Owlpen derives its name, it is thought, from the Saxon thegn, Olla, who first set up his pen, or enclosure, by the springs that rise under the foundations of the manor, about the 9th century.
There are records of the de Olepenne family 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 approximately 900 years of ownership in one family.
Owlpen Manor
Owlpen Manor is a Grade I listed manor house and the home of Sir Nicholas and Lady Karin Mander. The Tudor manor house and early 17th-century terraced gardens have been open to the public since 1966. Listed buildings on the estate include the Grist Mill and Court House, today included among cottages available as holiday accommodation. A medieval cider barn is used as a restaurant and for weddings.
Owlpen House
The Stoughton family 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 1955–1956 for the value of its building materials, though outbuildings including the gas works, lodges and stable block remain.
Owlpen Church
The Church of the Holy Cross stands above the manor house. Of medieval origins, the nave was rebuilt by the architect Samuel Manning in 1828 and the chancel added with restoration by James Piers St Aubyn in 1876. The result includes a number of interior mosaics, with opus sectile tiles designed by Charles Hardgrave and made by James Powell and Sons of the Whitefriars Glassworks; encaustic floor tiles by William Godwin & Son of Lugwardine; and stained glass windows, by Powells and Heaton, Butler and Bayne. A baptistery with further mosaics and Cosmatesque pavement was added in 1912–1913, when the old Norman font was installed. It has been described as ‘the most elaborate Victorian-Edwardian interior in the Cotswolds’. The church has been used as a filming location, including in 2008 for the BBC's four-part drama series, Tess of the d'Urbervilles. The benefice was from medieval times a chapelry of the rectory of the nearby parish of Newington Bagpath, but has been united with Uley since the late 19th century, since when the united benefice has been referred to as "Uley-cum-Owlpen".