In the early 2000s, couple Richard Wernham and Julia West, along with father-son duo John R. Latimer and David "Lub" Latimer, imagined of a co-educational school in Toronto that would be an alternative to the foremost independent schools in Toronto, which were mostly single sex and offered the International Baccalaureate.

Founding principal David Thompson left Greenwood in June 2008 become the Headmaster at Lakefield College School.

[3] Founding principal David Thompson left Greenwood in June 2008 to become the Headmaster at Lakefield College School.

[6] Greenwood's outdoor education program includes trips in the fall and winter, considered to be essential character-building experiences that encourage the development of perseverance and leadership.

[8] On Wednesdays, classes start late to give staff the opportunity to participate in professional development sessions as students take part in community service.