Help me find a retirement town near Boston

I appreciate the info on MA publics. Grandkids are a few years out and who knows what the educational landscape will look like. I know people who live in towns with unimpressive schools who just send their kids to the Catholic schools. I understand that there is a large Catholic high school, Bishop Fenwick, in Peabody and various K-8 elementaries around.


Haven’t been on this thread in a while. @kiddie, have you found a place to live?

I have lived, owned property, or had offices in several parts of the Boston area over much of my adult life. I prefer the Western suburbs but you have to go pretty far out for the price levels to work for @kiddie. Would towns like Stow, Littleton or Ayer work price-wise? I think they have quaint downtowns. Lots of apple orchards. Supermarket shopping is probably fine. Not so sure about Target or Walmart. With the possible exception of pizza and the $550K price tag, I think West Concord meets your criteria quite well. As someone mentioned, there is a condo complex called Concord Greene with prices probably in your range. There are some other new developments, but I think they are rental complexes rather than condos.

I’ve lost track, but given the high price levels, there are outlying towns that I don’t really know but that could be a lot less expensive like Southborough, Westborough, North Brookfield (I think). There is a train that stops in Southborough and Westborough. Also, has anyone suggested the South Shore? I think that a train stops in some of those towns and there was also a commuter ferry at one point. Not sure which of those towns are less expensive but some are pretty quaint.

We recently sold our home and our condo in Brookline. In each case, we got letters from prospective buyers telling us why they were great buyers for the house or condo. I found them pretty funny. But, when we bought our first house in the town, we were asked to write a letter to the seller explaining why we would be good owners. I was a bit unclear as to why, but OK.

Finally, what does it mean that rentals are slow? We own a roughly 1000 sf condo with a sleeping loft. We bought the place for $50K back in the dark ages when they used to call the town “Slummerville.” It is now chic. We hadn’t really done any renovations in decades and a couple of years ago ShawWife did a really nice head to toe renovation. The place looks like something that would be in the Boston Globe Sunday Magazine photo shoot on exciting urban living. We asked what we could rent the place for and the RE agent told us $2500+. We rented it out for $2500, which shocked us as the prior rent was something like $1300. Our tenants have moved out after almost two years and the same RE agent is having trouble finding tenants at $2300.

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City rentals are slow, and there are many vacancies. Outside the city there are no apartments and 15 people show up for a viewing. I am on the North Shore and in my town there are zero rentals right now. Somerville is probably slow. If it were $2k I would rent your place!

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From my limited viewpoint it seems that “city” rentals (Cambridge etc.) are the equivalent of a mortgage so why not try to buy someplace else. That was the math my kids did. At least you’re paying yourself.

Rents have definitely gone down in Cambridge/Somerville. I have seen lots of “no fees” and “two months free” kind of thing. A nice place like yours should indeed go for more than $2500 and will again once the universities start up again in person. Grad students make up a large portion of area tenants, and professionals who can work remotely have fled the city. I think rents will rebound. Right now it is less about price and more about who wants to be in the city at all. The reasons for being in the city: proximity to school or work, public transportation access, and the cultural life of museums, concerts, films and other gatherings, have all been removed by COVID at the moment.

Agreed. And with interest rates so low what you can buy for the equivalent of $2500/3000 per month is rent is a lot (providing you can get together the down payment and find a place).

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The real estate market is frozen here, very little inventory and prices at an all-time high. Despite low interest rates, does it make sense to buy at a high point? Also, not everyone stays in one place long term, so you have to consider closing and commission costs as well as taxes and upkeep.


That is true. I’m well aware of the crazy real estate situation. Demand at an all time high and supply really, really low. I get inquiries (including personal letters!) in my mailbox every week asking if we want to sell.

I think there are so many things to weigh when deciding where to live - it depends on where you are in your life, what lifestyle you want, and how long you intend on being in a particular place.

My young professional daughter cashed in on low rents in Boston proper when she moved in January. Buying doesn’t make sense for her because at this stage in her life she isn’t settled. Young families in Boston are an entirely different situation. They want out of the city, but right now the commutable suburbs have very high prices and no inventory.

For me, at the retirement stage, I have different choices to make. My current house in a commutable NJ suburb is probably at an all time high. I can take those monies and bank them and rent somewhere for a while. Or, I can take that money and invest in a new home. My needs are not the same as when I bought my current home. Don’t need to commute to work, don’t need great schools, can live in a 55+ community, and we want to be near my daughter in Boston (with an easy trip by train or car to visit).

I am actively looking now in that Westborough area somebody mentioned. Thinking that living in a town that doesn’t have its own train station, but where I can drive 15-20 minutes to another station, is a good idea.

BTW - seems like 55+ have not been as effected by the price increases as much as other communities. Most of the price jump in Boston suburbs were fueled by young families leaving the city.


Actually Westborough does have a commuter rail station.

My daughter, a grad student who shares an apartment in Jamaica Plain, house sat in Westborough for two months this past fall.

She enjoyed the town.

It has cute neighborhoods and a cute downtown, but is close to Route 9 with its plethora of shopping options – there is a Wegman’s in the area.

One thing I noted is that it is politically mixed – saw signs for both presidential candidates.

I am targeting 15-20 minute drive to a train station in that area - Ashland, Grafton, Westborough, or Southborough, maybe not actually in that town but in a neighboring town instead. We are going up in a couple of weeks to check out the area (and see our daughter).


Friend’s son lives an apartment in Westwood. Apartment has a Wegmans right there, along with several restaurants. He walks to the commuter rail and I think is only 4 stops to South Station. Super easy.

DH and I are renting in Medford starting this summer. In looking around, there were plenty of 2 bed/bath in the Boston area that were reasonable. I almost jumped on one that was in Back Bay with a parking space included for a little over $3000. I paid over a $1200 in the 90’s for a 2 bedroom in Back Bay- so prices look cheap to me right now!


Actually Westborough to South Station is 15 stops (about an hour).

Sorry meant Westwood, MA.

My apologies, you said Westwood in your post!

We learned a few things going to see a new 55+ retirement place this weekend.

  • Prices are higher than they appear - all of the new home prices on websites are practically lies - lot not included, new group of homes being released at a higher price, etc.
  • Not sure we want to live in a condo. We have concerns about HOA and their various rules. Having always lived in our own home, we are used to doing what we want.
  • New construction is nice - beautiful kitchens and baths, open floor plans, lots of light.
  • We were excited by the bigger models, maybe we aren’t mentally ready to downsize right now.
  • Living on a smaller property felt fine (didn’t feel cramped). After, having lived on a huge property for so long.
  • Now that we can travel freely (no pandemic restrictions and my husband being retired), we can visit my daughter more frequently even with the 4 hour trip. So, although we want to be closer, not sure we feel pressured into doing it right now.
  • The market is indeed crazy. Houses that won’t be done for over a year are already bought. Yes, we will get record price on our current house, but we will pay a record price for the one we move to.

Newburyport, Rockport, and Portsmouth, NH.

Actually these shore towns (like Rockport) fit my initial idea better than the places I have been looking at lately. I originally wanted a walkable town.

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