21,299

Bennington County, VT Homes

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  • /39

    $219,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 988 Sq Ft

    215 Orchard St, Pownal, VT 05261

    Welcome to this adorable bungalow in the heart of Pownal the opportunity you’ve been waiting for! If you’ve been searching for a home in Pownal but haven’t been able to find the right fit or move quickly enough, this charming 2 bedroom, 1 bath home may be exactly what you’ve been looking for.Featuring an updated kitchen, a cozy pellet stove that primarily heats the home, and a bright enclosed

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 636-5434

    215 Orchard St, Pownal, VT 05261
  • /48

    $45,000 Per Month

    • 4 Beds
    • 4 Baths
    • 5,624 Sq Ft
    • House for Rent

    37 Burnt Hill Rd, Winhall, VT 05340

    Now available for the 26-27 ski season! This spacious, luxurious post-and-beam mountain home has been owner-occupied for past winter weekends, and is now available as the ultimate ski rental just a 7-minute drive to Stratton's base lodge. Beginning with the property's 2-car garage-barn, enviable curb appeal extends throughout. An expansive, well-equipped chef's kitchen offers duel ranges and

    Jamie Luke TPW Real Estate

    37 Burnt Hill Rd, Winhall, VT 05340
  • /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 $491,421

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

    245 Southshire Dr, Bennington, VT 05201
    • /8

      Not Listed For Sale

      79 Heartwellville View Rd, Readsboro, VT 05350

      79 Heartwellville View Rd, Readsboro, VT 05350

      Last Sold Summary

      • 167 Days On Market

  • /33

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    8 West St, Bennington, VT 05201

    Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 551-3900

    8 West St, Bennington, VT 05201
  • /40

    $185,000

    Sold Jul 25, 2025

    305 Grove St, Bennington, VT 05201

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Built 2016

    Last Sold Summary

    • 3% Above List Price
    • $231/SF
    • 28 Days On Market

    Current Estimated Value $182,566

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    305 Grove St, Bennington, VT 05201
    • /39

      Est $357,853

      Not Listed For Sale

      744 Dunlap Farm Rd, Arlington, VT 05250

      • 3 Beds
      • 2 Baths
      • 1,306 Sq Ft
      • Built 1985
      744 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 89 Days On Market

  • /6

    $100,000

    Pending
    • Land
    • 26.2 Acres
    • $3,817 per Acre

    0 Magee Rd Unit 202616239, Stamford, VT 05352

    Uncover this hidden and exceptional 26.2-acre property featuring two prime lots, perfect for development or creating your personal retreat. Thispicturesque Vermont landscape is highlighted by small streams and even a tranquil pond, complete with wide trails that ensure easy navigation throughout the propertyfor access, exercise and recreational vehicles. Complete with remarkable stone outcrops

    Agent Photo

    Gary Fuls Jr

    Gary L Fuls DBA Re/MAX Transit

    (802) 884-2362

    0 Magee Rd Unit 202616239, Stamford, VT 05352
  • /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 $197,903

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    111 Hicks Ave, Bennington, VT 05201
    • /27

      Est $180,571

      Not Listed For Sale

      731 Main St, Bennington, VT 05201

      • 2 Beds
      • 1.5 Baths
      • 1,155 Sq Ft
      • Built 1900
      731 Main St, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

  • /51

    $755,000

    $25K PRICE DROP
    • 3,423 Sq Ft

    85 Limerick Ln, Arlington, VT 05250

    Vermont lifestyle meets income potential! Set in the scenic Taconic and Green Mountain valley along the Battenkill River and 8 shared acres, this spacious 4-bedroom, 5-bath home, built in 2001, offers peaceful country living with versatile use. Low cost HOA offers mowing, plowing, trash removal and water/ sewer. The property features three living sections with separate entrances, each with at

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 500-7734

    85 Limerick Ln, Arlington, VT 05250
  • /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

      Not Listed For Sale

      740 Vt Route 9, Woodford, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,648 Sq Ft
      • Built 1993
      740 Vt Route 9, Woodford, VT 05201

      Last Sold Summary

      • 139 Days On Market

  • /60

    $799,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,462 Sq Ft

    636 Dexter Rd, Shaftsbury, VT 05262

    In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 727-7584

    636 Dexter Rd, Shaftsbury, VT 05262
  • /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
    • /36

      Est $413,285

      Not Listed For Sale

      21 Birches Way, Peru, VT 05152

      • 3 Beds
      • 2 Baths
      • 1,275 Sq Ft
      • Built 1975
      21 Birches Way, Peru, VT 05152

