There are records of the de Olepenne family (who must have named themselves after the place) settled at Owlpen by 1174. They were local landowners, benefactors to abbeys and hospitals, and henchmen to their feudal overlords, the Berkeleys of Berkeley Castle, whose wills and charters they regularly attest.

In 1464 the male line failed after twelve generations of Olpennes and the manor and lands passed to the Daunt family on the marriage of Margery de Olepenne to John Daunt of Wotton-under-Edge. The Daunts were clothiers who had been settled in Wotton since the 14th century. They later acquired land in Munster, Ireland, where by 1595 they had their principal estate at Gortigrenane Castle, near Carrigaline in County Cork. In the nineteenth century, the fortunes of the manor suffered after the Stoughton family inherited in 1815. They built a new mansion c. 1848, called Owlpen House, a mile to the east of the original settlement, to the Italianate designs of Samuel Sanders Teulon.  It was demolished in 1955-6, though outbuildings including the gas works, lodges and stable block remain. Today Owlpen is widely known as the site of one of the finest early manor houses in England. The manor house as it stands, of medieval origins, was largely built and rebuilt by Daunt family, between 1464 and 1616. Since then it has hardly been touched except for small improvements early in the eighteenth century, when the east wing of the house, and the gardens, church and Grist Mill, were reordered by Thomas Daunt IV 1719-1726.

By the end of the 19th century the old manor had become celebrated as an icon of the Arts and Crafts movement. It lay in its remote valley as a Sleeping Beauty which had not been inhabited for nearly a hundred years, a picturesque ruin much decayed, overrun with ivy, and dwarfed by enormous yews. There was concern for its survival and the Society for the Protection of Ancient Buildings recommended that it should be vested in the National Trust, which however had no funds available for its repair.

Finally, in 1924-25, the Owlpen estate was sold, by auction, for the first time in nearly a thousand years. The future of the manor house was assured when it was acquired and sensitively repaired by Norman Jewson, a distinguished Cotswold Arts and Crafts architect who had worked with Ernest Gimson and the brothers Sidney and Ernest Barnsley (who was his father-in-law) in Sapperton. He has described how he saved the ancient house from ruin in 1925�? in his classic memoir, By Chance I did Rove (1951, twice reprinted).

Today Owlpen Manor is the home of Sir Nicholas and Lady (Karin) Mander, who since 1974 have carefully repaired the manor house and outbuildings, with the cottages and estate, giving them a new and integrated life for the conditions of today.  The Mander family gave Wightwick Manor to the National Trust in 1937. Sir Nicholas Mander succeeded as the fourth Mander baronet of The Mount in 2006.