21,299

Bennington County, VT Homes

Section Image
    • /30

      Est $460,127

      Not Listed For Sale

      414 Matteson Rd, North Bennington, VT 05257

      • 3 Beds
      • 2.5 Baths
      • 1,429 Sq Ft
      • Built 1981
      414 Matteson Rd, North Bennington, VT 05257

      Last Sold Summary

      • 4 Days On Market

  • /60

    $574,900

    $5K PRICE DROP
    • 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
  • /36

    $850,000

    Sold Dec 04, 2025

    109 Nichols Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 2.5 Baths
    • 1,946 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $437/SF
    • 30 Days On Market

    Current Estimated Value $856,847

    Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    109 Nichols Hill Ln, Dorset, VT 05251
    • /29

      Est $357,106

      Not Listed For Sale

      3 Polygraphic Ln, North Bennington, VT 05257

      • 4 Beds
      • 2 Baths
      • 2,247 Sq Ft
      • Built 1946
      3 Polygraphic Ln, North Bennington, VT 05257

      Last Sold Summary

      • 20 Days On Market

  • /27

    $645,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    4928 Main St Unit 2, Manchester Center, VT 05255

    Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

    David Halligan Four Seasons Sotheby's Int'l Realty

    4928 Main St Unit 2, Manchester Center, VT 05255
  • /40

    $1,000,000

    Sold Feb 24, 2026

    19 Roundtree Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 80 Days On Market

    Current Estimated Value $1,006,033

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /40

      Est $434,845

      Not Listed For Sale

      23 Church St, North Bennington, VT 05257

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1847
      23 Church St, North Bennington, VT 05257

      Last Sold Summary

      • 6 Days On Market

  • /15

    $389,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft

    319 Chester Knoll Dr, Bennington, VT 05201

    Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

    Lilli West Maple Leaf Real Estate

    319 Chester Knoll Dr, Bennington, VT 05201
  • /44

    $702,000

    Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $688,047

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /39

      Est $266,412

      Not Listed For Sale

      3 Church St, North Bennington, VT 05257

      • 3 Beds
      • 1.5 Baths
      • 1,238 Sq Ft
      • Built 1920
      3 Church St, North Bennington, VT 05257

      Last Sold Summary

      • 78 Days On Market

  • /60

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    57 Pearl Buck Dr, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr, Bondville, VT 05340
  • /20

    $500,000

    Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $495,313

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /34

      Est $324,857

      Not Listed For Sale

      6 Bank St, North Bennington, VT 05257

      • 6 Beds
      • 2 Baths
      • 2,986 Sq Ft
      • Built 1918
      6 Bank St, North Bennington, VT 05257

      Last Sold Summary

      • 61 Days On Market

  • /52

    $289,000

    • 3 Beds
    • 1.5 Baths
    • 1,411 Sq Ft

    262 Union St, Bennington, VT 05201

    Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

    William Paquin Maple Leaf Real Estate

    262 Union St, Bennington, VT 05201
  • /60

    $420,000

    Sold Jun 26, 2025

    123 Bank St, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 2,753 Sq Ft
    • Built 1952

    Last Sold Summary

    • 6% Below List Price
    • $153/SF
    • 31 Days On Market

    Current Estimated Value $423,989

    Last Listing Agent Margretta Fischer Wohler Realty Group

    123 Bank St, North Bennington, VT 05257
    • /60

      Est $875,037

      Not Listed For Sale

      551 Winter St, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,664 Sq Ft
      • Built 2003
      551 Winter St, Manchester Center, VT 05255

      Last Sold Summary

      • 53 Days On Market

  • /20

    $179,900

    $45K PRICE DROP 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
  • /59

    $3,200,000

    Sold Jun 08, 2026

    220 Camptown Rd, Manchester Center, VT 05255

    • 5 Beds
    • 4.5 Baths
    • 5,905 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $542/SF
    • 24 Days On Market

    Current Estimated Value $2,414,751

    Last Listing Agent Christiane Carroccio TPW Real Estate

    220 Camptown Rd, Manchester Center, VT 05255
    • /35

      Est $842,255

      Not Listed For Sale

      290 Mending Walls Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 2,424 Sq Ft
      • Built 2005
      290 Mending Walls Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

  • /32

    $265,000

    • 3 Beds
    • 1.5 Baths
    • 1,392 Sq Ft

    110 State Line Dr, Pownal, VT 05261

    Well-built and lovingly maintained through the years, this 3-bedroom, 2-bath ranch offers the ease of single-level living with both a deck and covered porch to take in the mountain views. An attached two-car garage, full basement, and storage shed provide plenty of room for hobbies, outdoor gear, and all the extras. Perched atop 1.4 acres on a gentle hill in Pownal, you'll enjoy a peaceful

