Ring and bailey or motte and bailey seen as earthworks. The castle mound is scarped out of the natural slope of the spur to enclose a sub-oval area about 80 metres north to south by about 60 metres east to west. Only in the north arc is an inner counter-scarp bank 0.8 metres in height. There is a moat surrounding the castle. The bailey lies to the north of the castle and is badly mutilated.
Between Aylesbury and Winslow, and on W. side of the village of Whitechurch, is a spot called Market Hill, where was formerly the Castle of Bolebec, and close to Weir Lane, where was the entrance to it, was a drawbridge, which was remaining at the end of the last century. Although no vestiges of the walls or of any buildings above ground remain, there is a high bank of earth, with four or five tumuli and traces of a moat, being part of the site of this castle, and which are objects of curiosity, being visible from a distance. This is all that is left of the ancient seat of the Bolebecs, and of their successors, the De Veres, in this part of the country, the site now being the property of Mr. H. Chapman.
Hugh de Bolebec, a follower and kinsman of Duke William, received in reward of his services and zeal large estates in this and other counties; his son Hugh founded the castle about the time that his brother Walter founded Woburn Abbey in Beds, and who succeeded Hugh at Bolebec. His daughter and heiress, Isabel, married Robert de Vere, third Earl of Oxford (see HEDINGHAM, ESSEX), and this estate thereafter followed the fortunes of that family. Edward, seventeenth Earl of Oxford, died seised of the honour of Whitechurch in 1548. In the reign of Elizabeth the manor passed to the family of Waterhouse, and afterwards to many other persons. In 1857 it was purchased by J. Guy, of Clearsby, and it continues in his family. After remaining in a ruinous state for a long period, Bolebec Castle was finally destroyed at the end of the Civil Wars of the seventeenth century. (Castles Of England, Sir James D. Mackenzie, 1896)