20,610

Bennington County, VT Homes

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  • /28

    $209,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    107 Jefferson Ave, Bennington, VT 05201

    Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Jefferson Ave, Bennington, VT 05201
  • /41

    $480,000

    Sold Dec 22, 2025

    245 Southshire Dr, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,116 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $227/SF
    • 145 Days On Market

    Current Estimated Value $520,344

    Last Listing Agent Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    245 Southshire Dr, Bennington, VT 05201
    • /38

      Est $456,565

      Not Listed For Sale

      27 Horton Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 2,082 Sq Ft
      • Built 1948
      27 Horton Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /25

    $675,000

    $35K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    184 W View Estates, Manchester Center, VT 05255

    Welcome to this well maintained 3-bedroom, 2.5-bath Colonial combining classic style with comfortable modern living. From the inviting front porch to the covered rear porch, patio, and fire pit, this home offers exceptional spaces for relaxing and entertaining both indoors and outdoors. The recently updated kitchen serves as the heart of the home with tasteful finishes and excellent

    Annette Gallo Real Broker LLC

    184 W View Estates, Manchester Center, VT 05255
  • /44

    $781,000

    Sold Aug 03, 2026

    74 Pond View Rd, Winhall, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 2,980 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $262/SF
    • 43 Days On Market

    Current Estimated Value $811,199

    Last Listing Agent Christine Chovan

    74 Pond View Rd, Winhall, VT 05340
    • /60

      Est $446,549

      Not Listed For Sale

      123 Bank St, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 2,753 Sq Ft
      • Built 1952
      123 Bank St, North Bennington, VT 05257

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /50

    $150,000

    $10K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,575 Sq Ft

    127 Dewey St, Bennington, VT 05201

    Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

    Lindsey Martin Maple Leaf Real Estate

    127 Dewey St, Bennington, VT 05201
  • /15

    $199,900

    Sold Jan 16, 2026

    111 Hicks Ave, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1936

    Last Sold Summary

    • $160/SF
    • 13 Days On Market

    Current Estimated Value $203,292

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    111 Hicks Ave, Bennington, VT 05201
    • /37

      Est $404,641

      Not Listed For Sale

      181 Dunham Ave, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1955
      181 Dunham Ave, North Bennington, VT 05257

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Abi Gregorio

  • /23

    $120,000

    Pending
    • 2 Beds
    • 1 Bath
    • 880 Sq Ft

    818 Old Depot Rd, Shaftsbury, VT 05262

    Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway, vacation rental, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy

    Lisa Friedman Great American Dream Realty

    818 Old Depot Rd, Shaftsbury, VT 05262
  • /51

    $434,000

    Sold Feb 27, 2026

    12 Stratton West Rd Unit 12, Winhall, VT 05340

    • 5 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $230/SF
    • 6 Days On Market

    Last Listing Agent Robert Sabol Wohler Realty Group

    12 Stratton West Rd Unit 12, Winhall, VT 05340
    • /40

      Est $542,918

      Not Listed For Sale

      287 Hewitt Dr, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 2,236 Sq Ft
      • Built 1974
      287 Hewitt Dr, North Bennington, VT 05257

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Angela Bevin Maple Leaf Real Estate

  • /15

    $169,900

    • 2 Beds
    • 1.5 Baths
    • 819 Sq Ft

    432 South St Unit A11, Bennington, VT 05201

    Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add

    Colt Hazell Flex Realty

    432 South St Unit A11, Bennington, VT 05201
  • /24

    $1,025,000

    Sold Oct 10, 2025

    10 Middle Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $475/SF
    • 5 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    10 Middle Ridge Rd, Winhall, VT 05155
    • /29

      Est $544,525

      Not Listed For Sale

      9378 Vt Route 9, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1985
      9378 Vt Route 9, Bennington, VT 05201

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Lisa Mirando Deerfield Valley Real Estate

  • /32

    $534,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    764 Myers Rd, Shaftsbury, VT 05262

    This charming, beautifully updated Cape sits on a sprawling 2-acre lot in a highly sought-after section of Shaftsbury, offering breathtaking panoramic mountain views. Boasting character and gleaming hardwood floors throughout. The first floor features a large living room with built-in bookshelves and cozy wood stove, a primary bedroom, full bath, and spacious country kitchen with granite

    Matt Waddington Hoffman Real Estate

    764 Myers Rd, Shaftsbury, VT 05262
  • /16

    $54,900

    Sold Oct 24, 2025

    255 Vermont 8, Searsburg, VT 05363

    • Land
    • 36,154 Sq Ft
    • $66,145 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    255 Vermont 8, Searsburg, VT 05363
    • /47

      Est $433,047

      Not Listed For Sale

      201 Erbs Way, Bennington, VT 05201

      • 3 Beds
      • 3.5 Baths
      • 2,686 Sq Ft
      • Built 1974
      201 Erbs Way, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /53

    $2,850,000

    Under Contract
    • 5 Beds
    • 5.5 Baths
    • 6,182 Sq Ft

    86 Church St, Dorset, VT 05251

    Set on the north side of the Dorset Green, 86 and 78 Church Street present a rare village compound in the heart of Dorset. Fully renovated with exceptional attention to detail, this refined micro-estate blends timeless New England character with sophisticated modern living. Encompassing the main residence, guest cottage, gardens, and garage, the property is both gracious in scale and intimate in

