21,114

Bennington County, VT Homes

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  • /51

    $1,875,000

    • 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

    (802) 521-2796

    276 Wilcox Hollow Rd, Sandgate, VT 05250
  • /10

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • House for Rent

    127 Mountain Ridge Rd, Peru, VT 05152

    If you're looking for a year-round rental in the Peru/Londonderry area, this contemporary mountain home has so much to offer. The inviting open-concept layout features a kitchen, living and dining space that extends out to a charming sun porch and back deck. Nestled close to Flood Brook, Bromley, and all that Londonderry and Peru have to offer, the location is convenient. And across the street

    Jamie Luke TPW Real Estate

    127 Mountain Ridge Rd, Peru, VT 05152
  • /3

    $452,500 Sold Aug 28, 2025

    3460 Sunderland Hill Rd, Arlington, VT 05250

    • 3 Beds
    • 3 Baths
    • 2,935 Sq Ft
    • Built 1920

    Last Sold Summary

    • 14% Below List Price
    • $154/SF
    • 17 Days On Market

    Current Estimated Value $501,232

    Last Listing Agent William Mariano

    3460 Sunderland Hill Rd, Arlington, VT 05250
    • /40

      Est $3,283,457 Not Listed For Sale

      440 Marcia Ln, Dorset, VT 05251

      • 5 Beds
      • 7.5 Baths
      • 8,700 Sq Ft
      • Built 2004
      440 Marcia Ln, Dorset, VT 05251

      Last Sold Summary

      • 22% Above List Price
      • $310/SF
      • 254 Days On Market

      Last Sold Price $2,700,000

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /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
  • /7

    $850 per month

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

    318 School St Unit 125 Adams, Bennington, VT 05201

    318 School St Unit 125 Adams, Bennington, VT 05201
  • /28

    $265,000 Sold Dec 15, 2025

    26 Cyr Ct, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 2000

    Last Sold Summary

    • $255/SF
    • 5 Days On Market

    Current Estimated Value $263,680

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    26 Cyr Ct, Bennington, VT 05201
    • /22

      Not Listed For Sale

      16 Clark Rd, Rupert, VT 05776

      • 4 Beds
      • 4 Baths
      • 2,708 Sq Ft
      • Built 1989
      16 Clark Rd, Rupert, VT 05776

      Last Sold Summary

      • $240/SF
      • 19 Days On Market

      Last Sold Price $649,000

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

  • /26

    $295,000 Pending

    • 6 Beds
    • 3 Baths
    • 2,640 Sq Ft

    235 Elm St Unit 3, Bennington, VT 05201

    This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

    Agent Photo

    Erica Hale

    Ridgeline Real Estate

    (802) 210-4437

    235 Elm St Unit 3, Bennington, VT 05201
  • /23

    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • House for Rent

    65 Cranberry Hill Rd, Bondville, VT 05340

    Never before offered: This Strattonwald contemporary ski house is a well cared-for home base for all who love the mountain lifestyle, in a private woodland setting just 9 minutes to Stratton's Main Base. The expansive living room is the ultimate gathering spot from morning to night, with soaring cathedral ceilings, a super-cozy wood stove, and extraordinary windows looking out at the private

    Jamie Luke TPW Real Estate

    65 Cranberry Hill Rd, Bondville, VT 05340
  • /38

    $390,000 Sold Aug 11, 2025

    626 Brookman Rd, Pownal, VT 05261

    • 3 Beds
    • 2 Baths
    • 3,274 Sq Ft
    • Built 1976

    Last Sold Summary

    • 18% Above List Price
    • $119/SF
    • 201 Days On Market

    Current Estimated Value $317,230

    Last Listing Agent Linda Benoit Highland Realty

    626 Brookman Rd, Pownal, VT 05261
    • /31

      Not Listed For Sale

      12 Stratton Rd W Unit 12, Winhall, VT 05340

      • 5 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 1968
      12 Stratton Rd W Unit 12, Winhall, VT 05340

      Last Sold Summary

      • $201/SF
      • 5 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Sandy Laserte 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 69 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 views. A

