20,611

Bennington County, VT Homes

Section Image
    • /29

      Est $588,215

      Not Listed For Sale

      335 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1987
      335 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /38

    $775,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 3,520 Sq Ft

    12 Stratton Ridge Rd, Winhall, VT 05340

    First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

    Carrie Mathews Winhall Real Estate

    12 Stratton Ridge Rd, Winhall, VT 05340
  • /53

    $495,000

    Sold Oct 17, 2025

    200 Applewood Ln, Manchester Center, VT 05255

    • 2,746 Sq Ft
    • Built 1986

    Last Sold Summary

    • $180/SF
    • 4 Days On Market

    Current Estimated Value $543,721

    Last Listing Agent Zachary Zupan EXP Realty

    200 Applewood Ln, Manchester Center, VT 05255
    • /37

      Est $771,117

      Not Listed For Sale

      173 N Ridge Run, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,829 Sq Ft
      • Built 1992
      173 N Ridge Run, Manchester Center, VT 05255

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /54

    $460,000

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,312 Sq Ft

    498 Townline Rd, Bennington, VT 05201

    If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

    Betty McEnaney Diamond Realty

    498 Townline Rd, Bennington, VT 05201
  • /42

    $529,000

    Sold Apr 15, 2026

    941 Myers Rd, Shaftsbury, VT 05262

    • 4 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 1900

    Last Sold Summary

    • $281/SF
    • 2 Days On Market

    Current Estimated Value $556,199

    Last Listing Agent Abi Gregorio

    941 Myers Rd, Shaftsbury, VT 05262
    • /43

      Est $608,667

      Not Listed For Sale

      78 Stoney Fields Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 1,710 Sq Ft
      • Built 1964
      78 Stoney Fields Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 61 Days On Market

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

  • /45

    $255,000

    $40K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /21

    $120,000

    Sold Mar 09, 2026

    1319 Vail Rd, Bennington, VT 05201

    • Land
    • 20 Acres
    • $6,000 per Acre

    Last Sold Summary

    • 143 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    1319 Vail Rd, Bennington, VT 05201
    • /31

      Est $481,259

      Not Listed For Sale

      6344 Main St, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 1,244 Sq Ft
      • Built 1950
      6344 Main St, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /60

    $735,000

    $64K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft

    2734 Mad Tom Rd, East Dorset, VT 05253

    Vermont's rustic charm will welcome you in a warm embrace every time you enter this custom built post and beam home on 37.5 private acres. The home features 2 bedrooms plus loft and 2 baths with tons of natural woodwork. The property also includes a detached post and beam garage with additional space above, perfect for an art studio, writer's workshop or plenty of extra storage. The property

    David Citron RE/MAX Four Seasons

    2734 Mad Tom Rd, East Dorset, VT 05253
  • /48

    $306,250

    Sold Dec 05, 2025

    4581 Main Rd, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft
    • Built 1967

    Last Sold Summary

    • 18% Above List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $326,595

    Last Listing Agent Susan Colvin MONARCH REALTY, INC.

    4581 Main Rd, Stamford, VT 05352
    • /34

      Est $879,299

      Not Listed For Sale

      50 Ways Ln, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 3,196 Sq Ft
      • Built 1970
      50 Ways Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Tyler Hirchak

  • /48

    $1,990,000

    • 4 Beds
    • 3.5 Baths
    • 3,844 Sq Ft

    209 Jack Cross Rd, Shaftsbury, VT 05262

    "Stone Meadows" a quintessential Vermont farmhouse set on more than 72 acres of rolling meadows, historic stone walls & peaceful countryside in Shaftsbury. Tucked along a quiet country road, this is the kind of property that captures the feeling so many people come to Vermont to find privacy, open land, character & and a home that feels connected to its surroundings. Serene and peaceful yet 17

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

    209 Jack Cross Rd, Shaftsbury, VT 05262
  • /41

    $400,000

    Sold Sep 24, 2026

    2984 Vt Route 313 W, Arlington, VT 05250

    • 5 Beds
    • 2 Baths
    • 1,963 Sq Ft
    • Built 1945

    Last Sold Summary

    • 1% Above List Price
    • $204/SF
    • 4 Days On Market

    Current Estimated Value $390,122

    Last Listing Agent Derryl Lang Four Seasons Sotheby's Int'l Realty

    2984 Vt Route 313 W, Arlington, VT 05250
    • /29

      Est $612,519

      Not Listed For Sale

      271 Nottingham Park, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,422 Sq Ft
      • Built 1986
      271 Nottingham Park, Manchester Center, VT 05255

      Last Sold Summary

      • 55 Days On Market

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

  • /41

    $415,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    87 B Hill Rd, Pownal, VT 05261

