20 Main Street, Rathfriland, Newry, Co Down, BT34 5PS

20 Main Street, Rathfriland, is a three-storey commercial building with attic space, dating from the early 19th century. It occupies the north side of Main Street and retains much original fabric on its upper floors, though its ground level and rear have been significantly altered.

The pitched roof is covered in natural slate with cement skews and a modern red brick chimney to the west gable. Three cast iron skylights sit on the rear pitch, and semicircular metal rainwater goods run around the building. The front elevation is lined cement rendered and painted. It features a two-stage moulded rendered eaves and alternating pairs of V-channelled stucco quoins, though these are missing at ground floor left. Marks in the render, the missing quoins and a lead flashing set in the render between ground and first floors indicate that an original timber shop front has been removed.

The current ground floor shop front consists of two large modern picture windows flanking a modern door with sidelights and transoms. At the extreme left is a former doorway with transom, now glazed as a window. Modern wall-mounted letters read "Stewart & James".

The first and second floors are identical in treatment. A central bay contains a 2/2 exposed box sliding sash window with horns, moulded stucco architrave and painted granite cill. The left and right bays each have larger tripartite windows comprising 2/2 sashes flanked by narrower 1/1 sashes, all with horns, architraves and matching cills. The heads of the second floor tripartite windows break the eaves mouldings, suggesting these windows have been enlarged at some point. A lower building abuts the left gable, with its exposed painted gable smooth rendered. A similar lower building abuts the right gable with a smooth rendered but unpainted exposed gable.

The rear elevation has been much altered and extended. A two-storey return with pitched roof to the right has been extended to the left filling the rest of the elevation, creating extensions of no architectural interest. A large rear yard serves the building.

Historical records show that buildings occupied this plot from at least 1776 (documented on the Meade Estate map). The 1834 Valuation book records two separate buildings here, each 25 feet high with frontages of 15 and 17 feet, both extending back 28 feet 6 inches. However, the circa 1862 Second Valuation describes two buildings with frontages of 16 feet 6 inches and 24 feet (both extending 28 feet 6 inches as before) and both 3.5 storeys high; the accompanying map shows a coach arch between them. It remains unclear the extent to which the earlier recorded buildings relate to the present structure. The buildings may have been raised in height, or alternatively rebuilt and made wider overall. No change in valuation after the Second Valuation suggests the present building represents a later refurbishment rather than a complete rebuild. The building's modern shop front, stripped ground floor and large rear extensions have detracted from its overall character, though the timber staircase and upper floor original fabric remain intact.