299-305 High Street, Kirkcaldy

299-305 High Street in Kirkcaldy is a three-storey tenement building with a wallhead attic, likely designed by A MacMaster around 1900. The exterior is constructed of ashlar stone featuring raised quoin strips. It has a mutuled cavetto cornice above the ground and second floors, with raised and tabbed margins on the first and second floors. The attic windows are segmentally pedimented and have stone mullions.

On the south elevation facing High Street, there are three shops at ground level beneath a common cornice, which includes a traditional fascia with flanking pendant finials and carved bosses. Delicate Ionic pilasters frame a panelled timber door with a small-paned oval fanlight located off-centre to the right. One shop features an in-canted centre door with flanking display windows to the right of centre, while another shop to the left of centre has a door on the left and a display window on the right, all beneath a deep fanlight. There is a pilaster beyond to the left and a further shop on the outer left. The first and second floors contain windows in the second and third bays, as well as bipartite windows in the outer bays. The attic features windows to the right and left of centre, flanked by a scooped wallhead with pedimented windows in the outer bays, and a further scooped wallhead above all windowheads that breaks the eaves. A chimney gablet with a hoodmoulded and keystoned round-headed niche on corbelled brackets is located over the centre bays.

The glazing patterns include 8- and 12-pane designs in the bays to the left of centre on the first floor and attic, with plate glass glazing elsewhere. All windows are timber sash and case, except for the bays to the right of centre in the attic, which have modern pivot windows. The ground level features fixed display windows. The roof is covered with grey slates, and there are cavetto-coped ashlar stacks with a full complement of cans and ashlar coped skews. Decorative cast-iron downpipes are present on the southwest side.

Inside, the shop at No 305 features egg and dart cornicing.