The best places to live in and around Boston

Updated on April 26, 2022

On Sunday, the Boston Globe Magazine published its annual “Top Spots to Live in Greater Boston” feature, which I’ve been fortunate enough to write for the past five years.

For want of a better metric, the list is based on the spots with the biggest jumps in median home prices compared to five years ago — the idea being that prices go up when more people want to live in a place. It’s an imperfect measure, to be sure (and not my own), and, naturally, people get all worked up about that. But home price data is measurable, and the market does move with demand, which is mostly (though not entirely) driven by desirability, so it’s not a bad way to land on some winners.

Of course, where we choose to live is a deeply personal decision that taps into both our practical concerns (How far is it to work? To family? Can you afford it? And will your kids be safe and get a good education?) and emotional instincts (Does it remind you of the neighborhood you loved growing up in? Does the architecture or natural beauty appeal to you? Does the diversity or vibrant street energy inspire you?). So the best place for one person is rarely going to be the same best place for someone else.

But there are some common, appealing factors a lot of people agree on. We don’t value them all in exactly the same way. Some people (especially after the claustrophobia of Covid), prioritize a large yard over convenience to the city, for example, while others would trade a subway station and a deck for a one-acre yard they have to mow. But most of us would probably like all of those things if possible, along with trees and parks and well-funded schools and the ability to walk to restaurants and shops. And there are some communities just seem that tick a lot of boxes for a lot of people.

I look at houses in towns all over Eastern Massachusetts each weekend for the Globe’s “On the Block” column, and my wife and I researched the hell out of every community within 15 miles of Boston when we were looking to buy our own home a decade ago. So for what it’s worth, here are my very biased, totally unscientific picks for the best places to live in and around Boston, depending on your budget and some other factors.

We’ll use median home prices, which include both single-family houses and condos, from the first quarter of 2022, courtesy of Redfin. In my view, that’s a good figure to look at, because it represents what real people are paying to buy in these places, regardless of the type of home they end up in. But it does mean that in Boston, Cambridge, and other areas where condos make up the bulk of home purchases, the median more closely reflects the price of an average condo, and a single-family is probably a lot more expensive.

I wrote a book! It’s called ‘Home Buying 101: Your Essential Guide to Buying Your First Home‘ and you can get it from Amazon, Bookshop.org, Barnes & Noble, or your local bookstore.

The best places to live in Boston if you’re wicked rich…

Newton

• Median home price: $1.36 million

I love a streetcar suburb (near-urban areas that experienced a lot of growth around trolley lines in the late 19th and early 20th centuries, like Kevin McAllister’s neighborhood in ‘Home Alone‘), and Newton is a perfect example of the style. It’s just a Green Line ride from downtown, and the various villages offer walkable, dense clusters of leafy streets lined with charming single- and two-family homes, shops, and restaurants.

Cambridge

• Median home price: $1.1 million

One of the most historic yet forward-thinking cities in the U.S., Cambridge is both beautiful and booming. It boasts a mix of Revolutionary War-era Colonials, turn-of-the-20th-century triple-deckers, ultramodern Passivhaus condos, and everything in between, all at a very comfortable and walkable human scale. You’re on the Red Line into downtown (and can get there just by walking over the Charles River in some spots), but with so many restaurants, bars, music venues, parks, playgrounds, and other things to do — not to mention the biotech and academic capitals of North America — there’s little reason to leave.

Brookline

• Median home price: $992,500

If you can afford to buy a home here (and a parking spot, if you have a car, since overnight street parking is banned), you’ll have easy access to downtown (you can easily walk to Longwood or Back Bay from many areas) and city-caliber eateries and shopping, all in a more tree-lined, picturesque package.

South End

• Median home price: $1.1 million

We lived in the Back Bay for three years, on a brick-clad street with gas lanterns, and it was lovely — but not as lovely as the South End, and here’s why: In the Back Bay, you are surrounded by tourists. It gets to be exhausting after a while. I went out for bagels one Sunday morning on Marlborough Street, and stepped outside to find a group of people taking pictures of our brownstone (and me, in my sweatpants). Just blocks away, meanwhile, the more residential South End has America’s largest collection of Victorian row houses, and better yet, it’s still the reigning restaurant capital of the Boston area. The South End is a beautiful, livable, and diverse urban neighborhood, and easily one of the best places to live in Boston proper.

Wellesley

• Median home price: $1.75 million

Home to Wellesley College — one of the famed and acclaimed all-women’s schools that comprise the “Seven Sisters” — Wellesley is both a beautiful, leafy Boston suburb and a destination in and of itself. The combination of 2,500 college students and a median household income of over $213,000 supports a variety of restaurants and other businesses downtown, while the housing stock is similar to Newton’s. Routes 9 and 128 are traffic-laden most of the day, of course, but the commuter rail has two stops in Wellesley.

