The elaborate gates and lodge were built at the same time as the main house to designs by the architect George Brown.

The gardens and grounds, including the artificial lake, were designed by the leading landscape architect of the time, William Sangster. The brick and cement tank, capable of holding 9000 gallons of water, supplied water to the house and grounds

The property was sold by the Clarke family in 1922 to manufacturer Hugh Victor McKay. The pastoralist William Naughton bought Rupertswood in 1926 and the property was subdivided. Since 1927 Rupertswood has been owned by the Salesian order.

Rupertswood has historical, architectural and social importance to the state of Victoria.

Rupertswood, one of the largest houses built in Victoria, has considerable historical and social importance as an expression of an extraordinary way of life based on great affluence. Rupertswood became one of the principal social centres in Victoria, with hundreds of guests arriving at the estate's private railway platform to attend hunt meets, balls and house parties. The estate also had its own half battery of horse artillery when Sir William Clarke formed a small permanent force in 1885. The drill hall and the vault remain as reminders of this privately sponsored regiment.

Rupertswood has important historical and social associations with landowner, stud-breeder and philanthropist Sir William Clarke (1831-1897). The elaborate mansion with its large estate demonstrates the important status of Clarke whose prominence as a colonist was recognised in 1882 by his appointment as a baronet.

The property also has an association with Hugh Victor McKay (1865-1926) who owned the Sunshine Harvester Works, for many years the largest factory in Australia. McKay achieved his long-held ambition of owning Rupertswood in 1922.

Rupertswood has significant historical associations with the Catholic Church. The Salesian order of priests, who have occupied the property since 1927, was formed in Turin, Italy by Saint John Bosco who set up schools and homes for the underprivileged of the city. The order arrived in Australia in 1923 and priests and brothers were welcomed in Melbourne by Archbishop Mannix in 1925. Rupertswood, from 1931 to 1981, was the site for Eucharistic Festivals, the major annual devotional event of the Catholic Church in Victoria.

Rupertswood is also of historical interest for its association with the Ashes, cricket's most illustrious trophy. After a social match on the property with members of the English touring cricket team in 1882, Lady Janet Clarke burnt a bail and presented the ashes in an urn to the victorious English captain, Ivo Bligh.

Rupertswood demonstrates outstanding craftsmanship and interior decoration. The stained glass windows by Ferguson and Urie are particularly noteworthy.