21,174

Bennington County, VT Homes

Section Image
    • /35

      Est $776,576 Not Listed For Sale

      2529 Main St, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft
      • Built 1780
      2529 Main St, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Above List Price
      • $290/SF
      • 9 Days On Market
      • Last Sold Price $731,000
      • Aug 16, 2024

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

  • /10

    $342,000

    • Land
    • 28.5 Acres
    • $12,000 per Acre

    11 Old County Rd E, Londonderry, VT 05148

    A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    11 Old County Rd E, Londonderry, VT 05148
  • /59

    $720,000 Sold Sep 12, 2025

    422 N Mason Hill Rd, Pownal, VT 05261

    • 4 Beds
    • 4 Baths
    • 4,844 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $149/SF
    • 5 Days On Market

    Current Estimated Value $699,412

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    422 N Mason Hill Rd, Pownal, VT 05261
    • /41

      Est $586,612 Not Listed For Sale

      1565 E Manchester Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,088 Sq Ft
      • Built 1967
      1565 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 9% Above List Price
      • $259/SF
      • 5 Days On Market
      • Last Sold Price $540,000
      • Nov 12, 2024

      Last Listing Agent Jessica Citera Cummings & Co

  • /48

    $227,500 Under Contract

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft

    47 Sycamore Ln, Shaftsbury, VT 05262

    Cute as a button! Located on a dead-end street in a desirable neighborhood in the village of Shaftsbury. This sweet two bedroom home sits on a nice sized lot with some backyard privacy and a beautiful view of the woods. The deep garage has plenty of room for your car and extra storage space in the back. Step into the three season porch where you can enjoy the outdoors without the bugs! The

    Justine Curry Maple Leaf Realty

    47 Sycamore Ln, Shaftsbury, VT 05262
  • /43

    $115,000 Sold Aug 29, 2025

    0000 Skiparee Rd, Pownal, VT 05261

    • Land
    • 25.7 Acres
    • $4,475 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

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

    0000 Skiparee Rd, Pownal, VT 05261
    • /11

      Est $603,606 Not Listed For Sale

      470 Johnnycake St, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,576 Sq Ft
      • Built 1950
      470 Johnnycake St, Manchester Center, VT 05255

      Last Sold Summary

      • 8% Above List Price
      • $354/SF
      • 41 Days On Market
      • Last Sold Price $557,500
      • Aug 17, 2023

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

  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /22

    $445,000 Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $449,583

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

    163 Vt Route 30, Winhall, VT 05340
    • /40

      Not Listed For Sale

      658 Finbars Forest Rd, Manchester Center, VT 05255

      • 5 Beds
      • 4 Baths
      • 2,602 Sq Ft
      • Built 1989
      658 Finbars Forest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • $250/SF
      • 5 Days On Market
      • Last Sold Price $650,000
      • Dec 11, 2023

      Last Listing Agent Lindsey Pinder Josiah Allen Real Estate, Inc.

  • /45

    $295,000

    • 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
  • /4

    $35,000 Sold Jan 20, 2026

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352

    • Land
    • 2 Acres
    • $17,500 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 106 Days On Market

    Last Listing Agent Duncan Honig Maple Leaf Realty

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
    • /32

      Est $956,781 Not Listed For Sale

      1145 Powderhorn Rd, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,728 Sq Ft
      • Built 1983
      1145 Powderhorn Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 19% Above List Price
      • $216/SF
      • 109 Days On Market
      • Last Sold Price $806,250
      • Apr 17, 2024

      Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  • /29

    $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
  • /55

    $707,500 Sold Jul 17, 2025

    697 Hamilton Hollow Rd, Arlington, VT 05250

    • 3 Beds
    • 2.5 Baths
    • 2,944 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Below List Price
    • $240/SF
    • 55 Days On Market

    Current Estimated Value $669,429

    Last Listing Agent Faith Rhodes Maple Leaf Realty

    697 Hamilton Hollow Rd, Arlington, VT 05250
    • /31

      Est $517,069 Not Listed For Sale

      109 Hillcrest Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1969
      109 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 8% Above List Price
      • $500/SF
      • 10 Days On Market
      • Last Sold Price $480,000
      • Apr 18, 2024

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

  • /43

    $1,895,000

    • 6 Beds
    • 5.5 Baths
    • 5,178 Sq Ft

    144 Taconic Rd, Manchester, VT 05255

    “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

    Tom Deck Josiah Allen Real Estate, Inc.

