20,639

Bennington County, VT Homes

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  • /53

    $529,000

    $166K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    58 Mount Anthony Rd, Bennington, VT 05201

    Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    58 Mount Anthony Rd, Bennington, VT 05201
  • /33

    $20,000 Per Month

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft
    • Condo for Rent

    16 Old Farm Rd Unit 1, Winhall, VT 05340

    16 OLD FARM ROADThe winter ski season is just around the corner! After a day on the slopes, unwind by the cozy brick wood-burning fireplace or relax in the comfortable living room, where the exposed beams and barn board wainscoting give you the warmth and charm of a classic Vermont ski retreat. The back door opens to a patio and level backyard, perfect for grilling your evening meal and

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    16 Old Farm Rd Unit 1, Winhall, VT 05340
  • /36

    $277,737

    Sold Feb 18, 2026

    109 Watershed Rd, Woodford, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1992

    Last Sold Summary

    • 7% Below List Price
    • $156/SF
    • 9 Days On Market

    Last Listing Agent Faith Rhodes Maple Leaf Real Estate

    109 Watershed Rd, Woodford, VT 05201
    • /32

      Est $43,843

      Not Listed For Sale

      339 S Stream Rd, Pownal, VT 05261

      • 5 Beds
      • 2 Baths
      • 2,204 Sq Ft
      • Built 1890
      339 S Stream Rd, Pownal, VT 05261

      Last Sold Summary

      • 115 Days On Market

      Last Listing Agent Lisa Friedman Great American Dream Realty

  • /52

    $359,000

    • 2 Beds
    • 1 Bath
    • 1,686 Sq Ft

    712 Vt Route 30, Dorset, VT 05251

    Nestled in a picturesque Dorset, Vermont setting, this classic 1850 farmhouse offers an affordable opportunity to create the home of your dreams. Situated on a manageable quarter-acre lot, the property features a detached two-car garage, two additional outbuildings, screened in porch, enclosed three season porch and established perennial plantings with classic New England character throughout.

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    712 Vt Route 30, Dorset, VT 05251
  • /3

    Starting at $1,750 Per Month

    • Studio - 2 Beds

    757 Main St, Bennington, VT 05201

    Newly Constructed Luxury Apartments in Bennington, VermontWelcome to 757 Main Street, a newly constructed apartment community offering modern living in a convenient Bennington location. Choose from a variety of thoughtfully designed studio, one-bedroom, and two-bedroom residences created for everyday comfort and easy living.The property is conveniently located near local dining,

    757 Main St, Bennington, VT 05201
  • /28

    $585,000

    Sold Mar 12, 2026

    550 Finbars Forest Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2 Baths
    • 1,958 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $299/SF
    • 142 Days On Market

    Current Estimated Value $590,938

    Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

    550 Finbars Forest Rd, Manchester Center, VT 05255
    • /43

      Est $184,068

      Not Listed For Sale

      858 Vt Route 9, Woodford, VT 05201

      • 2 Beds
      • 1 Bath
      • 1,061 Sq Ft
      • Built 1805
      858 Vt Route 9, Woodford, VT 05201

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Amy Hill EXP Realty

  • /58

    $1,650,000

    $225K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,368 Sq Ft

    276 Wilcox Hollow Rd, Sandgate, VT 05250

    Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    276 Wilcox Hollow Rd, Sandgate, VT 05250
  • /24

    $3,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    78 Franklin Rd, Manchester, VT 05255

    WINTER RENTAL 11/15/26 to 4/15/27'Tis the season, well, almost. Winter is just around the corner, and this classic, 1920s Vermont home awaits your stay. This traditional Manchester Village home is fully furnished and ready for your Winter Season rental.Turn off your electronics, curl up with a good book, spread out a board game, and just enjoy each other's company. Located on a quiet

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    78 Franklin Rd, Manchester, VT 05255
  • /39

    $215,000

    Sold Jul 21, 2026

    215 Orchard St, Pownal, VT 05261

    • 2 Beds
    • 1 Bath
    • 988 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $218/SF
    • 37 Days On Market

    Current Estimated Value $218,927

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    215 Orchard St, Pownal, VT 05261
    • /37

      Not Listed For Sale

      73 Woodford City Rd, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1984
      73 Woodford City Rd, Bennington, VT 05201

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Abi Gregorio

  • /41

    $550,000

    Under Contract
    • 5 Beds
    • 2 Baths
    • 1,974 Sq Ft

    971 S Stream Rd, Bennington, VT 05201

    Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    971 S Stream Rd, Bennington, VT 05201
  • /10

