In 1868, the parish of Derrylossory contained the following places:
"DERRYLOSSORY, (or Derralossary), a parish in the baronies of North Ballinacor and Newcastle, in the county of Wicklow, province of Munster, Ireland, 5 miles S.W. of Newtown Mount Kennedy. Annamoe is its post town. It is situated near Glendalough on the road from Dublin to Rathdrum. The surface is mountainous, with some bogs and numerous loughs. The river Avonmore traverses the interior. The soil varies in quality. The principal heights are "Wicklow Gap and Knocknacloghole in the interior; Sally Gap, Lugduff, Gravale, and some others, on the frontier. Lough-Dan is the principal lake. The living is a perpetual curacy in the diocese of Dublin, value £392, in the patronage of the archbishop. The church, which stands in an isolated district about a mile from the village of Roundwood, was enlarged in 1820 by means of a loan from the late Board of First Fruits. There are Roman Catholic chapels at Roundwood and Annamoe, which are united. The parish school is at Raheen, and there are two pay day schools within the parish. Derrybane, Castle Kevin, Roundwood Park, and Lake Park are the principal seats. There are extensive lead-mines at Glendascene, which are the property of the Irish Mining Company. Near Castle Kevin are the remains of an old castle formerly of the O'Toole family.
"ANNAMOE, a village in the parish of Derrylossory, barony of Ballinacor, in the county of Wicklow, prow, of Leinster, Ireland, 9 miles to the N.W. of Wicklow. It is situated in a charming valley by the Annamoe rivulet which runs down from Lough Dan to the river Ovoca. Not far from the village are the remains of Castle Kevin, an ancient fortress of the O'Tooles. It was in the form of a quadrangle. All that is left are the rampart and ditch, and some of the foundations. The principal seats are Castle Kevin, on a fine wooded hill, with extensive prospects; Dromeen and Lara House."
"LARAGH, a village in the parish of Derrylossory, in the barony of North Ballinacor, county Wicklow, province of Leinster, Ireland, 6 miles N.W. of Rathdrum. It is situated under the Laragh Mountain, near Glendalough. About 1 mile E. of the village is Laragh House."
"ROUNDWOOD, (or Togher), a village in the parish of Derrylossory, barony of Ballinacor, county Wicklow, province of Leinster, Ireland, 4½ miles S.S.W. of Newtown-Mount-Kennedy. It is situated on the road from Dublin to Seven Churches, and near the river Vartry, and Lough Dan. It is noted for its fine trout-fishing. Several seats surround the locality. There are a police station and a dispensary. Fairs are held in January, March, May, July, August, and September.