The Dripsey estate originally belonged to the MacCarthys. The fifteenth-century tower house at Carrignamuck was commissioned by Cormac McTeige MacCarthy, ninth Lord of Muskerry, and served as a residence for the tanist - the heir designated to succeed to nearby Blarney Castle. After a turbulent passage through the Tudor and Cromwellian wars, the estate passed to the Anglo-Norman Colthurst family. The Colthursts decided not to live in the medieval tower. They built a far more comfortable Georgian country house alongside it. Samuel Lewis's 1837 Topographical Dictionary of Ireland described the property as "Dripsey House, the residence of J.H. Colthurst, Esq." The Ordnance Survey name book of around the same period called the house and demesne a gentleman's seat. The old tower stood beside it as a kind of stone backdrop, a memory the new house could refer to without inhabiting.

Architecturally the National Inventory of Architectural Heritage describes Dripsey Castle as a detached, seven-bay, three-storey country house with a central pedimented three-bay breakfront. A canted bay window projects from the southern side. A three-bay, two-storey, flat-roofed wing extends to the north with a more recent extension beyond. Surviving historic features include the timber sash windows, a Venetian window in the breakfront - three lights, the central one arched - and a timber-panelled front door reached by a flight of stone steps. A separate farm complex of single- and double-storey buildings sits to the west, its own central pedimented breakfront mirroring the design of the main house. The entrance gate is marked by a single-storey gate lodge and a small circular ornamental tower - a folly built with a crenellated parapet and rubble stone walls.

The Colthursts intermarried with other Cork Protestant families through the nineteenth century. John Colthurst of Dripsey Castle married Jane Bowen of Oak Grove, Carrigadrohid. Their granddaughter Peggy married Alfred Greer, who purchased part of the Dripsey estate when it was advertised for sale in October 1851. Their daughter Georgina succeeded to Dripsey Castle, and in 1878 she married Robert Walter Travers Bowen. Four years later, in 1882, Bowen took the additional surname Colthurst - a common manoeuvre in landed Irish families to keep the name attached to the house, which was held to be the inheritable thing. He became Robert Walter Travers Bowen-Colthurst. His son, born in the same household, would carry the same hyphenated surname. The boy's name was John Bowen-Colthurst. And that name would change everything for the family at Dripsey.

During the Easter Rising in Dublin in April 1916, Captain John Bowen-Colthurst of the Royal Irish Rifles ordered the shooting of three civilians under arrest at Portobello Barracks. The most prominent was Francis Sheehy-Skeffington, a pacifist, suffragist, and journalist who had been arrested while trying to organise a citizens' patrol to prevent looting. He had committed no offence. He was shot against a wall in the barracks yard along with two other men. Bowen-Colthurst was court-martialled. The court found him guilty of murder but insane at the time of the offence, a verdict that allowed him to be committed to Broadmoor rather than imprisoned or executed. He was released in 1921, emigrated to Canada, and lived until 1965. The verdict did not satisfy his own neighbours in County Cork. The Bowen-Colthurst family was boycotted in the parish and eventually left Dripsey Castle. A killing in a Dublin barracks had emptied a Cork country house.

The O'Shaughnessy family - already owners of the nearby Dripsey Woollen Mills - bought the castle in 1922. The Irish Tourist Association survey of 1944 listed Dripsey Castle as the principal residence in the parish. The drawing room held a carved marble mantelpiece. The breakfast room contained a bookcase said to be made from timber salvaged from Carrigadrohid Castle, an older fortification a few kilometres upriver. The house was sold again in 2015 for €2 million, the buyer described in the press only as "an overseas buyer." It remains a private residence today and is not open to the public, though the gardens are sometimes used for local events. The medieval tower next door is also closed to visitors. The two buildings sit side by side on the river, ageing at different rates, holding the memory of MacCarthys and Colthursts and one terrible week in 1916.