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 944-4482

    215 & 221 Vt Route 30, Dorset, VT 05251
  • /10

    $1,200 per month

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

    318 School St Unit 318 School, Bennington, VT 05201

    318 School St Unit 318 School, Bennington, VT 05201
  • /20

    $90,000 Sold Apr 17, 2025

    105 Spring St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,520 Sq Ft
    • Built 1903

    Last Sold Summary

    • 10% Below List Price
    • $59/SF
    • 4 Days On Market

    Current Estimated Value $95,240

    Last Listing Agent Matt Waddington Hoffman Real Estate

    105 Spring St, Bennington, VT 05201
    • /36

      Est $810,207 Not Listed For Sale

      469 Laclair Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 3.5 Baths
      • 3,104 Sq Ft
      • Built 2011
      469 Laclair Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 12% Above List Price
      • $234/SF
      • 3 Days On Market

      Last Sold Price $725,000

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

  • /43

    $2,300,000

    • Land
    • 67 Acres
    • $34,328 per Acre

    215 Vermont 30, Dorset, VT 05251

    Opportunities are Knocking! Welcome to an extraordinary 67-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 most

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 300-4271

    215 Vermont 30, Dorset, VT 05251
  • /15

    $2,300 per month

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft
    • Condo for Rent

    214 Coombs Rd Unit 214, Manchester Center, VT 05255

    Carefree Living in the Heart of Manchester EastEnjoy the perfect blend of comfort and convenience in this spacious, one-level condominium. Located in the highly sought-after Manchester East community, this home is designed for those who want to spend less time on chores and more time enjoying everything the area has to offer. Key FeaturesSpacious Layout: Two bright bedrooms and one full

    Robin Apps Four Seasons Sotheby's Int'l Realty

    214 Coombs Rd Unit 214, Manchester Center, VT 05255
  • /60

    $1,450,000 Sold Oct 17, 2025

    17 Farwell Ln, Dorset, VT 05251

    • 3 Beds
    • 3.5 Baths
    • 3,294 Sq Ft
    • Built 1987

    Last Sold Summary

    • $440/SF
    • 0 Days On Market

    Current Estimated Value $1,167,485

    Last Listing Agent Charles Mauro Josiah Allen Real Estate, Inc.

    17 Farwell Ln, Dorset, VT 05251
    • /28

      Not Listed For Sale

      27 Mountain View Rd, Winhall, VT 05360

      • 6 Beds
      • 6.5 Baths
      • 5,896 Sq Ft
      • Built 2000
      27 Mountain View Rd, Winhall, VT 05360

      Last Sold Summary

      • $195/SF
      • 22 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Andrew King Stratton Real Estate

  • /30

    $225,000

    • 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
  • /22

    $995 per month

    • Studio
    • 1 Bath
    • 200 Sq Ft
    • Condo for Rent

    302 Silver St Unit 304.5, Bennington, VT 05201

    Thiis is a four unit right in town with great considerate tenants.

    302 Silver St Unit 304.5, Bennington, VT 05201
  • /27

    $285,000 Sold Apr 03, 2025

    46 NW Hill Rd, Pownal, VT 05261

    • 3 Beds
    • 2 Baths
    • 2,128 Sq Ft
    • Built 1900

    Last Sold Summary

    • 12% Below List Price
    • $134/SF
    • 193 Days On Market

    Current Estimated Value $298,976

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    46 NW Hill Rd, Pownal, VT 05261
    • /40

      Est $262,000 Not Listed For Sale

      112 County Rd, Stamford, VT 05352

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 County Rd, Stamford, VT 05352

      Last Sold Summary

      • 7% Above List Price
      • $255/SF
      • 5 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /47

    $599,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,836 Sq Ft

    162 Highland Ave, Manchester Center, VT 05255

    Easy Investment Opportunity! Three unit multi-family. Great passive income. Turn key money maker! Spacious layout with privacy for each unit. The main level unit offers an open living dining area, three bedrooms, one-bath with mountain views off the spacious deck. The second floor offers two separate one-bedroom, one-bath units. Each unit has its own entrance. The lower level provides storage for

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 317-7820

    162 Highland Ave, Manchester Center, VT 05255
  • /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
  • /27

    $203,000 Sold Jul 31, 2025

    806 Vt Route 313 W, Arlington, VT 05250

    • 3 Beds
    • 1 Bath
    • 1,332 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $152/SF
    • 6 Days On Market

