21,299

Bennington County, VT Homes

Section Image
    • /40

      Est $491,518

      Not Listed For Sale

      466 Laver Rd, Arlington, VT 05250

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 2006
      466 Laver Rd, Arlington, VT 05250

      Last Sold Summary

      • 369 Days On Market

  • /55

    $2,950,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /39

    $255,500

    Sold Jan 15, 2026

    77 Mcguire St, North Bennington, VT 05257

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $253/SF
    • 15 Days On Market

    Current Estimated Value $251,657

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    77 Mcguire St, North Bennington, VT 05257
    • /24

      Est $297,251

      Not Listed For Sale

      408 Dunlap Farm Rd, Arlington, VT 05250

      • 2 Beds
      • 1 Bath
      • 988 Sq Ft
      • Built 1984
      408 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 88 Days On Market

  • /60

    $415,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    358 Birch Grove, Arlington, VT 05250

    Have you dreamed of a home on a quiet cul-de-sac with over an acre of land and seasonal mountain views? Look no further! Situated on a wooded lot in a very desirable neighborhood, this spacious home has all you need. Flooded with natural light, the large living room includes a gas fireplace, cozy reading nook, and cute sunroom that is perfect for plants. It leads to a wraparound deck, also

    Justine Curry Maple Leaf Real Estate

    358 Birch Grove, Arlington, VT 05250
  • /3

    $110,000

    Sold Nov 17, 2025

    0 Maple Hill Rd, Shaftsbury, VT 05262

    • Land
    • 11.5 Acres
    • $9,565 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    0 Maple Hill Rd, Shaftsbury, VT 05262
    • /50

      Est $1,077,103

      Not Listed For Sale

      342 Lesure Rd, Stamford, VT 05352

      • 5 Beds
      • 4.5 Baths
      • 6,000 Sq Ft
      • Built 2007
      342 Lesure Rd, Stamford, VT 05352

      Last Sold Summary

      • 53 Days On Market

  • /29

    $449,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    2121 North Rd, Arlington, VT 05250

    Beautifully maintained split-level home offering a wonderful combination of comfort, flexibility, and privacy! Situated on a large, one-acre private lot, the property features a circular driveway and loose-laid rock wall that frames the landscape with classic rural charm. The main level boasts an open-concept layout with gleaming hardwood floors throughout, a spacious living room, and a kitchen

    Matt Waddington Hoffman Real Estate

    2121 North Rd, Arlington, VT 05250
  • /19

    $199,900

    Sold Sep 19, 2025

    42 Colvin Ave, Shaftsbury, VT 05262

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft
    • Built 1964

    Last Sold Summary

    • $210/SF
    • 28 Days On Market

    Current Estimated Value $201,471

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    42 Colvin Ave, Shaftsbury, VT 05262
    • /33

      Est $182,366

      Not Listed For Sale

      133 Tatro Rd, Stamford, VT 05352

      • 2 Beds
      • 1 Bath
      • 972 Sq Ft
      • Built 1995
      133 Tatro Rd, Stamford, VT 05352

      Last Sold Summary

      • 28 Days On Market

  • /6

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    2 Hamlin Ave, Bennington, VT 05201

    2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

    Lori Hurley Four Corner Properties LLC

    2 Hamlin Ave, Bennington, VT 05201
  • /55

    $945,000

    Sold Jun 05, 2026

    520 Moose Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 4,184 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $226/SF
    • 20 Days On Market

    Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    520 Moose Hollow Rd, Winhall, VT 05340
    • /33

      Est $270,667

      Not Listed For Sale

      864 East Rd, Stamford, VT 05352

      • 2 Beds
      • 1 Bath
      • 1,250 Sq Ft
      • Built 1985
      864 East Rd, Stamford, VT 05352

      Last Sold Summary

      • 59 Days On Market

  • /44

    $815,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 2,980 Sq Ft

    74 Pond View Rd, Winhall, VT 05340

    This spacious and well-maintained 4-bedroom, 4.5-bathroom condo in Stratton’s desirable Intervale community offers nearly 3,000 square feet of comfortable mountain living, just minutes from the Base Lodge with winter shuttle service. Nestled among the trees for added privacy, the home features an open-concept main level with cathedral ceilings, abundant natural light, a wood-burning fireplace,

