Castlefield, Castlebank Road, Cupar

Castlefield is a 2-storey and attic, 3-bay L-plan Plain Tudor villa built in 1851. It features a columned portico and a 2-storey canted bay window. The principal elevation is finished in sandstone ashlar, while the other elevations are predominantly squared and snecked tooled sandstone. Architectural details include a base course, a broken cill course, chamfered window openings, hoodmoulds, and gabled dormerheads that break the eaves.

On the west (principal) elevation, there is an off-centre 4-panel timber entrance door with a plain rectangular 2-pane fanlight, flanked by a simple corniced portico supported by a pair of Doric columns. Above the entrance, there is a single light window. To the right, both floors have windows in a slightly advanced panel, with the upper window featuring a hoodmould. To the left, there is an advanced one-bay gabled section with a canted window at both the ground and first floors, and a small attic window with a hoodmould above.

The south elevation is symmetrical with a 3-bay gable made of coursed sandstone. The east elevation has an off-centre gabled dormerhead breaking the eaves. To the left, there is a later first-floor projecting entrance doorway set at right angles, with concrete steps leading to the ground. To the right, there is a single-storey and attic wing set at right angles, featuring a near-central piended dormer that breaks the eaves. To the left of this wing, there is a recessed entrance doorway to the house, and to the far right, a doorway with a relocated earlier triangular heraldic stone panel above.

The villa predominantly has 8-pane timber sash and case windows and is covered with graded grey slates. It has gable end stacks and a near-central ridge stack on the wing at the east.

Inside, the villa is little altered, featuring timber panel doors, a decorative cornice, and a dark grey marble fire surround in the sitting room.

The gatepiers and boundary wall to the southeast consist of a pair of square corniced and chamfered gatepiers with gabled caps. To the north, there is a high wall made of loosely squared and snecked tooled sandstone with semicircular coping. To the south, the wall was initially punctuated with garages and an entrance doorway to the garden; further south, there is a high wall of loosely squared and snecked sandstone with semicircular coping that continues at right angles into East Road.