Monkstown, historically known as Carrickbrennan, is an area in south Dublin, located in Dun Laoghaire-Rathdown County, Ireland. It is on the coast, between Blackrock and Dún Laoghaire. The DART stations of Seapoint and Salthill and Monkstown serve the area.

In 1539, King Henry VIII awarded the Monkstown lands to Sir John Travers, Master of the Ordnance in Ireland. John Travers lived in his Castle at Monkstown from 1557 to his death in 1562 and is buried in the Carrickbrennan Graveyard where the property fell to James Eustace 3rd Viscount Baltinglass through his marriage to Mary Travers. In 1580, the Castle was used as a rebellion stronghold, after which it was awarded to Sir Henry Wallop, Vice-Treasurer of Ireland. The lands were later returned to Mary, the widow Baltinglass, who later married Gerald Alymer. On her death in 1610 the Castle was transferred to the Chevers family through the marriage of Mary Travers's sister Catherine to John Chevers, and the property passed directly to his second son Henry Chevers, who married Catherine, daughter of Sir Richard Fitzwilliam. Henry and Catherine Chevers lived here with their four children (Walter, Thomas, Patrick, Margaret).

Upon the death of Henry in 1640, the castle and lands were passed to Walter Cheevers. Walter and family were given command to vacate Monkstown in 1653 by the Cromwellian Commissioners, and transplanted to Killyan, County Galway. In 1660, Walter Chevers was restored to his estate at Monkstown Castle, until his death in 1678.

Monkstown was later purchased by Bishop of Armagh Michael Boyle where his son Murragh, Viscount Blessington enlarged the castle making it one of the finest residences.

Until about 1800, Monkstown was a rural area of open countryside, dotted here and there with large houses owned by the merchants of Dublin. The Monkstown Church (Church of Ireland) had been built - but was smaller than the present church. Two rivers met in the area now called Pakenham Road. The river known as Micky Briens originated in Sallynoggin. A lake beside Monkstown Castle had one small island. The coastline was ragged and rocky, with a harbour stretching over 100 yards inland at the mouth of the aforementioned rivers, adjacent to the area now occupied by the West Pier. Dun Laoghaire (then called Dunleary, and later Kingstown) was then a small group of houses in the area of the Purty Kitchen, and the present area of Dún Laoghaire was an area of rocky outcrops and later, quarries.
Wednesday, November 18, 1807 was South Dublin's night of disasters. In an horrific storm, two sailing ships, the Rochdale and the Prince of Wales were blown on to the rocks, one at Seapoint and the other at Blackrock. About 400 lives in total were lost on that night, many of them washed up on the shore at Monkstown. The disaster was one of the factors which led to the building of Dun Laoghaire Harbour. Most of the victims were buried in Carrickbrennan Churchyard.

The building of Dun Laoghaire harbour gave an impetus to the area, and Montpelier Terrace was the first of many terraces built in the area. The coming of the railway in 1837 had a much greater impact. Firstly, it changed the topology of the coast, and secondly, it led to Monkstown becoming a commuter suburb of the city of Dublin. Most of the houses along Monkstown Road and the avenues north of that road were constructed over the next 30 years. The maps of 1870 show this phase completed, but the rest of Monkstown consists of mansions surrounded by extensive gardens. For the following 50 years there was little change. The post-war developments of Castle Park, Richmond, Windsor, etc. and the more recent developments of Brook Court, Monkstown Valley, and Carrickbrennan Lawn mean that there is little opportunity for further development.

The diaries of the Rev John Thomas Hynes(1799-1868), a Catholic bishop who retired to Monkstown in 1861-1868 provide a valuable insight into daily life in Monkstown in that period. Hynes lived at Bloomwood, Monkstown Avenue (later renamed as Carrickbrennan Road), and later moved to Uplands, The Hill, Monkstown. The Hynes Diaries recount such details as the coming of gas lighting, the postal and travel facilities, church affairs, and lots of local gossip. The Hynes diaries are now preserved in Melbourne, but the full text has been made available online at www.unisanet.unisa.edu.au/research/condon/Hynes/index.htm