The original medieval buildings, Brotherhood Hall at centre, the former Smugglers Arms Inn far left and the surrounding cottages, are still in use and part of today's lower school. The 20th century upper school is at the other end of the town.
The history of the school began in 1614 when shortly before his death William Holland, a wealthy merchant from Steyning, left in his will these buildings and funds for the foundation and maintenance of a Free Grammar School. It was laid down that no Steyning boy should be refused admission if he was able to read and to pay a shilling to join the register. In the early days there was only one master and no more than 50 boys, with 6 boarders, and all lessons took place in one room within Brotherhood Hall. The building was originally a cloth merchants' Guild Hall dating back to around 1461.
In 1839, the school began to admit, from elsewhere, promising students and sons of titled gentry and civil servants. The surrounding cottages and former Inn were all purchased by the school in the early 20th century as the number of students increased, and subjects taught.
In 1944 it became a selective Grammar School for boys who passed the '11 Plus' exam. The comprehensive school for boys and girls we have today was formed when the Grammar School amalgamated with the Secondary Modern School in 1968.