21,299

Bennington County, VT Homes

Section Image
  • /46

    $399,000

    Sold Jul 28, 2025

    4 Bank St, Bennington, VT 05201

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Below List Price
    • $231/SF
    • 55 Days On Market

    Current Estimated Value $394,953

    Last Listing Agent Margretta Fischer Wohler Realty Group

    4 Bank St, Bennington, VT 05201
    • /25

      Est $755,691

      Not Listed For Sale

      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1968
      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 15 Days On Market

  • /32

    $534,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    764 Myers Rd, Shaftsbury, VT 05262

    This charming, beautifully updated Cape sits on a sprawling 2-acre lot in a highly sought-after section of Shaftsbury, offering breathtaking panoramic mountain views. Boasting character and gleaming hardwood floors throughout. The first floor features a large living room with built-in bookshelves and cozy wood stove, a primary bedroom, full bath, and spacious country kitchen with granite

    Matt Waddington Hoffman Real Estate

    764 Myers Rd, Shaftsbury, VT 05262
  • /4

    $225,000

    Sold Dec 19, 2025

    00 Margeaux Ln, Stratton, VT 05155

    • Land
    • 1.99 Acres
    • $113,065 per Acre

    Last Sold Summary

    • 189 Days On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    00 Margeaux Ln, Stratton, VT 05155
    • /35

      Not Listed For Sale

      15 Stratton View Rd, Bondville, VT 05340

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1964
      15 Stratton View Rd, Bondville, VT 05340

      Last Sold Summary

      • 1 Day On Market

  • /53

    $2,850,000

    Under Contract
    • 5 Beds
    • 5.5 Baths
    • 6,182 Sq Ft

    86 Church St, Dorset, VT 05251

    Set on the north side of the Dorset Green, 86 and 78 Church Street present a rare village compound in the heart of Dorset. Fully renovated with exceptional attention to detail, this refined micro-estate blends timeless New England character with sophisticated modern living. Encompassing the main residence, guest cottage, gardens, and garage, the property is both gracious in scale and intimate in

    Christiane Carroccio TPW Real Estate

    86 Church St, Dorset, VT 05251
  • /35

    $329,900

    Sold Aug 28, 2025

    170 Brambley Ln, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,459 Sq Ft
    • Built 1969

    Last Sold Summary

    • $226/SF
    • 4 Days On Market

    Current Estimated Value $320,067

    Last Listing Agent Matt Waddington Hoffman Real Estate

    170 Brambley Ln, Bennington, VT 05201
    • /11

      Est $649,495

      Not Listed For Sale

      1238 North Rd, East Arlington, VT 05252

      • 3 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2003
      1238 North Rd, East Arlington, VT 05252

      Last Sold Summary

      • 4 Days On Market

  • /26

    $450,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

    Exceptional Birch Hill residence showcasing one of the community’s most impressive renovations, designed for modern mountain living. At the heart of the home is a stunning kitchen that seamlessly blends style, function, and warmth — ideal for lively après-ski entertaining or relaxed Vermont weekends.With three well-appointed bedrooms plus an expansive den, there is ample space for family and

    Helen Nault

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
  • /13

    $60,500

    Sold May 18, 2026

    1488 Morgan St, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Above List Price
    • $48/SF
    • 14 Days On Market

    Current Estimated Value $256,667

    Last Listing Agent Dick Thackston R.H. Thackston & Company

    1488 Morgan St, Bennington, VT 05201
    • /14

      Est $411,961

      Not Listed For Sale

      535 Dunlap Farm Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1986
      535 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 55 Days On Market

  • /58

    $1,495,000

    Under Contract
    • 7 Beds
    • 5.5 Baths
    • 6,392 Sq Ft

    16 West Rd, Bennington, VT 05201

    Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless

    Kelley Mccarthy Mahar McCarthy Real Estate

    16 West Rd, Bennington, VT 05201
  • /47

    $365,000

    Sold Sep 11, 2025

    84 Jasper Ln, Arlington, VT 05250

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $190/SF
    • 69 Days On Market

    Current Estimated Value $356,960

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

    84 Jasper Ln, Arlington, VT 05250
    • /40

      Est $101,628

      Not Listed For Sale

      51 Chiselville Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 540 Sq Ft
      • Built 1820
      51 Chiselville Rd, Arlington, VT 05250

