21,114

Bennington County, VT Homes

Section Image
  • /8

    $65,000 Under Contract

    • Land
    • 1.02 Acres
    • $63,725 per Acre

    0 Stratton View Rd Unit 26, Winhall, VT 05340

    Stratton View Rd Lot # 59 , 1.02 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition lot MLS #5036988 available. Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Stratton View Rd Unit 26, Winhall, VT 05340
  • /22

    $210,000 Sold Jan 21, 2026

    52 Walker Meadow, Arlington, VT 05250

    • 2 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $109/SF
    • 4 Days On Market

    Current Estimated Value $237,623

    Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    52 Walker Meadow, Arlington, VT 05250
    • /13

      Est $283,094 Not Listed For Sale

      390 Tunnel St, Readsboro, VT 05350

      • 4 Beds
      • 2 Baths
      • 1,676 Sq Ft
      • Built 1968
      390 Tunnel St, Readsboro, VT 05350

      Last Sold Summary

      • 35% Above List Price
      • $125/SF
      • 3 Days On Market

      Last Sold Price $209,000

      Last Listing Agent Derek Greene Derek Greene

  • /45

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    9 Lower Taylor Hill Rd, Winhall, VT 05340

    Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

    Timothy Mich Doddridge Stratton Real Estate

    9 Lower Taylor Hill Rd, Winhall, VT 05340
  • /10

    $18,500 Sold Jan 09, 2026

    lot139&140 Bergrucken Ln, Readsboro, VT 05350

    • Land
    • 2.3 Acres
    • $8,043 per Acre

    Last Sold Summary

    • 20 Days On Market

    Last Listing Agent Christine Girard STEEPLEVIEW REALTY - N. ADAMS

    lot139&140 Bergrucken Ln, Readsboro, VT 05350
    • /39

      Est $260,761 Not Listed For Sale

      93 Depot St, Readsboro, VT 05350

      • 4 Beds
      • 2 Baths
      • 1,837 Sq Ft
      • Built 1800
      93 Depot St, Readsboro, VT 05350

      Last Sold Summary

      • 16% Above List Price
      • $122/SF
      • 1 Day On Market

      Last Sold Price $225,000

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /9

    $27,500

    • Land
    • 1.2 Acres
    • $22,917 per Acre

    0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

    Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

    Kelly Agrillo Southern Vermont Realty Group

    0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
  • /59

    $825,000 Sold Jun 30, 2025

    764 Barnumville Rd Unit 2, Manchester Center, VT 05255

    • 3 Beds
    • 4 Baths
    • 3,240 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Above List Price
    • $255/SF
    • 41 Days On Market

    Current Estimated Value $761,866

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    764 Barnumville Rd Unit 2, Manchester Center, VT 05255
    • /18

      Est $113,103 Not Listed For Sale

      78 Canal Dr, Readsboro, VT 05350

      • 3 Beds
      • 2 Baths
      • 1,024 Sq Ft
      • Built 1880
      78 Canal Dr, Readsboro, VT 05350

      Last Sold Summary

      • 74% Above List Price
      • $63/SF
      • 178 Days On Market

      Last Sold Price $65,000

      Last Listing Agent Duncan Honig Maple Leaf Realty

  • /43

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 3,780 Sq Ft

    1228 Skiparee Rd, Pownal, VT 05260

    Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

    Christiane Carroccio TPW Real Estate

    1228 Skiparee Rd, Pownal, VT 05260
  • /60

    $245,000 Sold Sep 22, 2025

    19 Robinson Ave, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Below List Price
    • $186/SF
    • 3 Days On Market

    Current Estimated Value $253,910

    Last Listing Agent Floyd Amidon Maple Leaf Realty

    19 Robinson Ave, Bennington, VT 05201
    • /40

      Est $582,960 Not Listed For Sale

      1456 Branch Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 2 Baths
      • 3,263 Sq Ft
      • Built 1991
      1456 Branch Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 20% Above List Price
      • $149/SF
      • 856 Days On Market

      Last Sold Price $487,000

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /60

    $579,900

    • 1 Bed
    • 1 Bath
    • 2,529 Sq Ft

    126 Simeon Dean Rd, Shaftsbury, VT 05262

    Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

    Denise Byers Green Mountain Premiere Properties

    126 Simeon Dean Rd, Shaftsbury, VT 05262
  • /33

    $740,000 Sold Jan 02, 2026

    G12 Cobble Ridge Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,764 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $268/SF
    • 1 Day On Market

