20,611

Bennington County, VT Homes

Section Image
  • /50

    $610,000

    Sold Sep 03, 2026

    3287 Route 7, Pownal, VT 05261

    • 3 Beds
    • 2.5 Baths
    • 2,504 Sq Ft
    • Built 1989

    Last Sold Summary

    • 10% Above List Price
    • $244/SF
    • 1 Day On Market

    Current Estimated Value $456,170

    Last Listing Agent Faith Rhodes Maple Leaf Real Estate

    3287 Route 7, Pownal, VT 05261
    • /40

      Est $628,904

      Not Listed For Sale

      143 Cedar Cir, Shaftsbury, VT 05262

      • 4 Beds
      • 4 Baths
      • 2,756 Sq Ft
      • Built 1977
      143 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /9

    $19,999

    Pending
    • Land
    • 1.5 Acres
    • $13,333 per Acre

    0 Lebensdorf Ln, Readsboro, VT 05350

    Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

    David White OwnerEntry.com

    0 Lebensdorf Ln, Readsboro, VT 05350
  • /50

    $449,000

    Sold Jun 08, 2026

    1284 Granger Hollow Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $320/SF
    • 19 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1284 Granger Hollow Rd, Shaftsbury, VT 05262
    • /29

      Est $400,842

      Not Listed For Sale

      202 Cedar Cir, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1985
      202 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 3 Days On Market

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

  • /27

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /13

    $47,000

    Sold May 22, 2026

    16 Schenk Rd, Stamford, VT 05352

    • Land
    • 10.64 Acres
    • $4,417 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 3 Days On Market

    Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

    16 Schenk Rd, Stamford, VT 05352
    • /40

      Est $303,602

      Not Listed For Sale

      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,006 Sq Ft
      • Built 1970
      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /51

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /45

    $352,500

    Sold Sep 03, 2026

    19 Royal St, North Bennington, VT 05257

    • 4 Beds
    • 1.5 Baths
    • 1,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $203/SF
    • 384 Days On Market

    Current Estimated Value $367,938

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    19 Royal St, North Bennington, VT 05257
    • /39

      Est $599,774

      Not Listed For Sale

      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 1981
      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /39

    $250,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 1.5 Baths
    • 1,458 Sq Ft

    301 Elm St, Bennington, VT 05201

    Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to

    Jenifer Prouty Hoffman Hoffman Real Estate

    301 Elm St, Bennington, VT 05201
  • /35

    $372,000

    Sold May 13, 2026

    303 Prospect St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,463 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 11 Days On Market

    Current Estimated Value $388,416

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    303 Prospect St, Bennington, VT 05201
    • /45

      Est $388,245

      Not Listed For Sale

      294 Tinkham Rd, North Bennington, VT 05257

      • 2 Beds
      • 2 Baths
      • 1,573 Sq Ft
      • Built 1975
      294 Tinkham Rd, North Bennington, VT 05257

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /39

    $59,900

    • Land
    • 40,075 Sq Ft
    • $65,109 per Acre

    14 The Ln, Stamford, VT 05352

    Escape to the beauty of VT with this unique cabin in charming Stamford VT. This is a beautiful almost 1 acre lot that has direct frontage on the North Branch of the Hoosic River. It is mostly cleared & level & has a quaint pathway leading down to the river, to enjoy nature. The property includes a cozy 16x10 cabin with solar powered battery system for lights and to plug things into. with 2

    Susan Colvin MONARCH REALTY, INC.

    14 The Ln, Stamford, VT 05352
  • /45

    $680,000

    Sold Jul 22, 2026

    146 Clover Ln, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Above List Price
    • $264/SF
    • 3 Days On Market

    Current Estimated Value $651,981

    Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    146 Clover Ln, Manchester Center, VT 05255
    • /52

      Est $436,558

      Not Listed For Sale

      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,535 Sq Ft
      • Built 1989
      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /10

    $695,000

    • Land
    • 117 Acres
    • $5,940 per Acre

    0 N Pownal Rd Unit 250712, Pownal, VT 05261

    Spectacular 117 acre parcel, with ample frontage on two roads, of about two thirds meadow ready for your dream home or development possibilities. Truly astonishing valley and mountain forever views southeast, south, and southwest to Massachusetts and New York State. Currently enrolled in the VT Current Use Program, this status can be continued or withdrawn by the future owner. A Land Use Change

    Maureen Dietze ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 N Pownal Rd Unit 250712, Pownal, VT 05261
  • /30

    $1,550,000

    Sold Apr 10, 2026

    147 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $388/SF
    • 9 Days On Market

    Current Estimated Value $1,297,558

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    147 High Meadow Rd, Winhall, VT 05340
    • /12

      Est $206,724

      Not Listed For Sale

      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 920 Sq Ft
      • Built 1935
      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Kevin Holmes Blue Slate Realty

  • /50

    $330,000

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,750 Sq Ft

    1141 Burgess Rd, Bennington, VT 05201

    Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

    Kate Barry EXP Realty

    1141 Burgess Rd, Bennington, VT 05201
  • /24

    $425,000

    Sold Jun 18, 2026

    141 Hillvale Rd, Manchester, VT 05255

    • 2 Beds
    • 3 Baths
    • 1,689 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $252/SF
    • 5 Days On Market

