21,114

Bennington County, VT Homes

Section Image
    • /52

      Est $415,246 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

      • 12% Above List Price
      • $242/SF
      • 6 Days On Market

      Last Sold Price $372,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /28

    $201,500 Sold Apr 03, 2025

    433 Squires Rd, Manchester Center, VT 05255

    • 2 Beds
    • 1 Bath
    • 1,142 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Above List Price
    • $176/SF
    • 9 Days On Market

    Current Estimated Value $224,494

    Last Listing Agent Linda Benoit Highland Realty

    433 Squires Rd, Manchester Center, VT 05255
    • /24

      Est $401,342 Not Listed For Sale

      318 Eleanors Way, North Bennington, VT 05257

      • 4 Beds
      • 3 Baths
      • 2,065 Sq Ft
      • Built 1968
      318 Eleanors Way, North Bennington, VT 05257

      Last Sold Summary

      • 6% Above List Price
      • $184/SF
      • 10 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /9

    $19,999

    • Land
    • 1.5 Acres
    • $13,333 per Acre

    0 Lebensdorf Ln, Readsboro, VT 05350

    Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

    David White OwnerEntry.com

    0 Lebensdorf Ln, Readsboro, VT 05350
  • /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 $390,705

    Last Listing Agent Catherine Cairns Maple Leaf Realty

    495 Fairview St, Bennington, VT 05201
    • /12

      Est $173,573 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

      • 45% Above List Price
      • $130/SF
      • 111 Days On Market

      Last Sold Price $120,000

      Last Listing Agent Kevin Holmes Blue Slate Realty

  • /6

    $74,900

    • Land
    • 5.3 Acres
    • $14,132 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 5-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

    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 $241,476

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    322 Burgess Rd, Bennington, VT 05201
    • /40

      Est $902,582 Not Listed For Sale

      16 Glastenbury Rd, Shaftsbury, VT 05262

      • 5 Beds
      • 3.5 Baths
      • 4,239 Sq Ft
      • Built 1800
      16 Glastenbury Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 1% Above List Price
      • $211/SF
      • 5 Days On Market

      Last Sold Price $895,000

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /50

    $4,500,000 Pending

    • 7 Beds
    • 10 Baths
    • 7,422 Sq Ft

    318 Spring Hill Ln, Dorset, VT 05251

    Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

    Richard Slocum Four Seasons Sotheby's Int'l Realty

    318 Spring Hill Ln, Dorset, VT 05251
  • /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 $507,981

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

    377 Glen Rd, Peru, VT 05152
    • /38

      Est $389,019 Not Listed For Sale

      726 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,588 Sq Ft
      • Built 1930
      726 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • $245/SF
      • 5 Days On Market

      Last Sold Price $389,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /45

    $1,075,000

    • 13 Beds
    • 12 Baths
    • 8,594 Sq Ft

    2759 Vt Route 11, Peru, VT 05152

    Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    2759 Vt Route 11, Peru, VT 05152
  • /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
    • /38

      Est $399,782 Not Listed For Sale

      1139 Old Depot Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1965
      1139 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 3% Above List Price
      • $205/SF
      • 76 Days On Market

      Last Sold Price $389,000

      Last Listing Agent Catherine Cairns Maple Leaf Realty

  • /6

    $35,000

    • Land
    • 1.7 Acres
    • $20,588 per Acre

    159 Oberdorf Rd, Readsboro, VT 05350

    Escape to the mountains with this ready-to-build 1.7-acre lot in scenic Alpenwald Village! Nestled beside National Forest land and bordered by a charming brook along the northern edge, this property offers a peaceful natural setting with endless outdoor adventure at your doorstep. Enjoy direct access to VAST snowmobile and VASA ATV trails, nearby hiking and mountain biking, and Dutch Hill for

    Lindsey Martin Maple Leaf Realty

    159 Oberdorf Rd, Readsboro, VT 05350
  • /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 $975,500 Not Listed For Sale

      498 Birch Hill Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 1997
      498 Birch Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • $371/SF
      • 12 Days On Market

      Last Sold Price $979,000

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /60

    $5,250,000

    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /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 $752,401

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /39

      Est $520,850 Not Listed For Sale

      127 Birch Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 3.5 Baths
      • 3,128 Sq Ft
      • Built 2000
      127 Birch Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 6% Above List Price
      • $157/SF
      • 65 Days On Market

      Last Sold Price $490,000

      Last Listing Agent David Citron RE/MAX

  • /11

    $780,000 Pending

    • Land
    • 663.95 Acres
    • $1,175 per Acre

    0 W Sandgate Rd, Sandgate, VT 05250

    This remarkable, partially conserved property is a true gem for conservation-minded buyers and outdoor enthusiasts alike. Encompassing two watersheds and a stretch of the pristine Green River, the land offers a rich tapestry of natural features and diverse terrain—ideal for exploring, observing wildlife, and enjoying every season to its fullest. The landscape ranges from gently rolling meadows to

    Andy Reed Four Seasons Sotheby's Int'l Realty

    0 W Sandgate Rd, Sandgate, 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 $195,616

    Last Listing Agent Erica Hale Ridgeline Real Estate

    105 County St, Bennington, VT 05201
    • /39

      Est $793,459 Not Listed For Sale

      192 Old Depot Rd, Shaftsbury, VT 05262

      • 4 Beds
      • 4 Baths
      • 3,206 Sq Ft
      • Built 1826
      192 Old Depot Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 11% Above List Price
      • $223/SF
      • 39 Days On Market

      Last Sold Price $715,000

      Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  • /23

    $119,900

    • 4 Beds
    • 2 Baths
    • 1,596 Sq Ft

    4697 Main Rd, Stamford, VT 05352

    Situated on a large 4+acre lot sits this adequately sized home!! 3-4 bedrooms with 1 3/4 bathrooms this home awaits your visions and ideas. With spacious rooms and a functional layout this home has many options. 1 car detached garage and vinyl siding are a plus!

