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My husband, my 6 month old son, and myself will be moving back to the area and are considering these three towns: Westwood, Natick and Milton.
We are mainly driven by the reputation for good schools and the housing, but remaining a short commuting distance to Boston for my husband's job.
We like to bring our dog hiking and get moving outside, so we would like hiking and parks available. We like having restaurants available, although that has changed with having a new baby. We mainly want to make sure this is a good community where we can live and raise our family.
I am also interested in what people like or dislike about these towns.
Is your husband commuting to Boston? Will you have a commute at any point? I think that any of the three towns would be fine, although the only town I've spent significant time in is Natick. So my personal bias would be to Natick, which is where I would move if Newton and Needham were not in my budget. I think the location is good, it has good accessibility to downtown, and has a nice downtown area itself, along with the commercial strip that has almost every chain in existence.
Oh, and keep going out to dinner while the baby is young. Once they become mobile and vocal, that's when going to a restaurant becomes a major ordeal and very stressful. When they're young enough to be in the carrier and sit quietly, that's the window of opportunity to enjoy going out.
These are all great communities and you really can't go wrong with any of them. They're all a bit different though.
Westwood is probably the sleepiest of the three. There's not really a town center in Westwood and aside from the new University Station shopping center in town shopping/dining options are very limited. Schools are excellent though and there are a lot of great neighborhoods in town. Commuting wise, the town does have a couple of train stations which is great but driving in/out of Westwood can be a bit of a bear depending upon where in town you live.
Milton is not a town I'm terribly familiar with but it's a nice town with solid schools is my understanding.
Natick on the other hand I'm incredibly familiar with. It has a nice town center and good schools. Lots of variety in the types of housing available as well. Little houses, big houses, condos, townhomes, and basically any other form of housing can be found in Natick. There's also a variety of housing environments too. South Natick can feel almost rural while the Natick Center area is very densely populated. Also, you'll find a lot more diversity of various type (economic, racial, etc.) in Natick than you would Westwood. Of course, you have easy access to the famous "Golden Triangle" shopping area with the Natick Mall, Shoppers World, etc. If you can't find what you want to buy in the triangle then it likely doesn't exist. I have tons of friends who live in Natick and I've helped a lot of people buy/sell there. They all love it.
You have the Blue Hills Reservation in Milton -- tons of hiking trails, Houghton's Pond, all that good outdoorsy stuff. There are also numerous parks around town too.
Milton would also be the shortest commute into Boston, depending on what side of town you're in. East Milton, all you do is hop on the Southeast Expressway. Horrible rush hours, however, but there are back roads through Dorchester to get you where you're going. There are three MBTA bus routes through town which will get you to the Red Line in either Quincy or Ashmont.
Schools, as Mike PRU said, and very solid and highly regarded, especially the French Immersion program.
I couldn't find them on Boston Magazine's list and they didn't get ranked on US News' list either. The ratings are pretty good on Great Schools. I didn't really dig any further than that and I don't have many friends in Milton who I could get personal feedback from.
You'd probably love Natick. It does have two commuter rail stops as well as easy access to the Mass Pike for commuting to Boston. The schools are also great, and somewhat underrated/shadowed by the surrounding higher-priced school-districts.
Milton would easily be the best commute into Boston. The schools are solid and the French Immersion program (where they instruct the children in French through most of grade school) is very popular. Westwood has very good schools and a major commuter rail station that goes straight into Boston. I'm not very familiar with Natick but my overall impression is the schools are good.
I do really like milton, I grew up there. Close to boston, beautiful homes, very historical. There schools seem good enough to me...im suprised they arent better quite honestly.
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