20,611

Bennington County, VT Homes

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  • /37

    $169,900

    • 1 Bed
    • 0.5 Baths
    • 789 Sq Ft

    3711 Main Rd, Stamford, VT 05352

    Meet "The Barrel House," a truly unique Vermont summer retreat! Tucked into the mountains of Stamford, this distinctive bow-roof seasonal cabin is believed to date to approximately 1938, a date set into its fieldstone fireplace along with the fitting words, "REST A WHILE." Nearly 90 years later, the invitation remains. Rich wood walls and ceilings, vintage details, warm wood floors, and an open

    Agent Photo

    Peter West

    Bishop West Real Estate, Inc.

    3711 Main Rd, Stamford, VT 05352
  • /17

    $7,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,512 Sq Ft
    • House for Rent

    195 Mystic Ln, Dorset, VT 05251

    WINTER SEASONAL: Just minutes from Dorset Village, this spacious 4 bed, 4.5 bath Cape offers the perfect winter getaway, surrounded by the beauty of nature. 3,512 SF of comfortable living space on 3.5 picturesque acres. Open layout kitchen, living and dining with 1st Floor bedroom and bath. 2 spacious bedrooms upstairs, hallway bath and finished basement space with bath, ideal for family and

    Laura Beckwith Josiah Allen Real Estate, Inc.

    195 Mystic Ln, Dorset, VT 05251
  • /39

    $735,000

    Sold May 01, 2026

    5 Wall St, Bondville, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,091 Sq Ft
    • Built 1972

    Last Sold Summary

    • $352/SF
    • 20 Days On Market

    Current Estimated Value $752,524

    Last Listing Agent Cheyanne Pugliese

    5 Wall St, Bondville, VT 05340
    • /56

      Not Listed For Sale

      321 Chester Knoll Dr, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 2024
      321 Chester Knoll Dr, Bennington, VT 05201

      Last Sold Summary

      • 156 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /56

    $550,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,394 Sq Ft

    1039 Berwal Rd, Arlington, VT 05250

    Set on over 5 picturesque acres in a peaceful country setting with beautiful Green Mountain views, this spacious 4 bedroom, 3 bath home offers the perfect blend of comfort, flexibility, and Vermont charm. Nestled just south of Manchester, the property provides an ideal balance of rural tranquility and convenient access to shopping, dining, recreation, and year-round attractions.Inside,

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    1039 Berwal 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

    $625,000

    Sold Aug 31, 2026

    34 Monument Ave, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,692 Sq Ft
    • Built 1850

    Last Sold Summary

    • 1% Above List Price
    • $232/SF
    • 9 Days On Market

    Current Estimated Value $612,188

    Last Listing Agent Jeffrey Dorman

    34 Monument Ave, Bennington, VT 05201
    • /41

      Est $405,857

      Not Listed For Sale

      653 Skyboro Rd E, Pownal, VT 05261

      • 2 Beds
      • 3 Baths
      • 1,761 Sq Ft
      • Built 1957
      653 Skyboro Rd E, Pownal, VT 05261

      Last Sold Summary

      • 12 Days On Market

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

  • /57

    $2,275,000

    $25K PRICE DROP
    • 9 Beds
    • 8 Baths
    • 5,512 Sq Ft

    288 Cedar Ln, Peru, VT 05152

    Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

    Agent Photo

    Jessica Citera

    Cummings & Co

    288 Cedar Ln, Peru, VT 05152
  • /35

    $35,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,472 Sq Ft
    • House for Rent

    8 Spring Hill Rd, Winhall, VT 05340

    Imagine arriving to your ski home and having the property giving you a giant hug. This is the house. A perfect combination of the old and the new with tastefully choses recent renovations which highlight architectural elements of yesterday while at the same time providing modern day comfort and luxury. This home has four beautiful bedrooms with a primary suite on the main floor.There is also

    Peggy O'neill Cummings & Co

    8 Spring Hill Rd, Winhall, VT 05340
  • /25

    $668,000

    Sold Aug 18, 2026

    184 W View Estates, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,108 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $317/SF
    • 66 Days On Market

    Current Estimated Value $671,431

    Last Listing Agent Annette Gallo Real Broker LLC

    184 W View Estates, Manchester Center, VT 05255
    • /22

      Est $835,843

      Not Listed For Sale

      185 Crooked Path Rd, Arlington, VT 05250

      • 4 Beds
      • 5.5 Baths
      • 3,463 Sq Ft
      • Built 2006
      185 Crooked Path Rd, Arlington, VT 05250

      Last Sold Summary

      • 9 Days On Market

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

  • /40

    $450,000

    • 3 Beds
    • 1.5 Baths
    • 1,650 Sq Ft

    349 Elm St, Bennington, VT 05201

    Location!Welcome to this charming and very well maintained home on desirable Elm Street. Featuring three bedrooms and two bathrooms, this sweet property offers plenty of space, character, and versatility.One of the bedrooms has been thoughtfully transformed into a spacious walk-in closet/dressing room, but it can easily be converted back into a bedroom to restore the home's full