    Starting at $1,500

    Total Monthly Price

    • 1 - 5 Beds

    940 Water St, North Bennington, VT 05257

    940 Water Street evolved from a late-19th-century factory complex into a modern mixed-use historic property, preserving a key piece of North Bennington’s industrial heritage. Housing renovations began in 2010 and continue through today and into 2017.Available Units We are currently expanding our selection of units and now offer 1+, 2, 3, 4, and 5-bedroom units. I am available to work

    940 Water St, North Bennington, VT 05257
  • /17

    $59,900

    Sold Jul 31, 2026

    0 Sunset Hill Rd Unit B, Pownal, VT 05261

    • Land
    • 2.38 Acres
    • $25,168 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 227 Days On Market

    Last Listing Agent Terri Edgerley Edge Realty Vermont

    0 Sunset Hill Rd Unit B, Pownal, VT 05261
    • /60

      Est $294,025

      Not Listed For Sale

      316 Jepson Rd, Stamford, VT 05352

      • 4 Beds
      • 2 Baths
      • 1,976 Sq Ft
      • Built 1887
      316 Jepson Rd, Stamford, VT 05352

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • /17

    $198,900

    • 2 Beds
    • 1 Bath
    • 1,332 Sq Ft

    348 Center St, Pownal, VT 05261

    Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a

    Agent Photo

    Sheryl Morehouse

    Bishop West Real Estate, Inc.

    348 Center St, Pownal, VT 05261
  • /26

    $5,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 1,994 Sq Ft
    • Condo for Rent

    39 Sage Hill Rd Unit 25, Manchester, VT 05255

    SUMMER RENTAL: 6/15/26 to 10/15/26WINTER SEASONAL RENTAL: 12/1/26 to 3/31/2027 Location is everything, and Torbank’s condominiums are the perfect choice! Just minutes from the heart of Manchester, Southern Vermont’s premier destination, you’ll have easy access to boutique shopping, dining, medical services, and year-round activities. In the winter, enjoy the convenience of nearby skiing at

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    39 Sage Hill Rd Unit 25, Manchester, VT 05255
  • /48

    $295,000

    Sold Jul 22, 2026

    166 Cardinal Ln, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 2,753 Sq Ft
    • Built 1964

    Last Sold Summary

    • $107/SF
    • 16 Days On Market

    Current Estimated Value $303,218

    Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

    166 Cardinal Ln, Bennington, VT 05201
    • /40

      Est $654,788

      Not Listed For Sale

      5529 Vt Route 7a, Shaftsbury, VT 05262

      • 3 Beds
      • 3 Baths
      • 3,173 Sq Ft
      • Built 1804
      5529 Vt Route 7a, Shaftsbury, VT 05262

      Last Sold Summary

      • 85 Days On Market

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

  • /33

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,911 Sq Ft

    21 Russett Dr, Bennington, VT 05201

    Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    21 Russett Dr, Bennington, VT 05201
  • /2

    $1,050 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    165 Benmont Ave, Bennington, VT 05201

    Property Id: 1488761 I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

    165 Benmont Ave, Bennington, VT 05201
  • /60

    $825,000

    Sold Jul 24, 2026

    1731 Three Maple Dr, Manchester Center, VT 05255

    • 4 Beds
    • 3.5 Baths
    • 3,237 Sq Ft
    • Built 1971

    Last Sold Summary

    • 6% Below List Price
    • $255/SF
    • 23 Days On Market

    Current Estimated Value $869,332

    Last Listing Agent David Citron RE/MAX Four Seasons

    1731 Three Maple Dr, Manchester Center, VT 05255
    • /14

      Est $292,383

      Not Listed For Sale

      400 South St, Bennington, VT 05201

      • 3 Beds
      • 3 Baths
      • 1,461 Sq Ft
      • Built 1825
      400 South St, Bennington, VT 05201

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent William Paquin Maple Leaf Real Estate

  • /56

    $1,200,000

    $1M PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,340 Sq Ft

    215 & 221 Vt Route 30, Dorset, VT 05251

    Two homes, multiple barns and outbuildings on 60 +/- incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    215 & 221 Vt Route 30, Dorset, VT 05251
  • /6

    $1,050 Per Month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Condo for Rent

    103 County St Unit 2, Bennington, VT 05201

    Property Id: 810906 1 bedroom apartment is located on second floor.Month to month lease where tenants pay for their utilities such as heat electric etc..