    Abi Gregorio

    110 State Line Dr, Pownal, VT 05261
  • /57

    $275,000

    Sold Aug 07, 2025

    115-117 Norton St, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • Built 1930

    Last Sold Summary

    • $162/SF
    • 0 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    115-117 Norton St, Bennington, VT 05201
    • /28

      Est $790,437

      Not Listed For Sale

      182 Mending Walls Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4 Baths
      • 1,955 Sq Ft
      • Built 2002
      182 Mending Walls Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

  • /12

    $399,500

    $11K PRICE DROP
    • 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 adventure

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    2937 Dorset Rd W, Dorset, VT 05251
  • /40

    $615,000

    Sold Aug 07, 2025

    5529 Vt Route 7a, Shaftsbury, VT 05262

    • 3 Beds
    • 3 Baths
    • 3,173 Sq Ft
    • Built 1804

    Last Sold Summary

    • 2% Below List Price
    • $194/SF
    • 85 Days On Market

    Current Estimated Value $642,648

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

    5529 Vt Route 7a, Shaftsbury, VT 05262
    • /24

      Est $676,469

      Not Listed For Sale

      94 E Manchester Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,649 Sq Ft
      • Built 2002
      94 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 113 Days On Market

  • /49

    $2,200,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 4,265 Sq Ft

    7537 Main St, Manchester Center, VT 05255

    Perched to capture sweeping easterly views of Vermont’s mountains, this re-imagined Manchester home lives large. Completely renovated and redesigned in 2022, the pristine property blends timeless materials with modern comforts and efficiency. Danby marble, light oak flooring, high-end fixtures, and antique barn beams anchor the Great Room, while expansive windows fill the home with natural light

    Elena Atwill Four Seasons Sotheby's Int'l Realty

    7537 Main St, Manchester Center, VT 05255
  • /26

    $290,000

    Sold Mar 26, 2026

    235 Elm St Unit 3, Bennington, VT 05201

    • 6 Beds
    • 3 Baths
    • 2,640 Sq Ft
    • Built 1880

    Last Sold Summary

    • 2% Below List Price
    • $110/SF
    • 8 Days On Market

    Current Estimated Value $286,283

    Last Listing Agent Erica Hale Ridgeline Real Estate

    235 Elm St Unit 3, Bennington, VT 05201
    • /40

      Est $1,016,056

      Not Listed For Sale

      160 Hemlock Ridge Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3.5 Baths
      • 4,139 Sq Ft
      • Built 2002
      160 Hemlock Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

  • /23

    $252,500

    $7K PRICE DROP
    • Land
    • 17.6 Acres
    • $14,347 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
  • /18

    $286,000

    Sold Jun 12, 2026

    124 Albe Dr, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Above List Price
    • $259/SF
    • 3 Days On Market

    Current Estimated Value $271,451

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    124 Albe Dr, Bennington, VT 05201
    • /40

      Est $919,574

      Not Listed For Sale

      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4.5 Baths
      • 2,814 Sq Ft
      • Built 1998
      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 2 Days On Market

  • /24

    $215,000

    $20K 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 mortgage with

    Melissa Nebelski Real Broker LLC

    340 Pleasant St, Bennington, VT 05201
  • /59

    $720,000

    Sold Sep 12, 2025

    422 N Mason Hill Rd, Pownal, VT 05261

    • 4 Beds
    • 4 Baths
    • 4,844 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $149/SF
    • 5 Days On Market

    Current Estimated Value $727,250

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    422 N Mason Hill Rd, Pownal, VT 05261
    • /29

      Est $1,200,023

      Not Listed For Sale

      667 Canterbury Rd, Manchester Center, VT 05255

      • 5 Beds
      • 5 Baths
      • 4,016 Sq Ft
      • Built 1990
      667 Canterbury Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 42 Days On Market

  • /42

    $345,000

    • 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
  • /43

    $115,000

    Sold Aug 29, 2025

    0000 Skiparee Rd, Pownal, VT 05261

    • Land
    • 25.7 Acres
    • $4,475 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

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

    0000 Skiparee Rd, Pownal, VT 05261
    • /31

      Est $617,447

      Not Listed For Sale

      350 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,177 Sq Ft
      • Built 1988
      350 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 170 Days On Market

  • /27

    $290,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 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
  • /22

    $445,000

    Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $442,030

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

    163 Vt Route 30, Winhall, VT 05340
    • /40

      Est $712,833

      Not Listed For Sale

      190 Meadow Ridge Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,564 Sq Ft
      • Built 1985
      190 Meadow Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 59 Days On Market

Showing Results 521 - 560, Page 14 of 18

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