Gloucester, Massachusetts, just got a serious bragging right: Travel + Leisure has crowned it one of the 10 best places to live on the East Coast. And honestly? Anyone who’s spent time on Cape Ann won’t be surprised.
Just 35 miles north of Boston, Gloucester offers 60 miles of coastline, sandy beaches that rank among New England’s most iconic and a working harbor where fishing boats still set the rhythm of daily life. It’s the kind of place where you can grab a lobster roll on the wharf, wander through galleries downtown and be kayaking on the Annisquam River before dinner.
Karen Hanson, license partner at Engel & Völkers By the Sea, calls Gloucester a “vibrant, tight-knit, and refreshingly diverse community,” adding that “you'll find fishermen, entrepreneurs, and artists enjoying time together for a boat ride on the Annisquam or over fresh-caught tuna tartare at Tonno.” It’s a reminder that this isn’t some sleepy seaside town—it’s very much alive and layered.
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The real estate picture is equally varied. Gloucester’s Eastern Point is dotted with shingle-style mansions that feel straight out of a movie set, while inland you’ll find more modest cottages and fixer-uppers with potential. The median listing price hovers just over $1 million, which puts it in rarefied company. But Hanson notes there are opportunities for those willing to roll up their sleeves: “If you are interested in purchasing in a vibrant waterfront community and your budget betrays you, doing renovations on a well-chosen home could be your answer.”
Beyond the homes and harbor views, Gloucester has something else going for it: personality. The town has long attracted artists, writers and salty characters who give it a certain edge. It’s not polished to perfection and that’s part of the appeal. Where some East Coast enclaves lean overly manicured, Gloucester has a patina that makes it feel lived-in, approachable and, yes, fun.
Add in easy access to Boston, top-notch seafood and four distinct New England seasons, and you can see why Gloucester made the cut. It’s a suburb with soul—and apparently, one of the very best addresses on the entire coast.