21,299

Bennington County, VT Homes

Section Image
  • /44

    $572,500

    Sold May 06, 2026

    475 Sunrise Ln, Arlington, VT 05250

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2002

    Last Sold Summary

    • 21% Below List Price
    • $191/SF
    • 214 Days On Market

    Current Estimated Value $616,421

    Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.

    475 Sunrise Ln, Arlington, VT 05250
    • /40

      Est $602,204

      Not Listed For Sale

      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 2,396 Sq Ft
      • Built 1971
      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 42 Days On Market

  • /4

    $18,000

    • Land
    • 1.1 Acres
    • $16,364 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /33

    $485,000

    Sold Apr 20, 2026

    3 Strattonwald Rd, Winhall, VT 05340

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $361/SF
    • 276 Days On Market

    Current Estimated Value $474,138

    Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Strattonwald Rd, Winhall, VT 05340
    • /40

      Est $605,371

      Not Listed For Sale

      143 Cedar Cir, Shaftsbury, VT 05262

      • 4 Beds
      • 4 Baths
      • 2,756 Sq Ft
      • Built 1977
      143 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 88 Days On Market

  • /8

    $1,900,000

    • Land
    • 199 Acres
    • $9,548 per Acre

    00 Vermont 11, Peru, VT 05152

    Bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains, this 199 +/- acre offering in Peru, Vermont captures the scale, landscape, and natural beauty that define Southern Vermont mountain living.Rolling terrain, wooded ridgelines, and changing elevation create exceptional natural light, long-range mountain vistas, and

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /60

    $230,500

    Sold Jul 18, 2025

    322 Burgess Rd, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 2,004 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $115/SF
    • 62 Days On Market

    Current Estimated Value $240,262

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    322 Burgess Rd, Bennington, VT 05201
    • /29

      Est $386,627

      Not Listed For Sale

      202 Cedar Cir, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1985
      202 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 3 Days On Market

  • /11

    $179,900

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft

    302 U S 7 S, Woodford, VT 05201

    Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

    Christine Lewis Brattleboro Area Realty

    302 U S 7 S, Woodford, VT 05201
  • /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
    • /40

      Est $269,226

      Not Listed For Sale

      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,006 Sq Ft
      • Built 1970
      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 18 Days On Market

  • /12

    $450,000

    • Land
    • 10.26 Acres
    • $43,860 per Acre

    4.1 Pearl Buck Dr, Winhall, VT 05340

    One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

    Kim Morgan-Wohler Wohler Realty Group

    4.1 Pearl Buck Dr, Winhall, VT 05340
  • /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 $501,634

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

    377 Glen Rd, Peru, VT 05152
    • /39

      Est $858,190

      Not Listed For Sale

      3842 Vt Route 7a, Shaftsbury, VT 05262

      • 5 Beds
      • 4.5 Baths
      • 4,312 Sq Ft
      • Built 1972
      3842 Vt Route 7a, Shaftsbury, VT 05262

      Last Sold Summary

      • 666 Days On Market

  • /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • /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 $649,092

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
    • /39

      Est $566,070

      Not Listed For Sale

      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 1981
      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 60 Days On Market

  • /25

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    393 Morse Hill Rd, East Dorset, VT 05253

    This beautifully maintained Dorset home with views is ready for its new owners. The main level features a generously sized eat-in kitchen with granite countertops that opens into the dining room. This floor also includes a large living room, a bedroom, and French doors that lead to a spacious deck overlooking a private yard. The ground floor offers a primary bedroom, a bathroom, and a laundry

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    393 Morse Hill Rd, East Dorset, VT 05253
  • /41

    $1,150,000

    Sold Jul 25, 2025

    35 Old Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 5.5 Baths
    • 4,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • 38% Below List Price
    • $238/SF
    • 369 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /45

      Est $380,920

      Not Listed For Sale

      294 Tinkham Rd, North Bennington, VT 05257

      • 2 Beds
      • 2 Baths
      • 1,573 Sq Ft
      • Built 1975
      294 Tinkham Rd, North Bennington, VT 05257

      Last Sold Summary

      • 4 Days On Market

  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

    Lindsey Martin Maple Leaf Real Estate

    113 Main 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
    • /52

      Est $427,632

      Not Listed For Sale

      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,535 Sq Ft
      • Built 1989
      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 6 Days On Market

