There is no perfect school, only fit school. Winsor is no exception. It's a Boston elite private girl school, what do you expect?
+s: 1. most of the dedicated teachers. Majority of the teachers (not from the athletic department) are very caring and nurturing.
2. small class size and wonderful academic programs in liberal art subjects, comparing with surrounding top public schools.
-s: socially, very cliquey, both students and parents (especially among the Winsor legacies and famous last names, with few exceptions). If you as parents are not part of the exclusive groups, your kids will not feel completely included and happy. Some social groups are even mean spirited. The general culture of the school is closed, cliquey and Boston local minded. It's a long way from educating girls to be the 21st century citizens, i.e., open minded, technology and global driven.
When a parent search for a school for your daughter, please pay less attention to the ranking and percentage going to ivy league etc. In the end, the school has to be a good fit for your daughter and family, in terms of the well being, socially and academically, in the long term.
My daughter has recently left the 8th grade at Winsor. It was a good school for her in 6th grade, and I have heard that the 5th grade at Winsor is even better than 6th grade. However, as the grades progress, the stress levels become higher and higher. Winsor is also very cliquey. The grade my daughter just exited is extremely mean and focuses on body type, looking good on social media, and being "popular". There are many promiscuous girls at Winsor that are focused on only boys. Although the college matriculations are very good, the academics are so stressful that some girls crack under the pressure. There is no sense of support throughout the class. Many of the leaders in the school only care about Winsor's preppy and pristine reputation rather than the actual well being of the student. Do not send your child to this school. There are many other good prep and public schools in Boston that are more inclusive and healthy for your child than Winsor.
My daughter just transitioned to Winsor from an average public school, and the difference is just tremendous. As a bright kid, she'd been bored and unhappy, and used to feel social pressure not to stand out or succeed academically. The environment and culture at Winsor is exactly the opposite. She is being challenged, in every class, every day. Her cohort (30 girls in her 5th grade class, broken into two sections of 15) is filled with active, interesting, friendly girls who celebrate each other's weirdness rather than mocking it, and who are wholly agreed that they're in school to learn. She's made a number of great friends in only two months, and there has (so far) been no clique-like behavior or exclusion, even though many of the families are a *lot* wealthier than we are. There's a lot of homework, but I haven't seen any that I could call busywork - it's all very intentional and useful, and she hasn't been overwhelmed yet (though sports don't start until next year). The new building will add a lot to the campus. The only real difficulty is the location - getting there in rush hour is hard. I love this school - go Wildcats!
Winsor is, of course, one of the top girls schools in the country. The matriculation list is astounding, SOME teachers are sooo overqualified, and all of the girls work extremely hard. As others mentioned, however, some parts of the staffing need some serious work. The math department, other than the fantastic Ms. Reynolds, is pitiful compared to the english and history departments. One teacher barely speaks english, one seems like teaching is the last thing he wants to be doing, and pretty much every teacher acts like they truly don't want you to succeed. I'm hoping the school takes the feedback it has gotten on the math department and steps it up. This is not a reason to go to a different school, but definitely something the school needs to work on.
I go to Winsor and it is such a great school! the academics are very rigorous and challenging but still very fun and enjoyable. You get a ton of homework but make amazing lifelong friends. Coming to Winsor was one of my best decisions! It is very well known for its outstanding college matriculation as well.