10, Middle Street, Chepstow is situated on an island site between Hawker's Hill and Middle Street in the centre of Chepstow, the lower end one of five. It is probably an encroachment on to a former medieval market area. It is a stone-built early-18th century, 2 ? storey structure with end-chimney, central entry and first-floor lateral fireplace. It is situated down-the-sloping ground. Its upper end part has C16th joists with a mullion window lintel to the early 19th century tri-partite window.

The south-east, Middle Street facade is of 19th century appearance, having a central doorway with flat hood, a shop front with bracketed cornice to right and a tri-partite window to left. Its first-floor fenestration consists of asymmetric 20th century casements, a 2-light to left and a 3-light to right. The lower north-east end-gable has two later doorways and a second-floor widow with small panes. The rear north-west elevation retains a low lateral chimney stack, but has been much altered by the C20th insertion of later windows and a doorway at mezzanine or Street level.

The interior has had partitions and some flooring removed, but must have been divided by a ceiling-beam and partition to right of the central south-east elevation doorway, in order to support existing longitudinal ceiling-beams. These beams have 'ogee' stops to medium chamfers and plain joists. There is a late18th century stair opposite the doorway, probably once with a partitioned passage to it. The line of it is shown by the spacing of the earlier joists, which stop at a point where a partition once existed. By the 19thcentury the upper-end part was probably sub-divided into a large kitchen to rear with iron range, bread-oven, window and a small parlour to front with tri-partite window. The lower-end part has a gable-end fireplace and was used as a shop. The fireplace has a chamfered timber lintel, with cut back stone work on each corner, possibly for ease of access through the later end doorways.

The north-west wall retains two splayed windows (one blocked) flanking a blocked splayed opening at mezzanine level damaged by a 20th century doorway insertion. The mezzanine window once lit the stair in its present position.

At first-floor there were formerly similar sized windows, one opening to the rear is in-situ, others are blocked. The first-floor has a lateral fireplace in the north-west wall and three (one removed) transverse ceiling-beams with straight-cut stops to narrow chamfers and plain joists. The original rooms may have been divided under the beams, one of two bays at the upper end with the lateral fireplace. The other lower-end room has a later brick gable-end fireplace, and may have been originally unheated.
The attic is lit from the lower gable-end by a square small-paned window and heated by an original gable-end fireplace with chamfered timber lintel.

There are 3 collar roof-trusses seated on timber wall pads, which support two pairs of trenched side-purlins, a diagonally set ridge-piece and flat section rafters. The present roof covering is of concrete tiles.

The closely set joists in the upper part of this building were formerly part of a 16th century timber-framed building with a jetty to its south-east side. The jetty was supported by the existing joists with an inset timber-framed wall, retaining a lintel for a 3-light mullion window. The wall was under-built by the present stone wall, when it was re-built or extended in stone to 2? storeys, largely as existing today, with alterations to fenestration in the 19th and 20th centuries. The early 18th century ground-floor layout once consisted of a kitchen with end-chimney at the lower end, divided by a central passage stair with parlour at the upper-end.
The two-bay, first-floor lateral chimney room suggests it had a typical, reception/great chamber for a town building of that early 18th century period.

Recorded as part of the emergency buildings programme, Geoff Ward & Louise Barker, 24/11/2005.