memory were gone within a decade.

The documentary record reaches back to between 1199 and 1206, when a Roger de Worcester restored the vill to his brother Philip, according to the Ormond Deeds. By 1308 to 1309, the town had burgesses, property holders who occupied burgages, a form of urban landholding typical of medieval planned towns, and paid six marks and threepence annually in rents of service. In 1358, the reeve and community were fined two shillings at the Pleas of Assizes in Clonmel for breach of the assize of bread and ale, a regulatory system that controlled the price and quality of staple foodstuffs. The manor passed through the hands of the Bermingham family during the fourteenth century, appearing in grants to James le Botiller, Earl of Ormond, in 1371, and to Thomas Bermingham in 1396. By the fifteenth century it had come to the Butlers of Dunboyne, remaining with them until it was confiscated in the aftermath of the 1641 Rising. Through all of this, the church sat at the crest of the hill and the castle lower down to the south-east, overlooking the river below.

A LiDAR survey carried out in 2011 added something the aerial photographs had only partially suggested: the village extended further south than previously mapped, with plot boundaries visible on both sides of the modern road. Interpreted alongside the older maps and photographs, this places the medieval church not at the edge of the settlement but roughly at its centre, with the castle positioned along the eastern flank. The modern road, in other words, runs through the middle of what was once a busy if modest market town, and the avenue leading to Kiltinan Castle follows a line that the original inhabitants would have recognised.