Castlebank, Castlebank Road, Cupar

Castlebank is a villa built around 1851, featuring two storeys and a basement with three bays in a castellated Tudor Gothic style. The principal elevation is constructed of coursed ashlar, while the other elevations are made of squared and snecked tooled sandstone. Notable architectural details include a base course, cill course, chamfered openings, and finials on the gables of the principal elevation.

The west elevation, which is the main facade, has a near-central single bay gabled section with a large porch that extends over the basement. This porch is corniced and features a blind quatrefoil balustrade with a central blank shield, flanked by tall circular angle pinnacles. The entrance is a pointed arch, with pointed arch side openings and a pierced quatrefoil balustrade. The single bay gables on either side have tripartite canted bay sections that are also castellated on the ground and first floors.

The north elevation includes a single bay gabled section on the left and an advanced gabled finialed blank section on the right. The south elevation has a blank, gabled finialed section to the left and a recessed gabled section to the right. The east elevation features an off-centre doorway that oversails the basement.

The villa predominantly has timber sash and case plate glass windows on the west elevation, while the east elevation mainly has 12-pane lying plane glazing in timber sash and case windows. The roof is covered with grey slates, and there are gable and ridge stacks on the north and south elevations. The timber door on the principal elevation has a pointed arch fanlight and sidelights.

Inside, there is a wide entrance hallway with a two-leaf timber and plate glass hall door, sidelights, and a wide full-width fanlight above. The interior features decorative cornices that have been filled in for a smooth finish, good quality woodwork, and a decorative iron banister on the staircase. Some original fire surrounds and fireplaces remain, although the basement has been altered to create a separate flat.

The property is also accompanied by gatepiers and boundary walls. The tall square corniced piers with gabled caps are located to the east, and a high rubble coped boundary wall runs north to south and east to west. To the west, there is a rubble gable-coped wall angled towards the driveway, which no longer has gatepiers.