The old Grammar School at the southern end of George Lane, is referred to by the Devon historian, W.G. Hoskins, who says, "Few schools in England can have such rich associations in the history of painting, but few towns in England can have been so unaware of their greatest son". JoshuaReynolds, the son of Samuel Reynolds, a Headmaster of this School, was born in the old school house in 1723. The house was pulled down in 1871, and there was no memorial to Reynolds until a tablet was put in the Church in 1904.
The School was known as Hele's School, Plympton, after Elize Hele who owned Sir Walter Raleigh's old manor house at Fardel, in the parish of Cornwood. The cost of the building completed in 1671, was £1,099. The School is built in a gothic style, possibly designed by the architect of Charles Church, Plymouth. A cloister of arches and columns decorated in contrasting bands of limestone and granite, supports the schoolroom. It has five large mullioned windows. Above the schoolroom door is a small gallery where the Headmaster could stand to watch his pupils at work.
The School was intended as a charitable school for boys of surrounding parishes but, such was its excellent reputation, the local gentry sent their sons too. John Parker of Saltram, who was to become the first Earl of Morley, used to walk daily to the School through Underwood. In 1973, on the occasion of the 250th anniversary of Reynolds' birth, the Civic Association, in conjunction with Plympton Grammar School, arranged various celebrations including the donation of wrought iron gates to the old School. They were ceremonially opened by Sir Thomas Monnington, the President of the Royal Academy.
Other notable pupils who also became artists include James Northcote (1746-1831), Benjamin Haydn (1786-1846) and Charles Lock Eastlake (1793-1865).
Another former pupil was Jack Russell, the famous hunting parson, and breeder of the terrier. He became, as he said, "Cock of the walk", after beating, in a fight, Bulteel, the son of a well-known local family.
During the latter half of the nineteenth century, an attempt to replace the classical curriculum of the School with commercial courses proved unsuccessful. Numbers dwindled, and the School closed in 1903. It was decided to re-open the School in 1921 on a co-educational basis. The School occupied Castle Barbican, purchased from the widow of J. Brooking Rowe, the author of "A History of Plympton Erle". By 1931, the growth of the Grammar School necessitated the use of the original old schoolroom. With continued growth in numbers, the School moved out of Plympton St. Maurice in 1937 to its present site in Stone Barton.