20,610

Bennington County, VT Homes

Section Image
  • /13

    $265,000

    Sold May 08, 2026

    13 Hall St, North Bennington, VT 05257

    • 4 Beds
    • 2 Baths
    • 1,882 Sq Ft
    • Built 1907

    Last Sold Summary

    • $141/SF
    • 3 Days On Market

    Current Estimated Value $269,328

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

    13 Hall St, North Bennington, VT 05257
    • /40

      Est $862,665

      Not Listed For Sale

      16 Glastenbury Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 3.5 Baths
      • 4,239 Sq Ft
      • Built 1800
      16 Glastenbury Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /42

    $250,000

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

    569 Buck Hill Rd, Arlington, VT 05250

    Back on Market July 22nd! 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

    Lisa Friedman Great American Dream Realty

    569 Buck Hill Rd, Arlington, VT 05250
  • /20

    $89,499

    Sold Sep 24, 2025

    72 Ethans Way, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 825 Sq Ft
    • Built 2024

    Last Sold Summary

    • 10% Below List Price
    • $108/SF
    • 120 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    72 Ethans Way, Bennington, VT 05201
    • /38

      Est $447,961

      Not Listed For Sale

      1139 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1965
      1139 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  • /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
  • /16

    $130,000

    Sold Nov 25, 2025

    76 Harvest Hills Dr, North Bennington, VT 05257

    • 3 Beds
    • 1 Bath
    • 1,290 Sq Ft
    • Built 1966

    Last Sold Summary

    • 16% Below List Price
    • $101/SF
    • 45 Days On Market

    Current Estimated Value $212,805

    Last Listing Agent Susan Bellville Bellville Realty

    76 Harvest Hills Dr, North Bennington, VT 05257
    • /40

      Est $890,500

      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

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /53

    $205,000

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

    305 Weeks St, Bennington, VT 05201

    Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

    Lindsey Martin Maple Leaf Real Estate

    305 Weeks St, Bennington, VT 05201
  • /21

    $280,000

    Sold Jun 12, 2026

    53 South Rd, East Arlington, VT 05252

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $187/SF
    • 30 Days On Market

    Current Estimated Value $286,629

    Last Listing Agent David White OwnerEntry.com

    53 South Rd, East Arlington, VT 05252
    • /39

      Est $571,406

      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

      Last Listing Agent David Citron RE/MAX Four Seasons

  • /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
  • /50

    $449,000

    Sold Jun 08, 2026

    1284 Granger Hollow Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $320/SF
    • 19 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1284 Granger Hollow Rd, Shaftsbury, VT 05262
    • /39

      Est $741,809

      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

      Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  • /43

    $1,795,000

    $100K PRICE DROP
    • 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

    Sara Buckley Josiah Allen Real Estate, Inc.

    144 Taconic Rd, Manchester, VT 05255
  • /13

    $47,000

    Sold May 22, 2026

    16 Schenk Rd, Stamford, VT 05352

    • Land
    • 10.64 Acres
    • $4,417 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 3 Days On Market

    Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

    16 Schenk Rd, Stamford, VT 05352
    • /32

      Est $360,723

      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

      Last Listing Agent Abi Gregorio

  • /9

    $19,999

    Pending
    • Land
    • 1.5 Acres
    • $13,333 per Acre

    0 Lebensdorf Ln, Readsboro, VT 05350

    Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

    David White OwnerEntry.com

    0 Lebensdorf Ln, Readsboro, VT 05350
  • /35

    $372,000

    Sold May 13, 2026

    303 Prospect St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,463 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 11 Days On Market

    Current Estimated Value $374,432

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    303 Prospect St, Bennington, VT 05201
    • /42

      Est $259,041

      Not Listed For Sale

      935 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 2 Beds
      • 1 Bath
      • 1,221 Sq Ft
      • Built 1965
      935 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /27

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /45

    $680,000

    Sold Jul 22, 2026

    146 Clover Ln, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Above List Price
    • $264/SF
    • 3 Days On Market

    Current Estimated Value $647,040

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

    146 Clover Ln, Manchester Center, VT 05255
    • /38

      Not Listed For Sale

      1058 Granger Hollow Rd, North Bennington, VT 05257

      • 3 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 2006
      1058 Granger Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 17 Days On Market

