21,299

Bennington County, VT Homes

Section Image
  • /8

    $50,000

    Sold Apr 15, 2026

    0 Stratton View Rd Unit 26, Winhall, VT 05340

    • Land
    • 1.02 Acres
    • $49,020 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 218 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    0 Stratton View Rd Unit 26, Winhall, VT 05340
    • /2

      Est $389,839

      Not Listed For Sale

      250 Lincoln St, Pownal, VT 05261

      • 5 Beds
      • 3 Baths
      • 3,598 Sq Ft
      • Built 1820
      250 Lincoln St, Pownal, VT 05261

      Last Sold Summary

      • 13 Days On Market

  • /7

    $997,000

    • Land
    • 23,086 Sq Ft
    • $1,881,132 per Acre

    153 Northside Dr, Bennington, VT 05201

    Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

    Lori Hurley Four Corner Properties LLC

    153 Northside Dr, Bennington, VT 05201
  • /6

    $9,000

    Sold Oct 03, 2025

    lot 305 Lebenschauung Cir, Stamford, VT 05352

    • Land
    • 1 Acre
    • $9,000 per Acre

    Last Sold Summary

    • 38% Below List Price
    • 76 Days On Market

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

    lot 305 Lebenschauung Cir, Stamford, VT 05352
    • /40

      Est $332,239

      Not Listed For Sale

      505 Cross Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 2003
      505 Cross Rd, Bennington, VT 05201

      Last Sold Summary

      • 2 Days On Market

  • /52

    $2,285,000

    • 5 Beds
    • 4.5 Baths
    • 4,647 Sq Ft

    543 Lower Hollow Rd, Dorset, VT 05251

    A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

    Britt Wohler

    543 Lower Hollow Rd, Dorset, VT 05251
  • /14

    $278,000

    Sold Aug 04, 2025

    400 South St, Bennington, VT 05201

    • 3 Beds
    • 3 Baths
    • 1,461 Sq Ft
    • Built 1825

    Last Sold Summary

    • 7% Above List Price
    • $190/SF
    • 38 Days On Market

    Current Estimated Value $279,966

    Last Listing Agent William Paquin Maple Leaf Real Estate

    400 South St, Bennington, VT 05201
    • /40

      Not Listed For Sale

      260 Tower Rd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 3,976 Sq Ft
      • Built 1981
      260 Tower Rd, Bennington, VT 05201

      Last Sold Summary

      • 115 Days On Market

  • /37

    $525,000

    Pending
    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft

    4 Stonehedge Dr, Bennington, VT 05201

    Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors,

    Kelley Mccarthy Mahar McCarthy Real Estate

    4 Stonehedge Dr, Bennington, VT 05201
  • /37

    $219,000

    Sold Aug 29, 2025

    261 Sycamore Ln, Shaftsbury, VT 05262

    • 3 Beds
    • 1 Bath
    • 1,156 Sq Ft
    • Built 1961

    Last Sold Summary

    • $189/SF
    • 4 Days On Market

    Current Estimated Value $222,585

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    261 Sycamore Ln, Shaftsbury, VT 05262
    • /24

      Est $155,743

      Not Listed For Sale

      354 NW Hill Rd, Pownal, VT 05261

      • 1 Bed
      • 816 Sq Ft
      • Built 1900
      354 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 6 Days On Market

  • /25

    $620,000

    • 4 Beds
    • 3 Baths
    • 1,768 Sq Ft

    35 Valley Pass St, Manchester, VT 05255

    Move right into this turnkey Cape offering 4 bedrooms and 3 bathrooms with extensive recent updates throughout. Combining classic New England charm with modern conveniences, this thoughtfully renovated home is designed for comfortable everyday living and effortless entertaining. The main level features a bright, open concept floor plan centered around a beautifully updated kitchen with quartz

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    35 Valley Pass St, Manchester, VT 05255
  • /53

    $1,388,000

    Sold Jul 11, 2025

    1325 Barnumville Rd, Manchester Center, VT 05255

    • 4 Beds
    • 5 Baths
    • 5,494 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $253/SF
    • 92 Days On Market

