Pitlessie House, Cupar Road, Pitlessie

The building is an early 19th century, 2-storey and attic house with a single-bay addition to the west from the mid 19th century and a later canted window on the east gable, designed by Gillespie and Scott in 1910. It features droved ashlar with ashlar dressings and rusticated quoins.

On the south elevation, there is a central panelled door with a fanlight and sidelights, topped by an entablature supported by two pairs of painted Tuscan columns. Above this, on the first floor, is a tripartite window, with single windows in the outer bays and in the single bay addition. Most windows are 4-pane sashes. The building has an eaves course, cornice, and blocking course, along with three modern flat-roofed dormers. The roof has straight skews with scrolled skewputts, end stacks, and is covered with slate.

On the north wall, there is a raised central attic stair window with a piended roof. To the north, there is an asymmetrical single and 2-storey L-plan former maltings with lofts, constructed of limewashed rubble with margins. Some segmental-headed carriageways are blocked, with oculi inserted at upper levels and two swept-roofed loft openings, one featuring a forestair. The roof of the maltings is made of pantiles and varies in levels.