No 5 (Incorporating No 2 Church Street)

No 5, incorporating No 2 Church Street, is a house that now serves as solicitors' offices. It dates from the 18th century and was re-roofed in the early 20th century. The building is constructed from local stone rubble with ashlar dressings and features a flat roof with a wide eaves overhang supported by wooden brackets. There is a late 20th-century wrought iron openwork balustrade on the east and south sides.

The south facade facing Church Street has three storeys and five bays, with the first two bays possibly being a later extension. It includes a cill course and rusticated quoins on the earlier section. The windows are generally 4-pane sash windows in plain openings, with stone lintels over the first two bays and architraved surrounds on the lower levels of bays three and five. The second floor has plain openings, while bay four features a 12-pane sash window only on the second floor. Bay five has three deep architraved plain windows on the ground floor, and there is a doorway set in a deep recess in bay two.

The east facade facing the Market Place has one bay with a wide three-light small-pane window at the ground floor, beneath a fascia. Above this is a double sash window in an architraved surround, followed by a plain opening with a 12-pane sash window on the second floor. The interior has not been seen. Historical photographs from the early 20th century show that the flat roof existed at that time, indicating that several flat roofs were being constructed in Wincanton around 1900 to 1910. This building is primarily included for its group value.