21,114

Bennington County, VT Homes

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  • /45

    $544,900

    • 2 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
  • /36

    $850,000 Sold Dec 04, 2025

    109 Nichols Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 2.5 Baths
    • 1,946 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $437/SF
    • 30 Days On Market

    Current Estimated Value $866,227

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

    109 Nichols Hill Ln, Dorset, VT 05251
    • /38

      Est $342,564 Not Listed For Sale

      683 Water St, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1934
      683 Water St, North Bennington, VT 05257

      Last Sold Summary

      • 15% Above List Price
      • $199/SF
      • 58 Days On Market

      Last Sold Price $299,000

      Last Listing Agent Angela Bevin Maple Leaf Realty

  • /36

    $399,000 Pending

    • 5 Beds
    • 3 Baths
    • 3,118 Sq Ft

    100 McCarthy Acres, North Bennington, VT 05257

    Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

    Nicholas Charest Maple Leaf Realty

    100 McCarthy Acres, North Bennington, VT 05257
  • /40

    $1,000,000 Sold Feb 24, 2026

    19 Roundtree Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 80 Days On Market

    Current Estimated Value $1,010,436

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /32

      Est $329,817 Not Listed For Sale

      159 Matteson Rd, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 1,552 Sq Ft
      • Built 1973
      159 Matteson Rd, North Bennington, VT 05257

      Last Sold Summary

      • 10% Above List Price
      • $193/SF
      • 34 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /8

    $35,000

    • Land
    • 1 Acre
    • $35,000 per Acre

    0 Barber Pond Rd, Pownal, VT 05261

    Tucked into the scenic rural landscape of Pownal, Vermont, this approximate one-acre parcel of raw land offers a blend of natural privacy and water frontage on Barber Pond. Ideal for recreational use or future development, subject to local zoning and permitting. Enjoy the charm of the southern Vermont countryside while remaining within easy reach of nearby towns and outdoor amenities. Known for

    Vicki Wilson Maple Leaf Realty

    0 Barber Pond Rd, Pownal, VT 05261
  • /44

    $702,000 Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $690,903

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /40

      Est $433,603 Not Listed For Sale

      23 Church St, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1847
      23 Church St, North Bennington, VT 05257

      Last Sold Summary

      • 3% Below List Price
      • $235/SF
      • 6 Days On Market

      Last Sold Price $446,500

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /13

    $17,000

    • Land
    • 1 Acre
    • $17,000 per Acre

    326A Bergabhang Dr, Stamford, VT 05352

    Affordable one-acre lot in Alpenwald Village, offering a charming country setting ideal for a primary residence or vacation retreat. With ample space to design and build, this parcel presents a wonderful opportunity to create the home you’ve always envisioned. The Alpenwald Village HOA fee is $450 annually and covers road maintenance; community guidelines include, but are not limited to, a

    Monique White Deerfield Valley Real Estate

    326A Bergabhang Dr, Stamford, VT 05352
  • /20

    $500,000 Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $511,075

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /30

      Est $308,650 Not Listed For Sale

      4 Church St, North Bennington, VT 05257

      • 3 Beds
      • 1 Bath
      • 1,296 Sq Ft
      • Built 1910
      4 Church St, North Bennington, VT 05257

      Last Sold Summary

      • 10% Above List Price
      • $217/SF
      • 7 Days On Market

      Last Sold Price $281,000

      Last Listing Agent Linda McLenithan SoVermont Realty

  • /39

    $895,000

    • 4 Beds
    • 4 Baths
    • 2,673 Sq Ft

    F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

    Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

    Mike England Michael England Real Estate

    F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
  • /30

    $25,000 Sold Apr 11, 2025

    0 Vermont Route 7a, Shaftsbury, VT 05262

    • Land
    • 3 Acres
    • $8,333 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 15 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    0 Vermont Route 7a, Shaftsbury, VT 05262
    • /39

      Est $256,599 Not Listed For Sale

      3 Church St, North Bennington, VT 05257

      • 3 Beds
      • 1.5 Baths
      • 1,238 Sq Ft
      • Built 1920
      3 Church St, North Bennington, VT 05257

      Last Sold Summary

      • 19% Above List Price
      • $174/SF
      • 78 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  • /5