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    349 Elm St, Bennington, VT 05201
  • /18

    $2,100

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • House for Rent

    61 Bell St, Woodford, VT 05201

    Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.3br MANUFACTURED HOME for rent!*Open Floor Plan**Covered Porch**Fireplace*Unit: B-061Apply To: Mountain View CommunityRent: $2100/moBeds/Baths: 3 beds 2 bathsSize: 1,624 square feetPets: Cat & Dog friendly, all

    61 Bell St, Woodford, VT 05201
  • /32

    $530,000

    Sold Aug 18, 2026

    764 Myers Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1964

    Last Sold Summary

    • 1% Below List Price
    • $291/SF
    • 26 Days On Market

    Current Estimated Value $536,524

    Last Listing Agent Matt Waddington Hoffman Real Estate

    764 Myers Rd, Shaftsbury, VT 05262
    • /21

      Est $281,647

      Not Listed For Sale

      1288 Brookman Rd, Pownal, VT 05261

      • 2 Beds
      • 1 Bath
      • 792 Sq Ft
      • Built 1969
      1288 Brookman Rd, Pownal, VT 05261

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Abi Gregorio

  • /7

    $55,000

    • Land
    • 22,215 Sq Ft
    • $107,843 per Acre

    24 Asa's Way, Bennington, VT 05257

    Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    24 Asa's Way, Bennington, VT 05257
  • /23

    $34,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft
    • House for Rent

    35 Strattonwald Rd, Winhall, VT 05340

    Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy space for après-ski

    Cheyanne Pugliese

    35 Strattonwald Rd, Winhall, VT 05340
  • /32

    $410,000

    Sold Apr 29, 2026

    8 Silver Birch Rd Unit 8, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Below List Price
    • $337/SF
    • 101 Days On Market

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    8 Silver Birch Rd Unit 8, Winhall, VT 05340
    • /35

      Est $2,732,012

      Not Listed For Sale

      171 High Fields Ln, Manchester, VT 05254

      • 5 Beds
      • 5.5 Baths
      • 7,574 Sq Ft
      • Built 2022
      171 High Fields Ln, Manchester, VT 05254

      Last Sold Summary

      • 291 Days On Market

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

  • /40

    $305,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,378 Sq Ft

    61 E Branch Farms Unit 1, Manchester Center, VT 05255

    East Branch Farms is in the most convenient location! This 3 bedroom and 2 and a half bath condo is ready for its next owners. Wood floors on the main level and new granite countertops in the kitchen. Full basement with both interior and exterior access for workshop space or extra storage. Located at the edge of lovely Manchester VT it is privately screened from the road with views of soaring

    Agent Photo

    Alison Cummings

    Cummings & Co

    61 E Branch Farms Unit 1, Manchester Center, VT 05255
  • /9

    $1,250 Per Month

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

    109 Mccall St Unit 3, Bennington, VT 05201

    *MANAGED BY HALE APARTMENTS*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!This charming apartment offers a cozy and comfortable living space with two bedroom and one bathroom. Immerse yourself in the rich history of Bennington as you explore the vibrant downtown area, just steps away from your doorstep. The apartment boasts a convenient location, allowing you to

    109 Mccall St Unit 3, Bennington, VT 05201
  • /53

    $2,850,000

    Sold Sep 18, 2026

    86 Church St, Dorset, VT 05251

    • 5 Beds
    • 5.5 Baths
    • 6,182 Sq Ft
    • Built 1840

    Last Sold Summary

    • $461/SF
    • 9 Days On Market

    Current Estimated Value $2,798,820

    Last Listing Agent Christiane Carroccio TPW Real Estate

    86 Church St, Dorset, VT 05251
    • /22

      Est $300,334

      Not Listed For Sale

      494 Atwood Dr, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,048 Sq Ft
      • Built 2006
      494 Atwood Dr, Pownal, VT 05261

      Last Sold Summary

      • 5 Days On Market

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

  • /13

    $229,000

    • Land
    • 0 Sq Ft

    468 Skyboro Rd, Pownal, VT 05261

    835+ FEET OF ROAD FRONTAGE 10+ ACRES - SUBDIVISION POTENTIAL!Developer and investor opportunity in Pownal, Vermont! This 10+ acre parcel offers approximately 835.9 feet of road frontage on Skyboro Road, providing valuable flexibility for evaluating potential homesites, and future development. The combination of acreage and exceptional road frontage creates an opportunity to explore

    Agent Photo

    Sheryl Morehouse

    BISHOP WEST REAL ESTATE

    468 Skyboro Rd, Pownal, VT 05261
  • /52

    $4,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,547 Sq Ft
    • Townhouse for Rent

    80 Murray Hill South Rd Unit 10, Manchester, VT 05255

    Winter Seasonal Rental – Downtown Manchester Center. Enjoy the best of Vermont this ski season in this beautiful 3 bedroom, 3 bath end unit offering breathtaking mountain views and an unbeatable location in the heart of downtown Manchester Center. With 1,567 square feet of comfortable living space, this bright and spacious condo features an open floor plan, wood pellet insert, abundant natural

    Laura Beckwith Josiah Allen Real Estate, Inc.