    Current Estimated Value $728,333

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

    G12 Cobble Ridge Rd, Winhall, VT 05340
    • /40

      Est $387,985 Not Listed For Sale

      1693 Branch Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 3 Baths
      • 2,259 Sq Ft
      • Built 1848
      1693 Branch Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 11% Above List Price
      • $155/SF
      • 14 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /33

    $815,000

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft

    158 Upland Downs Rd, Manchester Center, VT 05255

    This well-maintained home is nestled on an open, sunny lot with mountain views, offering a serene and picturesque setting. The property is in move-in condition and boasts one of Manchester's best locations, providing convenient access to the town, schools, and shops, all just minutes away. It is set back from the road, surrounded by beautifully landscaped lawn, gardens, and a spacious

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    158 Upland Downs Rd, Manchester Center, VT 05255
  • /37

    $233,000 Sold Aug 04, 2025

    73 Woodford City Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Above List Price
    • $221/SF
    • 73 Days On Market

    Last Listing Agent Abi Gregorio

    73 Woodford City Rd, Bennington, VT 05201
    • /25

      Est $94,433 Not Listed For Sale

      845 Bailey Hill Rd, Readsboro, VT 05350

      • 1 Bed
      • 586 Sq Ft
      • Built 1948
      845 Bailey Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 35% Above List Price
      • $119/SF
      • 19 Days On Market

      Last Sold Price $70,000

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /47

    $925,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 4,000 Sq Ft

    255 Hemlock Ridge Rd, Manchester Center, VT 05255

    Set at the end of a quiet private road, this light-filled, energy-efficient home offers exceptional privacy, expansive views, and convenient access to town. Less than five minutes from downtown Manchester and within easy reach of Bromley and Stratton, the property feels wonderfully rural while remaining highly accessible. The covered back porch and expanded deck overlook beautifully landscaped

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    255 Hemlock Ridge Rd, Manchester Center, VT 05255
  • /49

    $313,000 Sold Jul 21, 2025

    1385 N Bennington Rd, North Bennington, VT 05257

    • 4 Beds
    • 2 Baths
    • 2,050 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $153/SF
    • 53 Days On Market

    Current Estimated Value $314,429

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1385 N Bennington Rd, North Bennington, VT 05257
    • /15

      Est $426,012 Not Listed For Sale

      833 Freezing Hole Dr, Readsboro, VT 05350

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 1997
      833 Freezing Hole Dr, Readsboro, VT 05350

      Last Sold Summary

      • 2% Below List Price
      • $254/SF
      • 9 Days On Market

      Last Sold Price $432,500

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /20

    $179,900 Pending

    • 4 Beds
    • 1.5 Baths
    • 2,082 Sq Ft

    266 Robillard Rd, Stamford, VT 05352

    SOUTHERN VERMONT!~ PRICE DROP $45,000!! Great country location with over a 1/2 acre of beautiful lawns & perennial flower. Sitting porch, large kitchen with pantry opens to dining & living room. Oak hardwood floors on 1st floor. 2nd level has 4 good sized bedrooms & 3rd level has a private loft area with 2 very nice rooms & a 1/2 bath - great office space, laundry room or meditation room. Laundry

    Colleen Zajac Monarch Realty

    266 Robillard Rd, Stamford, VT 05352
  • /41

    $445,000 Sold Dec 19, 2025

    181 White Tail Run, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 2,246 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $198/SF
    • 5 Days On Market

    Current Estimated Value $458,348

    Last Listing Agent Margretta Fischer Wohler Realty Group

    181 White Tail Run, Arlington, VT 05250
    • /40

      Est $403,922 Not Listed For Sale

      470 Freezing Hole Dr, Readsboro, VT 05350

      • 3 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1964
      470 Freezing Hole Dr, Readsboro, VT 05350

      Last Sold Summary

      • 1% Above List Price
      • $376/SF
      • 8 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /12

    $399,500

    • Land
    • 2.7 Acres
    • $147,963 per Acre

    2937 Dorset Rd W, Dorset, VT 05251

    Prime Buildable Lot in Dorset! Embrace the Best of All Worlds!Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    2937 Dorset Rd W, Dorset, VT 05251
  • /30

    $400,000 Sold Oct 15, 2025

    38 Spruce Ln, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Below List Price
    • $248/SF
    • 0 Days On Market

    Current Estimated Value $395,631

    Last Listing Agent Lori Hurley Four Corner Properties LLC

    38 Spruce Ln, Arlington, VT 05250
    • /35

      Not Listed For Sale

      140 Odonnell Dr, Readsboro, VT 05350

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft
      • Built 2000
      140 Odonnell Dr, Readsboro, VT 05350

