287-295 High Street, Kirkcaldy

287-295 High Street in Kirkcaldy is an early 20th-century, four-storey tenement with an attic and five bays, featuring classical detailing. The building has a prominent central section with Ionic columns and shops on the ground floor. It is constructed of polished ashlar stone and includes decorative elements such as cornices on the ground and first floors, a cill course on the second floor, and an eaves cornice with a blocking course above the central bay. The entrance features a round-headed pend with voussoirs and stone mullions.

The south elevation facing High Street is symmetrical above the ground floor. The central entrance has a broad, deep-set panelled door with a semicircular fanlight above. Flanking the entrance are shops with in-canted centre doors. The shop on the outer right has been altered in 1996, featuring a centre door and display windows, with a projecting canted window above. The first floor has three windows in the slightly advanced central bay, bipartite windows in the flanking bays, and canted windows in the outer bays. A hexagonal clock on a bracket is located immediately to the left of the central bay. The second and third floors of the central bay are adorned with four fluted Ionic pilasters and an entablature with square dies, while the flanking bays mirror the first floor, with the outer bays featuring gables and attic windows.

The north elevation consists of seven bays above ground. It has flat-roofed extensions at the ground level and a timber bridge leading to the first floor, which includes a central door and windows in the flanking bays. The upper floors have regular fenestration, and there is a broad wallhead stack at the centre. A small, finialled ogee is present where the platform roof meets the pitched roof.

The building mainly features a glazing pattern of six-pane upper windows over two-pane lower windows in timber sash and case frames, although some modern windows are present on the first floor's outer left and right, and the third floor's outer right. The roof is covered with grey slates, and there are cavetto-coped ashlar ridge stacks and flat-coped wallhead stacks, all fitted with cans. The skews are ashlar-coped with flat skewputts, and terracotta ridge tiles are used. Decorative cast-iron downpipes with rainwater hoppers are also present.

The boundary walls at the rear are made of coped rubble.