In the 13th century, old Winchelsea was one of England's most prosperous ports, particularly involved in the wine trade from Gascony but was lost to the sea.

The returning route went through the Landgate or Pipewell Gate, down Ferry Hill and into the port area.

It is thought to be located behind the Fish Market and re-used parts of stone walls from earlier store houses in the Quay area.

A substantial farmhouse was built using the remains of these stone walls in 1425,[a] probably by the church to farm the land in front of the house as the port declined and the sea retreated.

[3] There is a collection of written correspondence relating to the workhouse in the Sussex Records Society archives dating from the early 19th century.

An example is give below: "PAR 511/35/1/21 1 Sep 1823 Letter from William Watson, Rye to the overseers of Winchelsea John West (the bearer hereof) having informed me that he has made application to be appointed master of the poorhouse at Winchelsea and that it is necessary for him to produce testimonials of his good conduct, I beg to say that I believe him to be a sober, honest and civil man and very trustworthy.

The two-storey timber-framed building's east wall has plaster infilling and exposed timber whereas the ground floor on north front is constructed with red brick and has tile hung above.

[5] Set in the grounds of Strand House is the jointly occupied two-storey timber-framed Crows Nest Cottage, built c. the 17th century or earlier.

Soldiers had been stationed in Winchelsea during the Napoleonic Wars to help guard the coast and along the Royal Military Canal which runs along the marshes below the town.