    Christiane Carroccio TPW Real Estate

    86 Church St, Dorset, VT 05251
  • /55

    $1,800,000

    Sold Mar 20, 2026

    139 Prospect St, Manchester, VT 05254

    • 3 Beds
    • 2.5 Baths
    • 3,450 Sq Ft
    • Built 1934

    Last Sold Summary

    • 3% Below List Price
    • $522/SF
    • 123 Days On Market

    Current Estimated Value $1,780,795

    Last Listing Agent Cheyanne Pugliese

    139 Prospect St, Manchester, VT 05254
    • /25

      Est $758,855

      Not Listed For Sale

      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1968
      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Helen Nault

  • /32

    $775,000

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

    20 Bishop Rd, Searsburg, VT 05363

    Sweeping long-range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton ridgelines from this stunning 2020 Moosehead log home. Situated on 7+ acres bordering thousands of acres of National Forest, the property offers direct access to VAST snowmobile trails, space to create your own private loops, and exceptional privacy — all while remaining just a short

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Bishop Rd, Searsburg, VT 05363
  • /23

    $125,000

    Sold Oct 07, 2025

    5089 Vt Route 7a, Arlington, VT 05250

    • 3 Beds
    • 3 Baths
    • 2,206 Sq Ft
    • Built 1976

    Last Sold Summary

    • 14% Above List Price
    • $57/SF
    • 6 Days On Market

    Current Estimated Value $234,949

    Last Listing Agent Susan Bellville Bellville Realty

    5089 Vt Route 7a, Arlington, VT 05250
    • /11

      Est $544,227

      Not Listed For Sale

      1238 North Rd, East Arlington, VT 05252

      • 3 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2003
      1238 North Rd, East Arlington, VT 05252

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  • /24

    $389,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,535 Sq Ft

    515 Buck Hill Rd, Arlington, VT 05250

    Completely renovated from top to bottom, this move-in-ready home perfectly blends modern updates with classic Vermont charm. 3 bedrooms and 1 bathroom with a layout that includes multiple practical options for adding a second bathroom. The layout also includes a unique, unfinished bonus area off the primary bedroom with its own private staircase to the backyard—a blank canvas ideal for an

    Lori Hurley Four Corner Properties LLC

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

    $242,500

    Sold May 06, 2026

    1645 Vermont Route 67 E, Shaftsbury, VT 05257

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2003

    Last Sold Summary

    • $160/SF
    • 6 Days On Market

    Last Listing Agent Morriah Adams BHG Masiello Brattleboro

    1645 Vermont Route 67 E, Shaftsbury, VT 05257
    • /14

      Est $447,391

      Not Listed For Sale

      535 Dunlap Farm Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1986
      535 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Sean Dillon Real Broker LLC

  • /19

    $209,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft

    7066 Main St, Readsboro, VT 05350

    Recently renovated & affordable 3-bedroom, 2-bath home comes with NEW Solar Panels INCLUDED in Price! The home has two full kitchens, one up and one down and comes partially furnished. Whether you're envisioning multigenerational living, a home-based business, or simply want to be close to skiing and outdoor adventure, this versatile layout adapts to fit your life. Recent renovations touch nearly

    Pam Tworig BISHOP WEST REAL ESTATE

    7066 Main St, Readsboro, VT 05350
  • /56

    $2,600,000

    Sold May 01, 2026

    25 Mountain Haunts Rd, Winhall, VT 05340

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft
    • Built 1960

    Last Sold Summary

    • 13% Below List Price
    • $391/SF
    • 366 Days On Market

    Current Estimated Value $2,552,242

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
    • /40

      Est $107,717

      Not Listed For Sale

      51 Chiselville Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 540 Sq Ft
      • Built 1820
      51 Chiselville Rd, Arlington, VT 05250

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Nicholas Charest Maple Leaf Real Estate

  • /16

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    447 Rock Bottom Ln, Peru, VT 05152

    Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

    Andy Reed Four Seasons Sotheby's Int'l Realty

    447 Rock Bottom Ln, Peru, VT 05152
  • /40

    $595,000

    Sold Nov 10, 2025

    4A Ridge, Winhall, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,886 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $315/SF
    • 31 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    4A Ridge, Winhall, VT 05340
    • /18

      Est $525,172

      Not Listed For Sale

      55 Wildflower Ln, Arlington, VT 05250

      • 3 Beds
      • 2.5 Baths
      • 2,514 Sq Ft
      • Built 1997
      55 Wildflower Ln, Arlington, VT 05250

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Sean Dillon Real Broker LLC

  • /55

    $2,850,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    JULY 23 - Significant new price change today! - 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

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /19

    $225,000

    Sold Aug 29, 2025

    1801 S Stream Rd, Bennington, VT 05201

    • Land
    • 16.68 Acres
    • $13,489 per Acre

    Last Sold Summary

    • 34 Days On Market

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1801 S Stream Rd, Bennington, VT 05201
    • /37

      Est $451,735

      Not Listed For Sale

      127 Flynn Hollow Rd, Sunderland, VT 05250

      • 3 Beds
      • 1.5 Baths
      • 1,718 Sq Ft
      • Built 1989
      127 Flynn Hollow Rd, Sunderland, VT 05250

      Last Sold Summary

      • 3 Days On Market

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

  • /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
  • /32

    $325,000

    Sold Jul 29, 2026

    21 Pageant St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,443 Sq Ft
    • Built 1950

    Last Sold Summary

    • $225/SF
    • 23 Days On Market

    Current Estimated Value $320,091

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    21 Pageant St, Bennington, VT 05201
    • /34

      Est $259,304

      Not Listed For Sale

      925 South Rd, East Arlington, VT 05252

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1972
      925 South Rd, East Arlington, VT 05252

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /6

    $199,900

    Pending
    • 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

Showing Results 201 - 240, Page 6 of 18

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