20,611

Bennington County, VT Homes

Section Image
  • /16

    $130,000

    Sold Jan 28, 2026

    755 Main St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft
    • Built 1890

    Last Sold Summary

    • 10% Below List Price
    • $88/SF
    • 141 Days On Market

    Current Estimated Value $148,509

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

    755 Main St, Bennington, VT 05201
    • /40

      Est $820,443

      Not Listed For Sale

      718 Montgomery Rd, Pownal, VT 05261

      • 5 Beds
      • 4 Baths
      • 3,879 Sq Ft
      • Built 1800
      718 Montgomery Rd, Pownal, VT 05261

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  • /26

    $165,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    128 Burgess Rd, Bennington, VT 05201

    Affordable homeownership awaits at 128 Burgess Road in Bennington! This compact 2-bedroom, 1-bath home offers approximately 840 square feet of living space with a practical layout and low utility costs. Several recent exterior improvements include brand-new siding, new rear entry stairs and a new electrical meter board in Spring 2026. The home also features vinyl replacement windows, including

    Emily Heyer Hoffman Real Estate

    128 Burgess Rd, Bennington, VT 05201
  • /11

    $780,000

    Sold Mar 23, 2026

    0 W Sandgate Rd, Sandgate, VT 05250

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

    Last Sold Summary

    • 110 Days On Market

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

    0 W Sandgate Rd, Sandgate, VT 05250
    • /19

      Est $244,218

      Not Listed For Sale

      169 Montgomery Rd, Pownal, VT 05261

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1970
      169 Montgomery Rd, Pownal, VT 05261

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Corey Bishop BISHOP WEST REAL ESTATE

  • /4

    $20,000

    $30K PRICE DROP Under Contract
    • Land
    • 43,124 Sq Ft
    • $20,202 per Acre

    0 Route 30 Unit 5099207, Winhall, VT 05340

    Wooded one acre parcel off Rt 30 in Winhall, just past the west entrance to French Hollow Rd. and by Green Mountain National Forest and VTRT 30. This is a sloping /wooded parcel that extends down to the Mill Brook. There seems to be a nice plateau/bench as a possible build site........All Buyers should/must do their Own due diligence.

    Mike England Michael England Real Estate

    0 Route 30 Unit 5099207, Winhall, VT 05340
  • /23

    $110,000

    Sold Mar 26, 2026

    4697 Main Rd, Stamford, VT 05352

    • 4 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1940

    Last Sold Summary

    • 35% Below List Price
    • $69/SF
    • 161 Days On Market

    Current Estimated Value $261,942

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

    4697 Main Rd, Stamford, VT 05352
    • /59

      Est $249,970

      Not Listed For Sale

      663 Sweet Rd, Pownal, VT 05261

      • 2 Beds
      • 2 Baths
      • 3,024 Sq Ft
      • Built 2010
      663 Sweet Rd, Pownal, VT 05261

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • /35

    $349,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft

    57 Paran Rd, Shaftsbury, VT 05262

    Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage.The spacious living room features wide

    Kelley Mccarthy Mahar McCarthy Real Estate

    57 Paran Rd, Shaftsbury, VT 05262
  • /40

    $125,000

    Sold May 01, 2026

    130 Lincoln St, Bennington, VT 05201

    • 4 Beds
    • 1 Bath
    • 1,156 Sq Ft
    • Built 1920

    Last Sold Summary

    • 9% Above List Price
    • $108/SF
    • 39 Days On Market

    Current Estimated Value $133,228

    Last Listing Agent Lisa Friedman Great American Dream Realty

    130 Lincoln St, Bennington, VT 05201
    • /52

      Est $269,297

      Not Listed For Sale

      351 Old Military Rd, Pownal, VT 05261

      • 4 Beds
      • 1 Bath
      • 1,378 Sq Ft
      • Built 1969
      351 Old Military Rd, Pownal, VT 05261

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • /24

    $179,000

    $56K PRICE DROP
    • 1,300 Sq Ft

    340 Pleasant St, Bennington, VT 05201

    Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout.Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your

    Melissa Nebelski Real Broker LLC

    340 Pleasant St, Bennington, VT 05201
  • /25

    $98,999

    Sold Jul 27, 2026

    78 Ethans Way, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft
    • Built 2024

    Last Sold Summary

    • $120/SF
    • 119 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    78 Ethans Way, Bennington, VT 05201
    • /40