    Current Estimated Value $274,640

    Last Listing Agent Joshua Lemieux Remax Summit

    806 Vt Route 313 W, Arlington, VT 05250
    • /31

      Not Listed For Sale

      6 Black Birch Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      6 Black Birch Rd, Winhall, VT 05340

      Last Sold Summary

      • $278/SF
      • 8 Days On Market

      Last Sold Price $338,000

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /40

    $1,245,000

    • 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
  • /39

    $1,275 per month

    • 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
  • /15

    $165,000 Sold Jun 18, 2025

    2793 Rupert Rd, Arlington, VT 05250

    • Land
    • 37 Acres
    • $4,459 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 50 Days On Market

    Current Estimated Value $167,662

    Last Listing Agent Faith Rhodes Maple Leaf Realty

    2793 Rupert Rd, Arlington, VT 05250
    • /40

      Est $533,409 Not Listed For Sale

      68 Willows Way Unit 4, Peru, VT 05152

      • 3 Beds
      • 3.5 Baths
      • 1,010 Sq Ft
      • Built 1984
      68 Willows Way Unit 4, Peru, VT 05152

      Last Sold Summary

      • 5% Below List Price
      • $556/SF
      • 116 Days On Market

      Last Sold Price $562,000

      Last Listing Agent Dylan Gage Bromley Real Estate

  • /17

    $270,000 Pending

    • 6 Beds
    • 3 Baths
    • 2,900 Sq Ft

    239 - 241 Elm St, Bennington, VT 05201

    Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

    Agent Photo

    Erica Hale

    Ridgeline Real Estate

    (802) 278-6021

    239 - 241 Elm St, Bennington, VT 05201
  • /19

    $35,000 per month

    • 3 Beds
    • 3 Baths
    • 2,920 Sq Ft
    • House for Rent

    2 Aspen Ln, Winhall, VT 05340

    *Available for a partial season discount.* Stratton views, sunlight, space, and location: this ski chalet has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill

    Jamie Luke TPW Real Estate

    2 Aspen Ln, Winhall, VT 05340
  • /37

    $615,000 Sold Apr 15, 2025

    29 Burnt Hill Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1982

    Last Sold Summary

    • 18% Below List Price
    • $410/SF
    • 39 Days On Market

    Current Estimated Value $621,612

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

    29 Burnt Hill Rd, Winhall, VT 05340
    • /40

      Est $344,531 Not Listed For Sale

      214 Pleasant St, Arlington, VT 05250

      • 4 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1890
      214 Pleasant St, Arlington, VT 05250

      Last Sold Summary

      • 1% Above List Price
      • $180/SF
      • 17 Days On Market

      Last Sold Price $339,500

      Last Listing Agent Lilli West Maple Leaf Realty

  • /37

    $175,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    4355 Sandgate Rd, Arlington, VT 05250

    Cozy cabin retreat waiting for you! This rustic two-bedroom, one-bath log home features a beautiful hearth with a stone fireplace and the charm of a true fisherman’s cabin in the woods. Enjoy easy, year-round access via a paved, town-maintained road and a newly constructed driveway leading directly to the home.The property offers waterfront access to the famous Green River—perfect for

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 330-5803

    4355 Sandgate Rd, Arlington, VT 05250
  • /12

    $1,700 per month

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

    48 Center Hill Rd Unit 48A, Manchester Center, VT 05255

    1 bedroom apartment available. Located in town within walking distance to schools, shopping, restaurants and parks. Wood floors, washer/dryer, air conditioned, vaulted ceiling. All utilities included.

    48 Center Hill Rd Unit 48A, Manchester Center, VT 05255
  • /6

    $122,500 Sold Apr 18, 2025

    10 Little Brook Rd, Winhall, VT 05340

    • Land
    • 2.2 Acres
    • $55,682 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 53 Days On Market

    Current Estimated Value $127,661

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    10 Little Brook Rd, Winhall, VT 05340
    • /9

      Not Listed For Sale

      78 Heartwellville View Rd, Readsboro, VT 05350

      78 Heartwellville View Rd, Readsboro, VT 05350

      Last Sold Summary

      • 167 Days On Market

      Last Sold Price $8,000

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

Showing Results 41 - 80, Page 2 of 18

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