    Current Estimated Value $447,942

    Last Listing Agent David Citron RE/MAX Four Seasons

    141 Hillvale Rd, Manchester, VT 05255
    • /40

      Est $893,275

      Not Listed For Sale

      16 Glastenbury Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 3.5 Baths
      • 4,239 Sq Ft
      • Built 1800
      16 Glastenbury Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /25

    $1,200,000

    Open House 10/10
    • 6 Beds
    • 3.5 Baths
    • 4,017 Sq Ft

    11 Founders Hill Rd, Winhall, VT 05360

    Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property can be sold furnished or unfurnished with closing before the ski season is here. 6 bedrooms and 3.5 bathrooms to accommodate your family and guests. Enjoy 2 primary suites with attached baths and one is on the main floor. Walk in

    Derek Greene Derek Greene

    11 Founders Hill Rd, Winhall, VT 05360
  • /45

    $272,500

    Sold Aug 28, 2026

    886 Hidden Valley Rd, Shaftsbury, VT 05262

    • 5 Beds
    • 2.5 Baths
    • 2,716 Sq Ft
    • Built 1978

    Last Sold Summary

    • 9% Below List Price
    • $100/SF
    • 9 Days On Market

    Current Estimated Value $301,571

    Last Listing Agent Julie Glover Mahar McCarthy Real Estate

    886 Hidden Valley Rd, Shaftsbury, VT 05262
    • /38

      Est $435,855

      Not Listed For Sale

      1139 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1965
      1139 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  • /10

    $190,000

    • Land
    • 3.8 Acres
    • $50,000 per Acre

    148 Vt Route 30, Winhall, VT 05340

    This exceptional 3.8-acre, partially-cleared Winhall lot offers potentially unobstructed views of Stratton mountain, and is permitted for a 4BR home perched at the top of the lot's slope. Nestled in pines, spruces, birches and maple trees, this private Vermont retreat offers an enviable sense of seclusion and natural beauty away from it all, yet with easy proximity to four seasons of fun

    Jamie Luke TPW Real Estate

    148 Vt Route 30, Winhall, VT 05340
  • /31

    $208,000

    Sold Oct 10, 2025

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 10 Days On Market

    Current Estimated Value $219,201

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350
    • /40

      Est $929,812

      Not Listed For Sale

      498 Birch Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 1997
      498 Birch Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /9

    $85,000

    • Land
    • 2.8 Acres
    • $30,357 per Acre

    0 W Mountain Rd, Shaftsbury, VT 05262

    Discover the possibilities offered by this 2.8±-acre wooded parcel in the desirable West Mountain Road area of Shaftsbury. Mature trees provide privacy and a peaceful country setting, while a level area within the property offers potential for a future homesite, subject to all required approvals. With selective clearing, the property may also offer beautiful mountain views. The lot features

    Jeffrey Dorman

    0 W Mountain Rd, Shaftsbury, VT 05262
  • /18

    $260,000

    Sold Apr 28, 2026

    940 Gage St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1945

    Last Sold Summary

    • 13% Below List Price
    • $166/SF
    • 58 Days On Market

    Current Estimated Value $284,054

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    940 Gage St, Bennington, VT 05201
    • /39

      Est $561,292

      Not Listed For Sale

      127 Birch Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 3.5 Baths
      • 3,128 Sq Ft
      • Built 2000
      127 Birch Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent David Citron RE/MAX Four Seasons

  • /49

    $429,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,096 Sq Ft

    928 Main Rd, Stamford, VT 05352

    Welcome to the heart of Stamford, Vermont, where small-town charm meets endless opportunity. Set on 3.99 level acres with beautiful mountain views, this former historic general store has been transformed into a spacious 3,096 sq. ft. residence designed for today's flexible lifestyle. The main home offers 3 bedrooms, open living spaces, and room for everyone, while the separate second-floor

    Christine Girard Lamacchia Realty, Inc. - North Adams

    928 Main Rd, Stamford, VT 05352
  • /44

    $572,500

    Sold May 06, 2026

    475 Sunrise Ln, Arlington, VT 05250

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2002

    Last Sold Summary

    • 21% Below List Price
    • $191/SF
    • 214 Days On Market

    Current Estimated Value $637,373

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

    475 Sunrise Ln, Arlington, VT 05250
    • /39

      Est $786,767

      Not Listed For Sale

      192 Old Depot Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 4 Baths
      • 3,206 Sq Ft
      • Built 1826
      192 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  • /60

    $4,995,000

    $255K PRICE DROP
    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /33

    $485,000

    Sold Apr 20, 2026

    3 Strattonwald Rd, Winhall, VT 05340

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $361/SF
    • 276 Days On Market

    Current Estimated Value $499,352

    Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Strattonwald Rd, Winhall, VT 05340
    • /40

      Est $657,525

      Not Listed For Sale

      5529 Vt Route 7a, Shaftsbury, VT 05262

      • 3 Beds
      • 3 Baths
      • 3,173 Sq Ft
      • Built 1804
      5529 Vt Route 7a, Shaftsbury, VT 05262

      Last Sold Summary

      • 85 Days On Market

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

  • /26

    $750,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain’s premier resort communities. Located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, and flexible living

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
  • /19

    $220,000

    Sold Jun 23, 2026

    14 Robinson Ave, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft
    • Built 1927

    Last Sold Summary

    • $175/SF
    • 309 Days On Market

    Current Estimated Value $236,343

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201

Showing Results 361 - 400, Page 10 of 18

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