By 1174, the de Olepenne family had lived at Owlpen for two generations. They were loyal subjects to their overlords, the Berkeleys of Berkeley Castle.

Margery de Olepenne married Thomas Daunt in c. 1462 and their son Christopher built the central hall and east wing of the existing manor house. Further alterations were made in 16th century but by 1706, the house fell into disrepair.

In 1720, Thomas Daunt IV inherited Owlpen and made changes to the house and remodelled the gardens. Thomas solved the problem of the steep hillside, by creating a terraced garden. The accounts of the period are in Gloucestershire Archives and list the ‘Acton stone for stepps’, the use of box (probably from Box and Boxell, both nearby), peach, nectarine and apricot trees, turf, gravel and ‘greens’.  Thomas VII died in 1803 and the house again was deserted.

In 1924, after years of neglect, Norman Jewson, a leading proponent of the Arts and Crafts Movement, bought Owlpen. Jewson wrote: ‘The terraced gardens with a yew parlour and groups of great clipped yews remained just as they were in the time of Queen Anne, a gardener being kept to look after them…In spite of the dilapidation of the house, which was so far advanced that one of the main roof trusses had given way, the great stone bay window had become almost detached from the wall and huge roots of ivy had grown right across some of the floors, it seemed to me that such an exceptionally beautiful and interesting old house might still be saved.’

Jewson restored the house and garden but after only two years, he sold it to Barbara Crohan, a cousin of Clive Bell. Crohan held numerous house-parties at Owlpen, with guests including Geoffrey Jellicoe, Vita Sackville-West and Gertrude Jekyll. Jekyll wrote: ‘Among little hillside gardens treated in a formal fashion, none is more delightful than that of Owlpen Manor…with what modesty the house nestles against the hillside and seeks to hide itself amidst regiments of yews.’

The estate is now owned by Sir Nicholas and Lady Mander.