Low earthworks on a gentle east-facing slope define two conjoined rectangular areas, now quietly absorbed into agricultural use. Further enclosures, platforms, and linear features spread outward to the east, north, and west, and aerial photography has revealed just how extensive this buried landscape really is.

The parkland surrounding Killoughter House appears to have escaped the heavier cultivation that would have erased such traces elsewhere, which is why so much survives. A well-defined sunken routeway, the kind of feature typical of deserted medieval settlements, can be followed for a considerable distance along a series of terraces south of the house. To its south, a cluster of rectangular features have been identified, and the pattern continues outward towards two nearby moated sites. A moated site is a defended medieval enclosure surrounded by a water-filled ditch, and Killoughter's neighbours in this landscape are significant ones. Castlegrange, whose name derives from an abbey founded in Wicklow town during the reign of Henry III (1216 to 1272), still retains fragments of its water-filled moats and masonry. Courtfoyle, another moated enclosure to the north-west, shows comparable associated earthworks extending in the same direction. The working interpretation, advanced by researcher D. L. Swan in 1996, is that these features collectively represent a single extensive medieval settlement, focused on the defended site at Killoughter and its adjacent church. Some of the rectangular enclosures may preserve field boundaries that pre-date even the medieval layout, underlying the modern field system rather than simply preceding it. In 2000, test trenching carried out in connection with the Hollybrook to Wicklow Gas Pipeline confirmed the presence of linear earthworks in the fields between the church and the moated site, though no datable material came to light.