County Buildings (West Section) St Catherine's Street, Cupar

The County Buildings comprise a group of buildings of varying dates, forming a neoclassical terrace along the south side of St Catherine's Street in Cupar. The original section was designed by Robert Hutchison and built between 1815 and 1817, likely following a plan by James Gillespie Graham from 1810. A nine-bay addition was added in 1924-25 by Thoms and Wilkie, based on plans dated 1907, creating a unified appearance.

The central council chamber block is symmetrical, two storeys high with a basement, and nine bays wide. It features channelled masonry on the ground floor. A prominent doorway is formed by twin engaged Roman-Doric columns, with a Diocletian window above. Roman-Doric pilasters support a balcony. The outer bays are slightly advanced, incorporating round-arched windows on the ground floor. A projecting cornice and balustraded blocking course top the building.

To the left is a former courtroom block, also two storeys and basement, spanning five bays. This section has a plain rendered façade, with a single door in the outer-right bay and a cill course running along the level of the upper windows. Interior alterations were carried out by William Burn in 1836, including remodelling the first-floor courtroom.

The 1925 addition to the far left is three storeys and basement, with nine bays, its outer bays slightly advanced and featuring round-arched windows on the ground floor. Above these are tripartite windows, echoing the style of the council chamber block.

The buildings have mainly plate glass glazing set in timber sash and case windows throughout. The roofs are covered in grey slates, and there are coped ashlar stacks. Rainwater goods are of cast iron.

Internally, the county chambers and original courtroom on the first floor remain largely intact. The main council chamber has bowed ends, featuring fluted Doric pilasters rising to ceiling height and a moulded cornice. A basket-arched minstrel's gallery with a balcony sits above the entrance double doors, flanked by fireplaces. Curved timber double doors provide access to a reception chamber to the west and a former library to the east. The 1836 courtroom by William Burn includes a segmentally-arched plasterwork ceiling with central roundels and ribs, culminating over full-height Roman-Doric pilasters. The basement, which previously housed cells, has corbelled vaulted ceilings, stone fireplaces, and studded timber doors. An engraved panel above one fireplace quotes a line from Hamlet: "There is nothing either good or bad, but thinking makes it so. To me it is a prison." Other interior features include a boarded timber open-well staircase with decorative timber newels.

Later additions, including a four-storey office block to the rear designed by John Needham (1947, built 1950-55) and a circa 1920 single-storey brick addition to the east, are not considered to be of special architectural or historic interest and are excluded from the listing.