      Last Sold Summary

      • $217/SF
      • 6 Days On Market

      Last Sold Price $555,000

      Last Listing Agent Monica Sumner BHG Masiello Brattleboro

  • /23

    $249,000

    • Land
    • 17.6 Acres
    • $14,148 per Acre

    88 Cedar Ln, Peru, VT 05152

    Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

    Joe Castaluccio Winhall Real Estate

    88 Cedar Ln, Peru, VT 05152
  • /38

    $635,000 Sold Nov 21, 2025

    825 Case Ln, Readsboro, VT 05350

    • 3 Beds
    • 2 Baths
    • 2,499 Sq Ft
    • Built 2006

    Last Sold Summary

    • 15% Above List Price
    • $254/SF
    • 7 Days On Market

    Current Estimated Value $597,518

    Last Listing Agent Melissa Nebelski Real Broker LLC

    825 Case Ln, Readsboro, VT 05350
    • /20

      Est $384,334 Not Listed For Sale

      603 Wiley Mountain Dr, Readsboro, VT 05350

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 2005
      603 Wiley Mountain Dr, Readsboro, VT 05350

      Last Sold Summary

      • $401/SF
      • 160 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /2

    $450,000 Pending

    • Land
    • 1.18 Acres
    • $381,356 per Acre

    97 N Branch Rd, Winhall, VT 05155

    The only undeveloped parcel of land on Stratton Lake. Underground utilities stubbed out to the road at entrance to lot. Stratton shuttle service, community water and sewer. Eastern exposure with views over the Stratton Lake. Adjacent to the Stratton Country Club golf course.

    John Sikes Stratton Real Estate

    97 N Branch Rd, Winhall, VT 05155
  • /44

    $275,000 Sold Jan 23, 2026

    211 Grandview St, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1955

    Last Sold Summary

    • 7% Below List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $295,418

    Last Listing Agent Flex Realty Group Flex Realty

    211 Grandview St, North Bennington, VT 05257
    • /24

      Est $370,431 Not Listed For Sale

      1680 W Hill Dr, Readsboro, VT 05350

      • 4 Beds
      • Built 1980
      1680 W Hill Dr, Readsboro, VT 05350

      Last Sold Summary

      • 48% Above List Price
      • $116/SF
      • 409 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /40

    $198,000 Pending

    • 5 Beds
    • 2 Baths
    • 2,201 Sq Ft

    317 Pleasant St, Bennington, VT 05201

    Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400). Unit 1 on the

    Michael Gilman 3GEN Real Estate Inc

    317 Pleasant St, Bennington, VT 05201
  • /36

    $265,000 Sold Jun 25, 2025

    82 Oakes St, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,512 Sq Ft
    • Built 1991

    Last Sold Summary

    • $175/SF
    • 57 Days On Market

    Current Estimated Value $266,991

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    82 Oakes St, Bennington, VT 05201
    • /58

      Est $297,450 Not Listed For Sale

      1806 Bosley Hill Rd, Readsboro, VT 05350

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1988
      1806 Bosley Hill Rd, Readsboro, VT 05350

      Last Sold Summary

      • 49% Above List Price
      • $128/SF
      • 126 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

  • /27

    $290,000

    • 4 Beds
    • 2 Baths
    • 2,190 Sq Ft

    196 Granger Hollow Rd, North Bennington, VT 05257

    Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large

    Steve Schoppmeyer BHG Masiello Brattleboro

    196 Granger Hollow Rd, North Bennington, VT 05257
  • /43

    $1,590,000 Sold Oct 23, 2025

    81 Pine Tree Ln, Manchester Center, VT 05255

    • 4 Beds
    • 3.5 Baths
    • 3,926 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $405/SF
    • 17 Days On Market

    Current Estimated Value $1,550,396

    Last Listing Agent Roger Danyew Diamond Realty

    81 Pine Tree Ln, Manchester Center, VT 05255
    • /23

      Est $181,909 Not Listed For Sale

      346 Vt Route 8, Readsboro, VT 05350

      • 2 Beds
      • 1 Bath
      • 942 Sq Ft
      • Built 1900
      346 Vt Route 8, Readsboro, VT 05350

      Last Sold Summary

      • 65% Above List Price
      • $117/SF
      • 11 Days On Market

      Last Sold Price $110,000

      Last Listing Agent Dick Thackston R.H. Thackston & Company

  • /21

    $120,000 Pending

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

    1319 Vail Rd, Bennington, VT 05201

    Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

    Lilli West Maple Leaf Realty

    1319 Vail Rd, Bennington, VT 05201

Showing Results 361 - 400, Page 10 of 18

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