20,611

Bennington County, VT Homes

Section Image
    • /31

      Est $419,564

      Not Listed For Sale

      2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 2 Beds
      • 1 Bath
      • 1,624 Sq Ft
      • Built 1961
      2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /40

    $1,699,000

    • 4 Beds
    • 4 Baths
    • 2,951 Sq Ft

    1949 South Rd, Peru, VT 05152

    Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

    Helen Nault

    1949 South Rd, Peru, VT 05152
  • /53

    $505,000

    Sold Aug 21, 2026

    58 Mount Anthony Rd, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 2,715 Sq Ft
    • Built 1928

    Last Sold Summary

    • 27% Below List Price
    • $186/SF
    • 223 Days On Market

    Current Estimated Value $547,599

    Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

    58 Mount Anthony Rd, Bennington, VT 05201
    • /32

      Est $358,884

      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

  • /47

    $1,500,000

    • Land
    • 38.57 Acres
    • $38,890 per Acre

    500 Nims Rd, Dorset, VT 05251

    This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

    Laura Beckwith Josiah Allen Real Estate, Inc.

    500 Nims Rd, Dorset, VT 05251
  • /15

    $175,000

    Sold Mar 09, 2026

    0 Alden Ln, Sunderland, VT 05250

    • Land
    • 40 Acres
    • $4,375 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 360 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    0 Alden Ln, Sunderland, VT 05250
    • /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

    $179,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • /47

    $502,500

    Sold Dec 15, 2025

    377 Glen Rd, Peru, VT 05152

    • 4 Beds
    • 4 Baths
    • 2,370 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $212/SF
    • 16 Days On Market

    Current Estimated Value $522,629

    Last Listing Agent Nancy Jensen Four Seasons Sotheby's Int'l Realty

    377 Glen Rd, Peru, VT 05152
    • /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

  • /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
  • /32

    $1,150,000

    Sold Aug 21, 2026

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155

    • 3 Beds
    • 3.5 Baths
    • 1,775 Sq Ft
    • Built 2004

    Last Sold Summary

    • $648/SF
    • 5 Days On Market

    Last Listing Agent Jamie Wylie Stratton Real Estate

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155
    • /39

      Est $207,000

      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

  • /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 RiverTucked 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
  • /35

    $707,500

    Sold May 01, 2026

    9 Old Route 30, Winhall, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft
    • Built 1948

    Last Sold Summary

    • 2% Above List Price
    • $261/SF
    • 4 Days On Market

    Current Estimated Value $688,800

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
    • /26

      Est $170,000

      Not Listed For Sale

      207 West Rd Unit N, Arlington, VT 05250

      • 3 Beds
      • 1 Bath
      • 1,660 Sq Ft
      • Built 1780
      207 West Rd Unit N, Arlington, VT 05250

      Last Sold Summary

      • 246 Days On Market

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /39

    $175,000

    • 2 Beds
    • 1 Bath
    • 810 Sq Ft

    220 Gage St, Bennington, VT 05201

    Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town.Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll

    Justine Curry Maple Leaf Real Estate

    220 Gage St, Bennington, VT 05201
  • /37

    $777,500

    Sold Jun 01, 2026

    34 Mountain View Rd, Winhall, VT 05360

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Below List Price
    • $311/SF
    • 15 Days On Market

    Last Listing Agent Jason Saphire www.HomeZu.com

    34 Mountain View Rd, Winhall, VT 05360
    • /55

      Est $706,222

      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

  • /9

    $269,000

    $26K PRICE DROP
    • 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
  • /43

    $755,000

    Sold Nov 14, 2025

    43 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 3,020 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $250/SF
    • 0 Days On Market

    Current Estimated Value $777,324

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /31

      Est $421,576

      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

  • /13

    $275,000

    $20K PRICE DROP
    • 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.

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201
  • /60

    $422,500

    Sold Jun 15, 2026

    2603 N Pownal Rd, Pownal, VT 05261

    • 3 Beds
    • 2.5 Baths
    • 1,764 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $240/SF
    • 12 Days On Market

    Current Estimated Value $428,902

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    2603 N Pownal Rd, Pownal, VT 05261
    • /33

      Est $217,709

      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

  • /48

    $314,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,337 Sq Ft

    78 Carbonti Cir, Arlington, VT 05250

    There is something special about a home that feels comfortable, welcoming, and full of possibility, and this Arlington property offers just that. Set in a wonderful neighborhood, this well-built 3-bedroom, 2-bath home provides easy one-level living along with the opportunity to add your own style and personality through a few cosmetic updates. Inside, the layout is practical and inviting, with a

    Faith Rhodes Maple Leaf Real Estate

    78 Carbonti Cir, Arlington, VT 05250
  • /30

    $277,000

    Sold Jul 10, 2026

    212 Dewey St, Bennington, VT 05201

    • 2 Beds
    • 2.5 Baths
    • 1,265 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $219/SF

    Current Estimated Value $273,930

    Last Listing Agent William Paquin Maple Leaf Real Estate

    212 Dewey St, Bennington, VT 05201
    • /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

  • /32

    $849,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,878 Sq Ft

    32 Benson Fuller Dr, Bondville, VT 05340

    Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout.Quality architectural details welcome you into a bright main level

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    32 Benson Fuller Dr, Bondville, VT 05340
  • /3

    $283,505

    Sold May 11, 2026

    11 Maltese Rd, Stamford, VT 05352

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1978

    Last Sold Summary

    • 3% Above List Price
    • $295/SF
    • 0 Days On Market

    Current Estimated Value $290,046

    Last Listing Agent Ann Greenwood Alton + Westall Real Estate Agency, LLC

    11 Maltese Rd, Stamford, VT 05352
    • /40

      Est $551,897

      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

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /59

    $989,900

    • 4 Beds
    • 3 Baths
    • 5,697 Sq Ft

    66 Somerset Rd, Searsburg, VT 05363

    LOW TAXES! Six oversized garage bays across two multi-level outbuildings, direct access to National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

    Erica Reynolds Southern Vermont Realty Group

    66 Somerset Rd, Searsburg, VT 05363
  • /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 $425,659

    Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

    848 Coleville Rd, Bennington, VT 05201
    • /40

      Est $433,234

      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

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /40

    $595,000

    $20K PRICE INCREASE Under Contract
    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    23 Loop Rd Unit 10, Bondville, VT 05340

    Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    23 Loop Rd Unit 10, Bondville, VT 05340
  • /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 $220,409

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

    52 Walker Meadow, Arlington, VT 05250
    • /15

      Est $460,595

      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

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /4

    $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
  • /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
    • /40

      Est $402,747

      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

      Last Listing Agent Monique White Deerfield Valley Real Estate

Showing Results 401 - 440, Page 11 of 18

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