example of a best old house in the neighborhood of bennington vermont
Photo: Kathryn Kelly
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Bennington, Vermont

It should come as no surprise that Bennington, a scenic Vermont town known for its antiques shops, pottery, art galleries, and hippie haven Bennington College, is home to dozens of celebrated poets, painters, and musicians. Robert Frost is buried here. And if the town looks like a Norman Rockwell painting, it's probably because his studio was just 20 miles outside downtown. The other part of its appeal is its convenient location: Nestled between the Taconic and Green Mountains in the southwestern corner of the state, it's the perfect weekend retreat for Boston and New York City urbanites looking to escape the grind. If the hometown hospitality doesn't lure you away for good, the Vermont maple syrup just might do the trick.

The Houses
Old Bennington, the site of a colonial settlement and one of three historic districts, has stately Greek Revival, Victorian, and Colonial Revival homes starting in the low $300,000s for fixer-uppers. Moving away from the center of town, 1930s Craftsman cottages list for under $200,000.

Why Buy Now?
Prices in Bennington are a little lower than Manchester and surrounding cities, so if you're looking for small-town living that's close to the great outdoors—and still within reach of a big city—Bennington fits the bill.

Among the best for: College Towns, Fixer-Uppers, Gardening, Northeast, Outdoor Activities, Retirees, Small Town, Walkability
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