Bennington County, VT Homes

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  /31

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /50

  $675,000

  Sold Nov 03, 2025

  7 Landgrove Rd, Landgrove, VT 05148

  • 4 Beds
  • 3 Baths
  • 2,570 Sq Ft
  • Built 1925

  Last Sold Summary

  • 12% Above List Price
  • $263/SF
  • 1 Day On Market

  Current Estimated Value $641,480

  Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

  7 Landgrove Rd, Landgrove, VT 05148
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  /37

  Est $1,380,954

  Not Listed For Sale

  6777 Main St, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 4,894 Sq Ft
  • Built 1790

  6777 Main St, Manchester Center, VT 05255

  Last Sold Summary

  • 200 Days On Market
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  /7

  $145,000

  $30K PRICE DROP

  • Land
  • 15.49 Acres
  • $9,361 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /49

  $245,000

  Sold Sep 03, 2025

  130 Sycamore Ln, Shaftsbury, VT 05262

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1959

  Last Sold Summary

  • 4% Below List Price
  • $284/SF
  • 28 Days On Market

  Current Estimated Value $243,602

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  130 Sycamore Ln, Shaftsbury, VT 05262
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  /33

  Est $533,112

  Not Listed For Sale

  367 Carlen St, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 2,228 Sq Ft
  • Built 1992

  367 Carlen St, Manchester Center, VT 05255

  Last Sold Summary

  • 76 Days On Market
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  /46

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 6,129 Sq Ft

  1035 Holy Smoke Rd, Shaftsbury, VT 05262

  Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

  Lori Hurley Four Corner Properties LLC

  1035 Holy Smoke Rd, Shaftsbury, VT 05262
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  /35

  $870,000

  Sold May 13, 2026

  24 Sugarbush Dr, Jamaica, VT 05343

  • 5 Beds
  • 3 Baths
  • 2,897 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $300/SF
  • 8 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate

  24 Sugarbush Dr, Jamaica, VT 05343
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  /42

  Est $488,043

  Not Listed For Sale

  256 Lathrop Ln, Manchester Center, VT 05255

  • 6 Beds
  • 4 Baths
  • 2,174 Sq Ft
  • Built 1820

  256 Lathrop Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 37 Days On Market
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  /38

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft

  1 Beaver St, Bondville, VT 05340

  Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

  Carrie Mathews Winhall Real Estate

  1 Beaver St, Bondville, VT 05340
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  /17

  $89,000

  Sold Jan 21, 2026

  0 State Line Rd, Shaftsbury, VT 05262

  • Land
  • 12 Acres
  • $7,417 per Acre

  Last Sold Summary

  • 13% Above List Price
  • 22 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  0 State Line Rd, Shaftsbury, VT 05262
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  /38

  Est $999,610

  Not Listed For Sale

  1144 Powderhorn Rd, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 3,843 Sq Ft
  • Built 1986

  1144 Powderhorn Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 3 Days On Market
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  /36

  $359,000

  $40K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,938 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Real Estate

  100 McCarthy Acres, North Bennington, VT 05257
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  /41

  $1,775,000

  Sold May 08, 2026

  43 Middle Ridge Rd Unit 416, Winhall, VT 05155

  • 4 Beds
  • 4 Baths
  • 2,401 Sq Ft
  • Built 2004

  Last Sold Summary

  • $739/SF
  • 2 Days On Market

  Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  43 Middle Ridge Rd Unit 416, Winhall, VT 05155
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  /23

  Est $493,732

  Not Listed For Sale

  69 Cottage St, Manchester Center, VT 05255

  • 2 Beds
  • 1.5 Baths
  • 1,675 Sq Ft
  • Built 1920

  69 Cottage St, Manchester Center, VT 05255

  Last Sold Summary

  • 6 Days On Market
• 

  

  /32

  $575,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

  This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

  David Halligan Four Seasons Sotheby's Int'l Realty

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
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  /41

  $319,250

  Sold Oct 24, 2025

  391 Weldon Dr, Sandgate, VT 05250

  • 2 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1960

  Last Sold Summary

  • 9% Below List Price
  • $193/SF
  • 29 Days On Market

  Current Estimated Value $308,630

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  391 Weldon Dr, Sandgate, VT 05250
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  /30

  Est $412,978

  Not Listed For Sale

  141 Green Mountain Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  141 Green Mountain Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 3 Days On Market
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  /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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  /36

  $355,000

  Sold May 29, 2026

  695 Dermody Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,748 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $376,270

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201

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