48-50 High Street, Kirkcaldy

44-46 High Street in Kirkcaldy is a three-storey and attic, eight-bay tenement building dating from around 1820, featuring shops on the ground floor. The structure is constructed of polished ashlar, harl with ashlar quoins, and rubble, with a cornice at the ground floor and an eaves course.

On the north elevation facing High Street, there is a corniced doorway with a timber door and a small-pane fanlight located in the bay to the left of the center. To the left, there is a public house with a door and window to the right and a tripartite window to the left, all set within a timber panelled facade beneath a traditionally lettered fascia. To the right of the center is a post office with a traditional shop front, featuring an in-canted door to the left and a display window to the right. A modern shop is located further to the right, along with another door at the outer right. The upper floors have regular fenestration.

The south elevation consists of six bays, with the left of center being rubble. The ground floor is obscured by a boundary wall. There is a four-storey round stair tower with a window on each floor, breaking the eaves in the penultimate bay to the left. Windows are present on the first and second floors in the flanking bays and to the right of center, with a flat-roofed extension projecting beyond to the right below two second-floor windows. Piended and slated dormer windows are positioned over bays one, three, four, and six.

The east elevation, facing Charlotte Street, features a blank gable end with a broad gablehead stack, and a flat-roofed extension to the outer left that is not included in this listing. The building has 12-pane and plate glass glazing patterns in timber sash and case windows, as well as fixed display windows for the shops. The roof is covered with grey slates, and there are coped ashlar stacks with cans and ashlar-coped skews.