21,010

Bennington, VT Homes

Section Image
    • /12

      Est $372,718 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,123 Sq Ft

      140 Church St, Shaftsbury, VT 05262

      140 Church St, Shaftsbury, VT 05262
  • /17

    $485,000

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft

    1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

    Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

    Lori Hurley Four Corner Properties LLC

    1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
  • /29

    $363,825 Sold Jun 06, 2025

    • 1,215 Sq Ft
    • $299/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1968

    30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340

    Discover the ease of Mountain living with the complimentary Birch Hill Shuttle, providing seamless access to winter adventures. This bright and welcoming end-unit townhouse offers plenty of space for family and friends to gather and unwind. With two inviting living areas, three comfortable bedrooms, and two well-appointed bathrooms, there's room for everyone to relax. The spacious entryway is

    Christine Chovan

    30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340
    • /40

      Est $253,041 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft

      69 Meadow Ln, Shaftsbury, VT 05262

      69 Meadow Ln, Shaftsbury, VT 05262
  • /18

    $389,900

    • 4 Beds
    • 2.5 Baths
    • 2,229 Sq Ft

    2842 Vermont Route 7a, Shaftsbury, VT 05262

    Elegant Country Estate with Panoramic Mountain Views – Shaftsbury, VT.Welcome to 2842 VT-7A — an exceptional single-level luxury residence set on over 5 private, landscaped acres in the tranquil hills of Shaftsbury. This custom-designed ranch-style home blends timeless Vermont charm with modern comfort, offering 2,229± sq ft of refined interior space, thoughtfully crafted for both relaxed

    Derek Greene Derek Greene

    2842 Vermont Route 7a, Shaftsbury, VT 05262
  • /20

    $345,000 Sold Jun 06, 2025

    • 1,693 Sq Ft
    • $204/SF
    • 64 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    200 Carlen St, Manchester Center, VT 05255

    Situated on one of the few full one acre lots in this neighborhood, this Cape-style residence offers abundant potential at an appealing price point that is rare to find these days. The main-level bedroom & adjacent three-quarter bath provide flexibility for single-level living. A welcoming, vaulted informal side entry room leads to the recently updated kitchen, complete w/ refreshed flooring,

    Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

    200 Carlen St, Manchester Center, VT 05255
    • /16

      Est $222,852 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft

      102 Meadow Ln, Shaftsbury, VT 05262

      102 Meadow Ln, Shaftsbury, VT 05262
  • /44

    $499,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft

    144 Oberdorf Rd, Readsboro, VT 05350

    Charming 4-Bedroom Chalet on 2 Acres in Scenic Readsboro, VermontEscape to the beauty of southern Vermont. Whether you're looking for a full-time residence or the perfect vacation getaway, this beautifully updated home offers comfort, style, and proximity to all-season recreation.Step inside to discover thoughtful upgrades throughout, including fully renovated bathrooms and a

    Evan Russell Real Broker LLC

    144 Oberdorf Rd, Readsboro, VT 05350
  • /18

    $400,000 Sold Jun 06, 2025

    • 2,139 Sq Ft
    • $187/SF
    • 92 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1980

    94 Murray Hill Woods Rd Unit 61, Manchester, VT 05255

    Perched at the top of Murray Hill’s sought-after Woods section, this end-unit condo offers some of the best panoramic mountain views in the community. 3 bedrooms, 3 1/2 bathrooms. From the moment you step in, breathtaking mountain views unfold through new sliding glass doors leading to an expansive deck overlooking the association’s open common land. The covered entry features a convenient

    Christiane Carroccio TPW Real Estate

    94 Murray Hill Woods Rd Unit 61, Manchester, VT 05255
    • /24

      Est $286,887 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,588 Sq Ft

      855 Vt Route 7a, Shaftsbury, VT 05262

      855 Vt Route 7a, Shaftsbury, VT 05262
  • /16

    $324,000

    • Land
    • 10 Acres
    • $31,921 per Acre

    0 Foote Rd Unit 5053891, Dorset, VT 05251

    Discover the perfect blend of privacy, natural beauty, and convenience with this stunning 10.15-acre parcel located on peaceful Foote Road in Dorset, Vermont. Tucked away in a quiet and quaint setting, this exceptional property offers the ideal canvas for your dream home or getaway retreat.The land features a harmonious mix of cleared and wooded acreage, providing both open space for

    David Shehadi Josiah Allen Real Estate, Inc.

    0 Foote Rd Unit 5053891, Dorset, VT 05251
  • /38

    $215,000 Sold Jun 06, 2025

    • 1,271 Sq Ft
    • $169/SF
    • 81 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1880

    230 Beech St, Bennington, VT 05201

    Charming 1880s home with 3 bedrooms and 2 full baths. Highly desirable "one floor living" with the kitchen, dining, living room, primary suite and laundry all on the main level. Two bedrooms are upstairs, which has lower ceilings. Both bathrooms have tiled floors, pedestal sinks, and fiberglass tub/shower units. Kitchen has warm maple cabinets, soft green laminate countertops and tin-look

