1, High Street

No 1 High Street is a 16th-century framed structure. It features half-timbering with brick infilling on the ground floor and plaster infilling above, set on a stone plinth. The left side has a projecting two-storey gable-ended facade, with an oversailing first floor supported by rough wooden brackets and exposed timber joists. There is a square bay oriel window on the first floor, which has mullions and a moulded headpiece and frame, along with diamond-paned glazing. The under reveal and area above the window are plastered. On the right side, there is a square projecting bay with wooden mullioned windows extending up two storeys, topped by a gable end, also featuring diamond-paned glazing. A small plain boarded door is located to the right of the bay, with a small hood above it. The building has a continuous ridge tile roof and the side elevation displays exposed framing with brick infilling. A National Trust plaque is placed at the corner. Nos 1 to 4 (consecutive), No 6, The Castle Inn, and the gate to Chiddingstone Castle form a group.