Boarders have been at Wesley from the day the School opened. In fact the very first student Freddie Binks, 9 years old, was a boarder. Boys as young as 7 were boarders though over time the age limit was raised and by the 1970s it was rare that anyone younger than 15 was a boarder. Many of the early Prospectuses showcased the high standard of accommodation for boarders as a selling point. For much of the time the boys lived on the top floor of the main building. In the late 1970s some of them moved to a leased house- Kafore on High Street Road. As part of the House system the boarders were originally labeled the Blue section, then as Adamson House from 1926.
During Headmaster Frederick's time the Junior boarding school closed, and some of the senior boys moved into their previous house facing Punt Road, nicknamed 'Toorak'.
The 1960s saw 'Cock House' a trophy which was awarded for the winners of House Sports competitions - they were the Rulers of the Roost.
In 1980 boarding ceased.
In October 2016 boarding was reintroduced under the name Learning in Residence, located at Glen Waverley campus, with purpose built small houses to accommodate students from the State, overseas and the Yirramalay studio school in the Kimberley.