While there may be reason to suggest that the town may occupy the site of an earlier settlement of the Donegans, Carrig Donegan, the origins of the present town are clearly and distinctly Norman, and closely connected with the settlement of the Barrys from the 13th century. Here they built their principal stronghold in North Cork.
Buttevant is located on the N20 road between Limerick and Cork and the R522 regional road. The Dublin–Cork railway line passes by the town, but the station, from which at the outbreak of World War I in 1914, newly raised battalions of the Royal Munster Fusiliers and the Royal Dublin Fusiliers who had completed their training at the local military barracks, set out for the Western Front.
Henry III of England, by grant of 26 September 1234, conceded a market at Buttevant to David Og de Barry to be held on Sundays, and a fair on the vigil and day of St. Luke the Evangelist (17 October and 18 October), and on six subsequent days. This was done to further the economic prosperity of the borough and connected with a widespread network of such markets and fairs which indicate "an extensive network of commercial traffic and an important part of the infrastructure of the growing agrarian and mercantile economy". The most important markets and all fairs were associated with the major boroughs and can be used as a gauge of their economic and social significance as also the 1301 quo warranto proceedings in Cork at which John de Barry "claimed the basic baronial jurisdiction of gallows, infangetheof, vetitia namia and fines for shedding blood (where 'Englishmen' were involved) in his manors of Buttevant, Castlelyons, Rathbarry and Lislee".
The town of Buttevant accumulated a series of such grants over several centuries. Fairs and markets were held at Buttevant for cattle sheep and pigs on 23 January, 30 April, 27 May, 27 August, and 21 November. Cattle and sheep fairs were held on 27 March, 14 October, 17 December. Pig markets were held on 11 July. Fairs falling on Saturdays were held on Mondays. Fridays were devoted to egg markets. Horse fairs were held on the Fourth Monday in October. Cahirmee Horse Fair, the only surviving fair, is held on 12 July.
The development of the settlement followed a pattern frequently repeated in the Norman colonies of North Cork and Limerick. The original nucleus of the town consisted of a keep situated on an elevation on the south side of the town. Opposite the keep, on a pre-Norman site, was built the parish church, dedicated to St. Brigit, sister of St. Colman of Cloyne. A mill, another characteristic element of Norman settlements, was located on the river, to the north of the keep. In addition, a hospice for lepers was established about a mile to the North East outside of the town wall. This basic structure was repeated in nearby Castletownroche, where it is still clearly to be seen, in Glanworth, Mallow, and in Kilmallock and Adare.
A further feature of Norman settlements in North Cork was their concomitant religious foundations. Early colonial sites, such as Buttevant and Castletownroche, saw the introduction of the more traditional monastic communities which were housed in foundations outside of the town walls. The Augustinian priories of Bridgetown (ante 1216) and Ballybeg (1229) being respectively founded by the Roches and the de Barry contiguous to the settlements of Castletownroche and Buttevant. With the rise of the new mendicant orders, essentially urban in character and mission, the Norman settlements saw the foundation of mendicant houses within the town walls as with the Franciscans in Buttevant (1251), and the Dominicans in Kilmallock (1291) and Glanworth (c. 1300).
The burgage of Buttevant developed to the north of the keep and eventually increased in size to about enclosed by walls for which Murage grants had been made by the crown in 1317. The native inhabitants were excluded from residence within the walled area and confined to a quarter of their own to the north west of the walled town.
A bridge, still extant, was built over the river Awbeg around 1250.
In 1317, the 11th. of Edward II of England, John fitz David de Barry requested and obtained from the exchequer a grant of £105 for the commonality and town of Buttevant for its walling. A further grant was made on 6 August 1375, the 49th. of Edward III, to the provost and commonality of the town together with the customs of its North Gate.
Buttevant also has many literary associations: Edmund Spencer, from his manor at Kilcolman, referred to it and the gentle Mullagh (the Awbeg River) in The Faerie Queen ; Anthony Trollope passed through in his novel Castle Richmond; James Joyce played a game of hurling there in his Portrait of an Artist as a Young Man; the revered Canon Sheehan of Doneraile mentions Buttevant in several of his novels, not least in Glenanaar in the setting of the fatal events of the Fair of Rathclare; and Elizabeth Bowen mentions it in her elegiacal family history Bowen's Court.
Clotilde Augusta Inez Mary Graves, otherwise Clotilde Graves (1863–1932), the daughter of Major W.H. Graves and Antoinette Dean of Harwich, was born at Buttevant castle on 3 June 1863. She was cousin of Alfred Perceval Graves, the father of the poet Robert Graves. Convent educated in Lourdes, she converted to Catholicism and embarked on a literary career. She was a successful London and New York playwright who enjoyed considerable literary acclaim in the first decades of the 20th century. In 1911, under the pseudonym of Richard Dehan, she published The Dop Doctor, which was made into a film in 1915 by Fred Paul. The film gave considerable offence in South Africa because if its harsh portrayal of English and Dutch characters. It was eventually banned under the Defence of the Realm Act. The story hinges around a drunken and disgraced doctor who eventually makes his way to South Africa where he redeems his honour at the siege of Mafeking. Albert Gérard, in his European-language writing in Sub Saharan Africa ISBN 963-05-3832-6, regards the book's description of the siege of Mafeking "as a heroic justification of British Imperial strategy and the vindication of a belief in the righteousness and superiority of the British cause. The Dop Doctor contains pro-Jingo arguments of the type which offers the stereotypical portrait of the Boer as backward and despicably primitive, and the black man as a shadow figure behind the civilizing foreground, an appendage of an argument over what to do with his labour". Between Two Thieves and One Braver Thing followed in 1914.
In the Gaelic tongue, An tAthar Peadair O Laoghaire makes unflattering mention of garrisoned Buttevant in Mo Sceal Fein; while the great Irish antiquarian of the 18th century, An tAthar Séamus O Conaire, one time member of the Royal Society of Antiquities, rests westward facing outside of the Friary portal.