21,299

Bennington County, VT Homes

Section Image
    • /40

      Est $919,000

      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

  • /45

    $299,900

    Under Contract
    • 5 Beds
    • 2.5 Baths
    • 2,716 Sq Ft

    886 Hidden Valley Rd, Shaftsbury, VT 05262

    Escape to the rustic charm of this beautiful 5 bedroom, 2.5 bath log cabin nestled on 2 peaceful acres in the highly desirable town of Shaftsbury. From the moment you step inside, you’ll fall in love with the warm log features throughout, exposed beam ceilings, and the cozy fireplace that anchors the inviting living room. The charming country kitchen flows into a dedicated dining room, creating

    Julie Glover Mahar McCarthy Real Estate

    886 Hidden Valley Rd, Shaftsbury, VT 05262
  • /45

    $405,000

    Sold Apr 20, 2026

    848 Coleville Rd, Bennington, VT 05201

    • 4 Beds
    • 3 Baths
    • 2,030 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $200/SF
    • 151 Days On Market

    Current Estimated Value $405,457

    Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

    848 Coleville Rd, Bennington, VT 05201
    • /39

      Est $530,268

      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

  • /20

    $524,900

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    1180 North Rd, East Arlington, VT 05252

    Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

    Jason Saphire www.HomeZu.com

    1180 North Rd, East Arlington, VT 05252
  • /35

    $220,000

    Sold Sep 16, 2025

    115 Jefferson Ave, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 1930

    Last Sold Summary

    • 18% Below List Price
    • $142/SF
    • 83 Days On Market

    Current Estimated Value $231,274

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    115 Jefferson Ave, Bennington, VT 05201
    • /39

      Est $783,650

      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

  • /19

    $219,500

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
  • /59

    $1,082,500

    Sold Aug 29, 2025

    4 Garden Loop Rd, Winhall, VT 05340

    • 3 Beds
    • 3.5 Baths
    • 4,054 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $267/SF
    • 45 Days On Market

    Current Estimated Value $1,138,416

    Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

    4 Garden Loop Rd, Winhall, VT 05340
    • /32

      Est $342,232

      Not Listed For Sale

      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft
      • Built 1986
      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 27 Days On Market

  • /4

    $14,000

    Under Contract
    • Land
    • 1.2 Acres
    • $11,667 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1.2-acre lot offers the perfect blend of privacy and convenience. Power is already available on the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /32

    $38,000

    Sold Aug 11, 2025

    339 S Stream Rd, Pownal, VT 05261

    • 5 Beds
    • 2 Baths
    • 2,204 Sq Ft
    • Built 1890

    Last Sold Summary

    • 31% Below List Price
    • $17/SF
    • 115 Days On Market

    Current Estimated Value $43,413

    Last Listing Agent Lisa Friedman Great American Dream Realty

    339 S Stream Rd, Pownal, VT 05261
    • /39

      Est $232,599

      Not Listed For Sale

      1618 W Sandgate Rd, Arlington, VT 05250

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft
      • Built 1969
      1618 W Sandgate Rd, Arlington, VT 05250

      Last Sold Summary

      • 64 Days On Market

  • /53

    $599,000

    $96K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    58 Mount Anthony Rd, Bennington, VT 05201

    Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

    Monique Geannelis Mahar McCarthy Real Estate

    58 Mount Anthony Rd, Bennington, VT 05201
  • /22

    $210,000

    Sold Jan 21, 2026

    52 Walker Meadow, Arlington, VT 05250

    • 2 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $109/SF
    • 4 Days On Market

    Current Estimated Value $221,090

    Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    52 Walker Meadow, Arlington, VT 05250
    • /31

      Est $428,799

      Not Listed For Sale

      1388 Pawlet Mountain Rd, Pawlet, VT 05761

      • 1 Bed
      • 1 Bath
      • 1,088 Sq Ft
      • Built 2004
      1388 Pawlet Mountain Rd, Pawlet, VT 05761

      Last Sold Summary

      • 20 Days On Market

  • /2

    $425,000

    • Land
    • 3 Acres
    • $141,667 per Acre

    lot B Frost Pond Rd, Dorset, VT 05251

    Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

    Charles Mauro Josiah Allen Real Estate, Inc.

    lot B Frost Pond Rd, Dorset, VT 05251
  • /10

    $18,500

    Sold Jan 09, 2026

    lot139&140 Bergrucken Ln, Readsboro, VT 05350

    • Land
    • 2.3 Acres
    • $8,043 per Acre

    Last Sold Summary

    • 20 Days On Market

    Last Listing Agent Christine Girard Lamacchia Realty, Inc. - North Adams

    lot139&140 Bergrucken Ln, Readsboro, VT 05350
    • /33

      Est $201,532

      Not Listed For Sale

      476 Tunnel St, Readsboro, VT 05350

      • 3 Beds
      • 1 Bath
      • 1,320 Sq Ft
      • Built 1880
      476 Tunnel St, Readsboro, VT 05350

      Last Sold Summary

      • 20 Days On Market

  • /43

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    683 Water St, North Bennington, VT 05257

    Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    683 Water St, North Bennington, VT 05257
  • /59

    $825,000

    Sold Jun 30, 2025

    764 Barnumville Rd Unit 2, Manchester Center, VT 05255

    • 3 Beds
    • 4 Baths
    • 3,240 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Above List Price
    • $255/SF
    • 41 Days On Market

    Current Estimated Value $812,199

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    764 Barnumville Rd Unit 2, Manchester Center, VT 05255
    • /13