  • /48

    $429,000

    • 2 Beds
    • 2 Baths
    • 7,000 Sq Ft

    3310 Vermont 346, Pownal, VT 05260

    Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

    Paul Harsch HARSCH ASSOCIATES

    3310 Vermont 346, Pownal, VT 05260
  • /21

    $73,500

    Sold Aug 04, 2025

    0 Sunset Dr Unit 5005504, Bennington, VT 05201

    • Land
    • 7 Acres
    • $10,500 per Acre

    Last Sold Summary

    • 26% Below List Price
    • 297 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    0 Sunset Dr Unit 5005504, Bennington, VT 05201
    • /24

      Est $435,843

      Not Listed For Sale

      318 Eleanors Way, North Bennington, VT 05257

      • 4 Beds
      • 3 Baths
      • 2,065 Sq Ft
      • Built 1968
      318 Eleanors Way, North Bennington, VT 05257

      Last Sold Summary

      • 10 Days On Market

  • /45

    $625,000

    $60K PRICE INCREASE
    • 3 Beds
    • 1.5 Baths
    • 1,594 Sq Ft

    191 Pleasant Street Extension, East Dorset, VT 05253

    "COME TAKE A PEEK, IT'S JUST ACROSS THE CREEK.....Enjoy an inviting front porch to unwind and breathe in the serene surroundings! Unwind and take in the lovely mountain views, all set on the scenic Tom River in East Dorset! Charming saltbox style (1982 circa), the design is open living spaces with abundant light through out... As an added bonus this property boasts an over sized two car garage

    Sunny Breen Josiah Allen Real Estate, Inc.

    191 Pleasant Street Extension, East Dorset, VT 05253
  • /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 $746,856

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /12

      Est $180,541

      Not Listed For Sale

      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 920 Sq Ft
      • Built 1935
      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 111 Days On Market

  • /50

    $555,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    3287 Route 7, Pownal, VT 05261

    Lovingly custom built in 1989 and offered for the first time, this beautifully maintained expanded Cape is a rare opportunity to own a home that has been cherished by its original family from the very beginning. Thoughtfully designed with generous room sizes and a timeless floor plan, the home offers warmth, comfort, and quality throughout. Inside, generous room sizes, timeless design, and

    Faith Rhodes Maple Leaf Real Estate

    3287 Route 7, Pownal, VT 05261
  • /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 $419,760

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    2603 N Pownal Rd, Pownal, VT 05261
    • /40

      Est $881,298

      Not Listed For Sale

      16 Glastenbury Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 3.5 Baths
      • 4,239 Sq Ft
      • Built 1800
      16 Glastenbury Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 5 Days On Market

  • /45

    $365,000

    • 4 Beds
    • 1.5 Baths
    • 1,735 Sq Ft

    19 Royal St, North Bennington, VT 05257

    Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the

    Lindsey Martin Maple Leaf Real Estate

    19 Royal St, North Bennington, VT 05257
  • /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 $273,865

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

    11 Maltese Rd, Stamford, VT 05352
    • /38

      Est $381,398

      Not Listed For Sale

      726 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,588 Sq Ft
      • Built 1930
      726 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 5 Days On Market

  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /37

    $895,000

    Sold Jul 11, 2025

    505 Powderhorn Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2 Baths
    • 2,089 Sq Ft
    • Built 1976

    Last Sold Summary

    • $428/SF
    • 40 Days On Market

    Current Estimated Value $856,428

    Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.

    505 Powderhorn Rd, Manchester Center, VT 05255
    • /38

      Est $415,509

      Not Listed For Sale

      1139 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1965
      1139 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 76 Days On Market

  • /45

    $650,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft

    146 Clover Ln, Manchester Center, VT 05255

    Come take a look at this charming Cape-style home set on nearly 4 acres, offering river frontage and beautiful mountain views. Bring your fishing pole or a canoe and head down to the river or relax and enjoy the sunshine on your own private beach as the water flows by.Inside, the home features an open-concept living and dining area, along with a first-floor primary suite for added

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    146 Clover Ln, Manchester Center, VT 05255
  • /37

    $256,250

    Sold Sep 03, 2025

    1236 Morgan St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,259 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $204/SF
    • 7 Days On Market

    Current Estimated Value $255,663

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1236 Morgan St, Bennington, VT 05201

Showing Results 361 - 400, Page 10 of 18

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