+ Acton: there are a couple dozen 1,500 sqft. split levels that come on the market per year. Good commuter rail access to the red line. Top 20 state school system.
+ Andover/Burlington/Frankling are all top 50 school districts, have a limited selction of affordable, though mostly much older houses. You're still looking at an hour to boston, but if you want to work at Oracle, iRobot, Philips, etc. you'll be right there.
+ Westford: You'll find a decent stock of older 1,000-1,500 sqft. places. Top 20 state school system. Horrible commute into Boston proper, but not bad if you work on the 95/128 belt.
Medford and Malden are gentrifying, the former more quickly than the latter, but you're making a pretty big trade-off in terms of school quality.
If your office is walking distance to South Station, or North Station, there are some farther flung suburbs with commuter rail access that would be workable. E.g. Newburyport has a cool seaside vibe and a commuter train into the heart of the city, though you're looking at an over an hour of travel time.
Southern NH is iffy. Windham is the main town for families, has reasonable prices and houses go very quickly in terms of sales. Salem, Hampstead, Pelham, Derry, Londonderry, not so much. You could theoretically commute from Nashua, but that seems insane to me.
If you can afford something in the $750K range you'll find ok townhouses in hip cities like Somerville and Arlington. That sum will get your foot in the door of a fixer-upper in tonier towns like Winchester and Lexington.
As you might be able to guess, I'm in the market as well, so if you've got any advice on hidden gems of towns, I'm all ears :)
I'd agree with that. A friend of mine basically gave up on Malden a couple years back, sold his place, and moved to Winchester.
When I lived in Houston, I lived in a beautiful flat, a 20 minute walk from my office, and did so making the equivalent of $18/hr. I can't think of many places that'd be possible in the Boston area.
Anyway, off the top of my head: Medford, Quincy, Braintree. Schools might not knock it out of the park like Lexington but they're not crap either. A decent MA school is better than a lot of "good" schools in other states. However, a "tiny" house is in the eye of the beholder. I'd consider 1500sqft pretty decent whereas some people would want 2000+ with an attached garage, which is incongruent with urban living. The "real T" access alleviates a lot of commute woes; T delays are blown out of proportion compared to the daily car-crash-induced traffic jam.
I'm not complaining, just noting that it's the tax of working in cities with a lot of economic activity. The major alternative is moving to a smaller city with fewer job options, but higher quality of life, e.g. Salt Lake City, which only has 3-4 unicorns, but balances that with 5 minute commutes to gorgeous new construction. Pick your poison!
My larger point is I used to live in the 4th largest city in the US and could afford a relatively new, relatively nice house for a pittance, a short distance from my office. I could spend more or less for a better school district, or use the savings for a private school.
Boston and SF seem happy saying "Good schools, affordable house, hellish commute - choose 2" to their residents.
(For what it's worth, I assume that you know most of what I'm about to write but I'm making the point anyway for others who might read.)
You said in another reply that the city in which you used to live was Houston. The key difference between Houston (or Dallas/Fort Worth or San Antonio or almost anywhere in Texas--yes, including Austin) is that it is a relatively flat, geographically plain metropolitan area. In Houston and in Dallas, housing can sprawl for days. I'm from Texas, the Dallas area specifically, and the areas where housing and other development has been built is staggering to me. The entire DFW metro area has developed across a five-county area that's 1/3rd the physical size of the entire state of Massachusetts. I haven't even run the numbers on the Houston metro area but I'd wager it's a quarter again as large.
Meanwhile, Boston is on a harbor and backs up to an area that was pretty urban back when Galveston was the main hub of Texas commerce and Houston was a sleepy town an hour north on the river. Boston--and San Francisco--are constrained by buildable area, geography (all that water, both on the coast and inland), and many, many years of "we build small areas to live in" type of thinking.
My point is that the oft-made comparisons between east and west coast living to Texas are rather unequal. Texas is generally flat, dry, hot, and almost entirely dirt. You can build pretty much anything anywhere you're willing to connect to water and power. (Though that first bit is pretty hard to come by.) But it also means that a lot of those amenities that people really like are super difficult to access without at least two cars per household and the attendant problems of traffic--and where to put the roads[0] and who gets to pay for them[1]--infrastructure (back to that whole "water is getting scarce" thing), and the rest that come along with them.
0 - The Houston metro area is home to the widest freeway in the country, Katy Freeway, which is 26 lanes at its widest point including service roads.
1 - That's one thing Texas was happy to import from the northeast: toll roads literally everywhere. I don't think TxDOT has built a new or even expanded, taxpayer-funded, limited-access freeway in the past decade.