21,175

Bennington County, VT Homes

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  • /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
  • /43

    $401,000 Sold May 23, 2025

    515 Hillside Dr, Pownal, VT 05261

    • 3 Beds
    • 2.5 Baths
    • 2,692 Sq Ft
    • Built 1932

    Last Sold Summary

    • $149/SF
    • 124 Days On Market

    Current Estimated Value $385,832

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    515 Hillside Dr, Pownal, VT 05261
    • /35

      Est $691,951 Not Listed For Sale

      602 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,907 Sq Ft
      • Built 1960
      602 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Above List Price
      • $341/SF
      • 5 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  • /8

    $150,000

    • Land
    • 2.26 Acres
    • $66,372 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-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

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

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • /60

    $534,000 Sold Nov 24, 2025

    272 Oak Hill Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2.5 Baths
    • 3,637 Sq Ft
    • Built 2001

    Last Sold Summary

    • 24% Below List Price
    • $147/SF
    • 111 Days On Market

    Current Estimated Value $581,972

    Last Listing Agent Faith Rhodes Maple Leaf Realty

    272 Oak Hill Rd, Shaftsbury, VT 05262
    • /31

      Est $532,078 Not Listed For Sale

      373 Highland Ave, Manchester Center, VT 05255

      • 4 Beds
      • 1.5 Baths
      • 1,830 Sq Ft
      • Built 1905
      373 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 1% Above List Price
      • $287/SF
      • 5 Days On Market

      Last Sold Price $525,000

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

  • /25

    $975,000 Under Contract

    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /48

    $296,500 Sold Nov 21, 2025

    4 Rockwood St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Below List Price
    • $156/SF
    • 6 Days On Market

    Current Estimated Value $297,391

    Last Listing Agent Justine Curry Maple Leaf Realty

    4 Rockwood St, Bennington, VT 05201
    • /34

      Est $734,148 Not Listed For Sale

      196 Ways Ln, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 2,304 Sq Ft
      • Built 1929
      196 Ways Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 5% Above List Price
      • $303/SF
      • 7 Days On Market

      Last Sold Price $699,000

      Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

  • /34

    $579,000

    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft

    4 Pearl Buck Dr, Winhall, VT 05340

    Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time,

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    4 Pearl Buck Dr, Winhall, VT 05340
  • /22

    $795,000 Sold Sep 17, 2025

    185 Crooked Path Rd, Arlington, VT 05250

    • 4 Beds
    • 5.5 Baths
    • 3,463 Sq Ft
    • Built 2006

    Last Sold Summary

    • $230/SF
    • 9 Days On Market

    Current Estimated Value $769,577

    Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    185 Crooked Path Rd, Arlington, VT 05250
    • /17

      Est $320,915 Not Listed For Sale

      1581 E Manchester Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 1952
      1581 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 13% Above List Price
      • $299/SF
      • 8 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Patti Trudel RE/MAX

  • /2

    $2,190,000

    • Land
    • 1.16 Acres
    • $1,887,931 per Acre

    301 Northside Dr, Bennington, VT 05201

    Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

    Paul Carroccio TPW Real Estate

    301 Northside Dr, Bennington, VT 05201
  • /30

    $290,000 Sold Jul 17, 2025

    221 Grandview St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,042 Sq Ft
    • Built 1948

    Last Sold Summary

    • 2% Below List Price
    • $278/SF
    • 75 Days On Market

    Current Estimated Value $288,318

    Last Listing Agent Angela Bevin Maple Leaf Realty

    221 Grandview St, Bennington, VT 05201
    • /40

      Est $1,622,377 Not Listed For Sale

      2894 West Rd, Manchester Center, VT 05255

      • 3 Beds
      • 6 Baths
      • 3,556 Sq Ft
      • Built 1970
      2894 West Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 2% Below List Price
      • $464/SF
      • 60 Days On Market

      Last Sold Price $1,650,000

      Last Listing Agent Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  • /29

    $210,000

    • 9 Beds
    • 5 Baths
    • 3,810 Sq Ft

    6982 Main St, Readsboro, VT 05350

    Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    6982 Main St, Readsboro, VT 05350
  • /2

    $275,000 Sold Jul 22, 2025

    0 Tunic Rd, Shaftsbury, VT 05262

    • Land
    • 138.31 Acres
    • $1,988 per Acre

    Last Sold Summary

    • 54 Days On Market

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

    0 Tunic Rd, Shaftsbury, VT 05262
    • /20

      Est $594,687 Not Listed For Sale

      290 Deer Meadow Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 1,635 Sq Ft
      • Built 1970
      290 Deer Meadow Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 10% Above List Price
      • $330/SF
      • 57 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Donna Murray Varick Associates Ltd

  • /50

    $249,500

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft

    3264 Route 153, West Rupert, VT 05776

    This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

    Scott McChesney McChesney RE, Inc.

