20,610

Bennington County, VT Homes

Section Image
    • /24

      Est $554,779

      Not Listed For Sale

      159 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft
      • Built 1972
      159 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 8 Days On Market

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

  • /54

    $480,000

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,312 Sq Ft

    498 Townline Rd, Bennington, VT 05201

    If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

    Betty McEnaney Diamond Realty

    498 Townline Rd, Bennington, VT 05201
  • /44

    $340,000

    Sold Jan 23, 2026

    989 Carpenter Hill Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,660 Sq Ft
    • Built 1986

    Last Sold Summary

    • 7% Below List Price
    • $205/SF
    • 85 Days On Market

    Current Estimated Value $346,218

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    989 Carpenter Hill Rd, Bennington, VT 05201
    • /27

      Est $629,472

      Not Listed For Sale

      211 Little John Dr, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1980
      211 Little John Dr, Manchester Center, VT 05255

      Last Sold Summary

      • 68 Days On Market

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

  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /60

    $534,000

    Sold Nov 24, 2025

    272 Oak Hill Rd, Shaftsbury, VT 05262

    • 3 Beds
    • 2.5 Baths
    • 3,637 Sq Ft
    • Built 2001

    Last Sold Summary

    • 24% Below List Price
    • $147/SF
    • 111 Days On Market

    Current Estimated Value $562,052

    Last Listing Agent Faith Rhodes Maple Leaf Real Estate

    272 Oak Hill Rd, Shaftsbury, VT 05262
    • /31

      Est $534,453

      Not Listed For Sale

      1 Cass Terrace, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 1913
      1 Cass Terrace, Manchester Center, VT 05255

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /23

    $249,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    18 Old Route 9, Wilmington, VT 05363

    Approximately 10 years new, this well-maintained and recently refreshed home offers the perfect combination of modern construction and country charm in the Green Mountains. Set on 2.0± acres in Searsburg, Vermont, a one-lane dirt road separates you from thousands of acres of National Forest land to explore literally right outside your door. The lot offers plenty of mature plantings, a stonewall

    Jacki Murano Southern Vermont Realty Group

    18 Old Route 9, Wilmington, VT 05363
  • /48

    $296,500

    Sold Nov 21, 2025

    4 Rockwood St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Below List Price
    • $156/SF
    • 6 Days On Market

    Current Estimated Value $305,514

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    4 Rockwood St, Bennington, VT 05201
    • /40

      Est $1,049,011

      Not Listed For Sale

      292 Johnnycake St, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 3,228 Sq Ft
      • Built 1984
      292 Johnnycake St, Manchester Center, VT 05255

      Last Sold Summary

      • 100 Days On Market

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

  • /45

    $269,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /22

    $795,000

    Sold Sep 17, 2025

    185 Crooked Path Rd, Arlington, VT 05250

    • 4 Beds
    • 5.5 Baths
    • 3,463 Sq Ft
    • Built 2006

    Last Sold Summary

    • $230/SF
    • 9 Days On Market

    Current Estimated Value $810,593

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

    185 Crooked Path Rd, Arlington, VT 05250
    • /24

      Est $634,821

      Not Listed For Sale

      2071 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,792 Sq Ft
      • Built 1980
      2071 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Robert Sabol Wohler Realty Group

  • /60

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft

    2734 Mad Tom Rd, East Dorset, VT 05253

    Vermont's rustic charm will welcome you in a warm embrace every time you enter this custom built post and beam home on 37.5 private acres. The home features 2 bedrooms plus loft and 2 baths with tons of natural woodwork. The property also includes a detached post and beam garage with additional space above, perfect for an art studio, writer's workshop or plenty of extra storage. The property

    David Citron RE/MAX Four Seasons

    2734 Mad Tom Rd, East Dorset, VT 05253
  • /3

    $199,000

    Sold Jul 16, 2026

    43 Limerick Ln, Arlington, VT 05250

    • Land
    • 9,147 Sq Ft
    • $947,619 per Acre

    Last Sold Summary

    • 1 Day On Market

    Current Estimated Value $201,333

    Last Listing Agent Margretta Fischer Wohler Realty Group

    43 Limerick Ln, Arlington, VT 05250
    • /37

      Est $888,954

      Not Listed For Sale

      505 Powderhorn Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,089 Sq Ft
      • Built 1976
      505 Powderhorn Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.

  • /41

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    87 B Hill Rd, Pownal, VT 05261

    Welcome to your own private Vermont retreat. Nestled on 3.2 acres in the mountains of Pownal, this Adirondack-style home offers the perfect blend of rustic charm, thoughtful craftsmanship, and everyday comfort.Surrounded by walking trails, blueberry and raspberry bushes, fruit trees, and abundant wildlife, the property is designed for those who appreciate the outdoors. Enjoy mountain views

    Lilli West Maple Leaf Real Estate

    87 B Hill Rd, Pownal, VT 05261
  • /22

    $175,000

    Sold Sep 11, 2025

    6967 Main St, Readsboro, VT 05350

    • 6 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • Built 1870

    Last Sold Summary

    • 22% Below List Price
    • $83/SF
    • 70 Days On Market

    Current Estimated Value $183,925

    Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

    6967 Main St, Readsboro, VT 05350
    • /33

      Est $552,309

      Not Listed For Sale

      367 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,228 Sq Ft
      • Built 1992
      367 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 76 Days On Market

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

  • /31

    $1,200,000

    • 1 Bath
    • 950 Sq Ft

    109 Winhall Hollow Rd, Winhall, VT 05340

    Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    109 Winhall Hollow Rd, Winhall, VT 05340
  • /53

