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Massey College is a graduate residential college at the University of Toronto that was established, built and partially endowed in 1962 by the Massey Foundation and officially opened in 1963, though women were not admitted until 1974. It was modeled around the traditional Cambridge and Oxford collegiate system and features a central court and porters lodge. Similar to St. John's College, Cambridge, and All Souls College, Oxford, senior and junior fellows of Massey College are nominated from the university community and occasionally the wider community, and are elected by the governing board of the college. The President of the University of Toronto, the Dean of graduate studies and three members of the Massey Foundation are ex officio members of the governing board, chaired by the elected member of the governing board. Members of the governing board are elected for five years; the principal of the college is elected for seven years. The college is well connected with prominent figures of the national establishment, and is the sponsor and host of the annual Massey Lectures. It hosted the Man Booker International Prize of 2007.

Massey College was conceived by Vincent Massey, the 18th Governor General of Canada, who attended University College, Toronto, as an undergraduate. Of the establishment of a new graduate college, Massey wrote, "It is of great importance that it should, in its form, reflect the life which will go on inside it and should possess certain qualities—dignity, grace, beauty, and warmth." The Massey Foundation, for which Vincent Massey served as a trustee, provided the financial endowment. Opened officially in 1963, the college was designed by Canadian architect Ron Thom, who subsequently designed the master plan for Trent University. Alan Beddoe designed the Massey College coat of arms, which derives from the arms of Vincent Massey. The founding head of Massey College (1963–81) was the celebrated Canadian journalist and author Robertson Davies. Professor Patterson Hume was the second head (1981–88), and Professor Ann Saddlemyer was the third one (1988–95). The fourth head of the college (1995–2014) was journalist John Fraser. On July 1, 2014, Hugh Segal, formerly a member of the Senate of Canada, became the fifth head of the college for a seven year term, but he resigned in 2019. The sixth principal was Justice Nathalie Des Rosiers, a former Liberal member of the Legislative Assembly of Ontario. The current interim Principal is Professor Jonathan Rose. During the 2006–07 academic year, Massey College hosted the King and Queen of Sweden, held a special tribute in honour of the founding head of the college, Robertson Davies, and was the host of the Man Booker International Prize in April 2007.

Ron Thom's design for Massey College was inspired by the medieval Oxbridge style college. As in Oxford and Cambridge, the buildings of Massey College all centre around one court which is accessible through only two gates. The main gate is at the foot of the tower, along with the porter's lodge. The quad contains a large pond with fish and fountains as well as the St. Catherine's Bell in the clock tower attached to the porch. The bells are rung three times a day during the school term to mark meal times. Around the quad are a total of five residence houses on the east, north, and west sides. The ground floors of these houses contain some administration offices. The largest building, containing the majority of the public space available to members of the fellowship, is on the south side along with the principal's house. Public space at Massey College includes the large dining hall, a small private dining room, a college common room and bar, an upper library, the lower library, the "puffy couch room" (an informal common room with television and games), the Colin Friesen seminar room, a computer room, and non resident study carrels. The college buildings are frequently studied by architecture students. In 2013, which marked its 50th anniversary, Massey College received two prestigious architecture awards. The 2013 Prix du XXe siècle, awarded by The Royal Architectural Institute of Canada, recognizes "the enduring excellence of nationally significant architecture, such as landmark buildings in the historical context of Canadian Architecture. The award can go to a building in Canada, designed by an architect from any country, or a building anywhere designed by a Canadian architect." The commentary from the award’s jury reads as follows: "Massey College is a skillful and humane interpretation of Arts and Crafts sensibilities in a modernist idiom. It is remarkable for its seamless integration of exterior and interior design, including the rich detailing of its custom furnishings and fittings. It has aged well, and is one of the University of Toronto’s most treasured modern buildings." The 2013 Landmark Award was awarded to Massey College by the Ontario Association of Architects. "Recognizing buildings that demonstrate architecture’s beauty, endurance and lasting contribution to the community and to society", a Landmark building "establishes a design excellence standard for future generations, enhances its environment and the public realm, recognizes and respects its surroundings; and contributes to the neighbourhood, the community or the city through its unique identity." Fall 2013 issue of Perspectives magazine, published by OAA, was dedicated to Ron Thom and featured Massey College. The Robertson Davies Library, also known as the lower library, houses the college's librarian as well as an office for the University of Toronto's Book History and Print Culture Program. This library contains display cases for exhibitions curated from the collection by Book History students and Massey students. The Library includes a collection of working 19th century printing presses. The Library's Bibliography Room has the largest collection of wood type in North America (some 350+ pieces). Several working hand presses are housed here. The most frequently used presses are two Albion presses, an Imperial Press, and a Washington Press. Some students work here as apprentices under the college printer. Printed keepsakes for college events are often made here.