Needham

• Median home price: $1.35 million

Just over Route 128 from Newton, Needham has a cute and vibrant town center with more boutique shops and legitimately great restaurants than you’d have a right to expect from a town of 31,000. Charming, tree-lined blocks full of Victorians, farmhouses, and Colonials fan outward in various directions (though, as in Wellesley and Newton, some of that charm is being torn down in favor of gross McMansions). Throw in a high-caliber school system and two commuter rail stops, and Needham is the epitome of New England suburban life.

Hingham

• Median home price: $1.1 million

Eleanor Roosevelt called Hingham’s Main Street the most beautiful in America, and with good reason: With stately antique Colonials and towering trees, it’s positively picturesque, like a Norman Rockwell painting. There’s a farmer’s market by the ocean, beautiful parks (including dog paradise Bare Cove and the Trustees-owned World’s End), and the best commute in all of Boston, aboard the MBTA ferry.

The best places if you’re just kinda rich…

Arlington

• Median home price: $929,000

Formerly a working-class town, Arlington has been drawing priced-out Cantabrigians for so long that it’s now a sought-after destination of its own. Like Cambridge, it has leafy side streets with a neighborhood feel, plus a commercial spine along Mass. Ave. with small businesses, restaurants, and an independent theater. It’s also on the Minuteman Bikeway, a paved 10-mile rail trail that runs from Cambridge all the way through Lexington to Bedford, and offers a safe cycling link to Davis Square and the rest of Somerville (via the new Somerville Community Path Extension) as well. The only thing Arlington is missing is the subway, though it’s an easy enough bike or bus ride to Alewife from East Arlington.

Medford

• Median home price: $835,000

Medford is to Somerville what Arlington is to Cambridge — an overflow option that’s a desirable community in its own right. It shares Tufts with Somerville and keeps you very close to the city, but there are more residential neighborhoods (Brooks Estate is positively idyllic) and gorgeous outdoor spaces including the Mystic Lakes (with swimming and boating programs), Wright’s Pond, and the 2,575-acre Middlesex Fells Reservation.

Jamaica Plain

• Median home price: $799,000

We had our hearts set on JP when we were house hunting over a decade ago. Unfortunately, so did everyone else, and everything we looked at spiraled out of our price range. There’s a reason prices never really dipped here during or after the recession: It’s got Orange Line and bike path access to downtown; the beautiful Jamaica Pond, Olmsted Park, and Arnold Arboretum, all jewels of Boston’s Emerald Necklace; a lively, walkable stretch of small shops, bars, and restaurants along Centre Street; and free-spirited ethos that celebrates diversity and community.

Milton

• Median home price: $850,000

Just over the Neponset River from Boston, Milton reminds me of Newton in a lot of ways… only it’s a few hundred thousand dollars cheaper. The schools are great — they even offer full French immersion programs — and there are sprawling, historic, multimillion-dollar estates, but also dense pockets of not-outrageously-priced homes on tree-lined streets with sidewalks. There’s bucolic beauty in the 6,000-acre Blue Hills Reservation, plus the more bustling commercial districts of East Milton Square and Lower Mills.

Marblehead

• Median home price: $788,000

It’s a bit off the beaten path — a drive to the commuter rail — but the winding streets and 18th-century maritime homes of Marblehead’s Old Town are so damned charming it’s well worth it. (Plus, you can probably just sail to work from one of the several yacht clubs.) There are more spread-out neighborhoods, too, from 1920s-style city blocks to cul-de-sac developments.

Melrose

• Median home price: $783,500

Melrose is, in my opinion, the nicest of the three middle-class “M” towns just north of Boston (along with Medford and also-booming Malden). It’s got beautiful, family-friendly neighborhoods and parks, a nice housing stock with lots of Victorians, plus some little shopping districts and commuter rail service. Prices here have gone crazy, however; a Realtor told me his clients offered more than $200,000 over the asking price on a Victorian here last year, and still lost the bidding war.

The best places ordinary people could possibly, theoretically afford to live…

Reading

• Median home price: $724,500

Reading has a lot of ingredients for a great town: It’s got ample commuter rail service to Boston, a bonafide town center with shops and restaurants (and, naturally, given the town name, a beautiful library), well-regarded schools, a beautiful historic district filled with charming homes (like the one pictured atop this post), and it’s at the intersection of two major highways. It’s gotten too pricey, in my opinion, but I think it offers much of what Needham does at a good discount.

