19 And 21, Winchester Street

19 and 21 Winchester Street are two buildings located on the north side of the street, with origins dating back to around 1500. They were rebuilt in the 17th century and again around 1800. Positioned at a corner site with Rollestone Street, the buildings are two storeys tall with an attic and are faced with stucco. The gable end features an old tile roof with paired thin out brackets supporting a flat eaves cornice. There are three casement dormers and five windows on the first floor, although the second from the left is blocked. The tall sashes on the first floor have flush architrave framing and intact glazing bars.

The ground floor of No 19 has a modern bowed shop window, while No 21 features a central six-panel double door with a rectangular fanlight that has an oval and curved diamond glazing pattern. Flanking the door are engaged fluted Doric columns, with a reeded frieze and a central panel decorated with acanthus leaves, a key pattern soffit, and a moulded dentil cornice. To the left of the door is a tripartite sash window with glazing bars, which has a mask keystone above it. There is also a small glazed secondary door to the right in a plain arched opening, with reeded springers and a mark keystone overhead.

The front facing Rollestone Street has a similar design, with a gable end to the left and a cornice that extends across. It features two blind roundels in the gable and one dormer. The first floor originally had five windows, three of which are now blocked, while the ground floor has four windows, two of which are blocked on the left side, and a door to the right with a plain fanlight in an architrave surround, complemented by roundel corner blocks and a small cornice. All ground floor windows showcase attractive mask keystones.

Inside, the first floor to attic features a 17th-century oak staircase with a solid heavy string, turned moulded balusters, a chamfered rail, and square newels topped with ball finials. The ground floor displays exposed ceiling beams and joists. The Winchester Street range retains elements of a 15th-century roof or circa 1500, with trusses, a chamfered raised centre collar, and remnants of former curved braces. The Rollestone Street range has a 17th-century three-bay roof structure with two plain collar principals and housed purlins.

Nos 17 to 21 Winchester Street form a group.