21,299

Bennington County, VT Homes

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  • /34

    $699,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 4,683 Sq Ft

    2744 Danby Mountain Rd, Dorset, VT 05251

    Welcome to your mountain contemporary escape in beautiful, historic Dorset, Vermont. This property offers exceptional value in today’s market. Sellers have relocated out of state, creating a unique opportunity for a new owner. They are motivated to sell and all reasonable offers will be considered. The new wrap around Trex deck offers stunning views of lush gardens and mountain scenery, with easy

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    2744 Danby Mountain Rd, Dorset, VT 05251
  • /16

    $130,000

    Sold Nov 25, 2025

    76 Harvest Hills Dr, North Bennington, VT 05257

    • 3 Beds
    • 1 Bath
    • 1,290 Sq Ft
    • Built 1966

    Last Sold Summary

    • 16% Below List Price
    • $101/SF
    • 45 Days On Market

    Current Estimated Value $205,002

    Last Listing Agent Susan Bellville Bellville Realty

    76 Harvest Hills Dr, North Bennington, VT 05257
    • /16

      Est $247,160

      Not Listed For Sale

      102 Meadow Ln, Shaftsbury, VT 05262

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1974
      102 Meadow Ln, Shaftsbury, VT 05262

      Last Sold Summary

      • 0 Days On Market

  • /10

    $150,000

    • Land
    • 4 Acres
    • $37,500 per Acre

    0 Rocky Ln Unit 5082777, Dorset, VT 05253

    'THE GROUND BENEATH AN APRIL SNOWSTORM IS NOT DORMANT... IT IS AWAKENING!".... Come discover the perfect opportunity to craft the home of your dreams!! With Spring ready to bloom, this very special lot is vibrant and quite ready for your vision!Fully permitted for a five bedroom residence, this property combines privacy, natural beauty and convenience!Imagine waking up to serene views,

    Sunny Breen Josiah Allen Real Estate, Inc.

    0 Rocky Ln Unit 5082777, Dorset, VT 05253
  • /21

    $280,000

    Sold Jun 12, 2026

    53 South Rd, East Arlington, VT 05252

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $187/SF
    • 30 Days On Market

    Current Estimated Value $266,979

    Last Listing Agent David White OwnerEntry.com

    53 South Rd, East Arlington, VT 05252
    • /24

      Est $300,380

      Not Listed For Sale

      855 Vt Route 7a, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 2,188 Sq Ft
      • Built 1805
      855 Vt Route 7a, Shaftsbury, VT 05262

      Last Sold Summary

      • 239 Days On Market

  • /40

    $525,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,732 Sq Ft

    1138 Barber Pond Rd, Pownal, VT 05261

    Welcome to your Vermont dream home—where comfort, craftsmanship, and countryside charm come together beautifully.Set against a backdrop of serene Vermont landscape, this stunning ranch offers effortless one-level living with exceptional indoor and outdoor spaces designed for both relaxation and entertaining. From the moment you arrive, the inviting front porch and paved driveway set the tone

    Lilli West Maple Leaf Real Estate

    1138 Barber Pond Rd, Pownal, VT 05261
  • /50

    $449,000

    Sold Jun 08, 2026

    1284 Granger Hollow Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $320/SF
    • 19 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1284 Granger Hollow Rd, Shaftsbury, VT 05262
    • /17

      Est $257,352

      Not Listed For Sale

      591 Vt Route 67 E, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 2001
      591 Vt Route 67 E, Shaftsbury, VT 05262

      Last Sold Summary

      • 22 Days On Market

  • /6

    $69,900

    Pending
    • 2 Beds
    • 1 Bath
    • 1,352 Sq Ft

    32 French Hill Rd, Pownal, VT 05261

    Subject property currently has two buildings on the property. One is a ranch style home the other is a shed. Property has just under an acre of land with power, and town sewer at the street. Do not entry property without your buyer's agent with you. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner

    April Shepard Twin State Realty LLC

    32 French Hill Rd, Pownal, VT 05261
  • /13

    $47,000

    Sold May 22, 2026

    16 Schenk Rd, Stamford, VT 05352

    • Land
    • 10.64 Acres
    • $4,417 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 3 Days On Market

    Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

    16 Schenk Rd, Stamford, VT 05352
    • /34

      Est $373,116

      Not Listed For Sale

      191 Grove Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 1,771 Sq Ft
      • Built 1978
      191 Grove Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 141 Days On Market