    103 County St Unit 2, Bennington, VT 05201
  • /30

    $345,750

    Sold Oct 21, 2025

    374 Overlea Rd, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft
    • Built 1948

    Last Sold Summary

    • 5% Below List Price
    • $197/SF
    • 58 Days On Market

    Current Estimated Value $403,722

    Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

    374 Overlea Rd, North Bennington, VT 05257
    • /22

      Est $88,384

      Not Listed For Sale

      91 Nelson Rd, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 832 Sq Ft
      • Built 1963
      91 Nelson Rd, Bennington, VT 05201

      Last Sold Summary

      • 2 Days On Market

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

  • /29

    $255,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,458 Sq Ft

    2650 Rupert Rd, Arlington, VT 05250

    Mountain View Oasis – 17 Acres of Open & Wooded SerenityEscape to your own private retreat with this two-bedroom, one-bath home nestled on 17 acres of beautiful open and wooded forest land. Built in 1999, this solidly constructed home features a poured concrete foundation, underground power, conventional septic system, and durable metal roof — giving you peace of mind with all the major

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    2650 Rupert Rd, Arlington, VT 05250
  • /26

    $1,750

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Condo for Rent

    9 Mechanic St Unit B, North Bennington, VT 05257

    9 Mechanic St Unit B, North Bennington, VT 05257
  • /43

    $275,000

    Sold Jun 26, 2026

    86 Mill Rd, Stamford, VT 05352

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $275/SF
    • 9 Days On Market

    Current Estimated Value $268,407

    Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

    86 Mill Rd, Stamford, VT 05352
    • /37

      Est $246,059

      Not Listed For Sale

      213 Gage St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,510 Sq Ft
      • Built 1850
      213 Gage St, Bennington, VT 05201

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /58

    $495,000

    $55K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,504 Sq Ft

    136 Fox Run Rd, Arlington, VT 05250

    Perched above the Battenkill River Valley and surrounded by mountain views this two story Vermont Gem is waiting for you. The perfect size two bedrooms, two bath home offers maple hardwood flooring, oversized windows and soaring mountain views. Lovely perennial gardens, flowering apple trees and large meadows grace the 3.90 acre property. This thoughtfully constructed home was built in 2000 with

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    136 Fox Run Rd, Arlington, VT 05250
  • /22

    $1,795

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    4 Mechanic St Unit A, North Bennington, VT 05257

    Waterfront two bedroom duplex in superb location* RARELY AVAILABLE DUPLEX* Two bedrooms and a full bathroom upstairs* Living room, dining room, laundry room and kitchen on the first floor* Washer/dryer hookups in their own laundry room (there are no W/D units in the apartment) with a closet* Rear deck, new stove and fridge, new windows and doors, nice clean apartment with

    4 Mechanic St Unit A, North Bennington, VT 05257
  • /49

    $435,000

    Sold Oct 10, 2025

    458 Fox Hill Rd, Bennington, VT 05201

    • 4 Beds
    • 4 Baths
    • 3,040 Sq Ft
    • Built 2007

    Last Sold Summary

    • 2% Above List Price
    • $143/SF
    • 7 Days On Market

    Current Estimated Value $469,431

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    458 Fox Hill Rd, Bennington, VT 05201
    • /32

      Est $339,062

      Not Listed For Sale

      169 Bard Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,584 Sq Ft
      • Built 1975
      169 Bard Rd, Bennington, VT 05201

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  • /43

    $1,200,000

    $1M PRICE DROP
    • Land
    • 60 Acres
    • $20,000 per Acre

    215 Vermont 30, Dorset, VT 05251

    Opportunities are Knocking! Welcome to an extraordinary 50+ acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta—location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont’s

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    215 Vermont 30, Dorset, VT 05251
  • /39

    $1,275

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    18 Main St Unit C, North Bennington, VT 05257

    Centrally located 3 family house with awesome tenants and awesome neigbors.

    18 Main St Unit C, North Bennington, VT 05257
  • /7

    $345,000

    Sold Nov 07, 2025

    72 Mckee Rd, Arlington, VT 05250

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • Built 1985

    Last Sold Summary

    • 21% Below List Price
    • $252/SF
    • 127 Days On Market

    Current Estimated Value $353,716

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

    72 Mckee Rd, Arlington, VT 05250
    • /57

      Not Listed For Sale

      115-117 Norton St, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,701 Sq Ft
      • Built 1930
      115-117 Norton St, Bennington, VT 05201

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

Showing Results 1 - 40, Page 1 of 18

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