    Vermont retreat nestled on 3.2 acres in the mountains of Pownal: "Gateway to Vermont". Right in the corner of NY and Mass, this Adirondack-style home offers the perfect blend of rustic charm, thoughtful craftsmanship, and everyday comfort.Surrounded by walking trails, blueberry and raspberry bushes, fruit trees, and abundant wildlife, the property is designed for those who appreciate the

    Lilli West Maple Leaf Real Estate

    87 B Hill Rd, Pownal, VT 05261
  • /35

    $799,000

    Sold Jul 17, 2026

    63 Raspberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 3.5 Baths
    • 3,078 Sq Ft
    • Built 1980

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    63 Raspberry Hill Rd, Winhall, VT 05340
    • /17

      Est $376,615

      Not Listed For Sale

      7935 Main St, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 1,382 Sq Ft
      • Built 1775
      7935 Main St, Manchester Center, VT 05255

      Last Sold Summary

      • 229 Days On Market

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

  • /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
  • /27

    $300,000

    Sold Dec 11, 2025

    0 Rock Bottom Ln, Peru, VT 05152

    • Land
    • 53 Acres
    • $5,660 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 156 Days On Market

    Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

    0 Rock Bottom Ln, Peru, VT 05152
    • /27

      Est $642,762

      Not Listed For Sale

      211 Little John Dr, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1980
      211 Little John Dr, Manchester Center, VT 05255

      Last Sold Summary

      • 68 Days On Market

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

  • /7

    $145,000

    $30K PRICE DROP Pending
    • 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
  • /46

    $1,270,000

    Sold Mar 20, 2026

    33 Forest Haunts Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $274/SF
    • 487 Days On Market

    Current Estimated Value $1,410,146

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

    33 Forest Haunts Rd, Winhall, VT 05340
    • /31

      Est $536,317

      Not Listed For Sale

      1 Cass Terrace, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 1913
      1 Cass Terrace, Manchester Center, VT 05255

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /27

    $345,000

    $24K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft

    686 Route 30, Dorset, VT 05251

    Village Mixed Use zoned Residence and Separate cottage located in the Hamlett of South Dorset...nearby Dorset's elementary School and Sheldon's Market. Conveniently located 3 miles from Manchester Ctr to the South or Dorset Village to the North. The main house offers 1350 SF, 2 bedrooms with overflow room, large closet, and sunroom entrance... The cottage is 675 SF with one bedroom and a

    Laura Beckwith Josiah Allen Real Estate, Inc.

    686 Route 30, Dorset, VT 05251
  • /18

    $350,000

    Sold Sep 11, 2026

    526 Jennings Brook Dr, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Built 2026

    Last Sold Summary

    • $294/SF
    • 0 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    526 Jennings Brook Dr, Bennington, VT 05201
    • /40

      Est $1,024,132

      Not Listed For Sale

      292 Johnnycake St, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 3,228 Sq Ft
      • Built 1984
      292 Johnnycake St, Manchester Center, VT 05255

      Last Sold Summary

      • 100 Days On Market

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

  • /32

    $765,000

    • 3 Beds
    • 3 Baths
    • 2,322 Sq Ft

    72 Benson Fuller Dr, Winhall, VT 05340

    Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

    Christine Chovan

    72 Benson Fuller Dr, Winhall, VT 05340
  • /43

    $1,374,000

    Sold May 21, 2026

    12 Sunny Hill Rd, Manchester Center, VT 05255

    • 4 Beds
    • 3.5 Baths
    • 5,397 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $255/SF
    • 50 Days On Market

    Current Estimated Value $1,173,459

    Last Listing Agent Carrie Mathews Winhall Real Estate

    12 Sunny Hill Rd, Manchester Center, VT 05255
    • /24

      Est $609,663

      Not Listed For Sale

      2071 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,792 Sq Ft
      • Built 1980
      2071 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Robert Sabol Wohler Realty Group

  • /38

    $315,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    51 Pageant St, Bennington, VT 05201

    There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous

    Angela Bevin Maple Leaf Real Estate

    51 Pageant St, Bennington, VT 05201
  • /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 $664,081

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    7 Landgrove Rd, Landgrove, VT 05148
    • /37

      Est $842,247

      Not Listed For Sale

      505 Powderhorn Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,089 Sq Ft
      • Built 1976
      505 Powderhorn Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 40 Days On Market

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

  • /38

    $605,000

    $20K PRICE DROP
    • 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
  • /21

    $545,000

    Sold Aug 07, 2026

    43 Murray Hill Heights Rd Unit 37, Manchester, VT 05255

    • 2 Beds
    • 2.5 Baths
    • 1,596 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $341/SF
    • 4 Days On Market

    Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

    43 Murray Hill Heights Rd Unit 37, Manchester, VT 05255
    • /33

      Est $538,170

      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

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

  • /37

    $329,000

    $70K 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
  • /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
    • /42

      Est $517,033

      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

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

Showing Results 641 - 680, Page 17 of 18

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