  • /20

    $649,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    27 Owls Head Hill Ln, Dorset, VT 05251

    Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    27 Owls Head Hill Ln, Dorset, VT 05251
  • /35

    $372,000

    Sold May 13, 2026

    303 Prospect St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,463 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 11 Days On Market

    Current Estimated Value $361,535

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    303 Prospect St, Bennington, VT 05201
    • /20

      Est $362,266

      Not Listed For Sale

      136 Grove Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1979
      136 Grove Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 2 Days On Market

  • /44

    $269,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft

    935 Gage St, Bennington, VT 05201

    Nestled in the Village of Bennington, this charming three-bedroom, two-bath Cape-style home offers comfort, character, and beautiful outdoor living. Step inside to find all fresh flooring, just painted throughout, and inviting spaces filled with natural light. Fireplace in the living room and new glass slider to the deck. Second floor is one large room with spacious closet and full bath-an ideal

    Lilli West Maple Leaf Real Estate

    935 Gage St, Bennington, VT 05201
  • /17

    $285,000

    Sold Jul 01, 2025

    263 Clough Rd, Stamford, VT 05352

    • 2 Beds
    • 2 Baths
    • 1,415 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $201/SF
    • 206 Days On Market

    Current Estimated Value $274,301

    Last Listing Agent Duncan Honig Maple Leaf Real Estate

    263 Clough Rd, Stamford, VT 05352
    • /27

      Est $248,165

      Not Listed For Sale

      338 Twitchell Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1964
      338 Twitchell Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 100 Days On Market

  • /8

    $9,999

    $6K PRICE DROP Pending
    • Land
    • 1.2 Acres
    • $8,332 per Acre

    0 Alpendorf Ave, Readsboro, VT 05350

    Stake a claim on your own little piece of Vermont, at the foot of the Green Mountain National Forest. This 1.2-acre triangular lot rises up from the road and may allow peekaboo views of the surrounding valley starting in late-fall, once the region's famous foliage drops away. It's located in Alpenwald Village, with community-maintained roads rolling up and down the area's hilly topography. Today

    David White OwnerEntry.com

    0 Alpendorf Ave, Readsboro, VT 05350
  • /30

    $1,550,000

    Sold Apr 10, 2026

    147 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $388/SF
    • 9 Days On Market

    Current Estimated Value $1,169,084

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    147 High Meadow Rd, Winhall, VT 05340
    • /39

      Est $430,671

      Not Listed For Sale

      20 Eastview Dr, Shaftsbury, VT 05262

      • 2 Beds
      • 2.5 Baths
      • 1,586 Sq Ft
      • Built 1986
      20 Eastview Dr, Shaftsbury, VT 05262

      Last Sold Summary

      • 35 Days On Market

  • /30

    $634,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,250 Sq Ft

    23 Stonewall Ln, Dorset, VT 05251

    Nestled in one of Vermont's most coveted villages, this three-bedroom, two-bathroom home is a canvas waiting for your creative vision. Priced well below assessed value, this property represents a rare opportunity to build equity from day one while enjoying the charm of quintessential New England living. The generous lot gives you room to breathe, garden, or simply watch the seasons paint the

    Brian Hill Remax Summit

    23 Stonewall Ln, Dorset, VT 05251
  • /24

    $425,000

    Sold Jun 18, 2026

    141 Hillvale Rd, Manchester, VT 05255

    • 2 Beds
    • 3 Baths
    • 1,689 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $252/SF
    • 5 Days On Market

    Current Estimated Value $434,288

    Last Listing Agent David Citron RE/MAX Four Seasons

    141 Hillvale Rd, Manchester, VT 05255
    • /36

      Est $514,638

      Not Listed For Sale

      1530 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 2,116 Sq Ft
      • Built 1900
      1530 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 8 Days On Market

  • /60

    $1,100,000

    • 3 Beds
    • 4 Baths
    • 2,745 Sq Ft

    65 Lower Taylor Hill Rd, Winhall, VT 05340

    Nestled on 10 private acres just off the Stratton Mountain Access Road, 65 Lower Taylor Hill Road offers a rare opportunity to own a beautifully renovated Vermont retreat ideally positioned between Stratton Mountain Resort and the area's endless four-season recreation. Surrounded by mature woodlands and exceptional privacy, this property offers a three-bedroom, three-bath main house along with a