      Est $358,434

      Not Listed For Sale

      505 Cross Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 2003
      505 Cross Rd, Bennington, VT 05201

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /42

    $325,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 1 Bath
    • 1,768 Sq Ft

    2154 U S 7, Pownal, VT 05261

    Charming antique Cape full of character and opportunity. This 3-bedroom, 1-bath home offers timeless New England charm with warm, inviting living spaces and a flexible layout ready for your personal touch. A first-floor bedroom and first-floor laundry provide the convenience of single-level living, while additional bedrooms upstairs offer flexibility for guests or office space. Original details

    Angela Bevin Maple Leaf Real Estate

    2154 U S 7, Pownal, VT 05261
  • /8

    $71,200

    Sold Oct 09, 2025

    272 Twenty Acre Wood Rd, Arlington, VT 05250

    • Land
    • 7.12 Acres
    • $10,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 58 Days On Market

    Current Estimated Value $71,673

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

    272 Twenty Acre Wood Rd, Arlington, VT 05250
    • /34

      Est $334,749

      Not Listed For Sale

      224 Burrington Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 1,658 Sq Ft
      • Built 1915
      224 Burrington Rd, Pownal, VT 05261

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /27

    $269,900

    $50K PRICE DROP
    • 2,190 Sq Ft

    196 Granger Hollow Rd, North Bennington, VT 05257

    Currently being used as a primary home a vacant 2nd home, this property could be either a single family residence with/without an in-law house or as 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

    Steve Schoppmeyer BHG Masiello Brattleboro

    196 Granger Hollow Rd, North Bennington, VT 05257
  • /20

    $90,000

    Sold Sep 18, 2026

    1178 Oberdorf Rd Unit 189/90, Readsboro, VT 05350

    • 3 Beds
    • 2 Baths
    • 1,109 Sq Ft
    • Built 1968

    Last Sold Summary

    • 36% Below List Price
    • $81/SF
    • 4 Days On Market

    Last Listing Agent Melissa Nebelski Real Broker LLC

    1178 Oberdorf Rd Unit 189/90, Readsboro, VT 05350
    • /40

      Est $595,636

      Not Listed For Sale

      260 Tower Rd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 3,976 Sq Ft
      • Built 1981
      260 Tower Rd, Bennington, VT 05201

      Last Sold Summary

      • 115 Days On Market

      Last Listing Agent Allison Pacelli Pacelli Zepka Corporation

  • /24

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,035 Sq Ft

    84 Overlook Rd, East Dorset, VT 05253

    Commanding panoramic mountain views define this exceptional Dorset Overlook residence, where every room is designed to capture the beauty of Southern Vermont's ever-changing landscape. Bathed in natural light, the home's open floor plan creates an effortless flow between living, dining, and entertaining spaces, making everyday living as enjoyable as hosting family and friends.The thoughtfully

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

    84 Overlook Rd, East Dorset, VT 05253
  • /8

    $50,000

    Sold Apr 15, 2026

    0 Stratton View Rd Unit 26, Winhall, VT 05340

    • Land
    • 1.02 Acres
    • $49,020 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 218 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    0 Stratton View Rd Unit 26, Winhall, VT 05340
    • /24

      Est $165,029

      Not Listed For Sale

      354 NW Hill Rd, Pownal, VT 05261

      • 1 Bed
      • 816 Sq Ft
      • Built 1900
      354 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Nicholas Charest Maple Leaf Real Estate

  • /14

    $2,395,000

    $105K PRICE DROP
    • Land
    • 227 Acres
    • $10,551 per Acre

    00 Vermont 11, Peru, VT 05152

    Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living.Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /6

    $9,000

    Sold Oct 03, 2025

    lot 305 Lebenschauung Cir, Stamford, VT 05352

    • Land
    • 1 Acre
    • $9,000 per Acre

    Last Sold Summary

    • 38% Below List Price
    • 76 Days On Market

    Last Listing Agent Christine Girard Lamacchia Realty, Inc. - North Adams

    lot 305 Lebenschauung Cir, Stamford, VT 05352
    • /27

      Est $322,357

      Not Listed For Sale

      46 NW Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,128 Sq Ft
      • Built 1900
      46 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 193 Days On Market

      Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  • /50

    $279,500

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft

    257 Watrous Rd, Rupert, VT 05768

    Charming Vermont Chalet on 3 Pastoral Acres Backing Up to Merck Forest!Embrace the ultimate Vermont lifestyle with this versatile 1970s chalet on +/-3 pristine acres of open pasture and woods. Located on a quiet country road bordering the 3,000+ acre Merck Forest & Farmland Center, this property offers incredible privacy and direct outdoor access. Perfectly suited as a year-round home,

    Scott McChesney McChesney RE, Inc.