      Last Sold Summary

      • 7 Days On Market

  • /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
  • /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
    • /11

      Not Listed For Sale

      117 Elm St, Manchester Center, VT 05255

      • 12 Beds
      • 6 Baths
      • 3,682 Sq Ft
      • Built 1850
      117 Elm St, Manchester Center, VT 05255

      Last Sold Summary

      • 77 Days On Market

  • /21

    $2,525,000

    New Construction $100K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340
  • /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 $1,734,688

    Last Listing Agent Cheyanne Pugliese

    139 Prospect St, Manchester, VT 05254
    • /18

      Est $212,255

      Not Listed For Sale

      9 Palmer Dr, Pownal, VT 05261

      • 1 Bed
      • 1 Bath
      • 1,012 Sq Ft
      • Built 1850
      9 Palmer Dr, Pownal, VT 05261

      Last Sold Summary

      • 24 Days On Market

  • /28

    $1,495,000

    $205K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,363 Sq Ft

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155

    Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

    Edwin Kevil Stratton Real Estate

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155
  • /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 $227,857

    Last Listing Agent Susan Bellville Bellville Realty

    5089 Vt Route 7a, Arlington, VT 05250
    • /79

      Est $424,179

      Not Listed For Sale

      460 Sparrow Dr, Stamford, VT 05352

      • 4 Beds
      • 3 Baths
      • 3,721 Sq Ft
      • Built 1988
      460 Sparrow Dr, Stamford, VT 05352

      Last Sold Summary

      • 67 Days On Market

  • /28

    $339,900

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

    78 Carbonti Cir, Arlington, VT 05250

    Enjoy effortless one-level living in this wonderful Arlington home, offering 3 bedrooms, 2 bathrooms, and a bright, modern layout. Set in a lovely neighborhood, the home welcomes you with a west-facing living room window that frames beautiful mountain views. Two bedrooms are tucked into the northeast corner of the home, while the spacious primary suite—with its own full bathroom—sits privately on

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    78 Carbonti Cir, 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
    • /29

      Est $504,434

      Not Listed For Sale

      117 Nottingham Park, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 1,728 Sq Ft
      • Built 1972
      117 Nottingham Park, Manchester Center, VT 05255

      Last Sold Summary

      • 42 Days On Market

  • /28

    $499,000

    $51K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,992 Sq Ft

    2936 Hapgood Pond Rd, Peru, VT 05152

    This is Vermont the way it's supposed to feel. Escape the ordinary and settle into something slower. Nestled on 30 private acres in the heart of Vermont's Green Mountains, this charming 2-bedroom, 2-bath cabin is the kind of place where the outside world fades away. Inside you will find a cozy living room with a wood burning fireplace, 2 good sized bedrooms and a bonus room. The lower walk out

    Jamie Wylie Stratton Real Estate

    2936 Hapgood Pond Rd, Peru, VT 05152
  • /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 $2,653,946

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
    • /12

      Est $361,119

      Not Listed For Sale

      454 NW Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 1,901 Sq Ft
      • Built 1880
      454 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 10 Days On Market

  • /10

    $20,000

    • Land
    • 1.2 Acres
    • $16,667 per Acre

    0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350

    1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

    Community Lands Community Lands

    0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350
  • /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
    • /35

      Est $240,320

      Not Listed For Sale

      312 School St Unit 314, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1908
      312 School St Unit 314, Bennington, VT 05201

      Last Sold Summary

      • 3 Days On Market

  • /38

    $4,975,000

    • 5 Beds
    • 4 Baths
    • 6,998 Sq Ft

    527 Benson Rd, Manchester Center, VT 05255

    Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

    Story Jenks LandVest, Inc/Woodstock

    527 Benson Rd, Manchester Center, VT 05255
  • /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
    • /34

      Est $514,564

      Not Listed For Sale

      647 Fox Hill Rd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 1,901 Sq Ft
      • Built 2008
      647 Fox Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 133 Days On Market

  • /27

    $209,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft

    1083 Main St, Bennington, VT 05201

    Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    1083 Main St, Bennington, VT 05201
  • /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
    • /39

      Est $578,697

      Not Listed For Sale

      557 Fox Hill Rd, Bennington, VT 05201

      • 4 Beds
      • 3.5 Baths
      • 2,336 Sq Ft
      • Built 2009
      557 Fox Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 17 Days On Market

Showing Results 161 - 200, Page 5 of 18

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