    $575,000 Pending

    • 10 Beds
    • 8 Baths
    • 8,300 Sq Ft

    202-204 Beech St, Bennington, VT 05201

    Rare opportunity to own a high-performing multi-family portfolio on a spacious .75-acre lot in Bennington. This property features 9 total units spread across two well-maintained buildings. The primary 6-unit building has seen significant recent capital improvements, including a brand-new metal roof and five fully renovated apartments featuring modern finishes. The sixth unit remains occupied by a

    Lori Hurley Four Corner Properties LLC

    202-204 Beech St, Bennington, VT 05201
  • /60

    $420,000 Sold Jun 26, 2025

    123 Bank St, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 2,753 Sq Ft
    • Built 1952

    Last Sold Summary

    • 6% Below List Price
    • $153/SF
    • 31 Days On Market

    Current Estimated Value $420,827

    Last Listing Agent Margretta Fischer Wohler Realty Group

    123 Bank St, North Bennington, VT 05257
    • /34

      Est $305,114 Not Listed For Sale

      6 Bank St, North Bennington, VT 05257

      • 6 Beds
      • 2 Baths
      • 2,986 Sq Ft
      • Built 1918
      6 Bank St, North Bennington, VT 05257

      Last Sold Summary

      • 9% Above List Price
      • $94/SF
      • 61 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Justine Curry Maple Leaf Realty

  • /40

    $179,000

    • Land
    • 0.2 Acre
    • $895,000 per Acre

    10 Partridge Hill, Manchester, VT 05255

    One of the last remaining lots in the exceptional Partridge Hill Association. This beautiful lot is situated to capture wonderful views and abbuts common land and a huge undeveloped land parcel on it's boundaries- offering a private outdoor space. The building envelope benefits from the ability to approach the parcel through the adjacent common land. Underground power and cable at the lot.

    Kim Morgan-Wohler Wohler Realty Group

    10 Partridge Hill, Manchester, VT 05255
  • /29

    $455,000 Sold Mar 28, 2025

    2 Byington Ln Unit 5, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft
    • Built 1977

    Last Sold Summary

    • 7% Below List Price
    • $290/SF
    • 53 Days On Market

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

    2 Byington Ln Unit 5, Winhall, VT 05340
    • /36

      Est $908,008 Not Listed For Sale

      372 Canterbury Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 1996
      372 Canterbury Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 14% Above List Price
      • $284/SF
      • 12 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Kristin Comeau TPW Real Estate

  • /40

    $1,150,000

    • 5 Beds
    • 3.5 Baths
    • 4,017 Sq Ft

    11 Founders Hill Rd, Winhall, VT 05360

    Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    11 Founders Hill Rd, Winhall, VT 05360
  • /40

    $615,000 Sold Aug 07, 2025

    5529 Vt Route 7a, Shaftsbury, VT 05262

    • 3 Beds
    • 3 Baths
    • 3,173 Sq Ft
    • Built 1804

    Last Sold Summary

    • 2% Below List Price
    • $194/SF
    • 85 Days On Market

    Current Estimated Value $615,817

    Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

    5529 Vt Route 7a, Shaftsbury, VT 05262
    • /28

      Est $558,868 Not Listed For Sale

      217 Hillvale Dr, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,549 Sq Ft
      • Built 2007
      217 Hillvale Dr, Manchester Center, VT 05255

      Last Sold Summary

      • 7% Above List Price
      • $336/SF
      • 92 Days On Market

      Last Sold Price $520,000

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

  • /51

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,816 Sq Ft

    281 Old County Ln, Readsboro, VT 05350

    Nestled on more than two acres of beautifully maintained countryside and mature forest, this renovated 1892 farmhouse blends New England charm with peaceful seclusion and easy access to local attractions. Just 15 minutes from Mass MoCA, 25 minutes from Mount Snow, and close to hiking and ATV trails, it’s perfect for outdoor enthusiasts. Inside, you’ll find a warm and thoughtfully updated home

    Melissa Nebelski Real Broker LLC

    281 Old County Ln, Readsboro, VT 05350
  • /57

    $275,000 Sold Aug 07, 2025

    115-117 Norton St, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • Built 1930

    Last Sold Summary

    • $162/SF
    • 0 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    115-117 Norton St, Bennington, VT 05201
    • /35

      Est $829,530 Not Listed For Sale

      290 Mending Walls Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 2,424 Sq Ft
      • Built 2005
      290 Mending Walls Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 4% Above List Price
      • $330/SF
      • 4 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /16

