Former House of Guisborough Grammar School with attached cottage and outbuilding

The building is the former House of Guisborough Grammar School, which includes an attached cottage and outbuilding. It dates from the 17th and 18th centuries, with some later additions. The structure is made of rubble with a stone slate roof and stands two storeys high, featuring a rear outshut. There are four first floor windows in total. The central entrance has a 20th-century four-panel door set in an ashlar stone surround with straight tooling, positioned on a plinth. To the right, there is a bay with four-pane sash windows, and to the left, an additional bay of four-pane sash windows. The building has end stacks.

The cottage on the right has a part-glazed 20th-century door in a plain stone surround, with a three-light double-chamfered mullioned window to the left on the ground floor, and a four-pane sash window above. It features a shaped kneeler and ashlar coping on the right. The added outbuilding to the left has a board door in an ashlar stone surround with interrupted jambs, and a four-pane sash window above, along with a shaped kneeler and ashlar coping on the left.