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Hi, I'm a Milton grad. I went there for thirteen years. In terms of academics and college placement, there really won't be a lot of differences between the three schools. Sure, one school might have a different statistic than another, but if your particular child goes to any of the three, her chances of getting in to a good school will be about the same. What you should consider, however, is the atmosphere. This, in my opinion, is where the schools really do differ. Windsor, obviously, is a single-sex school. So, the students go to dances at various boys schools, have friends from a lot of different schools, etc. Also, the academic atmosphere is very rigorous. It's like that at Milton and Andover, too, but I've gotten the sense that there might be even more of a pressure-cooker feeling at Windsor because there are no slacker boys to lighten things up. Between Milton and Andover, Milton gives a more diverse, city feel and Andover is more of your traditional country boarding school. If your child is going to be a day student, she might prefer Milton because Andover has more of a boarding community.
At all of these schools, there is a ton of pressure on students to do well, get into good colleges, etc. I got a great education at Milton. I feel like I learned more there than I did in college or law school. In fact, I felt as if I didn't have to work very hard in college or law school because of the strong foundation that Milton gave me. College and law school almost felt "fake" after Milton. However, I have never felt more stressed out than when I was in high school (and that is saying a lot, considering that I am now an attorney at big law firm). At this point, I am not planning on sending my children to private school. My opinion might change since my children are not yet school age, but I want to give them a chance to be kids, and I don't feel like I got that. Another thing about any of these three schools is that your daughter's friends will be scattered around the metro area or, in the case of Milton and Andover, around the country and the globe. It was nice knowing people from all over, but it's kind of a bummer not to have many friends where I am from. All of my closest high school friends are scattered around the country and during college, we never came "home" to the same place.
Good luck with your decision. If your daughter got into all three of these schools, she is a smart cookie and she will be fine no matter what. Also, another little secret that I learned too late is that it doesn't really matter where you go to college, just that you get a very high GPA. People from colleges that I've barely heard of get into Harvard Law School because they get 4.0s and good test scores. So, it's really not as if going to a prestigious high school gets you a leg up on everyone for eternity.
Feel free to email me with any questions about Milton. I have a love/hate relationship with the place. The teachers and the academics are just amazing! Truly amazing. Lots of kids seem to have nervous breakdowns, though, or start engaging in unhealthy behaviors to deal with the pressure.
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