I know there are lots of you on CC who live in New England. I am starting to scope out places to retire to near Boston. Here are my criteria -
• About 1 hour drive from Boston
• Ability to travel from Boston via train (with a 15 min max drive time at the end)
• Can be MA, NH, or RI
• Good public library
• Convenient to get to supermarket and other shopping (target, walmart, etc.)
• Good pizza within 15-20 minutes
• Some “downtown” walkable area with stores and restaurants (would be nice)
• Movie theater or book store in town (would be nice)
Any suggestions?
Budget? The Boston area is pretty pricy. Are you looking for a house, condo, 55+ community?
Wellesley is a great little town but all those western burbs are pricey.
I agree the budget is an important piece of the puzzle. Is being near the water important? If so, I’d say somewhere like Hingham is nice.
To give you a flavor of how pricy, I just went to Trulia and the lowest price house listed in Wellesley is a 1344 sq ft home for $650k. Can you afford that, or is there a budget limit, as well?
Looking for either a condo, 55+, or house with small property - I am done with maintaining property after 35 years of almost 1/2 acre to keep up. Although I do want at least space for a deck with a BBQ and chair to sit out and read.
I am thinking $550,000 as the max. I don’t need a town which is primarily a commuter town, as we don’t need to go into Boston every day (just on occasion). So not Newton, Wellesley, etc. as these are probably too close to Boston and are really commuter towns (where you will pay top dollar being that close).
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Nope no desire to be near the water.
I live an hour west of Boston. With the price you mentioned, you probably will need to look outside Route 495 with towns along or close to the Worcester- Boston commuter rail.
Towns in between Route 128/95 and Route 495 fit your criteria except for they are very expensive.
We are closer to retirement and are checking out other states that offer kinder and gentler than MA re. taxing retirees 
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Why Boston?
The further toward your hour away, the more reasonable. Plenty to do in RI or NH and rarely need Boston.
Many communities around 495 are bedroom areas and where families choose to raise kids.
Near Boston because my daughter lives there. I want to be able to visit her and her come see us (and she doesn’t have a car - so I would be fine picking her up from a train station). I don’t need a community of young families - so that is why about an hour away from Boston should be fine.
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Portsmouth, NH (getting expensive)
Exeter, NH
Other towns on NH’s seacoast.
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Portsmouth,NH is a little farther from Boston and not sure about train service. C & J Bus is great for getting to/from Boston and Logan if you want a major airport. Lovely downtown area. Bonus - close to Portland ME.
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I live in the MetroWest area near Boston.
The criteria you describe sounds like a very nice community and if you find something for $550k it will most likely be small and need some work.
Seems like there is a bit of a trend to have apartments rather than over 55 condos (see Avalon community in Sudbury and one is also being built in Maynard, which is close to the Acton commuter rail).
I suggest you look at Acton, Maynard, Natick or West Concord. Waltham might be a possibility, although it is more urban.
If you give me feedback on these, I’ll see if I can refine my suggestions. 
Editing to add: Property taxes are very high in this area. We pay about $12K a year.
How about Pennsylvania? Pittsburgh is a nice city.
No advice but I LOVE your living requirements!
Metrowest Boston is expensive - finding a home for 550k maybe possible but it would need lot of work. If that is a hassle - NH is the best option. NH is also getting expensive but 550k can take you much farther there - also there are many 55+ communities. NH does not have train but you can find many towns in 30mts driving range from Lowell/Lawrence commuter stations (also many of NH towns now have bus services to South Station and Logan).
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West Acton or West Concord are very nice communities right on the commuter rail line and they do have condos. If you are willing to go West of 495 to towns like Groton or Littleton, you will get more for your money. However, there are more single family homes than condos in those towns. Groton is close to Ayer, which has a commuter rail station; Littleton has its own rail station.
The Downeaster is the line that runs from Portland to Boston. Four trips per day with stops in Dover, Durham and Exeter.
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How about Natick, Framingham or Waltham?
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Exeter had been suggested to me by a friend and I think that has potential. There is an amtrak train from Boston to Exeter so that would work.
I think natick and waltham might work. I had a friend in Acton, so I am a little familiar with that area. I would rule out near there.
We are leaving NJ where all taxes are ridiculous (property, sales, and income). We pay about $12K now in property taxes - I would prefer to pay less for our retirement home.
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