The first school on the site opened in 1868 and was known as the 'Upper Harbour West School' and had 21 pupils.

The building consisted of a classroom and two small rooms used as a residence by the teacher. The sole furnishings of the school were a chair, three forms and a blackboard.

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In 1874 two rooms were added to the existing school to extend the teacher's residence and the school was officially renamed St Leonards School.

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In 1878 three-quarters of an acre of ground was purchased.

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The second school building was built in 1885. It had two rooms divided by a passageway.

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By May 1901 the school roll had reached 70.

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In March 1909 plans were in place to form the tennis courts and these were opened on 27 November of that year.

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The King George Hall beside the school was built and opened in 1912.

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The winter of 1916 saw the introduction of electric light in the schoolhouse.

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The school roll continued to increase and a pre-fab building was erected west of the hall in 1949.

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The pre-fab building was replaced with two classrooms, cloakrooms and offices in 1959. During this time the supper room in King George Hall was also used as a classroom.

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A third classroom was added to the school in 1970, elevated above the two existing classrooms.

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In 1970 the Education Board proposed the demolition of the 1885 building, but this was opposed by the community and ownership of this building was then transferred to the School Committee.

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The two rooms were used as an activity room and a library, and still have the same use today.

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The 125th Jubilee celebrations were held during Labour weekend in 1993, a 140th Jubilee was held on 5 December 2008 and the 150th Jubilee was during Labour weekend in 2018.