    Christine Chovan

    74 Pond View Rd, Winhall, VT 05340
  • /58

    $299,000

    Sold Jun 01, 2026

    207 Silver St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1846

    Last Sold Summary

    • $150/SF
    • 143 Days On Market

    Current Estimated Value $294,569

    Last Listing Agent Dan Mason Perrott Realty

    207 Silver St, Bennington, VT 05201
    • /43

      Est $430,899

      Not Listed For Sale

      394 East Rd, Stamford, VT 05352

      • 3 Beds
      • 3 Baths
      • 1,826 Sq Ft
      • Built 1988
      394 East Rd, Stamford, VT 05352

      Last Sold Summary

      • 24 Days On Market

  • /7

    $329,000

    • Land
    • 9.3 Acres
    • $35,376 per Acre

    1347 Morse Hill Rd, Dorset, VT 05251

    Discover the perfect blend of privacy and convenience with this 9.3 acre parcel situated in one of Southern Vermont's most desirable locations. Enjoy sweeping mountain views and peaceful surroundings just minutes from the charming and historic towns of Dorset and Manchester, known for boutique shopping, fine dining, and year-round cultural attractions. It's a short drive to skiing at Bromley,

    Deborah Hanst

    1347 Morse Hill Rd, Dorset, VT 05251
  • /42

    $655,000

    Sold Jun 03, 2026

    384 Alden Rd, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Above List Price
    • $347/SF
    • 7 Days On Market

    Current Estimated Value $589,560

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

    384 Alden Rd, Arlington, VT 05250
    • /27

      Est $283,528

      Not Listed For Sale

      3623 Main Rd, Stamford, VT 05352

      • 2 Beds
      • 1 Bath
      • 1,200 Sq Ft
      • Built 1972
      3623 Main Rd, Stamford, VT 05352

      Last Sold Summary

      • 173 Days On Market

  • /7

    $29,000

    • Land
    • 1.2 Acres
    • $24,167 per Acre

    00 Oberdorf Rd, Stamford, VT 05350

    This 1.2 acre rectangular lot is located in Alpenwald Village! The village roads are community-maintained, have electricity service through Green Mountain Power Company and is loaded with recreational perks! 1.4 miles to hiking/ biking trails on the Dutch Hill Backcountry Area of the Green Mountain National Forest. 1.9 miles to an ATV & snowmobile trailhead in Heartwellville. Situated in the town

    Casey Scott Southern Vermont Realty Group

    00 Oberdorf Rd, Stamford, VT 05350
  • /25

    $360,000

    Sold Feb 25, 2026

    00 Ross Rd, Winhall, VT 05340

    • Land
    • 41.1 Acres
    • $8,759 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 82 Days On Market

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

    00 Ross Rd, Winhall, VT 05340
    • /23

      Est $286,838

      Not Listed For Sale

      1635 Main Rd, Stamford, VT 05352

      • 3 Beds
      • 1 Bath
      • 1,692 Sq Ft
      • Built 1890
      1635 Main Rd, Stamford, VT 05352

      Last Sold Summary

      • 146 Days On Market

  • /46

    $1,275,000

    • 4 Beds
    • 2.5 Baths
    • 4,084 Sq Ft

    1677 Barnumville Rd, Manchester Center, VT 05255

    Imagine a time where taverns were the heart of the community, where laughter echoed off thick brick walls and stories were told by firelight. Now see yourself enjoying the ease of Single Floor Living that includes an enormous primary ensuite, with laundry! Start your day in the completely updated kitchen and move effortlessly into the dining area and living room with an easy to light cozy propane

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    1677 Barnumville Rd, Manchester Center, VT 05255
  • /23

    $235,000

    Sold Jul 31, 2025

    40 Bourn Brook Rd Unit 49, Manchester, VT 05255

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1986

    Last Sold Summary

    • $300/SF
    • 3 Days On Market

    Current Estimated Value $236,824

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

    40 Bourn Brook Rd Unit 49, Manchester, VT 05255
    • /32

      Est $320,127

      Not Listed For Sale

      1575 Main Rd, Stamford, VT 05352

      • 4 Beds
      • 2 Baths
      • 2,003 Sq Ft
      1575 Main Rd, Stamford, VT 05352