    Current Estimated Value $1,271,921

    Last Listing Agent Christiane Carroccio TPW Real Estate

    1325 Barnumville Rd, Manchester Center, VT 05255
    • /27

      Est $304,749

      Not Listed For Sale

      46 NW Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,128 Sq Ft
      • Built 1900
      46 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 193 Days On Market

  • /9

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,206 Sq Ft

    116 S Branch St Unit 118, Bennington, VT 05201

    Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

    Julie Glover Mahar McCarthy Real Estate

    116 S Branch St Unit 118, Bennington, VT 05201
  • /30

    $361,500

    Sold Oct 27, 2025

    64 Bergblume Cir, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,162 Sq Ft
    • Built 2007

    Last Sold Summary

    • 10% Below List Price
    • $167/SF
    • 49 Days On Market

    Last Listing Agent Pam Tworig BISHOP WEST REAL ESTATE

    64 Bergblume Cir, Stamford, VT 05352
    • /40

      Est $401,977

      Not Listed For Sale

      42 Maple Grove Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 2,163 Sq Ft
      • Built 1960
      42 Maple Grove Rd, Bennington, VT 05201

      Last Sold Summary

      • 87 Days On Market

  • /13

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,022 Sq Ft

    124 S Branch St, Bennington, VT 05201

    Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups—perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201
  • /58

    $975,000

    Sold Nov 27, 2025

    20 Jamie Ln, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 1987

    Last Sold Summary

    • $279/SF
    • 38 Days On Market

    Current Estimated Value $956,981

    Last Listing Agent David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
    • /34

      Est $293,284

      Not Listed For Sale

      543 Middle Pownal Rd, Pownal, VT 05261

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft
      • Built 1973
      543 Middle Pownal Rd, Pownal, VT 05261

      Last Sold Summary

      • 52 Days On Market

  • /5

    $350,000

    New Construction Pending
    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    525 Jennings Brook Dr, Bennington, VT 05201

    Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

    Lilli West Maple Leaf Real Estate

    525 Jennings Brook Dr, Bennington, VT 05201
  • /44

    $365,000

    Sold Feb 19, 2026

    2842 Vt Route 7a, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 2,661 Sq Ft
    • Built 1969

    Last Sold Summary

    • 8% Below List Price
    • $137/SF
    • 79 Days On Market

    Current Estimated Value $366,437

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    2842 Vt Route 7a, Shaftsbury, VT 05262
    • /24

      Est $383,703

      Not Listed For Sale

      78 Middle Pownal Rd, Pownal, VT 05261

      • 3 Beds
      • 1.5 Baths
      • 1,624 Sq Ft
      • Built 1922
      78 Middle Pownal Rd, Pownal, VT 05261

      Last Sold Summary

      • 50 Days On Market

  • /21

    $125,000

    Pending
    • Land
    • 4 Acres
    • $31,250 per Acre

    773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

    Set on 4 scenic acres in Shaftsbury Hollow, this special property offers a rare blend of open pasture, mature woodland, and frontage along the Little White Creek. The setting is both peaceful and recreational—ideal for those seeking a true Vermont escape. Enjoy natural shade along the water’s edge, spend summer days swimming or casting for brook trout, and gather around the campfire under the

    Jenifer Prouty Hoffman Hoffman Real Estate

    773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
  • /30

    $717,500

    Sold Feb 13, 2026

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $310/SF
    • 60 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
    • /40

      Est $371,339

      Not Listed For Sale

      1346 Barber Pond Rd, Pownal, VT 05261

      • 2 Beds
      • 2 Baths
      • 1,792 Sq Ft
      • Built 2006
      1346 Barber Pond Rd, Pownal, VT 05261

      Last Sold Summary

      • 11 Days On Market

  • /3

    $1,295,000

    • Land
    • 52.61 Acres
    • $24,615 per Acre

    00 Montgomery Rd, Pownal, VT 05261

    A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

    Ann Greenwood Alton + Westall Real Estate Agency, LLC

    00 Montgomery Rd, Pownal, VT 05261
  • /30

    $310,000

    Sold Jul 25, 2025

    198 Weeks St, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 2,032 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Below List Price
    • $153/SF
    • 54 Days On Market