    144 Taconic Rd, Manchester, VT 05255
  • /60

    $1,300,000 Sold Dec 10, 2025

    694 Sykes Hollow Rd, Rupert, VT 05776

    • 3 Beds
    • 2.5 Baths
    • 2,259 Sq Ft
    • Built 1789

    Last Sold Summary

    • 2% Above List Price
    • $575/SF
    • 15 Days On Market

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    694 Sykes Hollow Rd, Rupert, VT 05776
    • /35

      Est $691,951 Not Listed For Sale

      602 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,907 Sq Ft
      • Built 1960
      602 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Above List Price
      • $341/SF
      • 5 Days On Market
      • Last Sold Price $650,000
      • Oct 03, 2023

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

  • /31

    $329,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    103 Norton St, Bennington, VT 05201

    Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living.Step inside to find gleaming hardwood floors that flow throughout

    Timothy Corcoran Mahar McCarthy Real Estate

    103 Norton St, Bennington, VT 05201
  • /26

    $193,500 Sold Aug 06, 2025

    305 Weeks St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft
    • Built 1937

    Last Sold Summary

    • 3% Below List Price
    • $119/SF
    • 17 Days On Market

    Current Estimated Value $198,713

    Last Listing Agent Matt Waddington Hoffman Real Estate

    305 Weeks St, Bennington, VT 05201
    • /31

      Est $532,078 Not Listed For Sale

      373 Highland Ave, Manchester Center, VT 05255

      • 4 Beds
      • 1.5 Baths
      • 1,830 Sq Ft
      • Built 1905
      373 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 1% Above List Price
      • $287/SF
      • 5 Days On Market
      • Last Sold Price $525,000
      • Jan 14, 2025

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

  • /7

    $175,000

    • Land
    • 15.49 Acres
    • $11,298 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
  • /55

    $800,000 Sold Nov 17, 2025

    879 River Rd, Manchester, VT 05255

    • 3 Beds
    • 3.5 Baths
    • 2,340 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $342/SF
    • 34 Days On Market

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

    879 River Rd, Manchester, VT 05255
    • /34

      Est $734,148 Not Listed For Sale

      196 Ways Ln, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 2,304 Sq Ft
      • Built 1929
      196 Ways Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 5% Above List Price
      • $303/SF
      • 7 Days On Market
      • Last Sold Price $699,000
      • Aug 04, 2023

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

  • /44

    $199,000

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft

    106 Park St Unit 2, Bennington, VT 05201

    Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

    Vicki Wilson Maple Leaf Realty

    106 Park St Unit 2, Bennington, VT 05201
  • /15

    $640,000 Sold Feb 26, 2026

    105 Elm St, Manchester, VT 05255

    • 5 Beds
    • 4 Baths
    • 3,732 Sq Ft
    • Built 1850

    Last Sold Summary

    • $171/SF
    • 2 Days On Market

    Last Listing Agent David Citron RE/MAX Four Seasons

    105 Elm St, Manchester, VT 05255
    • /17

      Est $320,915 Not Listed For Sale

      1581 E Manchester Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 1952
      1581 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 13% Above List Price
      • $299/SF
      • 8 Days On Market
      • Last Sold Price $285,000
      • Apr 26, 2024