      Est $266,381

      Not Listed For Sale

      390 Tunnel St, Readsboro, VT 05350

      • 4 Beds
      • 2 Baths
      • 1,676 Sq Ft
      • Built 1968
      390 Tunnel St, Readsboro, VT 05350

      Last Sold Summary

      • 3 Days On Market

  • /30

    $275,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,265 Sq Ft

    212 Dewey St, Bennington, VT 05201

    Move right in or continue operating as a short-term rental—this fully furnished 2-bedroom, 2.5-bath ranch offers comfort, convenience, and flexibility all in one package. Currently used as an Airbnb, all contents are included, making this a true turnkey opportunity. Inside, you’ll find recently refinished hardwood floors, and skylights that fill the home with natural light. A pellet stove for

    William Paquin Maple Leaf Real Estate

    212 Dewey St, Bennington, VT 05201
  • /60

    $245,000

    Sold Sep 22, 2025

    19 Robinson Ave, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Below List Price
    • $186/SF
    • 3 Days On Market

    Current Estimated Value $247,111

    Last Listing Agent Floyd Amidon Maple Leaf Real Estate

    19 Robinson Ave, Bennington, VT 05201
    • /39

      Est $262,047

      Not Listed For Sale

      93 Depot St, Readsboro, VT 05350

      • 4 Beds
      • 2 Baths
      • 1,837 Sq Ft
      • Built 1800
      93 Depot St, Readsboro, VT 05350

      Last Sold Summary

      • 1 Day On Market

  • /42

    $250,000

    $50K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,952 Sq Ft

    569 Buck Hill Rd, Arlington, VT 05250

    Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home’s historic appeal. The spacious primary bedroom stretches 25 feet and offers two separate

    Lisa Friedman Great American Dream Realty

    569 Buck Hill Rd, Arlington, VT 05250
  • /23

    $388,800

    Sold Jun 10, 2026

    317 Chester Knoll Dr, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 2026

    Last Sold Summary

    • $240/SF

    Last Listing Agent Lilli West Maple Leaf Real Estate

    317 Chester Knoll Dr, Bennington, VT 05201
    • /40

      Est $547,576

      Not Listed For Sale

      1456 Branch Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 2 Baths
      • 3,263 Sq Ft
      • Built 1991
      1456 Branch Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 856 Days On Market

  • /34

    $850,000

    • 2,060 Sq Ft

    609 Depot St, Manchester Center, VT 05255

    Rare opportunity to own TWO prime town center buildings in the heart of the Manchester Depot. This unique offering includes a charming multi unit front home with two well maintained apartments and a separate commercial building currently occupied by a successful well established business! The current business/owner would like to continue operating the business and remain as a tenant, thus

    Sunny Breen Josiah Allen Real Estate, Inc.

    609 Depot St, Manchester Center, VT 05255
  • /50

    $4,150,000

    Sold Mar 18, 2026

    318 Spring Hill Ln, Dorset, VT 05251

    • 7 Beds
    • 10 Baths
    • 7,422 Sq Ft
    • Built 1941

    Last Sold Summary

    • 15% Below List Price
    • $559/SF
    • 181 Days On Market

    Current Estimated Value $3,327,781

    Last Listing Agent Richard Slocum Four Seasons Sotheby's Int'l Realty

    318 Spring Hill Ln, Dorset, VT 05251
    • /40

      Est $400,042

      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

  • /3

    $79,900

    • Land
    • 10.1 Acres
    • $7,911 per Acre

    0 Old County Ln, Readsboro, VT 05350

    Escape to the tranquil countryside of Readsboro with this stunning 10.10-acre parcel offering exceptional privacy and natural beauty. The property showcases a picturesque mix of open level areas and gentle rolling hills, complemented by mature apple and cherry trees, thriving blueberry bushes, and a charming brook that winds its way through the land.Whether you envision a full-time residence,

    Raelene Robinson-Garrow Real Broker LLC

    0 Old County Ln, Readsboro, VT 05350
  • /33

    $740,000

    Sold Jan 02, 2026

    G12 Cobble Ridge Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,764 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $268/SF
    • 1 Day On Market

    Current Estimated Value $770,333

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

    G12 Cobble Ridge Rd, Winhall, VT 05340
    • /15

      Est $444,112

      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

  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /37

    $233,000

    Sold Aug 04, 2025

    73 Woodford City Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Above List Price
    • $221/SF
    • 73 Days On Market

    Last Listing Agent Abi Gregorio

    73 Woodford City Rd, Bennington, VT 05201
    • /40

      Est $390,038

      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

  • /26

    $180,000

    Pending
    • Land
    • 3.1 Acres
    • $58,065 per Acre

    00 Finbar's Forest Rd, Manchester, VT 05255

    Set on a knoll. Stunning mountain view of Mt Aeolus. This private 3.1 acre lot is ready to be built on with the driveway installed and lot cleared. Vt State Wastewater permit WW-8-2024 for a 3 bedroom home. Owner has staked the land to show the well and septic location. Added topsoil and seeded. Short drive to the center of Manchester and just around the corner to the Manchester Country Club.

    Patti Trudel RE/MAX Four Seasons

    00 Finbar's Forest Rd, Manchester, VT 05255
  • /49

    $313,000

    Sold Jul 21, 2025

    1385 N Bennington Rd, North Bennington, VT 05257

    • 4 Beds
    • 2 Baths
    • 2,050 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $153/SF
    • 53 Days On Market

    Current Estimated Value $314,777

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1385 N Bennington Rd, North Bennington, VT 05257
    • /35

      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

Showing Results 401 - 440, Page 11 of 18

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