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

  • /51

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /30

    $1,550,000

    Sold Apr 10, 2026

    147 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $388/SF
    • 9 Days On Market

    Current Estimated Value $1,341,298

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    147 High Meadow Rd, Winhall, VT 05340
    • /39

      Est $210,000

      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

      Last Listing Agent Lisa Friedman Great American Dream Realty

  • /39

    $250,000

    $10K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,458 Sq Ft

    301 Elm St, Bennington, VT 05201

    Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to

    Jenifer Prouty Hoffman Hoffman Real Estate

    301 Elm St, Bennington, VT 05201
  • /24

    $425,000

    Sold Jun 18, 2026

    141 Hillvale Rd, Manchester, VT 05255

    • 2 Beds
    • 3 Baths
    • 1,689 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $252/SF
    • 5 Days On Market

    Current Estimated Value $434,103

    Last Listing Agent David Citron RE/MAX Four Seasons

    141 Hillvale Rd, Manchester, VT 05255
    • /55

      Est $675,060

      Not Listed For Sale

      697 Hamilton Hollow Rd, Arlington, VT 05250

      • 3 Beds
      • 2.5 Baths
      • 2,944 Sq Ft
      • Built 1997
      697 Hamilton Hollow Rd, Arlington, VT 05250

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  • /25

    $1,200,000

    • 6 Beds
    • 3.5 Baths
    • 4,017 Sq Ft

    11 Founders Hill Rd, Winhall, VT 05360

    Located .25 of a mile from the Stratton Mtn Gondola, Village and Resort. Corner lot with mature, professionally planned landscaping to enjoy all year. New roof and skylights were installed in 2024. One large expansion to the whole side of the house, all 3 levels, was 30 years ago. Lovingly maintained but needs a new kitchen floor and floor refinishing of the hard woods. Recently the bamboo

    Derek Greene Derek Greene

    11 Founders Hill Rd, Winhall, VT 05360
  • /60

    $900,000

    Sold Aug 25, 2025

    368 Bowen Dr, Readsboro, VT 05350

    • 3 Beds
    • 2 Baths
    • 2,168 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Above List Price
    • $415/SF
    • 3 Days On Market

    Current Estimated Value $895,444

    Last Listing Agent Nick Sicard EXP Realty

    368 Bowen Dr, Readsboro, VT 05350
    • /31

      Est $437,747

      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

      Last Listing Agent Suanne Ohl Northland Real Estate

  • /60

    $950,000

    $750K PRICE DROP Under Contract
    • 6 Beds
    • 7 Baths
    • 5,400 Sq Ft

    2001 Depot St, Manchester Center, VT 05255

    LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 3.2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a

    Steven Bryant TPW Real Estate

    2001 Depot St, Manchester Center, VT 05255
  • /30

    $750,000

    Sold Aug 19, 2025

    379 Owls Head Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 4 Baths
    • 2,187 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $343/SF
    • 15 Days On Market

    Current Estimated Value $821,875

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

    379 Owls Head Hill Ln, Dorset, VT 05251
    • /33

      Est $235,917

      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

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /53

    $925,000

    $150K PRICE DROP Under Contract
    • 13 Beds
    • 12 Baths
    • 8,594 Sq Ft

    2759 Vt Route 11, Peru, VT 05152

    Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    2759 Vt Route 11, Peru, VT 05152
  • /31

    $208,000

    Sold Oct 10, 2025

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 10 Days On Market

    Current Estimated Value $219,543

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350
    • /39

      Est $272,497

      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

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /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
  • /18

    $260,000

    Sold Apr 28, 2026

    940 Gage St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1945

    Last Sold Summary

    • 13% Below List Price
    • $166/SF
    • 58 Days On Market

    Current Estimated Value $272,115

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    940 Gage St, Bennington, VT 05201

Showing Results 361 - 400, Page 10 of 18

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