The Retreat has been an important building in the history of the Town. It is a timber-framed house of great architectural interest.
The most likely date of the building is 15th century, considerable alterations being made at a later date.
The medieval cellar will its hollow-chamfered ribs belonged to an earlier building. It was probably the shop of a wholesale wine merchant who chose to store his wine in the cellar.
Between The Retreat and the Strand Gate is Tower Cottage. This house was built early in the 17th century. The Duke of Wellington stayed here when he reviewed his troops during the Napoleonic Wars. Dame Ellen Terry, probably the most famous actress of the 19th century, made Tower Cottage her home when she lived in Winchelsea from 1896 until 1906 before she moved to Smallhythe. Tourists came to Winchelsea to catch a glimpse of her. Famous as she was she still found time to attend and give advice on the town’s amateur theatricals.