Massey College is home to an ecumenical worship space, St. Catherine's Chapel, which Vincent Massey wanted included to "symbolize the position that religion should have in a house of learning." in recognition of the sesquicentennial of Canada, the relationship between Massey College and the Mississaugas of the Credit First Nation, and the only one with its own title in an Indigenous language.

Massey College sponsors the annual Massey Lectures broadcast across the country on CBC as well as the Walter Gordon Symposium on Public Policy. In conjunction with the University of Toronto's School of Graduate Studies, Massey fellows organize an annual symposium of interest to the broader community. There is an annual magazine for all its constituent members: Senior and Junior Fellows, Alumni (which include former Senior Residents, and members of its Quadrangle Society (non academic community members). Massey Grand Rounds (MGR) is composed of members of the Massey College community, including physicians, medical students and graduate students in areas related to medicine and health sciences. It convenes monthly during the school term and serves as a discussion forum for topics related to medicine, the health sciences, and issues of interest to students. Guest Mentors attend regularly. Planning for the Annual MGR Symposium is a significant element of these gatherings. The group is guided by Dr. Aubie Angel, CM, MD, FRCPC, Senior Resident/Fellow, President of Friends of CIHR. The Janet Rossant Lectureship was established at Massey College in 2018 in recognition of Dr. Rossant's distinguished career as a scientist, scholar, builder and leader in medical research. Her dedicated mentorship of young scientists and scholars is reflected in the purpose of this honour. This Lectureship will attract accomplished visiting scientists to engage graduate students and faculty members alike, as part of the Massey Grand Rounds (MGR) program at Massey College. The college has a strong connection to the Canadian establishments and Canadian journalism. The college also strives to preserve an Oxbridge type atmosphere by mandating the wearing of gowns at dinner, and incorporating regular High Tables—into its schedule; and balances this with very active outreach programs The mandated goal of the college is to demonstrate through its corporate life the interconnectedness among all learning. Massey College also hosts its own Junior Fellow Lecture Series, sometimes called WIDEN Massey, where graduate student members of the community are invited to talk about their research in a general way to their non specialist peers. Local and national arts organisations are affiliated with the college. Many college events feature singers from the Canadian Opera Company or musicians from the Talisker Players as well as many talented Junior Fellows who share their music after supper or at events.

The Clarkson Laureateships in Public Service are the highest honour the College awards annually to members of its community. Over the years, notable philanthropists, academics, community organizers, politicians, and activists have been awarded a Clarkson Laureateship, including Ursula Franklin, William Davis, and Mary Eberts. The awarding of Clarkson Laureateships was approved by the Governing Board in 2003 and the first awards were given out in 2004, during the final year that Madam Clarkson, a Senior Fellow of the College, was Governor General of Canada. The award honours her many years of service to Canada by recognizing those members of its community who also contribute to the common good. The Laureateships are usually awarded at the first High Table in January in the presence of the Laureates’ families and Massey College peers. It is tradition for the Laureates to donate the monetary component of the award to a charitable cause of their choosing, often detailed in their acceptance speech. The evening somewhat echoes the ceremonies Madam Clarkson presided over for the Order of Canada when she was Governor General and she herself attends, often joined by past Clarkson Laureates, to honour the awardees.

Massey College was used by David Cronenberg as a location for his 1970 film Crimes of the Future. In 2021, it was used as a location for Star Trek: Discovery. In 2023, Massey College appeared in the Amazon prime superhero series "Gen V"