      Last Sold Summary

      • 5 Days On Market

  • /32

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,443 Sq Ft

    21 Pageant St, Bennington, VT 05201

    This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite

    Kelley Mccarthy Mahar McCarthy Real Estate

    21 Pageant St, Bennington, VT 05201
  • /28

    $450,000

    Sold Apr 23, 2026

    354 New Ireland Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $323/SF
    • 73 Days On Market

    Current Estimated Value $481,330

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

    354 New Ireland Rd, Manchester Center, VT 05255
    • /14

      Est $275,571

      Not Listed For Sale

      169 Reservoir Rd, Shaftsbury, VT 05262

      • 1 Bed
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1965
      169 Reservoir Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 15 Days On Market

  • /40

    $899,000

    $301K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,252 Sq Ft

    E1 Rock Ridge Rd, Winhall, VT 05155

    Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

    Christine Chovan

    E1 Rock Ridge Rd, Winhall, VT 05155
  • /39

    $383,000

    Sold Jul 30, 2025

    224 Garbrooke Dr, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,207 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $174/SF
    • 61 Days On Market

    Current Estimated Value $389,858

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    224 Garbrooke Dr, Bennington, VT 05201
    • /29

      Est $338,788

      Not Listed For Sale

      289 Reservoir Rd, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1996
      289 Reservoir Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 11 Days On Market

  • /60

    $2,079,500

    • 3 Beds
    • 2.5 Baths
    • 3,504 Sq Ft

    59 Barrows Heights, Dorset, VT 05251

    Unmatched Dorset village Charm!!...In the heart of Historic Dorset, just steps away from all village amenities. Leave the car in the garage and stroll to your morning coffee at the Dorset Bakery, pick up groceries at the Union Store or meet friends for dinner at the beloved Barrows House or the historic Dorset Inn after a round of golf at the Field Club or post-theater at the Playhouse. This is a

    Sunny Breen Josiah Allen Real Estate, Inc.

    59 Barrows Heights, Dorset, VT 05251
  • /42

    $600,000

    Sold Nov 12, 2025

    126 Fox Hill Rd, Bennington, VT 05201

    • 5 Beds
    • 1.5 Baths
    • 2,450 Sq Ft
    • Built 1850

    Last Sold Summary

    • 25% Below List Price
    • $245/SF
    • 148 Days On Market

    Current Estimated Value $606,954

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    126 Fox Hill Rd, Bennington, VT 05201
    • /18

      Est $240,400

      Not Listed For Sale

      43 Buck Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1 Bath
      • 1,361 Sq Ft
      • Built 1903
      43 Buck Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 279 Days On Market

  • /54

    $1,749,000

    $346K PRICE DROP Under Contract
    • 5 Beds
    • 4.5 Baths
    • 3,218 Sq Ft

    5491 Vt Route 315, Rupert, VT 05776

    Luxury move in ready fully renovated 1909 Federal home on 5+ peaceful acres, protected mountain views and stream frontage, but just 5 minutes from the activities on the Dorset Green and the Dorset Field Club. A 3 year renovation by the areas most skilled workmen includes a custom walnut kitchen with high end appliances, island bar seating opening to dining room for entertainment and family life.

    Annette Gallo Real Broker LLC

    5491 Vt Route 315, Rupert, VT 05776
  • /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 $261,051

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

    13 Hall St, North Bennington, VT 05257
    • /12

      Est $333,356

      Not Listed For Sale

      140 Church St, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 2,123 Sq Ft
      • Built 1870
      140 Church St, Shaftsbury, VT 05262

      Last Sold Summary

      • 7 Days On Market

  • /21

    $215,000

    $20K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 938 Sq Ft

    55 Eden Way Unit 3, Bennington, VT 05201

    Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and

    Angela Bevin Maple Leaf Real Estate

    55 Eden Way Unit 3, Bennington, VT 05201
  • /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
    • /60

      Est $308,251

      Not Listed For Sale

      450 Cleveland Ave, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1920
      450 Cleveland Ave, Shaftsbury, VT 05262

      Last Sold Summary

      • 31 Days On Market

Showing Results 281 - 320, Page 8 of 18

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