    Dick Thackston R.H. Thackston & Company

    4697 Main Rd, Stamford, VT 05352
  • /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 $843,436

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

    505 Powderhorn Rd, Manchester Center, VT 05255
    • /32

      Est $338,771 Not Listed For Sale

      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft
      • Built 1986
      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

      Last Sold Summary

      • 6% Above List Price
      • $289/SF
      • 27 Days On Market

      Last Sold Price $319,000

      Last Listing Agent Abi Gregorio

  • /32

    $295,000

    • 1 Bed
    • 1.5 Baths
    • 1,680 Sq Ft

    318 North St, Bennington, VT 05201

    A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

    Jenifer Prouty Hoffman Hoffman Real Estate

    318 North St, Bennington, VT 05201
  • /37

    $256,250 Sold Sep 03, 2025

    1236 Morgan St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,259 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $204/SF
    • 7 Days On Market

    Current Estimated Value $251,802

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    1236 Morgan St, Bennington, VT 05201
    • /39

      Est $191,416 Not Listed For Sale

      1618 W Sandgate Rd, Arlington, VT 05250

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft
      • Built 1969
      1618 W Sandgate Rd, Arlington, VT 05250

      Last Sold Summary

      • 37% Above List Price
      • $80/SF
      • 64 Days On Market

      Last Sold Price $140,000

      Last Listing Agent Lisa Friedman Great American Dream Realty

  • /12

    $35,300 Pending

    • 2 Beds
    • 1 Bath
    • 1,302 Sq Ft

    933 East Rd, Bennington, VT 05201

    Built in 1965, this one level home offers approximately 1302 finished square feet, two bedrooms and one full bath, fireplace, unfinished basement and deck. This home sits on an approximate 44867 sqft lot. This property is in uninhabitable condition and boarded up. UNSAFE TO ENTER, foundation cracked, fallen and caved in.

    Sherry Price REALHome Services and Solutions, Inc.

    933 East Rd, Bennington, VT 05201
  • /35

    $220,000 Sold Sep 16, 2025

    115 Jefferson Ave, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 1930

    Last Sold Summary

    • 18% Below List Price
    • $142/SF
    • 83 Days On Market

    Current Estimated Value $221,961

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    115 Jefferson Ave, Bennington, VT 05201
    • /31

      Est $424,716 Not Listed For Sale

      1388 Pawlet Mountain Rd, Pawlet, VT 05761

      • 1 Bed
      • 1 Bath
      • 1,088 Sq Ft
      • Built 2004
      1388 Pawlet Mountain Rd, Pawlet, VT 05761

      Last Sold Summary

      • 9% Above List Price
      • $358/SF
      • 20 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Suanne Ohl Northland Real Estate

  • /40

    $114,900

    • 4 Beds
    • 1 Bath
    • 1,156 Sq Ft

    130 Lincoln St, Bennington, VT 05201

    Convenient location walking distance to downtown Bennington shops and amenities. Spacious eat-in kitchen, formal dining room, and adjoining porch flow perfectly for entertaining. The rustic living room has a beautiful wood ceiling and plenty of windows letting in copious amounts of natural light. The 198' deep backyard is perfect for tossing a ball and enjoying backyard barbeques. Two porches are

    Lisa Friedman Great American Dream Realty

    130 Lincoln St, Bennington, VT 05201
  • /59

    $1,082,500 Sold Aug 29, 2025

    4 Garden Loop Rd, Winhall, VT 05340

    • 3 Beds
    • 3.5 Baths
    • 4,054 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $267/SF
    • 45 Days On Market

    Current Estimated Value $1,110,307

    Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

    4 Garden Loop Rd, Winhall, VT 05340
    • /30

      Est $405,473 Not Listed For Sale

      513 Sykes Hollow Rd, Pawlet, VT 05761

      • 3 Beds
      • 1 Bath
      • 1,764 Sq Ft
      • Built 1930
      513 Sykes Hollow Rd, Pawlet, VT 05761

      Last Sold Summary

      • 20% Above List Price
      • $192/SF
      • 2 Days On Market

      Last Sold Price $338,500

      Last Listing Agent Donna Murray Varick Associates Ltd

  • /25

    $98,999 New Construction

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    78 Ethans Way, Bennington, VT 05201

    Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    78 Ethans Way, Bennington, VT 05201
  • /32

    $38,000 Sold Aug 11, 2025

    339 S Stream Rd, Pownal, VT 05261

    • 5 Beds
    • 2 Baths
    • 2,204 Sq Ft
    • Built 1890

    Last Sold Summary

    • 31% Below List Price
    • $17/SF
    • 115 Days On Market

    Current Estimated Value $44,916

    Last Listing Agent Lisa Friedman Great American Dream Realty

    339 S Stream Rd, Pownal, VT 05261
    • /33

      Est $199,853 Not Listed For Sale

      476 Tunnel St, Readsboro, VT 05350

      • 3 Beds
      • 1 Bath
      • 1,320 Sq Ft
      • Built 1880
      476 Tunnel St, Readsboro, VT 05350

      Last Sold Summary

      • 11% Above List Price
      • $136/SF
      • 20 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

Showing Results 321 - 360, Page 9 of 18

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