20,610

Bennington County, VT Homes

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  • /12

    $450,000

    • Land
    • 10.26 Acres
    • $43,860 per Acre

    4.1 Pearl Buck Dr, Winhall, VT 05340

    One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

    Kim Morgan-Wohler Wohler Realty Group

    4.1 Pearl Buck Dr, Winhall, VT 05340
  • /15

    $96,906

    Sold Jul 11, 2026

    10 Cassie Ln, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $125/SF
    • 286 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    10 Cassie Ln, Bennington, VT 05201
    • /36

      Est $544,446

      Not Listed For Sale

      1530 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 2,116 Sq Ft
      • Built 1900
      1530 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • /19

    $426,000

    Sold Jan 16, 2026

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340

    • 2 Beds
    • 2 Baths
    • 1,798 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $237/SF
    • 1 Day On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340
    • /34

      Not Listed For Sale

      1858 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,088 Sq Ft
      • Built 1984
      1858 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  • /35

    $570,000

    $75K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251

    This Pretty White Cape is located on a low traveled dead end road right off Dorset's Morse Hill Road... equidistance to Manchester and Dorset and an easy walk to the newly transitioning Green Ridge Elementary K-5, for the 26-27 school year. Beautifully maintained, this residence offers a lovely open Dining/Kitchen /Living great-room with vault that beholds sunlight all day long. The quartz

    Laura Beckwith Josiah Allen Real Estate, Inc.

    185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251
  • /9

    $65,000

    Sold May 27, 2026

    0 Evergreen Dr, Bennington, VT 05201

    • Land
    • 9.24 Acres
    • $7,035 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    0 Evergreen Dr, Bennington, VT 05201
    • /33

      Est $684,901

      Not Listed For Sale

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      • 2 Beds
      • 2.5 Baths
      • 2,145 Sq Ft
      • Built 1998
      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /25

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    393 Morse Hill Rd, East Dorset, VT 05253

    This beautifully maintained Dorset home with views is ready for its new owners. The main level features a generously sized eat-in kitchen with granite countertops that opens into the dining room. This floor also includes a large living room, a bedroom, and French doors that lead to a spacious deck overlooking a private yard. The ground floor offers a primary bedroom, a bathroom, and a laundry

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    393 Morse Hill Rd, East Dorset, VT 05253
  • /44

    $375,000

    Sold Jun 12, 2026

    4991 Vt Route 313 W, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $268/SF
    • 75 Days On Market

    Current Estimated Value $370,884

    Last Listing Agent Margretta Fischer Wohler Realty Group

    4991 Vt Route 313 W, Arlington, VT 05250
    • /40

      Est $529,910

      Not Listed For Sale

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft
      • Built 2000
      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

    Lindsey Martin Maple Leaf Real Estate

    113 Main St, Bennington, VT 05201
  • /39

    $255,500

    Sold Jan 15, 2026

    77 Mcguire St, North Bennington, VT 05257

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $253/SF
    • 15 Days On Market

    Current Estimated Value $237,055

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    77 Mcguire St, North Bennington, VT 05257
    • /40

      Est $882,087

      Not Listed For Sale

      1279 W Mountain Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 5 Baths
      • 3,096 Sq Ft
      • Built 1977
      1279 W Mountain Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Flex Realty Group Flex Realty

  • /48

    $429,000

    • 2 Beds
    • 2 Baths
    • 7,000 Sq Ft

    3310 Vermont 346, Pownal, VT 05260

    Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

    Paul Harsch HARSCH ASSOCIATES

    3310 Vermont 346, Pownal, VT 05260
  • /3

    $110,000

    Sold Nov 17, 2025

    0 Maple Hill Rd, Shaftsbury, VT 05262

    • Land
    • 11.5 Acres
    • $9,565 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    0 Maple Hill Rd, Shaftsbury, VT 05262
    • /48

      Est $669,891

      Not Listed For Sale

      1516 W Mountain Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2.5 Baths
      • 1,738 Sq Ft
      • Built 1979
      1516 W Mountain Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 192 Days On Market

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /45

    $525,000

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,594 Sq Ft

    191 Pleasant Street Extension, East Dorset, VT 05253

    "COME TAKE A PEEK, IT'S JUST ACROSS THE CREEK.....Enjoy an inviting front porch to unwind and breathe in the serene surroundings! Unwind and take in the lovely mountain views, all set on the scenic Tom River in East Dorset! Charming saltbox style (1982 circa), the design is open living spaces with abundant light through out... As an added bonus this property boasts an over sized two car garage

    Sunny Breen Josiah Allen Real Estate, Inc.

