Roundwood lays claim to being the highest village in Ireland and stands about 240 metres above sea level. The modern village developed in the 19th century around the Catholic Church of St Laurence O’ Toole and contains a number of examples of Tudor Revival architecture, most notably the Coach House Hotel. There is evidence of earlier settlement in the area in the form of three ecclesiastical sites at Ballinafunshoge, Knockatemple and Derrylossary, all within a mile of the village. A bullaun stone and an example of rock art can be seen on the northern and southern approaches to the village. The old name for Roundwood was Togher, which denotes a timber or stone causeway built across boggy land in ancient Ireland.
Several notable figures have associations with Roundwood. General Joseph Holt (1756-1826) was a key rebel leader during the uprising of the United Irishmen in 1798. After the defeat of the United Irishmen at Vinegar Hill, he led a guerrilla campaign in the Wicklow Mountain, where his knowledge of the terrain allowed him to hold out for several months. He eventually negotiated a surrender and was transported to Australia, but later returned to Ireland. In 1998, a memorial to him was unveiled at Mullinaveige to the north Roundwood, where he lived.
Sean T. O’ Kelly (1882-1966), the second President of Ireland, lived at Roundwood Park just south of the village. He was in the GPO during the 1916 Rising, was elected to the first Dáil and became a close associate of Eamon de Valera during the independence struggle. Later he was a founding member of Fianna Fáil and held several cabinet posts in the 1930s and 1940s. He served two terms as President from 1945 to 1959.
Today Roundwood is an important gateway to the Wicklow Mountains and is within easy reach of the lakes and peaks as well as heritage sites like Glendalough and the Vartry Reservoir. St. Kevin’s Bus company was established here in the 1920s and ran a private bus service between Dublin and Glendalough. The Roundwood PURE Mile walk leads north-west from the village and passes places of local heritage interest along quiet country roads.