Bennington County, VT Homes

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  /26

  $795,000 Sold Aug 21, 2025

  5 Founders Hill Rd, Winhall, VT 05360

  • 3 Beds
  • 3 Baths
  • 1,624 Sq Ft
  • Built 1970

  Last Sold Summary

  • $490/SF
  • 0 Days On Market

  Last Listing Agent Jamie Wylie Stratton Real Estate

  5 Founders Hill Rd, Winhall, VT 05360
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  /21

  Est $499,435 Not Listed For Sale

  77 Dorset Hollow Rd, Dorset, VT 05251

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft
  • Built 1968

  77 Dorset Hollow Rd, Dorset, VT 05251

  Last Sold Summary

  • 11% Above List Price
  • $516/SF
  • 37 Days On Market

  Last Sold Price $451,150

  Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty
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  /37

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  17 Roundtree Rd, Winhall, VT 05340

  Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

  Sarah Nichols Winhall Real Estate

  17 Roundtree Rd, Winhall, VT 05340
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  /46

  $405,000 Sold Oct 10, 2025

  447 Farm Rd, Arlington, VT 05250

  • 2 Beds
  • 2 Baths
  • 1,564 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $259/SF
  • 27 Days On Market

  Current Estimated Value $393,756

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  447 Farm Rd, Arlington, VT 05250
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  /16

  Est $626,337 Not Listed For Sale

  21 Peace St, Dorset, VT 05251

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1800

  21 Peace St, Dorset, VT 05251

  Last Sold Summary

  • 5% Above List Price
  • $394/SF
  • 8 Days On Market

  Last Sold Price $595,000

  Last Listing Agent Carol O`Connor Four Seasons Sotheby's Int'l Realty
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  /5

  $440,000

  • Land
  • 5.54 Acres
  • $79,422 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
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  /46

  $645,000 Sold Oct 27, 2025

  197 N Ridge Run, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 1,945 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $332/SF
  • 5 Days On Market

  Current Estimated Value $639,297

  Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  197 N Ridge Run, Manchester Center, VT 05255
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  /16

  Est $548,040 Not Listed For Sale

  85 Benedict Rd, East Dorset, VT 05253

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft
  • Built 1965

  85 Benedict Rd, East Dorset, VT 05253

  Last Sold Summary

  • 60% Above List Price
  • $161/SF
  • 177 Days On Market

  Last Sold Price $342,000

  Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
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  /48

  $550,000 Sold Oct 09, 2025

  441 Woodcock Rd, Arlington, VT 05250

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Below List Price
  • $218/SF
  • 31 Days On Market

  Current Estimated Value $563,159

  Last Listing Agent Faith Rhodes Maple Leaf Realty

  441 Woodcock Rd, Arlington, VT 05250
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  /32

  Est $379,189 Not Listed For Sale

  5085 Route 30, Dorset, VT 05251

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft
  • Built 1960

  5085 Route 30, Dorset, VT 05251

  Last Sold Summary

  • 15% Above List Price
  • $371/SF
  • 8 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /16

  $139,000

  • Land
  • 1.62 Acres
  • $85,802 per Acre

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

  wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

  Mike England Michael England Real Estate

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
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  /33

  $335,000 Sold Dec 05, 2025

  379 Swallow Hill Rd, Pownal, VT 05261

  • 3 Beds
  • 1.5 Baths
  • 1,666 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $201/SF
  • 111 Days On Market

  Current Estimated Value $339,492

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  379 Swallow Hill Rd, Pownal, VT 05261
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  /27

  Est $607,043 Not Listed For Sale

  2533 Route 30, Dorset, VT 05251

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft
  • Built 1940

  2533 Route 30, Dorset, VT 05251

  Last Sold Summary

  • 21% Above List Price
  • $293/SF
  • 15 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.
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  /58

  $349,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  27 Broken Pines Dr, Bennington, VT 05201

  Welcome to your peaceful country retreat just over the Bennington town line in Shaftsbury! This 3BR/2BA ranch offers effortless one-level living on a generous 3.5-acre lot surrounded by nature and abundant wildlife. The heart of the home features a modern eat-in kitchen with granite countertops, custom Kraftmaid cabinets installed in 2022 and durable vinyl plank flooring throughout, creating a

  Vicki Wilson Maple Leaf Realty

  27 Broken Pines Dr, Bennington, VT 05201
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  /57

  $2,200,000 Sold Sep 12, 2025

  349 Kent Hill Rd, Dorset, VT 05251

  • 7 Beds
  • 6.5 Baths
  • 6,358 Sq Ft
  • Built 1928

  Last Sold Summary

  • 9% Below List Price
  • $346/SF
  • 57 Days On Market

  Current Estimated Value $1,971,455

  Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  349 Kent Hill Rd, Dorset, VT 05251
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  /27

  Est $827,889 Not Listed For Sale

  216 Church St, Dorset, VT 05251

  • 5 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1920

  216 Church St, Dorset, VT 05251

  Last Sold Summary

  • 201% Above List Price
  • $106/SF
  • 163 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty
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  /6

  $470,000

  • Land
  • 6.93 Acres
  • $67,821 per Acre

  lot#2 Margeaux Ln, Stratton, VT 05155

  This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  lot#2 Margeaux Ln, Stratton, VT 05155
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  /22

  $389,000 Sold Feb 23, 2026

  2 Lower Stratton Valley Rd, Winhall, VT 05340

  • 4 Beds
  • 1.5 Baths
  • 1,344 Sq Ft
  • Built 1978

  Last Sold Summary

  • $289/SF
  • 26 Days On Market

  Current Estimated Value $388,549

  Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

  2 Lower Stratton Valley Rd, Winhall, VT 05340
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  /31

  Est $1,004,029 Not Listed For Sale

  161 Dorset Hill Rd, East Dorset, VT 05253

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1972

  161 Dorset Hill Rd, East Dorset, VT 05253

  Last Sold Summary

  • 48% Above List Price
  • $262/SF
  • 5 Days On Market

  Last Sold Price $679,500

  Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.

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