21,172

Bennington County, VT Homes

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  • /47

    $1,500,000

    • Land
    • 38.57 Acres
    • $38,890 per Acre

    500 Nims Rd, Dorset, VT 05251

    This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 634-4776

    500 Nims Rd, Dorset, VT 05251
  • /19

    $4,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • House for Rent

    937 Route 30, Dorset, VT 05251

    Welcome home! This beautiful and well maintained 4 bedroom, 1.5-bath home is in the charming town of Dorset. It offers over 1,404 sq feet of single-story living. This very well thought out and comfortable floor plan features a bright, large living and dining room and many windows throughout the entire house. A separate dining area perfect for gatherings. Enjoy the outdoors on the large back deck

    Martina Dvorak-Grattan Wohler Realty Group

    937 Route 30, Dorset, VT 05251
  • /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 $288,372

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    112 Norton St, Bennington, VT 05201
    • /29

      Not Listed For Sale

      2 Byington Ln Unit 5, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,570 Sq Ft
      • Built 1977
      2 Byington Ln Unit 5, Winhall, VT 05340

      Last Sold Summary

      • $290/SF
      • 53 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

  • /41

    $1,775,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 2,401 Sq Ft

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155

    Experience the pinnacle of alpine sophistication in this completely renovated turn-key residence. Located in Rising Bear, this 4-bedroom, 4-bath condo blends modern design with an unbeatable location that defines luxury mountain lifestyle. Park your car in one of two designated spots in the heated underground garage and leave it, there's no need drive anywhere during your stay! Whether you prefer

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 802-9370

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155
  • /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
  • /21

    $375,000 Sold May 05, 2025

    61 Birch Hill Rd Unit 6, Winhall, VT 05340

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

    Last Sold Summary

    • $309/SF
    • 42 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    61 Birch Hill Rd Unit 6, Winhall, VT 05340
    • /37

      Est $639,522 Not Listed For Sale

      29 Burnt Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1982
      29 Burnt Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 4% Above List Price
      • $410/SF
      • 39 Days On Market

      Last Sold Price $615,000

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

  • /4

    $100,000

    • Land
    • 26.2 Acres
    • $3,817 per Acre

    0 Magee Rd Unit 73504013, Stamford, VT 05352

    Uncover this hidden and exceptional 26.2-acre property featuring two prime lots, perfect for development or creating your personal retreat. This picturesque Vermont landscape is highlighted by small streams and even a tranquil pond, complete with wide trails that ensure easy navigation throughout the property for access, exercise and recreational vehicles. Complete with remarkable stone outcrops

    Agent Photo

    Gary Fuls Jr

    RE/MAX Transitions

    (802) 523-2113

    0 Magee Rd Unit 73504013, Stamford, VT 05352
  • /23

    $34,000 per month

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

    35 Strattonwald Rd, Winhall, VT 05340

    $28,000 Winter Rental Rate | 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

    Cheyanne Pugliese

    35 Strattonwald Rd, Winhall, VT 05340
  • /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 $147,691

    Last Listing Agent Lindsey Martin Maple Leaf Realty

    235 Maple St, Bennington, VT 05201
    • /55

      Not Listed For Sale

      3496 Main St, Manchester, VT 05255

      • 6 Beds
      • 4.5 Baths
      • 6,145 Sq Ft
      • Built 1900
      3496 Main St, Manchester, VT 05255

      Last Sold Summary

      • $379/SF
      • 2 Days On Market

      Last Sold Price $2,327,000

      Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  • /41

    $939,000

    • 5 Beds
    • 6 Baths
    • 3,031 Sq Ft

    3191 Vermont 30, Dorset, VT 05251

    Dorset Village Investor's choice! Village Commercial... Currently Presenting a 5 unit, 3030 SF residence that can not be reproduced locally. This building has been lifted and a full (includes a small crawl) poured concrete foundation installed... dry as can be... clean as any basement can be hoped for! There are a mix of one bedrooms and studios... The configuration can be easily altered to

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 416-3525

    3191 Vermont 30, Dorset, VT 05251
  • /26

    $1,300 total monthly price

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

    178 S Branch St Unit 178, Bennington, VT 05201

    Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

    178 S Branch St Unit 178, Bennington, VT 05201
  • /34

    $450,000 Sold Feb 13, 2026

    356 Elm St, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 2,273 Sq Ft
    • Built 1934

    Last Sold Summary

    • $198/SF
    • 0 Days On Market

    Current Estimated Value $444,023

    Last Listing Agent Angela Bevin Maple Leaf Realty

    356 Elm St, Bennington, VT 05201
    • /22

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 63 Days On Market

      Last Sold Price $55,000

      Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

  • /60

    $1,600,000

    • 5 Beds
    • 4.5 Baths
    • 4,243 Sq Ft

    397 Fern Hill, Dorset, VT 05251

    Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 347-9044

    397 Fern Hill, Dorset, VT 05251
  • /29

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    90 Turkey Run Rd, Winhall, VT 05340

    Intervale Rental. Available for the 26-27 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom serves the

    Christiane Carroccio TPW Real Estate

    90 Turkey Run Rd, Winhall, VT 05340
  • /20

    $345,000 Sold Jun 06, 2025

    200 Carlen St, Manchester Center, VT 05255

    • 2 Beds
    • 2 Baths
    • 1,693 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $204/SF
    • 64 Days On Market

