21,175

Bennington County, VT Homes

Section Image
    • /17

      Est $243,948 Not Listed For Sale

      591 Vt Route 67 E, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 2001
      591 Vt Route 67 E, Shaftsbury, VT 05262

      Last Sold Summary

      • 2% Above List Price
      • $109/SF
      • 22 Days On Market

      Last Sold Price $240,000

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

  • /35

    $370,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,463 Sq Ft

    303 Prospect St, Bennington, VT 05201

    Nestled on a quiet residential street, this beautifully maintained home effortlessly blends timeless charm with modern convenience, creating a space that is as inviting as it is impressive. From the moment you arrive, you’ll appreciate the character and warmth that set this property apart. At the heart of the home is a thoughtfully designed kitchen featuring modern appliances, rich cherry

    Angela Bevin Maple Leaf Realty

    303 Prospect St, Bennington, VT 05201
  • /30

    $750,000 Sold Aug 19, 2025

    379 Owls Head Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 4 Baths
    • 2,187 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $343/SF
    • 15 Days On Market

    Current Estimated Value $756,609

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

    379 Owls Head Hill Ln, Dorset, VT 05251
    • /34

      Est $370,817 Not Listed For Sale

      191 Grove Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 1,771 Sq Ft
      • Built 1978
      191 Grove Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 1% Below List Price
      • $212/SF
      • 141 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  • /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
  • /31

    $208,000 Sold Oct 10, 2025

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 10 Days On Market

    Current Estimated Value $205,863

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    379 Heartwellville View Rd Unit lot 71 Section 8, Readsboro, VT 05350
    • /39

      Est $240,483 Not Listed For Sale

      192 Grove Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 1,146 Sq Ft
      • Built 1976
      192 Grove Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 12% Above List Price
      • $188/SF
      • 8 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /24

    $435,000

    • 2 Beds
    • 3 Baths
    • 1,689 Sq Ft

    141 Hillvale Rd, Manchester, VT 05255

    This is quite possibly the in-town Manchester home that you have been looking for. Offering convenient one level living and move-in ready condition with two bedrooms and two baths, hardwood floors, living room with woodstove, kitchen and sunroom. The finished basement offers additional living space with large family room, office, additional 3/4 bath and laundry. Don't forget about the attached

    David Citron RE/MAX Four Seasons

    141 Hillvale Rd, Manchester, VT 05255
  • /46

    $800,000 Sold May 21, 2025

    1 Monument Ave, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 3,560 Sq Ft
    • Built 1790

    Last Sold Summary

    • 1% Above List Price
    • $225/SF
    • 34 Days On Market

    Current Estimated Value $828,861

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    1 Monument Ave, Bennington, VT 05201
    • /20

      Est $339,125 Not Listed For Sale

      136 Grove Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1979
      136 Grove Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 10% Below List Price
      • $312/SF
      • 2 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

  • /18

    $300,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft

    940 Gage St, Bennington, VT 05201

    Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

    Christine Lewis Brattleboro Area Realty

    940 Gage St, Bennington, VT 05201
  • /53

    $400,000 Sold Sep 22, 2025

    495 Fairview St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,309 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $306/SF
    • 12 Days On Market

    Current Estimated Value $393,662

    Last Listing Agent Catherine Cairns Maple Leaf Realty

    495 Fairview St, Bennington, VT 05201
    • /27

      Est $262,659 Not Listed For Sale

      338 Twitchell Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1964
      338 Twitchell Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 12% Below List Price
      • $227/SF
      • 100 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Faith Rhodes Maple Leaf Realty

  • /19

    $219,500

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
  • /33

    $485,000 Sold Apr 20, 2026

    3 Strattonwald Rd, Winhall, VT 05340

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $361/SF
    • 276 Days On Market

    Current Estimated Value $491,724

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /39

      Est $408,556 Not Listed For Sale

      20 Eastview Dr, Shaftsbury, VT 05262

      • 2 Beds
      • 2.5 Baths
      • 1,586 Sq Ft
      • Built 1986
      20 Eastview Dr, Shaftsbury, VT 05262

      Last Sold Summary

      • 15% Above List Price
      • $224/SF
      • 35 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Brandy Lesser

  • /4

    $14,000 Under Contract

    • Land
    • 1.2 Acres
    • $11,667 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1.2-acre lot offers the perfect blend of privacy and convenience. Power is already available on the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this

    Flex Realty Group Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /60

    $230,500 Sold Jul 18, 2025

    322 Burgess Rd, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 2,004 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $115/SF
    • 62 Days On Market

    Current Estimated Value $247,281

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    322 Burgess Rd, Bennington, VT 05201
    • /36

      Est $494,040 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

      • $234/SF
      • 8 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Kelley Mccarthy Mahar McCarthy 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
  • /15

    $175,000 Sold Mar 09, 2026

    0 Alden Ln, Sunderland, VT 05250

    • Land
    • 40 Acres
    • $4,375 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 360 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    0 Alden Ln, Sunderland, VT 05250
    • /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

      • $427/SF
      • 49 Days On Market

      Last Sold Price $892,000

      Last Listing Agent Faith Rhodes Maple Leaf Realty

  • /37

    $795,000

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    34 Mountain View Rd, Winhall, VT 05360