    191 Pleasant Street Extension, East Dorset, VT 05253
  • /19

    $199,900

    Sold Sep 19, 2025

    42 Colvin Ave, Shaftsbury, VT 05262

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft
    • Built 1964

    Last Sold Summary

    • $210/SF
    • 28 Days On Market

    Current Estimated Value $203,252

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    42 Colvin Ave, Shaftsbury, VT 05262
    • /40

      Est $624,956

      Not Listed For Sale

      143 Cedar Cir, Shaftsbury, VT 05262

      • 4 Beds
      • 4 Baths
      • 2,756 Sq Ft
      • Built 1977
      143 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /49

    $335,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,480 Sq Ft

    164 Skyboro Rd W, Pownal, VT 05261

    Filled with natural light and designed for comfortable living, this charming 3-bedroom, 3-bath contemporary home offers a spacious, versatile floor plan with room to live, work, and create. Light wood flooring and multiple skylights enhance the warm, inviting interior, while thoughtfully designed living spaces provide comfort and flexibility for today's lifestyle. The main level features two

    Angela Bevin Maple Leaf Real Estate

    164 Skyboro Rd W, Pownal, VT 05261
  • /55

    $945,000

    Sold Jun 05, 2026

    520 Moose Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 4,184 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $226/SF
    • 20 Days On Market

    Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    520 Moose Hollow Rd, Winhall, VT 05340
    • /29

      Est $407,342

      Not Listed For Sale

      202 Cedar Cir, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1985
      202 Cedar Cir, Shaftsbury, VT 05262

      Last Sold Summary

      • 3 Days On Market

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

  • /50

    $555,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    3287 Route 7, Pownal, VT 05261

    Lovingly custom built in 1989 and offered for the first time, this beautifully maintained expanded Cape is a rare opportunity to own a home that has been cherished by its original family from the very beginning. Thoughtfully designed with generous room sizes and a timeless floor plan, the home offers warmth, comfort, and quality throughout. Inside, generous room sizes, timeless design, and

    Faith Rhodes Maple Leaf Real Estate

    3287 Route 7, Pownal, VT 05261
  • /58

    $299,000

    Sold Jun 01, 2026

    207 Silver St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1846

    Last Sold Summary

    • $150/SF
    • 143 Days On Market

    Current Estimated Value $304,490

    Last Listing Agent Dan Mason Perrott Realty

    207 Silver St, Bennington, VT 05201
    • /40

      Est $303,602

      Not Listed For Sale

      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,006 Sq Ft
      • Built 1970
      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /45

    $357,500

    $8K PRICE DROP Under Contract
    • 4 Beds
    • 1.5 Baths
    • 1,735 Sq Ft

    19 Royal St, North Bennington, VT 05257

    Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience, just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the

    Lindsey Martin Maple Leaf Real Estate

    19 Royal St, North Bennington, VT 05257
  • /42

    $655,000

    Sold Jun 03, 2026

    384 Alden Rd, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Above List Price
    • $347/SF
    • 7 Days On Market

    Current Estimated Value $643,292

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

    384 Alden Rd, Arlington, VT 05250
    • /39

      Est $613,603

      Not Listed For Sale

      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 1981
      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /25

    $360,000

    Sold Feb 25, 2026

    00 Ross Rd, Winhall, VT 05340

    • Land
    • 41.1 Acres
    • $8,759 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 82 Days On Market

    Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

    00 Ross Rd, Winhall, VT 05340
    • /45

      Est $381,789

      Not Listed For Sale

      294 Tinkham Rd, North Bennington, VT 05257

      • 2 Beds
      • 2 Baths
      • 1,573 Sq Ft
      • Built 1975
      294 Tinkham Rd, North Bennington, VT 05257

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /45

    $299,900

    Under Contract
    • 5 Beds
    • 2.5 Baths
    • 2,716 Sq Ft

    886 Hidden Valley Rd, Shaftsbury, VT 05262

    Escape to the rustic charm of this beautiful 5 bedroom, 2.5 bath log cabin nestled on 2 peaceful acres in the highly desirable town of Shaftsbury. From the moment you step inside, you’ll fall in love with the warm log features throughout, exposed beam ceilings, and the cozy fireplace that anchors the inviting living room. The charming country kitchen flows into a dedicated dining room, creating

    Julie Glover Mahar McCarthy Real Estate

    886 Hidden Valley Rd, Shaftsbury, VT 05262
  • /28

    $450,000

    Sold Apr 23, 2026

    354 New Ireland Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $323/SF
    • 73 Days On Market

    Current Estimated Value $465,665

    Last Listing Agent Carol O`Connor Four Seasons Sotheby's Int'l Realty

    354 New Ireland Rd, Manchester Center, VT 05255
    • /52

      Est $445,115

      Not Listed For Sale

      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,535 Sq Ft
      • Built 1989
      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /2

    $425,000

    • Land
    • 3 Acres
    • $141,667 per Acre

    lot B Frost Pond Rd, Dorset, VT 05251

    Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

    Charles Mauro Josiah Allen Real Estate, Inc.

    lot B Frost Pond Rd, Dorset, VT 05251
  • /42

    $600,000

    Sold Nov 12, 2025

    126 Fox Hill Rd, Bennington, VT 05201

    • 5 Beds
    • 1.5 Baths
    • 2,450 Sq Ft
    • Built 1850

    Last Sold Summary

    • 25% Below List Price
    • $245/SF
    • 148 Days On Market

    Current Estimated Value $625,245

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    126 Fox Hill Rd, Bennington, VT 05201
    • /12

      Est $202,636

      Not Listed For Sale

      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 920 Sq Ft
      • Built 1935
      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Kevin Holmes Blue Slate Realty

  • /43

    $319,900

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    683 Water St, North Bennington, VT 05257

    Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    683 Water St, North Bennington, VT 05257

Showing Results 321 - 360, Page 9 of 18

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