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    65 Lower Taylor Hill Rd, Winhall, VT 05340
  • /60

    $900,000

    Sold Aug 25, 2025

    368 Bowen Dr, Readsboro, VT 05350

    • 3 Beds
    • 2 Baths
    • 2,168 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Above List Price
    • $415/SF
    • 3 Days On Market

    Current Estimated Value $883,826

    Last Listing Agent Nick Sicard EXP Realty

    368 Bowen Dr, Readsboro, VT 05350
    • /34

      Not Listed For Sale

      1858 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,088 Sq Ft
      • Built 1984
      1858 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 49 Days On Market

  • /52

    $650,000

    $75K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,274 Sq Ft

    490 Barnumville Rd, Manchester Center, VT 05255

    490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

    David Shehadi Josiah Allen Real Estate, Inc.

    490 Barnumville Rd, Manchester Center, VT 05255
  • /30

    $750,000

    Sold Aug 19, 2025

    379 Owls Head Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 4 Baths
    • 2,187 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $343/SF
    • 15 Days On Market

    Current Estimated Value $767,394

    Last Listing Agent Carol O`Connor Four Seasons Sotheby's Int'l Realty

    379 Owls Head Hill Ln, Dorset, VT 05251
    • /33

      Est $706,250

      Not Listed For Sale

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 2 Beds
      • 2.5 Baths
      • 2,145 Sq Ft
      • Built 1998
      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 4 Days On Market

  • /55

    $10,300,000

    New Construction
    • 6 Beds
    • 9 Baths
    • 10,993 Sq Ft

    551 West Fields, Manchester, VT 05254

    Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

    Sunny Breen Josiah Allen Real Estate, Inc.

    551 West Fields, Manchester, VT 05254
  • /31

    $208,000

    Sold Oct 10, 2025

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 10 Days On Market

    Current Estimated Value $209,494

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350
    • /40

      Est $558,524

      Not Listed For Sale

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft
      • Built 2000
      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 47 Days On Market

  • /59

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    219 Shamrock Hill, Arlington, VT 05250

    Escape to your own private Vermont retreat with this exceptional move-in-ready 3-bedroom, 2-bath home set amidst the breathtaking mountain landscapes of Sandgate. Surrounded by peaceful countryside and stunning panoramic views, this property offers the perfect blend of natural beauty, privacy, and modern comfort.Step inside to discover an elegant open-concept design where spacious living,

    Lindsey Martin Maple Leaf Real Estate

    219 Shamrock Hill, Arlington, VT 05250
  • /18

    $260,000

    Sold Apr 28, 2026

    940 Gage St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1945

    Last Sold Summary

    • 13% Below List Price
    • $166/SF
    • 58 Days On Market

    Current Estimated Value $278,811

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    940 Gage St, Bennington, VT 05201
    • /40

      Est $826,385

      Not Listed For Sale

      1279 W Mountain Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 5 Baths
      • 3,096 Sq Ft
      • Built 1977
      1279 W Mountain Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 104 Days On Market

  • /15

    $96,906

    New Construction Under Contract
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    10 Cassie Ln, Bennington, VT 05201

    Welcome to 10 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    10 Cassie Ln, Bennington, VT 05201
  • /53

    $400,000

    Sold Sep 22, 2025

    495 Fairview St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,309 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $306/SF
    • 12 Days On Market

    Current Estimated Value $393,970

    Last Listing Agent Catherine Cairns Maple Leaf Real Estate

    495 Fairview St, Bennington, VT 05201
    • /48

      Est $633,480

      Not Listed For Sale

      1516 W Mountain Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2.5 Baths
      • 1,738 Sq Ft
      • Built 1979
      1516 W Mountain Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 192 Days On Market

  • /27

    $650,000

    $25K PRICE INCREASE
    • 4 Beds
    • 4.5 Baths
    • 3,864 Sq Ft

    6265 Vt Route 7a, Sunderland, VT 05250

    Extensively Renovated Classic Vermont ColonialThis beautifully updated 1935 Vermont Colonial offers the perfect blend of classic charm and modern convenience, with thoughtful additions completed in 1972 and 2016. With nearly 3,900 square feet of living space, this spacious home features 4 bedrooms, 4.5 bathrooms, two dedicated office spaces, and a versatile third-story bonus room, ideal for a

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    6265 Vt Route 7a, Sunderland, VT 05250

Showing Results 321 - 360, Page 9 of 18

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