20,622

Bennington County, VT Homes

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  • /31

    $365,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    12 Hall St, North Bennington, VT 05257

    Located in the heart of the charming North Bennington Village, this beautifully renovated home offers the perfect blend of classic character and modern convenience. Completely renovated interior in 2022, including a new roof, this move-in-ready home features three bedrooms and two beautifully updated bathrooms, with the added convenience of a first-floor bedroom and main-level laundry. The

    Kelley Mccarthy Mahar McCarthy Real Estate

    12 Hall St, North Bennington, VT 05257
  • /53

    $400,000

    Sold Sep 22, 2025

    495 Fairview St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,309 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $306/SF
    • 12 Days On Market

    Current Estimated Value $409,321

    Last Listing Agent Catherine Cairns Maple Leaf Real Estate

    495 Fairview St, Bennington, VT 05201
    • /40

      Est $423,316

      Not Listed For Sale

      1693 Branch Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 3 Baths
      • 2,259 Sq Ft
      • Built 1848
      1693 Branch Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Monique White Deerfield Valley 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
  • /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 $655,715

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

    475 Sunrise Ln, Arlington, VT 05250
    • /15

      Est $471,650

      Not Listed For Sale

      833 Freezing Hole Dr, Readsboro, VT 05350

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 1997
      833 Freezing Hole Dr, Readsboro, VT 05350

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /26

    $825,000

    $25K 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. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
  • /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 $494,496

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /40

      Est $417,565

      Not Listed For Sale

      470 Freezing Hole Dr, Readsboro, VT 05350

      • 3 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1964
      470 Freezing Hole Dr, Readsboro, VT 05350

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /40

    $1,699,000

    • 4 Beds
    • 4 Baths
    • 2,951 Sq Ft

    1949 South Rd, Peru, VT 05152

    Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

    Helen Nault

    1949 South Rd, Peru, VT 05152
  • /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 $227,725

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
    • /49

      Est $546,037

      Not Listed For Sale

      1450 King Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 2 Baths
      • 3,104 Sq Ft
      • Built 1983
      1450 King Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /47

    $1,500,000

    • Land
    • 38.57 Acres
    • $38,890 per Acre

    500 Nims Rd, Dorset, VT 05251

    This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

    Laura Beckwith Josiah Allen Real Estate, Inc.

    500 Nims Rd, Dorset, VT 05251
  • /15

    $175,000

    Sold Mar 09, 2026

    0 Alden Ln, Sunderland, VT 05250

    • Land
    • 40 Acres
    • $4,375 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 360 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    0 Alden Ln, Sunderland, VT 05250
    • /35

      Est $551,652

      Not Listed For Sale

      140 Odonnell Dr, Readsboro, VT 05350

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft
      • Built 2000
      140 Odonnell Dr, Readsboro, VT 05350

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Monica Sumner BHG Masiello Brattleboro

  • /27

    $179,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • /47

    $502,500

    Sold Dec 15, 2025

    377 Glen Rd, Peru, VT 05152

    • 4 Beds
    • 4 Baths
    • 2,370 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $212/SF
    • 16 Days On Market

    Current Estimated Value $509,919

    Last Listing Agent Nancy Jensen Four Seasons Sotheby's Int'l Realty

    377 Glen Rd, Peru, VT 05152
    • /20

      Est $406,345

      Not Listed For Sale

      603 Wiley Mountain Dr, Readsboro, VT 05350

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 2005
      603 Wiley Mountain Dr, Readsboro, VT 05350

      Last Sold Summary

      • 160 Days On Market

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /20

    $139,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,109 Sq Ft

    1178 Oberdorf Rd Unit 189/90, Readsboro, VT 05350

    Opportunity awaits in Alpenwald Village! Situated on a 2.1 acre corner parcel consisting of two lots with frontage on both Oberdorf Road and Oberhugel Road, this property offers privacy, a cleared homesite, and an adjoining wooded lot with potential seasonal mountain views. The current owners have completed much of the interior clean-out and gutting, leaving a blank canvas for the next owner to

    Melissa Nebelski Real Broker LLC

    1178 Oberdorf Rd Unit 189/90, Readsboro, VT 05350
  • /35

    $707,500

    Sold May 01, 2026

    9 Old Route 30, Winhall, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft
    • Built 1948

    Last Sold Summary

    • 2% Above List Price
    • $261/SF
    • 4 Days On Market

    Current Estimated Value $667,986

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
    • /24

      Est $420,414

      Not Listed For Sale

      1680 W Hill Dr, Readsboro, VT 05350

      • 4 Beds
      • Built 1980
      1680 W Hill Dr, Readsboro, VT 05350

      Last Sold Summary

      • 409 Days On Market

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /2

    $4,177,625

    $802K PRICE DROP
    • 33,801 Sq Ft

    1000 Investors Ln, Manchester, VT 05255

    Exceptional opportunity to acquire a well-established Vermont investment portfolio consisting of 10 properties inclusive of 33 residential units and 2 commercial units located across the desirable communities of Brattleboro, Ludlow, Manchester, Cavendish, Shaftsbury, Proctorsville, and Chester. This diverse portfolio has been thoughtfully maintained and professionally managed, with many long-term

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    1000 Investors Ln, Manchester, VT 05255
  • /37

    $777,500

    Sold Jun 01, 2026

    34 Mountain View Rd, Winhall, VT 05360

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Below List Price
    • $311/SF
    • 15 Days On Market

