You don't know me, but I've silently benefited from this site over the years (especially around exam times, when procrastination is needful) and I feel like I should give something back. I've noticed that questions about Massey College tend to go begging here, and that's a shame. Massey really is a unique place that can make your years at U of T law school very different from what they otherwise would be. I think I can safely say that most people who've lived at Massey and been part of the community can probably not imagine their time at U of T without the college. I'm not saying it's for everyone. Far from it. But it's much more than a place to live, and anyone applying there should know that.
You can learn a lot about Massey online. I'd suggest reading the college website and the wiki is also pretty good.
Probably the most important things you won't learn immediately from these sites are as follows. Massey admits approx 60 resident "junior fellows" (students, at U of T) each year, and around 70 additional non-resident junior fellows. Residents, obviously, live at the college while non-residents do not. Fees can be checked online - I'm not sure what they are currently. To live there it's relatively expensive, but you get a (small) private room and your own study. Shared bathroom on the hall. Meal plan that's pretty good. I'd call it an investment in living a certain way in school, but worth it. Bursaries available for those in need. Non-resident fees are relatively nominal (few hundred for the year?) and allow students not living at the college to participate fully in Massey life.
Important note. If you live at Massey you will probably, in a natural way, find yourself a full part of the community. If you don't live there, it's very easy to just pay your fees and not get much out of it. Non-resident junior fellowship takes, if anything, more careful thought than resident junior fellowship for this reason.
Massey admits students from every graduate and professional program at U of T. That's professional programs that come after undergraduate degrees - second entry. It strives for a mix. Many students cite this as Massey's most attractive feature. Whether you're doing a PhD in math or pursuing your medical degree or in law school, one does tend to get sick of being surrounded only by other people doing the same. As a community, Massey is a break for everyone. Your dinner conversation is much more likely to be about someone's research surrounding the culture of "found" food (meaning harvested in nature) than it is about the latest Supreme Court decision. That's just one example, of course.
Approximately 4-6 junior fellows each year (estimate, not guaranteed) are from the law school. I find it's a good number, especially if you join during first year. It gives you a few natural friends in first year and people you know. Massey can also be too much of a good thing in this regard. For many people at Massey, the college itself becomes more of a natural social hub than the program, in this case law school. Admission for law students tends to be fairly competitive. There are more applications than there are spots.
You can live in residence at the college for up to three years. Convenient for law students, save those in four year combined programs. PhD students tend to be forced to go non-resident by the time they are done. It's just to spread around the experience of living there.
I should mention some of the social advantages of being part of the Massey community. I'll sound like a snob as I write this, unavoidably, and I'm sorry. Just about any important speaker or guest of the university generally has a reception after the event at Massey. It's the natural place to go. Some of the university's most prominent scholars have their offices in the college (rooms literally down the hall from where you live) and every year there's a cohort of mid-career journalists at the college also. There are social events throughout the year, mentorship opportunities, you name it. A significant number of prominent jurists and lawyers are affiliated with the college through the "Quadrangle Society" (too complicated to explain) and yes, that can matter. Suffice it to say you can meet literally anyone at the college and that's essentially accurate. When the King and Queen of Sweden show up to judge the annual pumpkin carving contest (true story) that should give you some idea.
It would be very easy from the outside to get the sense that Massey is in some sense a snobbish or elite institution. The gowns at dinner don't help that impression. If it were populated entirely by law students that would probably become true. But remember that law students are only a small portion of the whole. Most junior fellows are pursuing academic degrees, and almost everyone at the college is some combination of quirky, laid-back, intellectual, desperately in need of distraction from their work, and wonderfully glad to be living at a college filled with people unlike themselves.
I didn't mean to write so much, but I could probably write for pages more and still not capture the essence of Massey college. It's wonderful in large part because it's small enough to be a real community. When you live there, you really do get to know everyone. It's so much more than just a residence. And while we've had the occasional person over the years who didn't know what they'd applied to and then they turned out to love it, I'd really recommend that anyone applying to the college should know what they are in for.
I'll gladly take questions, but if anyone wishes to reply I'd suggest you send me a private message also so I get some notice. I don't come here often.