    3264 Route 153, West Rupert, VT 05776
  • /53

    $495,000 Sold Oct 17, 2025

    200 Applewood Ln, Manchester Center, VT 05255

    • 2,746 Sq Ft
    • Built 1986

    Last Sold Summary

    • $180/SF
    • 4 Days On Market

    Current Estimated Value $501,107

    Last Listing Agent Zachary Zupan EXP Realty

    200 Applewood Ln, Manchester Center, VT 05255
    • /29

      Est $756,038 Not Listed For Sale

      110 Highland Ave, Manchester Center, VT 05255

      • 5 Beds
      • 3.5 Baths
      • 2,912 Sq Ft
      • Built 1890
      110 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Above List Price
      • $246/SF
      • 4 Days On Market

      Last Sold Price $715,000

      Last Listing Agent Jamie Luke TPW Real Estate

  • /22

    $895,000

    • Land
    • 24.08 Acres
    • $37,168 per Acre

    A Windsor Rd, Manchester, VT 05255

    Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

    Kim Morgan-Wohler Wohler Realty Group

    A Windsor Rd, Manchester, VT 05255
  • /42

    $529,000 Sold Apr 15, 2026

    941 Myers Rd, Shaftsbury, VT 05262

    • 4 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 1900

    Last Sold Summary

    • $281/SF
    • 2 Days On Market

    Current Estimated Value $467,825

    Last Listing Agent Abi Gregorio

    941 Myers Rd, Shaftsbury, VT 05262
    • /9

      Est $668,246 Not Listed For Sale

      207 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,176 Sq Ft
      • Built 1970
      207 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 7% Above List Price
      • $286/SF
      • 7 Days On Market

      Last Sold Price $622,500

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /55

    $239,500 Pending

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    38 Cyr Ct, Bennington, VT 05201

    This classic 1975 ranch offers comfortable single-level living with great potential to make it your own. Featuring three bedrooms, including a primary with its own bath. The home provides a functional layout suited to a variety of lifestyles. A spacious living area and eat-in kitchen create a welcoming foundation for everyday living and entertaining. While the home could benefit from some

    Catherine Cairns Maple Leaf Realty

    38 Cyr Ct, Bennington, VT 05201
  • /48

    $239,900 Sold Jun 06, 2025

    213 Maple St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • Built 1910

    Last Sold Summary

    • $166/SF
    • 2 Days On Market

    Current Estimated Value $247,916

    Last Listing Agent Matt Waddington Hoffman Real Estate

    213 Maple St, Bennington, VT 05201
    • /40

      Est $778,217 Not Listed For Sale

      521 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 2,270 Sq Ft
      • Built 1996
      521 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 7% Above List Price
      • $319/SF
      • 8 Days On Market

      Last Sold Price $725,000

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

  • /3

    $219,000

    • 2 Beds
    • 1 Bath
    • 1,872 Sq Ft

    17 Henry Hill, Stamford, VT 05352

    Sean Taylor Moresi Real Estate Partners

    17 Henry Hill, Stamford, VT 05352
  • /22

    $265,500 Sold Jul 15, 2025

    18 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1970

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 72 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /39

      Est $385,639 Not Listed For Sale

      90 Jennifer Ln, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 1,389 Sq Ft
      • Built 1970
      90 Jennifer Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 3% Above List Price
      • $270/SF
      • 19 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /25

    $289,000 Under Contract

    • 7 Beds
    • 6 Baths
    • 5,712 Sq Ft

    136 North St, Bennington, VT 05201

    Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail,

    Jeffrey Dorman

    136 North St, Bennington, VT 05201
  • /21

    $120,000 Sold Mar 09, 2026

    1319 Vail Rd, Bennington, VT 05201

    • Land
    • 20 Acres
    • $6,000 per Acre

    Last Sold Summary

    • 143 Days On Market

    Last Listing Agent Lilli West Maple Leaf Realty

    1319 Vail Rd, Bennington, VT 05201
    • /29

      Est $618,408 Not Listed For Sale

      36 Boulder Rd, Manchester Center, VT 05255

      • 4 Beds
      • 1.5 Baths
      • 2,512 Sq Ft
      • Built 1825
      36 Boulder Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 9% Above List Price
      • $225/SF
      • 7 Days On Market

      Last Sold Price $565,000

      Last Listing Agent Susan Bellville Bellville Realty

  • /41

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft

    7 Roundtree Rd, Winhall, VT 05340

    Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    7 Roundtree Rd, Winhall, VT 05340
  • /48

    $306,250 Sold Dec 05, 2025

    4581 Main Rd, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft
    • Built 1967

    Last Sold Summary

    • 18% Above List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $300,652

    Last Listing Agent Susan Colvin MONARCH REALTY, INC.

    4581 Main Rd, Stamford, VT 05352
    • /29

      Est $562,493 Not Listed For Sale

      335 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1987
      335 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 4% Above List Price
      • $331/SF
      • 4 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /26

    $199,000

    • 4 Beds
    • 2 Baths
    • 1,980 Sq Ft

    210 Division St, Bennington, VT 05201

    Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

    Lilli West Maple Leaf Realty

    210 Division St, Bennington, VT 05201
  • /34

    $335,000 Sold Jun 09, 2025

    290 Springhill Rd, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 2,354 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $142/SF
    • 208 Days On Market

    Current Estimated Value $344,144

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    290 Springhill Rd, Bennington, VT 05201
    • /33

      Est $738,288 Not Listed For Sale

      208 Winter St, Manchester Center, VT 05255

      • 5 Beds
      • 3 Baths
      • 1,172 Sq Ft
      • Built 1984
      208 Winter St, Manchester Center, VT 05255

      Last Sold Summary

      • 13% Above List Price
      • $559/SF
      • 3 Days On Market

      Last Sold Price $655,000

      Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  • /4

    $28,000

    • Land
    • 2.3 Acres
    • $12,174 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-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

    Flex Realty Group Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350

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