    80 Murray Hill South Rd Unit 10, Manchester, VT 05255
  • /36

    $300,000

    Sold Apr 02, 2026

    318 Chester Knoll Dr, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft
    • Built 2006

    Last Sold Summary

    • $161/SF
    • 5 Days On Market

    Current Estimated Value $327,437

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    318 Chester Knoll Dr, Bennington, VT 05201
    • /60

      Est $412,026

      Not Listed For Sale

      145 Main St, Pownal, VT 05261

      • 4 Beds
      • 2.5 Baths
      • 2,032 Sq Ft
      • Built 1742
      145 Main St, Pownal, VT 05261

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Nicholas Charest Maple Leaf Real Estate

  • /5

    $55,000

    • Land
    • 20,908 Sq Ft
    • $114,583 per Acre

    29 Asa's Way, Bennington, VT 05257

    Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    29 Asa's Way, Bennington, VT 05257
  • /7

    $1,250 Per Month

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

    207 Maple St Unit 3, Bennington, VT 05201

    *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS! Welcome to 207 Maple St. #3, located in the charming town of Bennington, VT. This cozy apartment offers 2 bedrooms and 1 bathroom, providing ample space for comfortable living. Situated in a prime location, this apartment is perfect for those seeking a convenient and hassle-free lifestyle.

    207 Maple St Unit 3, Bennington, VT 05201
  • /26

    $440,000

    Sold Jun 29, 2026

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Below List Price
    • $362/SF
    • 10 Days On Market

    Last Listing Agent Helen Nault

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
    • /43

      Est $1,453,331

      Not Listed For Sale

      164 Landmark Ln, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,990 Sq Ft
      • Built 1810
      164 Landmark Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 397 Days On Market

      Last Listing Agent Donna Murray Varick Associates Ltd

  • /31

    $595,000

    • Land
    • 23.62 Acres
    • $25,191 per Acre

    3213 West Rd, Bennington, VT 05201

    Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    3213 West Rd, Bennington, VT 05201
  • /60

    $12,500 Per Month

    • 4 Beds
    • 4.5 Baths
    • 4,393 Sq Ft
    • House for Rent

    163 Taconic Rd, Manchester, VT 05255

    Exclusive Taconic Avenue walk to Village Location... Rarely found, Recently Constructed in 2002 this High Country Colonial is on one acre seamlessly blending within the historic district. Aesthetically pleasing among the area's recently restored Houses of the Hildene era, this residence meets all expectations! Deep front porch entry to soaring foyer flanked with formal rooms while the family

    Laura Beckwith Josiah Allen Real Estate, Inc.

    163 Taconic Rd, Manchester, VT 05255
  • /46

    $290,000

    Sold Apr 10, 2026

    112 Norton St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,564 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $185/SF
    • 8 Days On Market

    Current Estimated Value $309,840

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    112 Norton St, Bennington, VT 05201
    • /40

      Est $938,174

      Not Listed For Sale

      67 Coventry Ln, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 2,774 Sq Ft
      • Built 1965
      67 Coventry Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 10 Days On Market

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

  • /60

    $995,000

    • 5 Beds
    • 5 Baths
    • 4,126 Sq Ft

    238 Seminary Ave, Manchester, VT 05254

    Manchester Village LivingExperience the charm of village life in this expansive Victorian home and guest cottage, ideally located in the heart of Manchester Village. Rich in character and architectural detail, the home features original woodwork, soaring ceilings, generously sized rooms, and timeless New England appeal—enhanced by a new roof, windows and heating system.The spacious main

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    238 Seminary Ave, Manchester, VT 05254
  • /59

    $6,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    3370 Main St, Manchester, VT 05255

    One of the oldest homes in Manchester Village, dating back to 1763, The Hoyt House is a beautifully revived antique that blends historic Vermont character with comfortable modern living. Ideally located in the heart of Manchester Village, this charming 3-bedroom, 2.5-bath home offers a thoughtfully designed layout. The first floor features a spacious primary suite with a private sitting room and

    Laura Beckwith Josiah Allen Real Estate, Inc.

    3370 Main St, Manchester, VT 05255
  • /41

    $141,000

    Sold Apr 01, 2026

    235 Maple St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,060 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Below List Price
    • $133/SF
    • 13 Days On Market

    Current Estimated Value $157,895

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    235 Maple St, Bennington, VT 05201
    • /34

      Est $510,223

      Not Listed For Sale

      32 County Rd, Stamford, VT 05352

      • 2 Beds
      • 2 Baths
      • 1,586 Sq Ft
      • Built 1989
      32 County Rd, Stamford, VT 05352

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rebecca Seymour Brattleboro Area Realty

Showing Results 81 - 120, Page 3 of 18

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