Using money left by Elize Hele, the school was founded in 1658 by John Maynard and Elize Stert. It was built by John Avent and completed in 1671. There is a date above the door that means nothing more than the year when the building reached that height. The first Master was appointed upon completion of the building and there were 15 masters during the life of the School, the most memorable being Samuel Reynolds, father of the remarkable artist Sir Joshua Reynolds. Other artists who received an education here were James Northcott, Benjamin Haydon and Charles Lock Eastlake. One of the Mudge sons was educated here as was Jack Russell.

Pupils were supposed to be the sons of men who could not afford fees but at times this proviso was forgotten. There were boarders from far and wide, but most of the boys came from local Parishes. Sometimes the school flourished and at other times the education was poor.

The school closed in 1903 and was then empty for some time. A new Grammar School was started up in 1921 at Castle Barbican and due to lack of space there the old school was once again used: now there were both boys and girls attending. Education continued at both sites until 1933 when the school in Stone Barton was ready.

From then on the Old Grammar School was used for many and varied educational purposes.

It has now come to the time when regretfully the Hele Trust has been instructed by the Charity Commission to sell the building in order to protect the charity.