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Top Places to Live 2024: Where to Find a Deal in Greater Boston’s Sky-High Market

With dwindling inventory, high interest rates, and even higher home prices, it’s no secret that for many buyers, finding a house in Greater Boston’s most desirable towns and neighborhoods is harder than ever. But for discerning house hunters, there’s good news: Sometimes, all you have to do is look a little beyond the usual suspects to find your dream home.

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Top Places to Live 2024
Here Are 2023 Condo Prices in Boston by Neighborhood
Greater Boston’s Single-Family Home Prices By Town in 2023

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IF YOU WANT…

Jamaica Plain

Like the South End before it, Jamaica Plain’s appeal with the creative class is the very thing that ultimately ensured it became less attainable over time. Folks who bought in J.P. during its gradual rise in popularity are now the beneficiaries of the once-burgeoning area coming to full maturity (see: the collective spike in property values). It’s not hard to see why the neighborhood is so beloved: J.P. boasts a more-diverse collection of housing stock and people than many other Boston neighborhoods, from the stately homes of Pond Street and J-Way that resemble the nearby Chestnut Hill to the renovated triple-deckers of Walk Hill Street. But after decades of fostering indie shops and restaurants, some of the very businesses that made J.P. unique are being shut out by rising prices, too. So for the new stream of chefs, artists, and musicians seeking “the next J.P.,” we say, welcome to Roslindale!

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Roslindale

It doesn’t really feel like there’s a border between Jamaica Plain and Roslindale; one neighborhood gently blends into the next. But once in Roslindale proper, you’ll recognize that it has its own identity. According to J.P. resident and William Raveis agent Gabby Baron, Roslindale “definitely breeds a sense of community—it’s the closest thing you’ll find to a small town within Boston.” Noting the recent influx of young artists and professionals, Baron adds, “You are beginning to see the types of activities that galvanized J.P.—art walks and farmers’ markets.” Plus, “you absolutely get more for your money in Roslindale, and there are a lot of new development projects.” Despite the influx of young buyers in Roslindale, at its heart, it’s still “Rozzie,” Boston’s “garden suburb,” where Tony DeBenedictis opened his Italian deli and butcher shop, Tony’s Market, in 1963 and at 85 years old is still doing the butchering every day.

By the Numbers: Jamaica Plain

By the Numbers: Roslindale

1,100-Square-Foot Comparison:
J.P. vs. Rozzie

By Elisabeth Hadjis

vs.

97 Brookley Rd., #2, Jamaica Plain, Boston

1,100 square feet

997 South St., #2, Roslindale, Boston

$735,000 $775,000 3 2 full

Sale Price Asking Price Bedrooms Bathrooms

$570,000 $559,000 3 1 full

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IF YOU WANT…

Wellesley

You can debate and annually re-rank towns based on infinite criteria, and still, Wellesley maintains its emeritus status as Boston’s premier suburb. It’s no accident: The town is close to Boston, at the axis of the main north/south and east/west arteries, and has great public and private schools, not to mention beautiful homes (including some new construction single-families and condos) and a fairy-tale downtown. Quaint but not so precious as to exclude actual commerce, it is precisely the appropriate size to meet every need of its resident families with parks, indie restaurants—Juniper, Café Mangal, Alta Strada, et cetera—and ample parking at Whole Foods. Remember your South End friends whose child reached school age and swore they “would miss Boston so much and be back in town all the time” after they moved to Wellesley? They lied.

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Natick

While Wellesley saw the construction of Route 9 in the 1930s as an unpleasant inconvenience, Natick saw it as an opportunity and has been a shopping destination ever since (hello, Natick Mall and its forthcoming pickleball oasis). But in recent years, the suburb (population: 37,000) has blossomed into something much more: According to Jane Neilson, a real estate agent with Pinnacle Group at Douglas Elliman, “Natick is very similar to Wellesley in a lot of ways, but it’s a lot more affordable to buy a home here…and there’s a more diverse mix of home styles.” Pair that with terrific schools, new construction (see: the Wayside at Graystone townhomes), a classic MetroWest-style downtown, popular restaurants and cafés, and strongly supported municipal arts programs, and you begin to see why the average home spent just over 30 days on the market here in 2023.

