37-39 Kirk Wynd, Kirkcaldy

This is an 18th-century house, with an addition built in 1901 by Robert Little, originally a home, now converted into legal offices. The main part of the building is two storeys and an attic, with three bays, constructed using harled (roughcast) walls accented with stone margins and quoin strips, while the 1901 wing is of ashlar stone. An eaves course runs along the top of the walls. The front (east) elevation features an architraved doorway, a deep-set timber door, a canted window with a blocking course, and timber sash and case windows. Stone mullions are also present.

The front elevation has a deep-set timber door in the centre, a window to the right, and a canted quadripartite window to the left, the latter featuring a delicate wrought-iron parapet. The first-floor windows are regularly spaced. A slightly recessed, single-storey extension with a panelled timber door and plate glass fanlight sits to the left, alongside a window to the right. The rear (south) elevation has a window at first-floor level and in the gablehead. The western elevation includes a flat-roofed extension, originally a garage or gig house, a stair window centrally, and windows in the outer bays at first-floor level, along with four modern rooflights.

The windows generally feature a 12-pane glazing pattern, with smaller panes over plate glass in the lower sashes of the canted window. Grey slates cover the roof. The gableheads have coped ashlar stacks with decorative cans and ashlar-coped skews. Decorative wrought-iron brattishing is present above the canted window and at the eaves on both the front and west elevations.

The interior retains original and late 19th-century decorative fixtures. Decorative cornicing and dado rails are present. A vestibule features a screen door (with flanking lights blocked) and a decorative astragalled fanlight. A curved staircase has decorative cast-iron balusters and a timber handrail. A ground floor office on the south side contains a carved fireplace and overmantel, panelled soffits, and a dentilled cornice to an architraved cupboard opening. The attic rooms have cast-iron fireplaces, including a round-headed fireplace with a cast-iron grate and a decorative Victorian fireplace with tiled cheeks. The 1901 extension has etched glass in the screen door and timber fireplaces in the angles of two rooms in the north wing, with overmantels of shelves and cupboards, and Art Nouveau style beaten copper lintels.

The property is enclosed by low saddleback-coped boundary walls and a semi-circular-coped rubble wall, with a window and a moulded ashlar arched pedestrian gateway to the Hunter Street elevation.