      Last Sold Summary

      • 6 Days On Market

  • /32

    $775,000

    • 5 Beds
    • 2 Baths
    • 3,500 Sq Ft

    20 Bishop Rd, Searsburg, VT 05363

    Sweeping long-range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton ridgelines from this stunning 2020 Moosehead log home. Situated on 7+ acres bordering thousands of acres of National Forest, the property offers direct access to VAST snowmobile trails, space to create your own private loops, and exceptional privacy — all while remaining just a short

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Bishop Rd, Searsburg, VT 05363
  • /37

    $950,000

    Sold Nov 20, 2025

    1589 Richville Rd, Manchester Center, VT 05255

    • 5 Beds
    • 4.5 Baths
    • 3,697 Sq Ft
    • Built 1850

    Last Sold Summary

    • 14% Below List Price
    • $257/SF
    • 91 Days On Market

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

    1589 Richville Rd, Manchester Center, VT 05255
    • /18

      Est $516,587

      Not Listed For Sale

      55 Wildflower Ln, Arlington, VT 05250

      • 3 Beds
      • 2.5 Baths
      • 2,514 Sq Ft
      • Built 1997
      55 Wildflower Ln, Arlington, VT 05250

      Last Sold Summary

      • 46 Days On Market

  • /44

    $1,050,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,584 Sq Ft

    5173 Route 30, Dorset, VT 05251

    Discover the ease and charm of Vermont living in this beautifully maintained farmhouse, thoughtfully designed for comfort and everyday convenience. Set on 0.85 acres of manicured grounds, this spacious home offers four bedrooms, five bathrooms, and an attached two-car garage.The open floor plan creates a welcoming flow, perfect for both quiet evenings and hosting family and friends. A

    David Halligan Four Seasons Sotheby's Int'l Realty

    5173 Route 30, Dorset, VT 05251
  • /28

    $401,000

    Sold Mar 27, 2026

    2023 North Rd, Arlington, VT 05250

    • 3 Beds
    • 1.5 Baths
    • 1,222 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $328/SF
    • 35 Days On Market

    Current Estimated Value $394,703

    Last Listing Agent Mandolyn McIntyre Crow Real Broker LLC

    2023 North Rd, Arlington, VT 05250
    • /37

      Est $460,647

      Not Listed For Sale

      127 Flynn Hollow Rd, Sunderland, VT 05250

      • 3 Beds
      • 1.5 Baths
      • 1,718 Sq Ft
      • Built 1989
      127 Flynn Hollow Rd, Sunderland, VT 05250

      Last Sold Summary

      • 3 Days On Market

  • /31

    $90,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    109 Evergreen Dr, Bennington, VT 05201

    House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

    Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
  • /35

    $810,000

    Sold May 29, 2026

    2930 Richville Rd, Manchester, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,882 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $281/SF
    • 14 Days On Market

    Last Listing Agent Sara Buckley Josiah Allen Real Estate, Inc.

    2930 Richville Rd, Manchester, VT 05255
    • /34

      Est $205,288

      Not Listed For Sale

      925 South Rd, East Arlington, VT 05252

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1972
      925 South Rd, East Arlington, VT 05252

      Last Sold Summary

      • 6 Days On Market

  • /24

    $399,000

    • 3 Beds
    • 1 Bath
    • 1,535 Sq Ft

    515 Buck Hill Rd, Arlington, VT 05250

    OPEN HOUSE SATURDAY 6/13 9am to 2pm. Completely renovated from top to bottom, this move-in-ready home perfectly blends modern updates with classic Vermont charm. 3 bedrooms and 1 bathroom with a layout that includes multiple practical options for adding a second bathroom. The layout also includes a unique, unfinished bonus area off the primary bedroom with its own private staircase to the

    Lori Hurley Four Corner Properties LLC

    515 Buck Hill Rd, Arlington, VT 05250
  • /21

    $465,000

    Sold Sep 12, 2025

    4195 Route 30, Dorset, VT 05251

    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft
    • Built 1757

    Last Sold Summary

    • 2% Above List Price
    • $316/SF
    • 2 Days On Market

    Current Estimated Value $516,433

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

    4195 Route 30, Dorset, VT 05251
    • /25

      Est $437,415

      Not Listed For Sale

      125 Chiselville Rd, Arlington, VT 05250

      • 4 Beds
      • 4 Baths
      • 1,593 Sq Ft
      • Built 1880
      125 Chiselville Rd, Arlington, VT 05250