      Last Listing Agent Patti Trudel RE/MAX

  • /35

    $1,175,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,425 Sq Ft

    3436 Main St, Manchester, VT 05254

    Set in the heart of Manchester Village, this beautifully renovated historic home blends timeless character with thoughtful modern updates. The result is a warm and inviting residence that honors its past while offering the comfort and style of today. The kitchen and great room are the true centerpiece of the home, stunning in both design and function, with high-end finishes and an open feel ideal

    Christiane Carroccio TPW Real Estate

    3436 Main St, Manchester, VT 05254
  • /38

    $291,065 Sold Jul 11, 2025

    121 Fillmore St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1946

    Last Sold Summary

    • 1% Above List Price
    • $168/SF
    • 66 Days On Market

    Current Estimated Value $303,825

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    121 Fillmore St, Bennington, VT 05201
    • /28

      Est $224,384 Not Listed For Sale

      433 Squires Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 1,142 Sq Ft
      • Built 1974
      433 Squires Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 11% Above List Price
      • $176/SF
      • 9 Days On Market
      • Last Sold Price $201,500
      • Apr 03, 2025

      Last Listing Agent Linda Benoit Highland Realty

  • /46

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 6,129 Sq Ft

    1035 Holy Smoke Rd, Shaftsbury, VT 05262

    Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

    Lori Hurley Four Corner Properties LLC

    1035 Holy Smoke Rd, Shaftsbury, VT 05262
  • /33

    $685,000 Sold Apr 16, 2026

    158 Upland Downs Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1983

    Last Sold Summary

    • 16% Below List Price
    • $393/SF
    • 147 Days On Market

    Current Estimated Value $787,088

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

    158 Upland Downs Rd, Manchester Center, VT 05255
    • /40

      Est $1,622,377 Not Listed For Sale

      2894 West Rd, Manchester Center, VT 05255

      • 3 Beds
      • 6 Baths
      • 3,556 Sq Ft
      • Built 1970
      2894 West Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 2% Below List Price
      • $464/SF
      • 60 Days On Market
      • Last Sold Price $1,650,000
      • Oct 07, 2024

      Last Listing Agent Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  • /36

    $399,000 Pending

    • 5 Beds
    • 3 Baths
    • 3,118 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 Realty

    100 McCarthy Acres, North Bennington, VT 05257
  • /60

    $235,000 Sold May 20, 2025

    1304 Vermont Route 100, Readsboro, VT 05350

    • Land
    • 5 Acres
    • $47,000 per Acre

    Last Sold Summary

    • 88 Days On Market

    Last Listing Agent Lisa Friedman Great American Dream Realty

    1304 Vermont Route 100, Readsboro, VT 05350
    • /20

      Est $594,687 Not Listed For Sale

      290 Deer Meadow Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 1,635 Sq Ft
      • Built 1970
      290 Deer Meadow Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 10% Above List Price
      • $330/SF
      • 57 Days On Market
      • Last Sold Price $540,000
      • Sep 08, 2023

      Last Listing Agent Donna Murray Varick Associates Ltd

  • /32

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,234 Sq Ft

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

    This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

    David Halligan Four Seasons Sotheby's Int'l Realty

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
  • /14

    $20,000 Sold Oct 30, 2025

    79 Skytop Dr Unit 6, Bennington, VT 05201

    • 1 Bed
    • 1 Bath
    • 561 Sq Ft
    • Built 1950

    Last Sold Summary

    • 27% Below List Price
    • $36/SF
    • 0 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    79 Skytop Dr Unit 6, Bennington, VT 05201
    • /29

      Est $756,038 Not Listed For Sale

      110 Highland Ave, Manchester Center, VT 05255

      • 5 Beds
      • 3.5 Baths
      • 2,912 Sq Ft
      • Built 1890
      110 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Above List Price
      • $246/SF
      • 4 Days On Market
      • Last Sold Price $715,000
      • Jun 13, 2024

      Last Listing Agent Jamie Luke TPW Real Estate

Showing Results 521 - 560, Page 14 of 18

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