21,114

Bennington County, VT Homes

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  • /56

    $2,999,000 Under Contract

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft

    25 Mountain Haunts Rd, Winhall, VT 05340

    Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4 ensuite bedroom, 3 stone fireplaces, huge lodge room w/ large beams

    Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
  • /35

    $329,900 Sold Aug 28, 2025

    170 Brambley Ln, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,459 Sq Ft
    • Built 1969

    Last Sold Summary

    • $226/SF
    • 4 Days On Market

    Current Estimated Value $324,328

    Last Listing Agent Matt Waddington Hoffman Real Estate

    170 Brambley Ln, Bennington, VT 05201
    • /14

      Est $274,971 Not Listed For Sale

      169 Reservoir Rd, Shaftsbury, VT 05262

      • 1 Bed
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1965
      169 Reservoir Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 11% Above List Price
      • $245/SF
      • 15 Days On Market

      Last Sold Price $247,100

      Last Listing Agent Jacob Barnes EXP Realty

  • /11

    $2,425,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340
  • /42

    $325,000 Sold Jun 03, 2025

    209 Washington Ave, Bennington, VT 05201

    • 4 Beds
    • 4 Baths
    • 3,230 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $101/SF
    • 52 Days On Market

    Current Estimated Value $333,133

    Last Listing Agent Wendy Larson Hooscik Realty

    209 Washington Ave, Bennington, VT 05201
    • /29

      Est $327,747 Not Listed For Sale

      289 Reservoir Rd, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1996
      289 Reservoir Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 14% Above List Price
      • $214/SF
      • 11 Days On Market

      Last Sold Price $288,000

      Last Listing Agent Gabrielle Burdge Hoffman Real Estate

  • /38

    $1,095,000

    • 4 Beds
    • 3 Baths
    • 3,252 Sq Ft

    E1 Rock Ridge Rd, Winhall, VT 05155

    Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

    Christine Chovan

    E1 Rock Ridge Rd, Winhall, VT 05155
  • /60

    $2,100,000 Sold May 02, 2025

    18 Rocky Dell Rd, Winhall, VT 05340

    • 7 Beds
    • 5.5 Baths
    • 6,195 Sq Ft
    • Built 2007

    Last Sold Summary

    • 14% Below List Price
    • $339/SF
    • 246 Days On Market

    Current Estimated Value $2,686,041

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    18 Rocky Dell Rd, Winhall, VT 05340
    • /40

      Est $667,014 Not Listed For Sale

      1004 Holy Smoke Rd, Shaftsbury, VT 05262

      • 2 Beds
      • 2 Baths
      • 1,982 Sq Ft
      • Built 2006
      1004 Holy Smoke Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 5% Above List Price
      • $320/SF
      • 736 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Nikki Lother Maple Leaf Realty

  • /12

    $410,000 Pending

    • 3 Beds
    • 1 Bath
    • 2,040 Sq Ft

    2511 Vermont 30, Dorset, VT 05251

    Tucked just south of Dorset Village, this inviting home offers the best of Vermont living with easy access to town, scenic trails, golf, and beloved local restaurants. Warm and welcoming, the house features charming moldings, hardwood floors, and a bright, comfortable layout that feels instantly like home. Curl up in the spacious living room by the marble, wood-burning fireplace, or gather in the

    Andy Reed Four Seasons Sotheby's Int'l Realty

    2511 Vermont 30, Dorset, VT 05251
  • /47

    $365,000 Sold Sep 11, 2025

    84 Jasper Ln, Arlington, VT 05250

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $190/SF
    • 69 Days On Market

    Current Estimated Value $352,008

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

    84 Jasper Ln, Arlington, VT 05250
    • /18

      Est $231,722 Not Listed For Sale

      43 Buck Hill Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 1 Bath
      • 1,361 Sq Ft
      • Built 1903
      43 Buck Hill Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 22% Above List Price
      • $140/SF
      • 279 Days On Market