    257 Watrous Rd, Rupert, VT 05768
  • /37

    $500,000

    Sold Jun 30, 2026

    4 Stonehedge Dr, Bennington, VT 05201

    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $157/SF
    • 20 Days On Market

    Current Estimated Value $508,997

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    4 Stonehedge Dr, Bennington, VT 05201
    • /40

      Est $445,061

      Not Listed For Sale

      42 Maple Grove Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 2,163 Sq Ft
      • Built 1960
      42 Maple Grove Rd, Bennington, VT 05201

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  • /40

    $434,500

    $45K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,861 Sq Ft

    120 Village St, East Dorset, VT 05253

    Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. . An addition followed in 1900, and thoughtful improvements over the years have created a gracious Colonial farmhouse with approximately 3,861 square feet of living space, an oversized two-car garage, and 1.1 acres. The expansive floor plan offers a primary suite with an oversized

    Dana Kingsley Josiah Allen Real Estate, Inc.

    120 Village St, East Dorset, VT 05253
  • /25

    $585,000

    Sold Sep 04, 2026

    35 Valley Pass St, Manchester, VT 05255

    • 4 Beds
    • 3 Baths
    • 1,768 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $331/SF
    • 51 Days On Market

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

    35 Valley Pass St, Manchester, VT 05255
    • /24

      Est $379,423

      Not Listed For Sale

      78 Middle Pownal Rd, Pownal, VT 05261

      • 3 Beds
      • 1.5 Baths
      • 1,624 Sq Ft
      • Built 1922
      78 Middle Pownal Rd, Pownal, VT 05261

      Last Sold Summary

      • 50 Days On Market

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

  • /39

    $350,000

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,256 Sq Ft

    261 Skyboro, Pownal, VT 05261

    Move-in ready Ranch offering comfortable one-level living in a peaceful setting with mountain views. Set on 1.89 acres and conveniently located for commuting to both Bennington and Williamstown, MA. This 3-bedroom, 1.5-bath home has been lovingly improved over the past five years. The owner has invested significant time and care into making the home warm, functional and easy to enjoy. Updates

    Emily Heyer Hoffman Real Estate

    261 Skyboro, Pownal, VT 05261
  • /30

    $361,500

    Sold Oct 27, 2025

    64 Bergblume Cir, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,162 Sq Ft
    • Built 2007

    Last Sold Summary

    • 10% Below List Price
    • $167/SF
    • 49 Days On Market

    Last Listing Agent Pam Tworig BISHOP WEST REAL ESTATE

    64 Bergblume Cir, Stamford, VT 05352
    • /36

      Not Listed For Sale

      1211 Carpenter Hill Rd, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 1930
      1211 Carpenter Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Peter West BISHOP WEST REAL ESTATE

  • /18

    $79,000

    $30K PRICE DROP
    • Land
    • 17 Acres
    • $4,647 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Significant price reduction! This gently sloping 17acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's throw

    Michelle O'Neil Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /58

    $975,000

    Sold Nov 27, 2025

    20 Jamie Ln, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 1987

    Last Sold Summary

    • $279/SF
    • 38 Days On Market

    Current Estimated Value $994,221

    Last Listing Agent David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
    • /31

      Est $535,605

      Not Listed For Sale

      695 Barber Pond Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1854
      695 Barber Pond Rd, Pownal, VT 05261

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Sandy Reavill

  • /13

    $1,295,000

    • Land
    • 52 Acres
    • $24,904 per Acre

    0 Montgomery Rd, Pownal, VT 05261

    A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 Montgomery Rd, Pownal, VT 05261
  • /44

    $365,000

    Sold Feb 19, 2026

    2842 Vt Route 7a, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 2,661 Sq Ft
    • Built 1969

    Last Sold Summary

    • 8% Below List Price
    • $137/SF
    • 79 Days On Market

    Current Estimated Value $387,624

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    2842 Vt Route 7a, Shaftsbury, VT 05262

Showing Results 481 - 520, Page 13 of 18

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