275-277 High Street, Kirkcaldy

275-277 High Street in Kirkcaldy is an early 19th-century tenement building that has undergone some alterations in the 20th century. It stands three stories high with an attic and features six bays, with shops located on the ground floor. The exterior is finished with ashlar, harl, and dry-dash, complemented by stone cills and quoins. The ground floor has a bracketed cornice and an eaves cornice, both adorned with mutules.

On the south elevation facing High Street, the ground floor includes a traditional shop positioned to the left of center, featuring an in-canted part-glazed door at the center and display windows on either side below a fascia. There is an ashlar pier at the center with decorative fluted brackets, and a modern shop is located to the right. The first and second floors each have six windows, while the attic is pedimented with two windows and a broad gablehead stack that breaks the eaves at the center. Piended timber dormer windows are present over the outer bays.

The north elevation has much of its detail obscured, but a central attic gablet similar to the south elevation is visible, along with a slightly lower part-crowstepped building to the north. The windows are timber sash and case with a 12-pane glazing pattern, and the shops feature fixed plate glass glazing. The roof is covered with grey slates, and there are ashlar coped skews and cavetto coped ashlar stacks, some fitted with cans. Additionally, there are cast-iron downpipes and a decorative rainwater hopper on the southeast side.