Norden's 1607 map of WinchesterPrevious investigations have shown that the site lies within a fortified Iron Age settlement. The Roman town of Venta Belgarum was built over this earlier settlement and grew to be the fifth largest town in Roman Britain.

Occupation of the town continued into the post-Roman period, when it became an important royal and ecclesiastical centre. During the reign of King Alfred in the late 9th century the Saxon town (burgh) was formed as streets and defences were rebuilt. Jewry Street probably came into existence at this time. In the medieval period major ecclesiastical monuments were built, most notably the present cathedral building which is less than 700m from the site and was started in 1079.

The current buildings on the site date from the 19th & 20th centuries. From 1865-1901 No. 19 was the Golden Lion Pub, No. 20 was first a coach-builders and then a cycle shop. Tea rooms took the place of the cycle shop and were themselves replaced by several other businesses over the years.