Five Chimneys was originally a series of cottages, now incorporated into one much larger building with a fine cellar beneath and large garden that is often open in June as part of the NGS Yellow Boook national gardens scheme.
Like many houses in Winchelsea Five Chimneys does not reveal its secrets easily. The oldest part, unseen from the street, is the barrel vaulted cellar built around the time of the creation of New Winchelsea in 1290. Its just visible entrance is from Castle street and runs parallel to Mill Rd. Note how the entrance is precisely opposite the entrance to Salutation Cellars underneath what was the old Salutation Inn.
The current house largely hidden behind hung tiling and altered over time is a Wealden hall house built during the 15th century, with a single bay medieval open hall. The open hall was floored over in the 16th century and a massive chimney built from Caen stone on the north side difficult to see from Castle St or Mill Rd. A cross wing was added in the 17th century and later the western side was underbuilt in local Tilgate stone and tile hung on the southern side. The entrance and hall passage way are probably original to the Wealden house and has fine flagstones at its entrance. An oriel window was added on the first floor after the Great War. The gararges were built on the site of a Mission Hall where services were held regularly from 1905 unitl 1921.
The building suffered severe damage as a result of a bomb that fell during the Second World War into the adjacent Castle Street. The bomb destroyed the buildings opposite, killing one local resident, and blowing almost all the tiles off Five Chimeys.