    Current Estimated Value $383,449

    Last Listing Agent Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

    200 Carlen St, Manchester Center, VT 05255
    • /6

      Est $119,487 Not Listed For Sale

      10 Little Brook Rd, Winhall, VT 05340

      10 Little Brook Rd, Winhall, VT 05340

      Last Sold Summary

      • 2% Below List Price
      • 53 Days On Market

      Last Sold Price $122,500

      Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  • /56

    $1,750,000

    • 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

    (802) 944-4482

    215 & 221 Vt Route 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
  • /12

    $100,000 Sold Sep 08, 2025

    242 North Rd, East Arlington, VT 05252

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1930

    Last Sold Summary

    • 26% Below List Price
    • $95/SF
    • 32 Days On Market

    Current Estimated Value $136,925

    Last Listing Agent Matt Waddington Hoffman Real Estate

    242 North Rd, East Arlington, VT 05252
    • /22

      Est $261,594 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

      • 6% Above List Price
      • $120/SF
      • 5 Days On Market

      Last Sold Price $246,000

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

  • /43

    $2,300,000

    • Land
    • 60 Acres
    • $38,333 per Acre

    215 Vermont 30, Dorset, VT 05251

    Opportunities are Knocking! Welcome to an extraordinary 60 +/- 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

    (802) 300-4271

    215 Vermont 30, Dorset, VT 05251
  • /26

    $1,300 total monthly price

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

    172 S Branch St Unit 172, Bennington, VT 05201

    First floor two bedroom- walk to town- living room, dining room, kitchen, full bathroom with shower stall, comes with newer electric stove and fridge, washer/dryer hookups- heat is forced hot air (fuel oil)- rent DOES NOT INCLUDE utilities- I pay for lawncare, plowing and garbage- I take first month's rent, last month's rent and one month's rent as a security deposit (3x

    172 S Branch St Unit 172, Bennington, VT 05201
  • /31

    $895,000 Sold Dec 12, 2025

    73 Cranberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $337/SF
    • 222 Days On Market

    Current Estimated Value $907,480

    Last Listing Agent Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
    • /60

      Est $382,394 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

      • 10% Below List Price
      • $209/SF
      • 11 Days On Market

      Last Sold Price $424,000

      Last Listing Agent Nicholas Charest Maple Leaf Realty

  • /30

    $225,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    92 Bourn Brook Rd Unit 67, Manchester Center, VT 05255

    2 bedroom, 1 bath townhouse offering a bright open concept layout across two levels. The main level features comfortable living and dining spaces, in-unit laundry, and hardwood flooring. Upstairs you’ll find two nicely sized bedrooms and a full bath. Ideally located in the heart of Manchester Center, just minutes from shopping, dining, schools, and everyday amenities, with easy access to multiple

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 357-7389

    92 Bourn Brook Rd Unit 67, Manchester Center, VT 05255
  • /44

    $1,350 total monthly price

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

    254 Union St Unit B, Bennington, VT 05201

    Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

    254 Union St Unit B, Bennington, VT 05201
  • /60

    $530,000 Sold Aug 15, 2025

    2354 Danby Mountain Rd, Dorset, VT 05251

    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft
    • Built 1968

    Last Sold Summary

    • 17% Below List Price
    • $261/SF
    • 244 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    2354 Danby Mountain Rd, Dorset, VT 05251
    • /32

      Est $1,610,968 Not Listed For Sale

      40 Nims, Dorset, VT 05251

      • 3 Beds
      • 3.5 Baths
      • 3,507 Sq Ft
      • Built 2006
      40 Nims, Dorset, VT 05251

      Last Sold Summary

      • 13% Above List Price
      • $405/SF
      • 8 Days On Market

      Last Sold Price $1,420,000

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

  • /56

    $925,000

    • 3 Beds
    • 4.5 Baths
    • 3,718 Sq Ft

    171 Mending Walls Rd, Manchester Center, VT 05255

    Looking for "NEW"? This is as close to new as any residence can be since it was "gutted to studs" and completely tastefully renovated on three levels! New quartz island kitchen, all new stainless appliances, new soft gray painted cabinetry, and completely open to dining and living areas. The foyer is two stories tile entrance with powder room. Peer through from the foyer, and a spacious vaulted

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 736-7720

    171 Mending Walls Rd, Manchester Center, VT 05255
  • /52

    $1,025,000 Sold Jul 18, 2025

    21 Shepards Ln, Manchester, VT 05255

    • 4 Beds
    • 4 Baths
    • 3,046 Sq Ft
    • Built 1845

    Last Sold Summary

    • 14% Below List Price
    • $337/SF
    • 54 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    21 Shepards Ln, Manchester, VT 05255
    • /40

      Est $928,792 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

      • 13% Above List Price
      • $297/SF
      • 10 Days On Market

      Last Sold Price $825,000

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

  • /40

    $1,245,000 Under Contract

    • 4 Beds
    • 6 Baths
    • 4,272 Sq Ft

    1016 West Rd, Manchester Center, VT 05255

    Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 357-7462

    1016 West Rd, Manchester Center, VT 05255
  • /36

    $220,000 Sold Aug 20, 2025

    1211 Carpenter Hill Rd, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Above List Price
    • $157/SF
    • 4 Days On Market

    Last Listing Agent Peter West BISHOP WEST REAL ESTATE

    1211 Carpenter Hill Rd, Bennington, VT 05201
    • /34

      Est $528,958 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

      • 4% Above List Price
      • $322/SF
      • 0 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Rebecca Seymour Brattleboro Area Realty

  • /35

    $379,900

    • 4 Beds
    • 2.5 Baths
    • 2,530 Sq Ft

    93 Russett Dr, Bennington, VT 05201

    Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 416-3661

    93 Russett Dr, Bennington, VT 05201
  • /36

    $435,000 Sold Mar 24, 2026

    1061 Granger Hollow Rd, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 1990

    Last Sold Summary

    • 13% Below List Price
    • $206/SF
    • 215 Days On Market

    Current Estimated Value $453,102

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1061 Granger Hollow Rd, North Bennington, VT 05257

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