20,611

Bennington County, VT Homes

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  • /33

    $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

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Bishop Rd, Searsburg, VT 05363
  • /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
    • /19

      Est $441,140

      Not Listed For Sale

      1 Division Place, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 975 Sq Ft
      • Built 1895
      1 Division Place, Bennington, VT 05201

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /25

    $379,000

    • 2 Beds
    • 1 Bath
    • 1,276 Sq Ft

    1580 Main Rd, Stamford, VT 05352

    Very well appointed 2 bedroom 1 bathroom home with new heat pumps, stainless steel appliances, oversized garage and a walk up attic. New fenced in yard on just over an acre.

    Sean Taylor Moresi Real Estate Partners

    1580 Main Rd, Stamford, VT 05352
  • /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
    • /27

      Est $286,953

      Not Listed For Sale

      239 Breezy Acres Dr, Vernon, VT 05354

      • 3 Beds
      • 1.5 Baths
      • 1,941 Sq Ft
      • Built 1992
      239 Breezy Acres Dr, Vernon, VT 05354

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent A.J. Bellville Bellville Realty

  • /34

    $349,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,808 Sq Ft

    390 Smith Dr, Readsboro, VT 05350

    This well-built, post and beam style home provides serene solitude in the Vermont town of Readsboro. Lovingly crafted by its current owners, the house is a perfect execution of their vision. The unassuming exterior gives way to beautiful interior craftsmanship. Warm tones from the natural wood envelope you throughout the home, with oversized windows providing views of the surrounding naturescape.

    Monica Sumner BHG Masiello Brattleboro

    390 Smith Dr, Readsboro, VT 05350
  • /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 $239,877

    Last Listing Agent Susan Bellville Bellville Realty

    5089 Vt Route 7a, Arlington, VT 05250
    • /26

      Est $392,020

      Not Listed For Sale

      183 Cross Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1980
      183 Cross Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

  • /17

    $199,900

    $24K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft

    7066 Main St, Readsboro, VT 05350

    Why Rent when You Can Own a Home?! First Time Homebuyers eligible for financing with very low down payment and help with closing costs. 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. Recent renovations touch nearly every corner of the home, including both

    Pam Tworig BISHOP WEST REAL ESTATE

    7066 Main St, Readsboro, VT 05350
  • /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 $1,791,526

    Last Listing Agent Cheyanne Pugliese

    139 Prospect St, Manchester, VT 05254
    • /21

      Est $193,983

      Not Listed For Sale

      106 Park St Unit 16, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1993
      106 Park St Unit 16, Bennington, VT 05201

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

  • /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
  • /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
    • /38

      Est $455,976

      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

  • /60

    $2,500,000

    New Construction $450K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    LABOR DAY WEEKEND BEGINS WITH A HUGE PRICE CHANGE! - 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

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /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 $2,611,190

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
    • /60

      Est $427,350

      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

  • /6

    $199,900

    • 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
  • /33

    $710,000

    Sold Aug 24, 2026

    2 Corner Rock Rd, Winhall, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Below List Price
    • $334/SF
    • 21 Days On Market

    Last Listing Agent Jessica Marullo TPW Real Estate

    2 Corner Rock Rd, Winhall, VT 05340
    • /37

      Est $382,151

      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

  • /7

    $299,000

    $30K PRICE DROP
    • Land
    • 9.3 Acres
    • $32,151 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
  • /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
    • /40

      Est $510,359

      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

  • /40

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 4,453 Sq Ft

    6 Old Ridge Rd, Winhall, VT 05340

    Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering,

    Trent Stephens Wohler Realty Group

    6 Old Ridge Rd, Winhall, VT 05340
  • /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 $318,589

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    21 Pageant St, Bennington, VT 05201
    • /43

      Est $183,485

      Not Listed For Sale

      858 Vt Route 9, Woodford, VT 05201

      • 2 Beds
      • 1 Bath
      • 1,061 Sq Ft
      • Built 1805
      858 Vt Route 9, Woodford, VT 05201

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Amy Hill EXP Realty

  • /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
  • /12

    $410,000

    Sold Apr 01, 2026

    2511 Vermont 30, Dorset, VT 05251

    • 3 Beds
    • 1 Bath
    • 2,040 Sq Ft
    • Built 1962

    Last Sold Summary

    • $201/SF
    • 3 Days On Market

    Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

    2511 Vermont 30, Dorset, VT 05251
    • /37

      Not Listed For Sale

      73 Woodford City Rd, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1984
      73 Woodford City Rd, Bennington, VT 05201

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Abi Gregorio

  • /12

    $49,000

    • Land
    • 9,147 Sq Ft
    • $233,333 per Acre

    2 Belvedere St, Bennington, VT 05201

    Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and

    Dan Mason Perrott Realty

    2 Belvedere St, Bennington, VT 05201
  • /38

    $1,700,000

    Sold Jun 09, 2026

    2589 W Sandgate Rd, Arlington, VT 05250

    • 5 Beds
    • 3 Baths
    • 6,323 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $269/SF
    • 261 Days On Market

    Current Estimated Value $1,451,362

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    2589 W Sandgate Rd, Arlington, VT 05250
    • /47

      Est $418,130

      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

  • /36

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,671 Sq Ft

    6 Dwyers Camp Rd, Shaftsbury, VT 05262

    Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

    Lori Hurley Four Corner Properties LLC

    6 Dwyers Camp Rd, Shaftsbury, VT 05262
  • /21

    $175,000

    Sold Dec 23, 2025

    2591 Chapel Rd, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 11 Days On Market

    Current Estimated Value $196,086

    Last Listing Agent Susan Bellville Bellville Realty

    2591 Chapel Rd, Bennington, VT 05201
    • /25

      Est $770,503

      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

  • /27

    $565,500

    • 2 Beds
    • 3 Baths
    • 5,574 Sq Ft

    425 Rt 30 N, Pawlet, VT 05775

    A true piece of Vermont history, this rustic 1880 timber frame barn embodies the craftsmanship and character of a bygone era. Encompassing approximately 5,500 square feet, the structure is exceptionally solid, showcasing the strength and character of its original hand-hewn beams and post and beam joinery offering soaring interior spaces and authentic architectural details. Set on 10.05

    Chris DeFelice Four Seasons Sotheby's Int'l Realty

    425 Rt 30 N, Pawlet, VT 05775
  • /55

    $762,000

    Sold Nov 03, 2025

    3221 Hapgood Pond Rd, Peru, VT 05152

    • 4 Beds
    • 4 Baths
    • 2,868 Sq Ft
    • Built 1950

    Last Sold Summary

    • 17% Above List Price
    • $266/SF
    • 6 Days On Market

    Current Estimated Value $789,355

    Last Listing Agent Jamie Wylie Stratton Real Estate

    3221 Hapgood Pond Rd, Peru, VT 05152
    • /14

      Est $436,386

      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

  • /15

    $65,000

    • Land
    • 17.3 Acres
    • $3,757 per Acre

    18 Hidden Valley Rd, Shaftsbury, VT 05262

    Ready to build 2.5 acre building lot with an aditional 14 acres of riding trails with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site and the trails on the lot make it a great opportunity for a horse paddock.

    Dan Mason Perrott Realty

    18 Hidden Valley Rd, Shaftsbury, VT 05262

Showing Results 201 - 240, Page 6 of 18

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