      Last Sold Price $190,000

      Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  • /38

    $1,995,000

    • 5 Beds
    • 3 Baths
    • 6,323 Sq Ft

    2589 W Sandgate Rd, Arlington, VT 05250

    Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

    Dia Jenks LandVest, Inc/Woodstock

    2589 W Sandgate Rd, Arlington, VT 05250
  • /37

    $950,000 Sold Nov 20, 2025

    1589 Richville Rd, Manchester Center, VT 05255

    • 5 Beds
    • 4.5 Baths
    • 3,697 Sq Ft
    • Built 1850

    Last Sold Summary

    • 14% Below List Price
    • $257/SF
    • 91 Days On Market

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

    1589 Richville Rd, Manchester Center, VT 05255
    • /12

      Est $329,041 Not Listed For Sale

      140 Church St, Shaftsbury, VT 05262

      • 3 Beds
      • 1.5 Baths
      • 2,123 Sq Ft
      • Built 1870
      140 Church St, Shaftsbury, VT 05262

      Last Sold Summary

      • 10% Above List Price
      • $141/SF
      • 7 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /2

    $125,000

    • Land
    • 1.45 Acres
    • $86,207 per Acre

    L/O River Rd, Winhall, VT 05340

    This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

    Cheyanne Pugliese

    L/O River Rd, Winhall, VT 05340
  • /21

    $465,000 Sold Sep 12, 2025

    4195 Route 30, Dorset, VT 05251

    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft
    • Built 1757

    Last Sold Summary

    • 2% Above List Price
    • $316/SF
    • 2 Days On Market

    Current Estimated Value $462,152

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

    4195 Route 30, Dorset, VT 05251
    • /60

      Est $306,497 Not Listed For Sale

      450 Cleveland Ave, Shaftsbury, VT 05262

      • 4 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1920
      450 Cleveland Ave, Shaftsbury, VT 05262

      Last Sold Summary

      • 6% Above List Price
      • $154/SF
      • 31 Days On Market

      Last Sold Price $289,000

      Last Listing Agent Floyd Amidon Maple Leaf Realty

  • /3

    $69,900

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft

    32 French Hill Rd, Pownal, VT 05261

    Subject property currently has two buildings on the property. One is a cape style home the other is a shed. Property has just under an acre of land with power, and town sewer at the street. Do not entry property without your buyer's agent with you.

    April Shepard Twin State Realty LLC

    32 French Hill Rd, Pownal, VT 05261
  • /54

    $225,000 Sold Sep 10, 2025

    304 North St Unit 6, Bennington, VT 05201

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Above List Price
    • $104/SF
    • 15 Days On Market

    Current Estimated Value $229,331

    Last Listing Agent Thomas Martins Maple Leaf Realty

    304 North St Unit 6, Bennington, VT 05201
    • /16

      Est $237,979 Not Listed For Sale

      102 Meadow Ln, Shaftsbury, VT 05262

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1974
      102 Meadow Ln, Shaftsbury, VT 05262

      Last Sold Summary

      • 3% Below List Price
      • $320/SF
      • 0 Days On Market

      Last Sold Price $246,000

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

  • /13

    $55,000 Pending

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

    1488 Morgan St, Bennington, VT 05201

    Priced to sell and ready for you to bring your imagination!!! Ranch style home with 2 car detached garage and a level 1.03 acre lot. Needs updating and repairs, but at this price, worth the efforts!!!

    Dick Thackston R.H. Thackston & Company

    1488 Morgan St, Bennington, VT 05201
  • /19

    $426,000 Sold Jan 16, 2026

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340

    • 2 Beds
    • 2 Baths
    • 1,798 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $237/SF
    • 1 Day On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340
    • /24

      Est $285,459 Not Listed For Sale

      855 Vt Route 7a, Shaftsbury, VT 05262

      • 3 Beds
      • 2 Baths
      • 2,188 Sq Ft
      • Built 1805
      855 Vt Route 7a, Shaftsbury, VT 05262

