Help me find a retirement town near Boston

I have lived in Massachusetts for most of my adult life. It was by accident. Grad school here plus my first job, which was the best first job in the world for my career path. I’d prefer the mountains in West (Canmore, AB or Boulder or someplace in New Mexico) or Marin County (not so much now with the fires) but ShawWife is rooted here. So we bought an extraordinary house here and hope to live a long life and expire in it.

Taxes really aren’t that bad but the people are what distinguishes the Boston area . Outside of the arts, there are more interesting people per capita here. The hospitals are great, the folks who work in biotech do really interesting things, the professors are often working on fascinating stuff. We had over for brunch a former professor who is trying to help companies account for sustainability (ESG) in financial reporting; a landscape architect; a former management consultant who is now working for a very large company that has had public problems trying to help them communicate with the market, the public, and regulators in a more effective way, a retired neurologist who focused on the neurology of reading, etc. Many of our friends are doing interesting things so it is fun to talk with them.

And, for the tax-phobic, they can do what the former owner of this house did. He made Florida his main home for tax purposes (actually fully legitimate in terms of usage as far as I can tell) and hence avoided MA income tax, which is now 5%. If I were to avoid state tax, I could finance a decent mortgage in Florida. But, we would legitimately have to live there for 6+ months a year, which would not excite my wife.

The much bigger effect, frankly, is that real estate is very expensive and property taxes rise with real estate prices. Although our property taxes are lower than NH, the base real estate value is higher than NH. According to that not totally accurate source Zillow, my house has risen $500K in value since we bought it in Jan 2020. We will have to pay for that for years to come.


You are at least fortunate to have paid $500k less then then it would cost now :slight_smile:


We lived in Boston for 8 years, and had a similar experience (the most interesting friends and acquaintances across a pretty wide socioeconomic spectrum, who had either super interesting jobs or fascinating hobbies ). I miss that. It felt to me that people valued intellect far above material consumption (unlike where I currently live). I had often told that to my D20, and when we moved her up there for school, as we drove through Newton on our way to her apartment in Cleveland Circle, she said (almost verbatim), “I understand what you meant now…I’ve never seen so many large beautiful homes with old beater cars parked in the driveway in my life.” LOL.


Ha, yea… bet you’d like Boulder CO too :wink:

" my house has risen $500K in value since we bought it in Jan 2020. We will have to pay for that for years to come." - Maybe yes, maybe no. It depends on how your town does it reassessments etc. Everybody’s home values went up, so it maybe be a wash.


I too had 12 good years living in Brookline Ma. I loved my internship, my job, my condo, and my friends. My son and DIL lived in Cambridge for years, but decided to move to CA.

I think people from NY have the same feelings of belonging.


Southfield in South Weymouth. Old Navel Air Station redeveloped. South of Boston, about 15 miles, has a commuter rail station. My MIL was in rehab in the nursing home there and we attended a professional rugby game there this past summer. Seems very nice.

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We have been renting an apartment in Medford for about a month. I was surprised to find out that the tax rate is lower in MA than NC. We might change our mind about residency. The town we have enjoyed walking to and eating at is Malden. Right on the T, so many restaurants and grocery store. It’s got a nice vibe.


Malden and Medford are both very nice towns. With lots of restaurants and walkable areas, and a fairly easy train ride to the city.


If you yearn for a vacation not-too-far-away, Cape Cod can be lovely this time of year.


@Colorado_mom, I do love Boulder. I have a close friend who lives there. Since we were in grad school, he and I have taken an annual retreat in the mountains for a few days to do what I call strategic planning for life. Since he moved to Boulder, we have done it in the mountains outside of Boulder. In the early 90s, I was leaving a job on Wall Street and wanted to move to somewhere like Boulder as I could do my work from anywhere near a good airport. Housing prices were unbelievably low at that point (there was a real estate recession) and the nicest highest in the nicest suburbs were a few hundred thousand. I could’t get my wife to consider it. Later, my friend moved there. Years later, we visited for a week and I tried to convince her to move. We met a number of his friends (I’d call them part of the touchy-feely intelligentsia) who were fascinating and welcoming. We looked at houses. Found one we liked on a lake at the edge of Boulder. ShawWife didn’t want to move outright (in part because the artist community is not particularly strong there or even in Denver) and wanted to maintain our house in the Boston area. I didn’t think that, at the time, we could afford a nice house in Boulder and a nice house in the Boston area. So, we didn’t buy one. If we moved outright, we could have bought a really nice house. Ah well.

In a couple of weeks I’m heading out to Colorado for our annual retreat, but we are going to a different area.

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Depending upon where you are in the Boston area, you can get to nice places on the South Shore, in NH and Maine to the North, or the Berkshires or Southern Vermont to the West.

Friends of ours have a condo on the water in Florida and plan to sell their house in Boston when he retires and buy a house in the Berkshires and go back and forth between the two places.

Colorado_mom - is it at all possible to buy land and build a small house in CO front range without spending like half a million $$? Just curious!!!

We are closing in on at least a temporary solution. Looking into renting an apartment about 30 minutes outside of Boston and keeping our home in NJ. Trying out living near Boston to see how we like it.


Curious to know which town, if you are comfortable sharing!

The Front Range (areas near Denver, Boulder etc) like most places has gotten pricey. Some of the distant rural areas, especially on the plains, are probably more affordable. Friends are renting a nice 3BR patio home in Greeley (city about 90 min NE of Denver), and it looked like they are in low 300s on zillow.

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@kiddie great strategy! There are always things that emerge as you experience the lay of the land. So smart to work these out of a test drive rental!

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Thanks for the first hand info, Colorado_mom. Two kids out there now so spending a lot of time looking westward… :blush:

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Wise choice to try it out.

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Tough to find rentals. Congrats!

Not in Denver. There might be some places north of Denver/Longmont, but wood prices are very expenses in Colorado. My brother builds houses near Steamboat and even the $1M ones cost a lot more this year.

My daughter and BF are looking for a house. They are outbid on $500k houses by $50k to $100k. In my 1952 neighborhood, houses that went for $400k two years ago are now $600k. They are 3 bd, 2 bath (sometimes only 1), nice size yards, sometimes a one car garage, sometimes a 2 car garage but those are separate buildings, and take up some of the nice sized yards.