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North Bennington, VT Homes for Sale with Acreage

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  • /52

    $725,000

    $170K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,424 Sq Ft

    2 Cold Spring Rd, North Bennington, VT 05257

    Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on 50

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    2 Cold Spring Rd, North Bennington, VT 05257
  • /43

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,501 Sq Ft

    856 Matteson Rd, North Bennington, VT 05257

    Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

    Faith Rhodes Maple Leaf Real Estate

    856 Matteson Rd, North Bennington, VT 05257
  • /27

    $290,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,190 Sq Ft

    196 Granger Hollow Rd, North Bennington, VT 05257

    Currently being used as a primary home a vacant 2nd home, this property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large

    Steve Schoppmeyer BHG Masiello Brattleboro

    196 Granger Hollow Rd, North Bennington, VT 05257
  • /49

    $650,000

    • 5 Beds
    • 3 Baths
    • 5,524 Sq Ft

    81 Honeysuckle Ln, North Bennington, VT 05257

    Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

    Kelley Mccarthy Mahar McCarthy Real Estate

    81 Honeysuckle Ln, North Bennington, VT 05257
  • /25

    $1,425,000

    • 3 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    1058 Granger Hollow Rd, North Bennington, VT 05257

    A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    1058 Granger Hollow Rd, North Bennington, VT 05257
  • /32

    $750,000

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,696 Sq Ft

    130 Ipan Rd, North Bennington, VT 05257

    Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

    Kelley Mccarthy Mahar McCarthy Real Estate

    130 Ipan Rd, North Bennington, VT 05257
  • /12

    $825,000

    $40K PRICE DROP
    • 5,568 Sq Ft

    1931 Vermont Route 67 E, Shaftsbury, VT 05262

    Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

    Julie Glover Mahar McCarthy Real Estate

    1931 Vermont Route 67 E, Shaftsbury, VT 05262
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