Headmaster's House, 40 Milton Road, Kirkcaldy

The Headmaster's House, located at 40 Milton Road in Kirkcaldy, was designed by Sir Robert Rowand Anderson in 1876. This two-storey, two-bay Gothic-style building is constructed from bull-faced squared rubble, featuring ashlar long and short quoins and dressings. Notable architectural elements include hoodmoulds with label-stops, stop-chamfered and chamfered reveals, as well as stone transoms and mullions.

On the north elevation, there is a broad advanced gable to the left of center, which includes a canted quadripartite transomed window at ground level. Above this, a trefoil-headed bipartite window is set in the gablehead, adorned with a floral motif in the tympanum and a glazed quatrefoil at the apex, all beneath a pointed-arch hoodmould. To the right, there is a broad hoodmoulded doorway that abuts the return of the advanced gable, featuring a round-headed door with voussoirs, a plate tracery-effect window with a blind arch-head quatrefoil, a boarded timber door, and an adjacent narrow light. Above, a pointed-arch bipartite stair window is located in the gablehead.

The south elevation features M-gables, each with a gablehead stack, and a small window at the center. To the right, there is a single-storey piend-roofed wing that has a small window to the left and a window (converted from a coal shute) to the right, along with a door on the return to the left.

On the east elevation, there is a window to the left at ground level and a smaller window at the center. Above, a dormerheaded bipartite window breaks the eaves to the left, while a tall wallhead stack is positioned to the right.

The west elevation has a window to the right of center at ground level and a smaller window at the center, with a dormerheaded window breaking the eaves to the right.

The windows throughout the building feature small-pane upper sashes over 4-pane and plate glass lower sections, all set in timber sash and case frames. The south elevation includes a bipartite window with small pane glazing over two-part timber casement windows, and the stair window has leaded small-pane glazing. The roof is covered with grey slates, and the building has coped ashlar stacks with cans, some of which are polygonal, along with stepped, ashlar-coped skews and decorative cast-iron downpipes with rainwater hoppers.

Inside, the ground floor sitting room boasts a decorative cornice, while the doorways feature stop-chamfered architraves. The interior also includes a timber fireplace and a staircase with plain cast-iron balusters and a timber handrail.

The property is complemented by saddleback-coped ashlar gatepiers and low boundary walls to the north, along with coped rubble boundary walls to the south, east, and west.