    Last Listing Agent Jason Saphire www.HomeZu.com

    34 Mountain View Rd, Winhall, VT 05360
    • /21

      Est $257,635

      Not Listed For Sale

      470 Alpenwald Ln Unit A57, Readsboro, VT 05350

      • 3 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1970
      470 Alpenwald Ln Unit A57, Readsboro, VT 05350

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Ruth Goyette Lamacchia Realty, Inc. - Adams

  • /7

    $997,000

    • Land
    • 23,086 Sq Ft
    • $1,881,132 per Acre

    153 Northside Dr, Bennington, VT 05201

    Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

    Lori Hurley Four Corner Properties LLC

    153 Northside Dr, Bennington, VT 05201
  • /43

    $755,000

    Sold Nov 14, 2025

    43 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 3,020 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $250/SF
    • 0 Days On Market

    Current Estimated Value $751,921

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /28

      Est $388,781

      Not Listed For Sale

      469 Swallow Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft
      • Built 1993
      469 Swallow Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 138 Days On Market

      Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

  • /58

    $1,599,000

    • 4 Beds
    • 2.5 Baths
    • 5,403 Sq Ft

    525 Andrea Dr, Stamford, VT 05352

    Paradise Found!Exquisite Vermont Retreat. Follow the gravel road to the end and you will discover this amazing wonderfully protected and private home on 37 acres in the peaceful town of Stamford. The best of Vermont skiing, boating, hiking, winter and summer recreation as well as the shopping, dining, art, and culture of the Berkshires of Massachusetts are also just a short drive away. Bright

    Paul Harsch Harsch Associates

    525 Andrea Dr, Stamford, VT 05352
  • /60

    $422,500

    Sold Jun 15, 2026

    2603 N Pownal Rd, Pownal, VT 05261

    • 3 Beds
    • 2.5 Baths
    • 1,764 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $240/SF
    • 12 Days On Market

    Current Estimated Value $419,336

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    2603 N Pownal Rd, Pownal, VT 05261
    • /39

      Est $430,858

      Not Listed For Sale

      375 Grapevine Ln, Pownal, VT 05261

      • 4 Beds
      • 3 Baths
      • 2,208 Sq Ft
      • Built 2011
      375 Grapevine Ln, Pownal, VT 05261

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /52

    $2,285,000

    • 5 Beds
    • 4.5 Baths
    • 4,647 Sq Ft

    543 Lower Hollow Rd, Dorset, VT 05251

    A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

    Britt Wohler

    543 Lower Hollow Rd, Dorset, VT 05251
  • /30

    $277,000

    Sold Jul 10, 2026

    212 Dewey St, Bennington, VT 05201

    • 2 Beds
    • 2.5 Baths
    • 1,265 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $219/SF

    Current Estimated Value $273,244

    Last Listing Agent William Paquin Maple Leaf Real Estate

    212 Dewey St, Bennington, VT 05201
    • /40

      Est $401,436

      Not Listed For Sale

      201 Sunset Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 1.5 Baths
      • 1,720 Sq Ft
      • Built 2003
      201 Sunset Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  • /25

    $599,000

    $21K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 1,768 Sq Ft

    35 Valley Pass St, Manchester, VT 05255

    Welcome to this beautifully updated Cape offering 4 bedrooms and 3 bathrooms in one of Manchester's most desirable neighborhoods. Thoughtfully renovated with extensive recent improvements, this turnkey home blends classic New England character with modern style, comfort, and efficiency. The heart of the home is the bright, open-concept living space, where a beautifully renovated kitchen features

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    35 Valley Pass St, Manchester, VT 05255
  • /3

    $283,505

    Sold May 11, 2026

    11 Maltese Rd, Stamford, VT 05352

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1978

    Last Sold Summary

    • 3% Above List Price
    • $295/SF
    • 0 Days On Market

    Current Estimated Value $284,001

    Last Listing Agent Ann Greenwood Alton + Westall Real Estate Agency, LLC

    11 Maltese Rd, Stamford, VT 05352
    • /27

      Est $586,916

      Not Listed For Sale

      503 Atwood Dr, Pownal, VT 05261

      • 3 Beds
      • 2.5 Baths
      • 2,160 Sq Ft
      • Built 2004
      503 Atwood Dr, Pownal, VT 05261

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /9

    $269,000

    $26K PRICE DROP
    • 2,206 Sq Ft

    116 S Branch St Unit 118, Bennington, VT 05201

    Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

    Julie Glover Mahar McCarthy Real Estate

    116 S Branch St Unit 118, Bennington, VT 05201
  • /37

    $256,250

    Sold Sep 03, 2025

    1236 Morgan St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,259 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $204/SF
    • 7 Days On Market

    Current Estimated Value $267,860

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1236 Morgan St, Bennington, VT 05201
    • /16

      Est $321,812

      Not Listed For Sale

      89 Field Way, Pownal, VT 05261

      • 2 Beds
      • 1.5 Baths
      • 1,152 Sq Ft
      • Built 2006
      89 Field Way, Pownal, VT 05261

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Lori Hurley Four Corner Properties LLC

  • /13

    $275,000

    $20K PRICE DROP
    • 2,022 Sq Ft

    124 S Branch St, Bennington, VT 05201

    Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201

Showing Results 401 - 440, Page 11 of 18

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