Best Places to Live 2014: Growing Family

The kids need a dedicated playroom. You need a big kitchen—and you’ve earned that master suite with the fireplace and walk-in closet. These towns offer sizable lots, superb services, and unique architecture.

best places to live boston growing family

Photograph by Steve Dunewell

— Winner —


Median home price: $825,000
One-year change: +18%

Think of Winchester as your dignified old-money auntie: You won’t find its name in the papers, and it’s not as flashy as other suburban towns—but it’s worth getting to know, because the fringe benefits are many. Residents adore its lantern-lit downtown bursting with stellar eateries, indie shops, and family-owned businesses; superb school system (an override just passed, providing funds for a high school renovation); and sporty retreats (it’s home to a portion of the Middlesex Fells Reservation, and the Winchester Country Club and Winchester Boat Club overlook Upper Mystic Lake). In the sidewalk-lined Winchester flats, find Queen Annes and Tudors with level yards, straight out of a John Hughes film. For privacy, aspire to Myopia Hill, where Federal-style fiefdoms are tucked into lush lots. Winchester maintains a low profile in large part because it lacks direct highway access, but there are two commuter-rail stops. And with such lovely architecture, shops, and recreation, why would you need to stray?


— Also worth a look —


Median home price: $667,000
One-year change: +8%

Think Concord, but with more space and fewer million-dollar-plus price tags (though such abodes are certainly on offer). The town shares a top-ranked high school with Concord, and it’s easy to zip into the center for shopping, services, and the commuter rail. Carlisle itself boasts plenty of acreage and pastoral estates. The new subdivision Hanover Hill, adjacent to Great Brook Farm State Park, offers houses on two-plus acres that embrace the town’s bucolic sensibilities— without sacrificing modern perks.


Median home price: $477,500
One-year change: +3%

Want to spread out on an acre-plus (in a 2,000-square-foot home) for under $500,000? This North Shore enclave has a quaint town center, a classic New England common, and strong community spirit. In winter, sled at Wheatland Hill; come summer, take a dip in Hood’s Pond; in the fall, visit the Topsfield Fair. Well-regarded Masconomet Middle School and High School serve Topsfield and its neighbors, Middleton and Boxford. Don’t let the rural vibe deceive you: It’s conveniently wedged between Route 1 and I-95.


On the Market

Address: 38 Summer St., Topsfield
Stats: Three bedrooms, two and a half baths
Listing Price: $699,900

Check out more of our Best Places to Live 2014 coverage.