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 as their attorneys and witnesses.
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 estates at Gortigrenane Castle, near Carrigaline, and at Tracton Abbey, near Kinsale, both in County Cork. The main line failed on the death of Thomas Daunt VI in 1803, when the Stoughton family, Anglo-Irish landowners from county Kerry, inherited. They sold the estate in 1925-1926, after some 900 years of ownership in one family.
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