By the Numbers: Wellesley

By the Numbers: Natick

4,100-Square-Foot Comparison:
Wellesley vs. Natick

vs.

47 Audubon Rd., Wellesley

4,100 square feet

33 Birch Rd., Natick

$2,410,000 $2,295,000 5 4 full, 1 half

Sale Price Asking Price Bedrooms Bathrooms

$1,599,000 $1,550,000 4 3 full, 1 half

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IF YOU WANT…

Marblehead

Like other former “summer” towns, Marblehead never intended to be a traditional Boston suburb. With a Chamber of Commerce that touts it as both the “Yachting capital of America” and the “Birthplace of the American Navy,” the collective gaze of Marblehead is undoubtedly seaward. Couple that with the beauty of what’s on shore, and you have one of New England’s most desirable towns. Also, one of its great party towns: In Marblehead, summer Saturday nights “have more in common with high-season Nantucket than they do seaside suburbs like Duxbury, Hingham, or Ipswich,” according to one resident. When it’s time to wind down, locals retire to neighborhoods like Old Town, an enclave of more than 200 pre–Revolutionary War homes, and Marblehead Neck, home to seaside manors on an exclusive sprite of land jutting out from an already exclusive peninsula, Marblehead itself.

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Swampscott

Surrounded by far noisier neighbors (we see you, Marblehead and Salem), Swampscott is more of the strong, silent type, content to go about its business as a lovely, livable seaside town. Though much of its waterfront is rockier and more scenic than swimmable, buyers are nonetheless drawn to the town’s beaches. They’re also drawn to the relatively easy commute. Unlike neighboring Marblehead (which can take forever to get in or out of thanks to a single two-lane road), Swampscott is on the commuter rail. You’ll fi nd many stately homes throughout town as well as more recently developed post-war tracts, and even newer condo developments like the Landing at Vinnin Square. Bonus points for having a few famous residents: Swampscott is the hometown of Barstool Sports founder David Portnoy, as well as the current home of NCAA prez and former Governor Charlie Baker.

By the Numbers: Marblehead

By the Numbers: Swampscott

1,900-Square-Foot Comparison:
Marblehead vs. Swampscott

vs.

8 Washington St., Marblehead

1,900 square feet

22 Shelton Rd., Swampscott

$1,128,000 $850,000 4 2 full, 1 half

Sale Price Asking Price Bedrooms Bathrooms

$769,000 $829,000 4 2 full

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IF YOU WANT…

Hingham

Like the Pilgrims four centuries before them, each evening, the citizens of Hingham arrive by boat via Massachusetts Bay, white sleeves and collars peeking out from below black outer garments (read: fleece vests), slip-on leather shoes adorned with decorative gold metal, and carrying the vestiges of international commerce. These modern pilgrims are the lifeblood of Boston’s thriving financial services industry, and it is because the MBTA’s commuter ferry offers the most relaxing and scenic commute to Boston that Hingham is the closest thing the suburbs have to a one-industry town. Toss in a beautiful Main Street, World’s End nature preserve, quality public and private schools, and arguably the most sophisticated downtown dining scene on the South Shore, and it is abundantly clear why the town has remained a scorching hot real estate market since the mid-1600s.

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Scituate

A short trip south on Route 3A is Scituate, a town with a beautiful waterfront as well as a sweet downtown featuring locally owned and operated shops, bars, and restaurants. Like many of the homes on the “Irish Riviera,” a term once used to describe the beaches of the South Shore, over the past few decades, Scituate itself has been converted from a summer respite to a year-round place to live. “If a potential buyer is interested in the South Shore, I’ll enthusiastically take them by the arm and say, ‘Have you been to Scituate?’ I absolutely love this town,” says Coldwell Banker sales associate Joe DeAngelo. He is not alone in his enthusiasm: In 2023, properties stayed on the market for just 33 days—not much of a surprise when you consider the town’s charming cedar-shingled homes not far from the Greenbush commuter-rail line, which connects the coastal towns of the South Shore to Boston.

By the Numbers: Hingham

By the Numbers: Scituate

1,900-Square-Foot Comparison:
Hingham vs Scituate

vs.