Newburyport

• Median home price: $703,000

If you like the charming, historic, waterfront pedestrian paradise of downtown Portsmouth, N.H. (and I sure do), Newburyport feels very similar — but it’s got an even bigger downtown, it’s in Massachusetts, and it’s on the commuter rail to Boston (albeit, a 60-minute ride to North Station).

Quincy

• Median home price: $605,000

After a lengthy home search 13 years ago, we ultimately decided that Quincy was one of the most undervalued areas around Boston, and narrowed our search to about a square mile between Wollaston Beach and the Wollaston T station. Prices have gone up here, by a lot (particularly in more residential neighborhoods like Wollaston, North Quincy, Merrymount, Montclair, West Quincy, and Adams Shore), but it still represents a great value if you’d like to be near the city: You’ve got 27 miles of Atlantic coastline (take that, western suburbs), four Red Line stops (suck it, Watertown), a surprisingly strong school system, plus a ton of restaurants and a “light-urban” patchwork of walkable, diverse neighborhoods. Like Medford, Quincy has an incredible amount of cheap or even free activities and day camps for kids. And our daughter will always be able to walk to school, or to a friend’s house; it’s a great place to raise a family.

Norwood 

• Median home price: $625,000

If you ignore the ugliness that is Route 1 and the “Automile” on the east side of town (which keeps the residential property tax rate quite low), Norwood is a really cute small city wedged between more expensive Westwood and Walpole. It’s got a historic and concentrated downtown, solid schools, a lot of adorable 1920s houses, and even some great breweries.

Sharon 

• Median home price: $660,000

This is admittedly anecdotal, but I’ve met three people from Sharon in my life, and they’re all pretty wonderful. More practically speaking, this town has a longstanding history of investing in its school system, and it draws families who share that priority (and appreciate the commuter rail stop). What’s more, Sharon is home to some beautiful nature and conservation land, including Mass Audubon’s Moose Hill Wildlife Sanctuary, and Lake Massapoag, which offers legit swimming beaches, kids’ camps, concerts, and boating in the center of town. Prices aren’t necessarily cheap here — but you certainly get a lot for your money.

Best places: The best bargains around Boston

Salem 

• Median home price: $525,000

With so much incredible history, an active (and largely pedestrian) downtown full of offbeat cafes and shops, salty taverns with exposed brick and beams, and pretty waterfront parks, Salem was our runner-up when house hunting. There’s a gorgeous town common, and the city sits at the convergence of two commuter rail lines, so, during rush hour at least, you’ve got trains coming almost as frequently as a subway line. It just felt a little too far away for us after having lived in the heart of Boston for so many years, and for some reason its schools continue to rank pretty poorly. Despite some big price gains since those days, I think Salem is still one of the best values in the Boston area.

Easton 

• Median home price: $538,000

I’m often surprised by the price when I tour a home in Easton: You can still get a very nice four-bedroom house here — with a yard, updated kitchen, the whole shebang – in the $500K range. It’s got a rural feel, yet it’s not that far from the city (and pretty near to Providence, R.I., too), there’s a college in town, and a very cute town center (plus a delightful children’s museum). There are loads of beautiful, historic homes, too — it’s not just your generic bedroom community full of mid-century ranches.

Worcester

• Median home price: $369,900

The second-largest city in New England offers commuter rail service and a daily express train to Boston, and offers some big-city attractions — an incredible science museum called the EcoTarium, some great restaurants and craft beer bars, and the Red Sox AAA team among them. But it’s also got a lot of immensely livable neighborhoods packed with charming, historic single-family homes with yards. If you feel like you missed out on the once-cheap collection of beautiful Victorians that were available in Dorchester 15 to 20 years ago, take a look at Worcester.

Plymouth

• Median home price: $530,000

It’s far from Boston, yes, but Plymouth is still on the commuter rail and enticingly priced. It’s huge and varied, with just about any type of housing you might want, from antique homes to sprawling McMansions to over-55 communities. And you can enjoy beautiful, Cape Cod-caliber beaches plus a local history that rivals that of Salem.

Lowell

• Median home price: $394,500

Lowell has been on a long, sometimes-difficult, upward trajectory since the 1990s. It’s got cobblestoned streets full of restaurants and bars, commuter rail service into Boston, a bonafide minor league baseball franchise, a lovely outdoor concert theater and summer music series, and one of the lynchpins in the University of Massachusetts system. You can find gorgeous new lofts in renovated brick mill buildings, and 19th-century mansions where mill owners once lived. Simply put, Lowell’s not perfect yet, but there’s a lot of good going on here.

So there you have it – my unofficial, completely subjective picks for the best places to live in and around Boston. What places would you add? What made you settle on where you live now? Feel free to tear me a new one in the comments.