    $215,000

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft

    40 Bourn Brook Rd Unit 50, Manchester, VT 05255

    Modern In-Town Living and Fully Renovated Bourn Brook Condo. Experience the best of Manchester Center in this meticulously renovated end-unit at Bourn Brook. Whether you are looking for an affordable primary residence or a sleek "lock-and-leave" weekend getaway, this condo delivers modern style in a prime, walkable location.Interior HighlightsNo detail was spared in this top-to-bottom

    Robin Apps Four Seasons Sotheby's Int'l Realty

    40 Bourn Brook Rd Unit 50, Manchester, VT 05255
  • /59

    $720,000 Sold Sep 12, 2025

    422 N Mason Hill Rd, Pownal, VT 05261

    • 4 Beds
    • 4 Baths
    • 4,844 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $149/SF
    • 5 Days On Market

    Current Estimated Value $711,382

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    422 N Mason Hill Rd, Pownal, VT 05261
    • /28

      Est $779,704 Not Listed For Sale

      182 Mending Walls Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4 Baths
      • 1,955 Sq Ft
      • Built 2002
      182 Mending Walls Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 8% Above List Price
      • $371/SF
      • 5 Days On Market

      Last Sold Price $725,000

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /17

    $160,000

    • Land
    • 2.9 Acres
    • $55,172 per Acre

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250

    This scenic undeveloped lot in Sunderland, Vermont, offers an exceptional opportunity to build in a peaceful yet convenient location. Set along a picturesque bike route, the property features level terrain that makes it ideal for easy construction and design flexibility. The land is already cleared, opening up the possibility for lovely mountain views and allowing you to envision your home

    Andy Reed Four Seasons Sotheby's Int'l Realty

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250
  • /43

    $115,000 Sold Aug 29, 2025

    0000 Skiparee Rd, Pownal, VT 05261

    • Land
    • 25.7 Acres
    • $4,475 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

    Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

    0000 Skiparee Rd, Pownal, VT 05261
    • /24

      Est $695,104 Not Listed For Sale

      94 E Manchester Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,649 Sq Ft
      • Built 2002
      94 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5% Above List Price
      • $400/SF
      • 113 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Annette Gallo Real Broker LLC

  • /52

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 4,650 Sq Ft

    20 Blackberry Ln, Peru, VT 05152

    Welcome to Bromley Village. This spacious 5 bedroom, 5 bath house offers everything you need to ensure the comfort of your group whether it’s large or small. The heart of this home is the magnificent great room with 20 foot ceilings, wood burning fireplace, slate floors, dining area and corner bar. The gourmet kitchen with red cabinets, soapstone counters, and top of the line appliances (Sub

    David Citron RE/MAX Four Seasons

    20 Blackberry Ln, Peru, VT 05152
  • /22

    $445,000 Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $439,270

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

    163 Vt Route 30, Winhall, VT 05340
    • /40

      Est $912,576 Not Listed For Sale

      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4.5 Baths
      • 2,814 Sq Ft
      • Built 1998
      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 1% Above List Price
      • $320/SF
      • 2 Days On Market

      Last Sold Price $900,000

      Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

  • /5

    $199,000 Pending

    • Land
    • 55 Acres
    • $3,618 per Acre

    0 Andrea Dr Unit 239393, Stamford, VT 05352

    55 acres of pristine sloping woodlands. Build your dream house here. Two very private adjacent lots on gravel road with timber value. Although not part of the Alpenwald development the road is plowed and maintained by the Association for $750/year ($350 per lot). Exceptional opportunity to own a piece of Vermont. Convenient to skiing, hiking, reservoir and 10 minutes to MASS MoCA and restaurants

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 Andrea Dr Unit 239393, Stamford, VT 05352
  • /25

    $825,000 Sold Mar 14, 2025

    0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $356/SF
    • 135 Days On Market

    Last Listing Agent Jamie Wylie Stratton Real Estate

    0 Cobble Ridge Rd Unit D2, Winhall, VT 05340
    • /26

      Est $633,852 Not Listed For Sale

      989 Beech St, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 1,924 Sq Ft
      • Built 1989
      989 Beech St, Manchester Center, VT 05255

      Last Sold Summary

      • 41% Above List Price
      • $234/SF
      • 20 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Faith Rhodes Maple Leaf Realty

  • /8

    $175,000

    • Land
    • 2.26 Acres
    • $77,434 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Shuttle service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water permit in place for a 4 bedroom home.

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

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