22 Eldridge Ct., Hingham

1,900 square feet

11 Lawson Rd., Scituate

$1,175,000 $1,149,000 3 2 full, 1 half

Sale Price Asking Price Bedrooms Bathrooms

$818,280 $849,000 3 2 full

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IF YOU WANT…

Milton

As close to Boston as Newton (and on the Red Line to boot!), Milton has the unique quality of feeling much farther away—sort of like if you moved Concord or Wellesley closer to downtown but were still able to maintain their charm, history, and beauty. As such, homes are priced accordingly, whether you gravitate toward a more-modest split-level in East Milton, a grand hilltop estate (check out the recent $8.9 million listing for the town’s fully restored Applecroft estate), or a Lower Mills condo in a converted building. Another reason the town is always highly in demand? Its embarrassment of educational riches, with strong public schools, the small private Curry College, and the highly esteemed Milton Academy, whose campus could easily be mistaken for a small university.

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Canton

Just 10 miles southwest of Milton, this close-in suburb has many similar qualities—most notably, its convenience factor. The town is approximately halfway between Cape Cod’s beaches and Wachusett’s ski slopes, Logan and TF Green airports, and Gillette Stadium and Fenway Park. And it’s only growing in popularity, thanks to some key improvements: Historically a manufacturing town, Canton has finally replaced the blight left by Plymouth Rubber Company factory with Copperworks, a new condo community featuring plenty of amenities (including a walkway to the commuter rail). Speaking of amenities: Downtown Canton’s commercial hub is anchored by plenty of franchises, but there are also a good number of indie stores and businesses. And truly, is there any greater Massachusetts bona fide than being the world headquarters of Dunkin’? We think not.

By the Numbers: Milton

By the Numbers: Canton

3,000-Square-Foot Comparison:
Milton vs Canton

vs.

52 Hilltop St., Milton

3,000 square feet

6 Pear Tree Dr., Canton

$1,670,000 $1,450,00 4 2 full, 1 half

Sale Price Asking Price Bedrooms Bathrooms

$785,000 $850,000 4 3 full, 1 half

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IF YOU WANT…

Concord

There are few communities in the United States that can claim the historical and literary significance of Concord. Home to Walden Pond, Louisa May Alcott’s Orchard House, Thoreau Farm, and the Home of Ralph Waldo Emerson, the town offers residents and visitors alike a comprehensive education in American history. If that isn’t enough, it’s home to two of the country’s most storied prep schools, along with the state-of-the-art Concord-Carlisle High School. Be alert for cyclists as you loop around Concord’s most scenic drive, taking in the Old North Bridge as well as the stunning homes and remaining farms that line Monument Street before turning onto Lowell Road to head back to the meticulous town center. Concord is still home to a thriving literary community and even offers a new writer-in-residence program (complete with a private office) at the public library.

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Bedford

Built up around a classic Colonial town square, Bedford has neither the name recognition nor the population of neighboring Concord and Lexington—and that seems to be just fine for Bedfordites. “It’s a town with a palpable pride in its schools, sports, homes, and businesses,” effuses Barrett Sotheby’s Realtor Rory Fivek, who works in both Concord and Bedford. Its housing stock tells a tale not only of the area’s Revolutionary War roots but also the development of the post–World War II suburbs: You’ll find everything from mid- to late-20th century tract homes to LEED certified new builds. And nature, too: Residents can hop on the Minuteman Bikeway, which originates at Bedford’s Narrow Gauge Rail Trail, and ride the former railway line all the way to the Alewife T stop. For some, it’s a leisurely way to get moving; for others, it’s an easy way to commute to Boston that we call the reverse Paul Revere.

By the Numbers: Concord, Mass.

By the Numbers: Bedford, Mass.

2,400-Square-Foot Comparison:
Concord vs Bedford

vs.

1362 Main St., Concord

2,400 square feet

11 Ruben Duren Way, Bedford

$1,651,362 $1,595,000 4 2 full, 1 half

Sale Price Asking Price Bedrooms Bathrooms

$1,337,000 $1,225,000 4 2 full, 1 half

First published in the print edition of the March 2024 issue, as part of our Top Places To Live 2024 cover package, with the headline, “The Bargain Next Door.”