The Nunnery Cottages are thought to stand near the site of a Medieval Priory founded in 1247 by Richard Clare, Earl of Gloucester. Records show this this was a very poor Order and in 1546 the Prioress, Margaret Loftus, surrendered to the King's Commissioners all its possessions and these were granted to Henry Lee.

The possible origins of the building as part of the Priory/Nunnery site cannot be entirely discounted, although it now seems certain that the main buildings of the Priory were located on the site of the twin-gabled building immediately to the north on the Desborough Road. It may be that The Nunnery Cottages are on the site of one of the outbuildings of The Priory complex and this is how they obtained their name.

The provision of barns and stables forming the west and north sides of the rear yard does suggest that the building was a farmhouse circa 1700, but there is also reason to believe that it might have been an Inn. This may account for the rather unusual layout of the barns; the cellar under the northern room, the mullioned windows facing the yard rather than the road and the very large parlour.

The Trust has sold one of the Cottages (no. 3 Desborough Road) for residential use but has retained ownership of the other Cottage (no 3A Desborough Road) as this was occupied by long-standing tenants.

The Bungalow was originally part of the Maltings belonging to Town Farm, which is situated to the south of the Nunnery Cottages. The end adjoining the Cottages were bricked off some time ago to make a small single-storey dwelling, with a low cellar beneath. This unit has been fully restored and sold and is now occupied. Putting this small residential unit back into use has enhanced the Nunnery Cottages themselves and given back to the community by creating new housing.

The Barns to the south of the Bungalow (the remainder of Town Farm Maltings) and the "L" shaped Barn to the rear of Nunnery Cottages are being restored by private individuals and it is hoped this will be done to a high standard to complete the restoration of this group. The Trust put in a tender for these barns but was unsuccessful.