    $495,000

    Sold Oct 17, 2025

    200 Applewood Ln, Manchester Center, VT 05255

    • 2,746 Sq Ft
    • Built 1986

    Last Sold Summary

    • $180/SF
    • 4 Days On Market

    Current Estimated Value $532,958

    Last Listing Agent Zachary Zupan EXP Realty

    200 Applewood Ln, Manchester Center, VT 05255
    • /42

      Est $513,757

      Not Listed For Sale

      256 Lathrop Ln, Manchester Center, VT 05255

      • 6 Beds
      • 4 Baths
      • 2,174 Sq Ft
      • Built 1820
      256 Lathrop Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 37 Days On Market

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

  • /7

    $145,000

    $30K PRICE DROP Pending
    • Land
    • 15.49 Acres
    • $9,361 per Acre

    00 Silk Rd, Bennington, VT 05201

    Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

    David White OwnerEntry.com

    00 Silk Rd, Bennington, VT 05201
  • /42

    $529,000

    Sold Apr 15, 2026

    941 Myers Rd, Shaftsbury, VT 05262

    • 4 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 1900

    Last Sold Summary

    • $281/SF
    • 2 Days On Market

    Current Estimated Value $542,004

    Last Listing Agent Abi Gregorio

    941 Myers Rd, Shaftsbury, VT 05262
    • /38

      Est $1,009,232

      Not Listed For Sale

      1144 Powderhorn Rd, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,843 Sq Ft
      • Built 1986
      1144 Powderhorn Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /37

    $439,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    15 Polygraphic Ln, North Bennington, VT 05257

    At the end of a quiet road in North Bennington, this beloved 1979 home is being offered for the first time by its original owner. Set on over an acre with a large private backyard, garden beds, wild blackberries, and a peaceful wooded backdrop, the property feels beautifully tucked away while remaining just a short walk to the Henry Bridge and the Walloomsac River. Inside, the home is timeless,

    Jenifer Prouty Hoffman Hoffman Real Estate

    15 Polygraphic Ln, North Bennington, VT 05257
  • /21

    $120,000

    Sold Mar 09, 2026

    1319 Vail Rd, Bennington, VT 05201

    • Land
    • 20 Acres
    • $6,000 per Acre

    Last Sold Summary

    • 143 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    1319 Vail Rd, Bennington, VT 05201
    • /23

      Est $516,894

      Not Listed For Sale

      69 Cottage St, Manchester Center, VT 05255

      • 2 Beds
      • 1.5 Baths
      • 1,675 Sq Ft
      • Built 1920
      69 Cottage St, Manchester Center, VT 05255

      Last Sold Summary

      • 6 Days On Market

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

  • /38

    $625,000

    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    1 Beaver St, Bondville, VT 05340

    Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

    Carrie Mathews Winhall Real Estate

    1 Beaver St, Bondville, VT 05340
  • /48

    $306,250

    Sold Dec 05, 2025

    4581 Main Rd, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft
    • Built 1967

    Last Sold Summary

    • 18% Above List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $317,130

    Last Listing Agent Susan Colvin MONARCH REALTY, INC.

    4581 Main Rd, Stamford, VT 05352
    • /30

      Est $409,525

      Not Listed For Sale

      141 Green Mountain Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1986
      141 Green Mountain Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Patti Trudel RE/MAX Four Seasons

  • /36

    $359,000

    $40K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,938 Sq Ft

    100 McCarthy Acres, North Bennington, VT 05257

    Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

    Nicholas Charest Maple Leaf Real Estate

    100 McCarthy Acres, North Bennington, VT 05257
  • /35

    $799,000

    Sold Jul 17, 2026

    63 Raspberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 3.5 Baths
    • 3,078 Sq Ft
    • Built 1980

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    63 Raspberry Hill Rd, Winhall, VT 05340
    • /40

      Est $383,010

      Not Listed For Sale

      1732 Barnumville Rd, Manchester Center, VT 05255

      • 4 Beds
      • 1 Bath
      • 1,456 Sq Ft
      • Built 1844
      1732 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Bonnie Chandler RE/MAX Four Seasons

  • /32

    $549,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,234 Sq Ft

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

    This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

    David Halligan Four Seasons Sotheby's Int'l Realty

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
  • /27

    $300,000

    Sold Dec 11, 2025

    0 Rock Bottom Ln, Peru, VT 05152

    • Land
    • 53 Acres
    • $5,660 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 156 Days On Market

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

    0 Rock Bottom Ln, Peru, VT 05152
    • /40

      Not Listed For Sale

      72 Jaquith Rd, Londonderry, VT 05148

      • 4 Beds
      • 2.5 Baths
      • 3,794 Sq Ft
      • Built 1991
      72 Jaquith Rd, Londonderry, VT 05148

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

  • /12

    $825,000

    $40K PRICE DROP Under Contract
    • 5,568 Sq Ft

    1931 Vermont Route 67 E, Shaftsbury, VT 05262

    Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

    Julie Glover Mahar McCarthy Real Estate

    1931 Vermont Route 67 E, Shaftsbury, VT 05262
  • /47

    $240,000

    Sold Sep 24, 2025

    120 Imperial Ave, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1895

    Last Sold Summary

    • 20% Below List Price
    • $100/SF
    • 114 Days On Market

    Current Estimated Value $278,592

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    120 Imperial Ave, Bennington, VT 05201
    • /23

      Est $785,682

      Not Listed For Sale

      88 Jaquith Rd, Londonderry, VT 05148

      • 3 Beds
      • 2.5 Baths
      • 2,742 Sq Ft
      • Built 1980
      88 Jaquith Rd, Londonderry, VT 05148

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

Showing Results 641 - 680, Page 17 of 18

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