      Last Sold Summary

      • 24% Above List Price
      • $105/SF
      • 239 Days On Market

      Last Sold Price $230,500

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

  • /8

    $9,999 Pending

    • Land
    • 1.2 Acres
    • $8,332 per Acre

    0 Alpendorf Ave, Readsboro, VT 05350

    Stake a claim on your own little piece of Vermont, at the foot of the Green Mountain National Forest. This 1.2-acre triangular lot rises up from the road and may allow peekaboo views of the surrounding valley starting in late-fall, once the region's famous foliage drops away. It's located in Alpenwald Village, with community-maintained roads rolling up and down the area's hilly topography. Today

    David White OwnerEntry.com

    0 Alpendorf Ave, Readsboro, VT 05350
  • /18

    $949,900 Sold Jun 02, 2025

    168 Meadow Ln, Dorset, VT 05251

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1954

    Last Sold Summary

    • $547/SF
    • 6 Days On Market

    Current Estimated Value $907,344

    Last Listing Agent Charles Mauro Josiah Allen Real Estate, Inc.

    168 Meadow Ln, Dorset, VT 05251
    • /17

      Est $249,918 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

      • 4% 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

  • /28

    $390,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,222 Sq Ft

    2023 North Rd, Arlington, VT 05250

    Rare opportunity to own a fully renovated home plus a subdivided, buildable lot with Mount Equinox views. 2023 North Rd offers turnkey living with exceptional future potential, just minutes to Manchester, Stratton, and Bromley. The main home was extensively renovated in Fall of 2025, inside & out. Exterior upgrades include new vinyl siding & trim, all new windows, upgraded insulation, a freshly

    Mandolyn McIntyre Crow Real Broker LLC

    2023 North Rd, Arlington, VT 05250
  • /39

    $255,500 Sold Jan 15, 2026

    77 Mcguire St, North Bennington, VT 05257

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $253/SF
    • 15 Days On Market

    Current Estimated Value $264,609

    Last Listing Agent Angela Bevin Maple Leaf Realty

    77 Mcguire St, North Bennington, VT 05257
    • /34

      Est $380,114 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% Above 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

  • /22

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340

    Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • /3

    $110,000 Sold Nov 17, 2025

    0 Maple Hill Rd, Shaftsbury, VT 05262

    • Land
    • 11.5 Acres
    • $9,565 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Lilli West Maple Leaf Realty

    0 Maple Hill Rd, Shaftsbury, VT 05262
    • /39

      Est $244,533 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

      • 14% Above List Price
      • $188/SF
      • 8 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /55

    $10,300,000 New Construction

    • 6 Beds
    • 9 Baths
    • 10,993 Sq Ft

    551 West Fields, Manchester, VT 05254

    Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

    Sunny Breen Josiah Allen Real Estate, Inc.

    551 West Fields, Manchester, VT 05254
  • /19

    $199,900 Sold Sep 19, 2025

    42 Colvin Ave, Shaftsbury, VT 05262

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft
    • Built 1964

    Last Sold Summary

    • $210/SF
    • 28 Days On Market

    Current Estimated Value $194,626

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    42 Colvin Ave, Shaftsbury, VT 05262
    • /20

      Est $403,492 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

      • 8% Above 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

  • /15

    $96,906 New Construction

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    10 Cassie Ln, Bennington, VT 05201

    Welcome to 10 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) 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

    Kate Barry EXP Realty

    10 Cassie Ln, Bennington, VT 05201
  • /45

    $750,500 Sold May 20, 2025

    688 Rice Ln, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 2,576 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Above List Price
    • $291/SF
    • 27 Days On Market

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    688 Rice Ln, Bennington, VT 05201
    • /27

      Est $259,222 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

      • 14% Below List Price
      • $227/SF
      • 100 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Faith Rhodes Maple Leaf Realty

  • /8

    $1,900,000

    • Land
    • 199 Acres
    • $9,548 per Acre

    00 Vermont 11, Peru, VT 05152

    199 +/- acre parcel in Peru Vermont bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains. The scale of the land, elevation and orientation provide exceptional privacy, consistent natural light and expansive long range mountain vistas. The property offers a rare combination of direct forest access and proximity to

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152

Showing Results 241 - 280, Page 7 of 18

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