21,299

Bennington County, VT Homes

Section Image
  • /43

    $1,795,000

    $100K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 5,178 Sq Ft

    144 Taconic Rd, Manchester, VT 05255

    “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

    Sara Buckley Josiah Allen Real Estate, Inc.

    144 Taconic Rd, Manchester, VT 05255
  • /41

    $445,000

    Sold Dec 19, 2025

    181 White Tail Run, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 2,246 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $198/SF
    • 5 Days On Market

    Current Estimated Value $452,471

    Last Listing Agent Margretta Fischer Wohler Realty Group

    181 White Tail Run, Arlington, VT 05250
    • /20

      Est $401,601

      Not Listed For Sale

      603 Wiley Mountain Dr, Readsboro, VT 05350

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 2005
      603 Wiley Mountain Dr, Readsboro, VT 05350

      Last Sold Summary

      • 160 Days On Market

  • /9

    $19,999

    Pending
    • Land
    • 1.5 Acres
    • $13,333 per Acre

    0 Lebensdorf Ln, Readsboro, VT 05350

    Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

    David White OwnerEntry.com

    0 Lebensdorf Ln, Readsboro, VT 05350
  • /30

    $400,000

    Sold Oct 15, 2025

    38 Spruce Ln, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Below List Price
    • $248/SF
    • 0 Days On Market

    Current Estimated Value $376,670

    Last Listing Agent Lori Hurley Four Corner Properties LLC

    38 Spruce Ln, Arlington, VT 05250
    • /24

      Est $377,119

      Not Listed For Sale

      1680 W Hill Dr, Readsboro, VT 05350

      • 4 Beds
      • Built 1980
      1680 W Hill Dr, Readsboro, VT 05350

      Last Sold Summary

      • 409 Days On Market

  • /27

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /38

    $635,000

    Sold Nov 21, 2025

    825 Case Ln, Readsboro, VT 05350

    • 3 Beds
    • 2 Baths
    • 2,499 Sq Ft
    • Built 2006

    Last Sold Summary

    • 15% Above List Price
    • $254/SF
    • 7 Days On Market

    Current Estimated Value $609,829

    Last Listing Agent Melissa Nebelski Real Broker LLC

    825 Case Ln, Readsboro, VT 05350
    • /21

      Est $248,918

      Not Listed For Sale

      470 Alpenwald Ln Unit A57, Readsboro, VT 05350

      • 3 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1970
      470 Alpenwald Ln Unit A57, Readsboro, VT 05350

      Last Sold Summary

      • 17 Days On Market

  • /6

    $56,900

    $18K PRICE DROP
    • Land
    • 4.2 Acres
    • $13,548 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 4-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /44

    $275,000

    Sold Jan 23, 2026

    211 Grandview St, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1955

    Last Sold Summary

    • 7% Below List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $282,027

    Last Listing Agent Colt Hazell Flex Realty

    211 Grandview St, North Bennington, VT 05257
    • /28

      Est $386,179

      Not Listed For Sale

      469 Swallow Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft
      • Built 1993
      469 Swallow Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 138 Days On Market

  • /12

    $325,000

    Under Contract
    • 2,476 Sq Ft

    343 Safford St, Bennington, VT 05201

    An investment gem or owner-occupied standout in the heart of Bennington, this renovated property features three distinct units, each offering the privacy and feel of a single-family home. Unlike traditional stacked apartments, all three units boast a two-story layout with 2 bedrooms and 1 full bath, ensuring no neighbors above or below. Each features modern finishes, bright living spaces, and a

    Lori Hurley Four Corner Properties LLC

    343 Safford St, Bennington, VT 05201
  • /36

    $265,000

    Sold Jun 25, 2025

    82 Oakes St, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,512 Sq Ft
    • Built 1991

    Last Sold Summary

    • $175/SF
    • 57 Days On Market

    Current Estimated Value $271,870

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    82 Oakes St, Bennington, VT 05201
    • /39

      Est $401,838

      Not Listed For Sale

      375 Grapevine Ln, Pownal, VT 05261

      • 4 Beds
      • 3 Baths
      • 2,208 Sq Ft
      • Built 2011
      375 Grapevine Ln, Pownal, VT 05261

      Last Sold Summary

      • 35 Days On Market

  • /51

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /49

    $595,000

    Sold May 18, 2026

    94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $278/SF
    • 38 Days On Market

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

    94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255
    • /40

      Est $386,719

      Not Listed For Sale

      201 Sunset Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 1.5 Baths
      • 1,720 Sq Ft
      • Built 2003
      201 Sunset Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 75 Days On Market

  • /59

    $419,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,119 Sq Ft

    131 Pine Cir, Bennington, VT 05201

    A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors

    Vicki Wilson Maple Leaf Real Estate

    131 Pine Cir, Bennington, VT 05201
  • /43

    $1,590,000

    Sold Oct 23, 2025

    81 Pine Tree Ln, Manchester Center, VT 05255

    • 4 Beds
    • 3.5 Baths
    • 3,926 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $405/SF
    • 17 Days On Market

    Current Estimated Value $1,528,898

    Last Listing Agent Roger Danyew Diamond Realty

    81 Pine Tree Ln, Manchester Center, VT 05255
    • /27

      Est $586,535

      Not Listed For Sale

      503 Atwood Dr, Pownal, VT 05261

      • 3 Beds
      • 2.5 Baths
      • 2,160 Sq Ft
      • Built 2004
      503 Atwood Dr, Pownal, VT 05261