    Current Estimated Value $318,225

    Last Listing Agent Margretta Fischer Wohler Realty Group

    198 Weeks St, Bennington, VT 05201
    • /31

      Est $545,762

      Not Listed For Sale

      695 Barber Pond Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1854
      695 Barber Pond Rd, Pownal, VT 05261

      Last Sold Summary

      • 12 Days On Market

  • /28

    $120,500

    • 4 Beds
    • 1 Bath
    • 1,368 Sq Ft

    113 Forgette Rd, Stamford, VT 05352

    Roll up your sleeves! This property needs complete rehab but will be well worth the effort. Private location set back from the road, large yard ready to enjoy. Short drive to North Adams for shopping. Don't hesitate to take a look this may be the one for you.

    Andrea Thackston R.H. Thackston & Company/Bellows Falls

    113 Forgette Rd, Stamford, VT 05352
  • /58

    $590,000

    Sold Feb 27, 2026

    1098 W Sandgate Rd, Arlington, VT 05250

    • 3 Beds
    • 2.5 Baths
    • 3,284 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $180/SF
    • 35 Days On Market

    Current Estimated Value $600,116

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

    1098 W Sandgate Rd, Arlington, VT 05250
    • /20

      Est $208,981

      Not Listed For Sale

      2685 N Pownal Rd, Pownal, VT 05261

      • 2 Beds
      • 1 Bath
      • 868 Sq Ft
      • Built 1950
      2685 N Pownal Rd, Pownal, VT 05261

      Last Sold Summary

      • 231 Days On Market

  • /59

    $899,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    178 High Meadow Rd, Winhall, VT 05340

    POSTPONED OPENHOUSE Spacious 4,000± sq. ft. contemporary home located in a sought-after ski resort community with convenient winter shuttle bus access to the slopes. Designed for both entertaining and everyday comfort, this property features an open-concept floor plan, abundant natural light, and generous living spaces throughout. The inviting family recreation room with bar offers the perfect

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    178 High Meadow Rd, Winhall, VT 05340
  • /22

    $595,000

    Sold Jan 26, 2026

    62 Owls Nest Cir Unit B8, Manchester, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 1,963 Sq Ft
    • Built 1985

    Last Sold Summary

    • $303/SF
    • 11 Days On Market

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

    62 Owls Nest Cir Unit B8, Manchester, VT 05255
    • /36

      Est $452,103

      Not Listed For Sale

      159 Vt Route 11, Peru, VT 05152

      • 5 Beds
      • 2.5 Baths
      • 2,280 Sq Ft
      • Built 1971
      159 Vt Route 11, Peru, VT 05152

      Last Sold Summary

      • 114 Days On Market

  • /60

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 3,295 Sq Ft

    142 Schenkar Rd, Pownal, VT 05261

    Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

    Erin McCormick KW Vermont

    142 Schenkar Rd, Pownal, VT 05261
  • /24

    $615,000

    Sold Aug 25, 2025

    129 Coventry Ln, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 68 Days On Market

    Current Estimated Value $637,717

    Last Listing Agent Joseph Cajzer Josiah Allen Real Estate, Inc.

    129 Coventry Ln, Manchester Center, VT 05255
    • /40

      Est $997,527

      Not Listed For Sale

      2347 Hapgood Pond Rd, Peru, VT 05152

      • 4 Beds
      • 2 Baths
      • 2,991 Sq Ft
      • Built 1815
      2347 Hapgood Pond Rd, Peru, VT 05152

      Last Sold Summary

      • 25 Days On Market

  • /43

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 3,780 Sq Ft

    1228 Skiparee Rd, Pownal, VT 05260

    Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

    Christiane Carroccio TPW Real Estate

    1228 Skiparee Rd, Pownal, VT 05260
  • /31

    $1,347,000

    Sold Nov 10, 2025

    951 Rupert Rd, Arlington, VT 05250

    • 5 Beds
    • 5 Baths
    • 6,200 Sq Ft
    • Built 2006

    Last Sold Summary

    • 15% Below List Price
    • $217/SF
    • 110 Days On Market

    Current Estimated Value $1,325,296

    Last Listing Agent Kristin Pirie Winhall Real Estate

    951 Rupert Rd, Arlington, VT 05250

Showing Results 481 - 520, Page 13 of 18

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