    Stratton Chalet with INCREDIBLE Mountain Views! Recently renovated this VT mountain retreat is the perfect place to enjoy all seasons in Southern VT. Enjoy the majestic views of the summit from your hot tub and firepit all year long. The interior layout is wonderful for larger groups to gather with an expansive open entertainment area on the ground level including the kitchen, dining and living

    Jason Saphire www.HomeZu.com

    34 Mountain View Rd, Winhall, VT 05360
  • /47

    $502,500 Sold Dec 15, 2025

    377 Glen Rd, Peru, VT 05152

    • 4 Beds
    • 4 Baths
    • 2,370 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $212/SF
    • 16 Days On Market

    Current Estimated Value $500,550

    Last Listing Agent Nancy Jensen Four Seasons Sotheby's Int'l Realty

    377 Glen Rd, Peru, VT 05152
    • /33

      Est $702,054 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

      • 1% Above List Price
      • $324/SF
      • 4 Days On Market

      Last Sold Price $695,000

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /60

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,764 Sq Ft

    2603 N Pownal Rd, Pownal, VT 05261

    Perched like a storybook retreat and affectionately known as “the treehouse,” this one-of-a-kind home rises from it’s owner-built frame, nestled atop a natural rock outcrop with sweeping views of the Taconic Range.Inside, the home unfolds with a sense of wonder. Sunlight dances beneath a dramatic 20-foot ceiling, softly illuminated from above, while a living rock outcrop emerges through the

    Lindsey Martin Maple Leaf Realty

    2603 N Pownal Rd, Pownal, VT 05261
  • /41

    $1,150,000 Sold Jul 25, 2025

    35 Old Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 5.5 Baths
    • 4,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • 38% Below List Price
    • $238/SF
    • 369 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /40

      Est $547,226 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

      • 6% Above List Price
      • $209/SF
      • 47 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /43

    $339,900

    • 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
  • /21

    $73,500 Sold Aug 04, 2025

    0 Sunset Dr Unit 5005504, Bennington, VT 05201

    • Land
    • 7 Acres
    • $10,500 per Acre

    Last Sold Summary

    • 26% Below List Price
    • 297 Days On Market

    Last Listing Agent Lilli West Maple Leaf Realty

    0 Sunset Dr Unit 5005504, Bennington, VT 05201
    • /40

      Est $879,946 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

      • 3% Above List Price
      • $276/SF
      • 104 Days On Market

      Last Sold Price $853,000

      Last Listing Agent Flex Realty Group Flex Realty

  • /3

    $275,000 Pending

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    11 Maltese Rd, Stamford, VT 05352

    Warm and comfortable light-filled three bedroom, one bath ranch home tucked away in Stamford Vermont. Very private location on 12 wooded acres with stream, makes it a lovely home and/or ideal get-away in excellent condition. A pellet stove in the living room allows for efficient supplemental heating and the Tesla power wall installed in basement offers 3 days of electrical power in the event of a

    Ann Greenwood Alton + Westall Real Estate Agency, LLC

    11 Maltese Rd, Stamford, VT 05352
  • /43

    $755,000 Sold Nov 14, 2025

    43 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 3,020 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $250/SF
    • 0 Days On Market

    Current Estimated Value $770,723

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /40

      Est $549,572 Not Listed For Sale

      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 2,396 Sq Ft
      • Built 1971
      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 3% Above List Price
      • $223/SF
      • 42 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Lilli West Maple Leaf Realty

  • /47

    $275,000

    • 5 Beds
    • 2 Baths
    • 2,952 Sq Ft

    569 Buck Hill Rd, Arlington, VT 05250

    Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home’s historic appeal. The spacious primary bedroom stretches 25 feet and offers two separate

    Lisa Friedman Great American Dream Realty

    569 Buck Hill Rd, Arlington, VT 05250
  • /24

    $190,000 Sold May 07, 2025

    105 County St, Bennington, VT 05201

    • 5 Beds
    • 3 Baths
    • 2,270 Sq Ft
    • Built 1910

    Last Sold Summary

    • $84/SF
    • 6 Days On Market

    Current Estimated Value $200,594

    Last Listing Agent Erica Hale Ridgeline Real Estate

    105 County St, Bennington, VT 05201
    • /40

      Est $562,344 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

      • 4% Above List Price
      • $196/SF
      • 88 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Lilli West Maple Leaf Realty

  • /3

    $79,900

    • Land
    • 10.1 Acres
    • $7,911 per Acre

    0 Old County Ln, Readsboro, VT 05350

    Escape to the tranquil countryside of Readsboro with this stunning 10.10-acre parcel offering exceptional privacy and natural beauty. The property showcases a picturesque mix of open level areas and gentle rolling hills, complemented by mature apple and cherry trees, thriving blueberry bushes, and a charming brook that winds its way through the land.Whether you envision a full-time residence,

    Raelene Robinson-Garrow Real Broker LLC

    0 Old County Ln, Readsboro, VT 05350
  • /37

    $895,000 Sold Jul 11, 2025

    505 Powderhorn Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2 Baths
    • 2,089 Sq Ft
    • Built 1976

    Last Sold Summary

    • $428/SF
    • 40 Days On Market

    Current Estimated Value $853,735

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

    505 Powderhorn Rd, Manchester Center, VT 05255
    • /40

      Est $252,539 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

      • 10% Above List Price
      • $229/SF
      • 18 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Lilli West Maple Leaf Realty

Showing Results 321 - 360, Page 9 of 18

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