      Last Sold Summary

      • 8 Days On Market

  • /60

    $950,000

    $750K PRICE DROP Under Contract
    • 6 Beds
    • 7 Baths
    • 5,400 Sq Ft

    2001 Depot St, Manchester Center, VT 05255

    LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 3.2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a

    Steven Bryant TPW Real Estate

    2001 Depot St, Manchester Center, VT 05255
  • /16

    $130,000

    Sold Jan 28, 2026

    755 Main St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft
    • Built 1890

    Last Sold Summary

    • 10% Below List Price
    • $88/SF
    • 141 Days On Market

    Current Estimated Value $140,495

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

    755 Main St, Bennington, VT 05201
    • /38

      Est $413,743

      Not Listed For Sale

      218 Puddingstone Rd, Pownal, VT 05261

      • 3 Beds
      • 1.5 Baths
      • 1,936 Sq Ft
      • Built 1971
      218 Puddingstone Rd, Pownal, VT 05261

      Last Sold Summary

      • 21 Days On Market

  • /53

    $925,000

    $150K PRICE DROP
    • 13 Beds
    • 12 Baths
    • 8,594 Sq Ft

    2759 Vt Route 11, Peru, VT 05152

    Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    2759 Vt Route 11, Peru, VT 05152
  • /11

    $780,000

    Sold Mar 23, 2026

    0 W Sandgate Rd, Sandgate, VT 05250

    • Land
    • 663.95 Acres
    • $1,175 per Acre

    Last Sold Summary

    • 110 Days On Market

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

    0 W Sandgate Rd, Sandgate, VT 05250
    • /16

      Est $167,290

      Not Listed For Sale

      86 Floyds Way, Pownal, VT 05261

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1972
      86 Floyds Way, Pownal, VT 05261

      Last Sold Summary

      • 6 Days On Market

  • /60

    $4,995,000

    $255K PRICE DROP
    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /23

    $110,000

    Sold Mar 26, 2026

    4697 Main Rd, Stamford, VT 05352

    • 4 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1940

    Last Sold Summary

    • 35% Below List Price
    • $69/SF
    • 161 Days On Market

    Current Estimated Value $254,595

    Last Listing Agent Dick Thackston R.H. Thackston & Company

    4697 Main Rd, Stamford, VT 05352
    • /40

      Est $872,283

      Not Listed For Sale

      718 Montgomery Rd, Pownal, VT 05261

      • 5 Beds
      • 4 Baths
      • 3,879 Sq Ft
      • Built 1800
      718 Montgomery Rd, Pownal, VT 05261

      Last Sold Summary

      • 29 Days On Market

  • /26

    $850,000

    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    46 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    46 Ridge Rd Unit C-4, Winhall, VT 05340
  • /40

    $125,000

    Sold May 01, 2026

    130 Lincoln St, Bennington, VT 05201

    • 4 Beds
    • 1 Bath
    • 1,156 Sq Ft
    • Built 1920

    Last Sold Summary

    • 9% Above List Price
    • $108/SF
    • 39 Days On Market

    Current Estimated Value $121,230

    Last Listing Agent Lisa Friedman Great American Dream Realty

    130 Lincoln St, Bennington, VT 05201
    • /19

      Est $249,948

      Not Listed For Sale

      169 Montgomery Rd, Pownal, VT 05261

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1970
      169 Montgomery Rd, Pownal, VT 05261

      Last Sold Summary

      • 10 Days On Market

  • /43

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,501 Sq Ft

    856 Matteson Rd, North Bennington, VT 05257

    Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

    Faith Rhodes Maple Leaf Real Estate

    856 Matteson Rd, North Bennington, VT 05257
  • /8

    $71,200

    Sold Oct 09, 2025

    272 Twenty Acre Wood Rd, Arlington, VT 05250

    • Land
    • 7.12 Acres
    • $10,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 58 Days On Market

    Current Estimated Value $67,237

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

    272 Twenty Acre Wood Rd, Arlington, VT 05250
    • /59

      Est $157,000

      Not Listed For Sale

      663 Sweet Rd, Pownal, VT 05261

      • 2 Beds
      • 2 Baths
      • 3,024 Sq Ft
      • Built 2010
      663 Sweet Rd, Pownal, VT 05261

      Last Sold Summary

      • 28 Days On Market

  • /27

    $189,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • /35

    $279,000

    Sold Aug 07, 2025

    65 Mountain View Dr, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $160/SF
    • 30 Days On Market

    Last Listing Agent Dan Mason Perrott Realty

    65 Mountain View Dr, Shaftsbury, VT 05262
    • /52

      Est $248,969

      Not Listed For Sale

      351 Old Military Rd, Pownal, VT 05261

      • 4 Beds
      • 1 Bath
      • 1,378 Sq Ft
      • Built 1969
      351 Old Military Rd, Pownal, VT 05261

      Last Sold Summary

      • 3 Days On Market

  • /25

    $98,999

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

    78 Ethans Way, Bennington, VT 05201

    Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. 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 energy-efficient

    Kate Barry EXP Realty

    78 Ethans Way, Bennington, VT 05201

Showing Results 441 - 480, Page 12 of 18

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