      Last Sold Summary

      • 31 Days On Market

  • /25

    $1,200,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,736 Sq Ft

    12 Beattie Ln, Manchester, VT 05254

    First Time on the Market! Beautifully positioned ranch-style home set on 4 scenic acres with mountain views. This bright and inviting property features abundant natural sunlight, with numerous windows in both the front and back of the home. Enjoy cathedral ceilings in the living and dining rooms. Family and living rooms with its own wood-burning fireplaces perfect for cozy gatherings. The

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    12 Beattie Ln, Manchester, VT 05254
  • /54

    $225,000

    Sold Sep 10, 2025

    304 North St Unit 6, Bennington, VT 05201

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Above List Price
    • $104/SF
    • 15 Days On Market

    Current Estimated Value $235,953

    Last Listing Agent Thomas Martins Maple Leaf Real Estate

    304 North St Unit 6, Bennington, VT 05201
    • /34

      Est $494,365

      Not Listed For Sale

      3600 North Rd, Arlington, VT 05250

      • 3 Beds
      • 2.5 Baths
      • 1,891 Sq Ft
      • Built 2004
      3600 North Rd, Arlington, VT 05250

      Last Sold Summary

      • 40 Days On Market

  • /28

    $729,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft

    21 Burnt Hill Rd, Winhall, VT 05341

    Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont! This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just minutes

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
  • /43

    $340,000

    Sold May 14, 2026

    80 Murray Hill South Rd Unit 11, Manchester, VT 05255

    • 2 Beds
    • 1.5 Baths
    • 1,163 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $292/SF
    • 3 Days On Market

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

    80 Murray Hill South Rd Unit 11, Manchester, VT 05255
    • /32

      Est $465,551

      Not Listed For Sale

      2128 North Rd, Arlington, VT 05250

      • 3 Beds
      • 2 Baths
      • 1,552 Sq Ft
      • Built 1987
      2128 North Rd, Arlington, VT 05250

      Last Sold Summary

      • 4 Days On Market

  • /23

    $550,000

    Open Sun 11AM - 1PM Pending
    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft

    144 Oak Knoll Rd, Arlington, VT 05250

    OPEN HOUSE SCHEDULED FOR 6/21/26 HAS BEEN CANCELED!!! SELLER HAS ACCEPTED AN OFFER! Completely Updated with Stunning Views and a Prime Central Location!This exceptional home truly has it all. From the moment you step inside, you'll be welcomed by a warm and inviting atmosphere that instantly feels like home. Thoughtfully designed with a seamless flow, the living spaces are both comfortable

    Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

    144 Oak Knoll Rd, Arlington, VT 05250
  • /19

    $426,000

    Sold Jan 16, 2026

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340

    • 2 Beds
    • 2 Baths
    • 1,798 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $237/SF
    • 1 Day On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340
    • /38

      Est $300,076

      Not Listed For Sale

      1469 Sunderland Hill Rd, Arlington, VT 05250

      • 3 Beds
      • 1.5 Baths
      • 1,268 Sq Ft
      • Built 1958
      1469 Sunderland Hill Rd, Arlington, VT 05250

      Last Sold Summary

      • 4 Days On Market

  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /9

    $65,000

    Sold May 27, 2026

    0 Evergreen Dr, Bennington, VT 05201

    • Land
    • 9.24 Acres
    • $7,035 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    0 Evergreen Dr, Bennington, VT 05201
    • /26

      Est $386,010

      Not Listed For Sale

      131 Mckee Rd, Arlington, VT 05250

      • 3 Beds
      • 3 Baths
      • 1,732 Sq Ft
      • Built 1985
      131 Mckee Rd, Arlington, VT 05250

      Last Sold Summary

      • 7 Days On Market

  • /7

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    447 Rock Bottom Ln, Peru, VT 05152

    Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

    Andy Reed Four Seasons Sotheby's Int'l Realty

    447 Rock Bottom Ln, Peru, VT 05152
  • /44

    $375,000

    Sold Jun 12, 2026

    4991 Vt Route 313 W, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $268/SF
    • 75 Days On Market

    Current Estimated Value $373,513

    Last Listing Agent Margretta Fischer Wohler Realty Group

    4991 Vt Route 313 W, Arlington, VT 05250

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home