    Jenifer Prouty Hoffman Hoffman Real Estate

    230 Beech St, Bennington, VT 05201
    • /23

      Est $232,249 Not Listed For Sale

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

      256 Sycamore Ln, Shaftsbury, VT 05262

      256 Sycamore Ln, Shaftsbury, VT 05262
  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /41

    $426,000 Sold Jun 04, 2025

    • 2,294 Sq Ft
    • $186/SF
    • 52 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    4690 Route 153, Rupert, VT 05776

    This very special Vermont Contemporary is perched above the road on 10+ beautiful acres of gardens and park-like forest. The property is located on the east side of VT Rte 153 in Rupert, an unspoiled northwest corner of Bennington County. Start your day enjoying sunrise in the breakfast sunroom for morning coffee or tea, and enjoy the evening light on the west-facing screen porch listening to

    Kristin Comeau TPW Real Estate

    4690 Route 153, Rupert, VT 05776
    • /40

      Est $230,499 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,940 Sq Ft

      261 Cleveland Ave, Shaftsbury, VT 05262

      261 Cleveland Ave, Shaftsbury, VT 05262
  • /12

    $119,000

    • Land
    • 1.00 Acre
    • $119,000 per Acre

    318 Skyboro Rd, Pownal, VT 05261

    Come see this 1 acre secluded lot located just 10 minutes to Bennington or Williamstown. The site work has been done. There is a driveway with a lawn area plenty space for a garden. The drilled well, septic and underground power are already installed. Renovate the mobilome on the land or it could be removed and a new home built. 1 hour from Albany international airport, less than 4

    Dan Mason Perrott Realty

    318 Skyboro Rd, Pownal, VT 05261
  • /19

    $141,000 Sold Jun 03, 2025

    • 819 Sq Ft
    • $172/SF
    • 46 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1989

    432 South St Unit C7, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This clean and bright 2BR, 1.5-BA ground-level, end unit is ready to welcome you home. Tucked at the edge of this well-kept community, you’ll love the extra privacy, natural light, and comfortable layout. Just minutes from downtown Bennington’s shops, restaurants, and cultural spots—plus close access to local parks, healthcare, and everything else you

    Abi Gregorio

    432 South St Unit C7, Bennington, VT 05201
    • /17

      Est $272,862 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft

      591 Vt Route 67 E, Shaftsbury, VT 05262

      591 Vt Route 67 E, Shaftsbury, VT 05262
  • /53

    $399,000

    • 5 Beds
    • 3 Baths
    • 2,568 Sq Ft

    100 McCarthy Acres, North Bennington, VT 05257

    Almost lake front! Come for the space, stay for the location! This 2,500+ sq. ft. home offers five bedrooms, three full bathrooms, a large home office in the finished basement, and an additional 250 sq. ft. bonus room off one of the upstairs bedrooms. The owners converted the original garage into a 600 sq. ft. primary bedroom (heated and cooled with an efficient mini-split and separated into a

    Nicholas Charest Maple Leaf Realty

    100 McCarthy Acres, North Bennington, VT 05257
  • /42

    $325,000 Sold Jun 03, 2025

    • 3,230 Sq Ft
    • $101/SF
    • 52 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1900

    209 Washington Ave, Bennington, VT 05201

    Gracious Victorian Lady in need of a new forever owner. Built as a doctor’s home and clinic, now two completed upstairs apartments, ready for a third, with office space and handicapped access downstairs. Beautiful, mature maples and a shady lawn with room to build a stand-alone studio or accessory dwelling. On Washington Avenue, two blocks to downtown. Perfect for a counselor, physiotherapist,

    Wendy Larson Maple Leaf Realty

    209 Washington Ave, Bennington, VT 05201
    • /34

      Est $377,270 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,325 Sq Ft

      191 Grove Rd, Shaftsbury, VT 05262

      191 Grove Rd, Shaftsbury, VT 05262
  • /32

    $398,000

    • 3 Beds
    • 2 Baths
    • 1,337 Sq Ft

    78 Carbonti Cir, Arlington, VT 05250

    Easy single-level living! Welcome to Arlington's Carbonti Circle. Updated three-bedroom, two-bath ranch nestled in a quiet neighborhood setting just minutes from downtown Arlington and the famous Battenkill River. Set on a .30-acre lot, this home offers the perfect blend of comfort, character and convenience. Experience easy living in this beautifully maintained single-level home! Enjoy a

    Margretta Fischer Wohler Realty Group

    78 Carbonti Cir, Arlington, VT 05250
  • /18

    $949,900 Sold Jun 02, 2025

    • 1,736 Sq Ft
    • $547/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1954

    168 Meadow Ln, Dorset, VT 05251

    A true village gem !!! One level living.Totally renovated in 2020. Gutted to the studs. All new--wiring, plumbing, insulation, sheet rock, roofing, windows, kitchen and baths. Beautiful bright sun room. On over an acre of land.Walk to the theater, library, restaurants, general store.This is a must see. Extremely charming and turn key.All dimensions are approximate.

    Charles Mauro Josiah Allen Real Estate, Inc.

    168 Meadow Ln, Dorset, VT 05251
    • /39

      Est $266,542 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,146 Sq Ft

      192 Grove Rd, Shaftsbury, VT 05262

      192 Grove Rd, Shaftsbury, VT 05262
  • /41

    $365,000

    • 2 Beds
    • 2 Baths
    • 1,542 Sq Ft

    509 Thompson Pond Rd, Pownal, VT 05261

    Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

    Kelley Mccarthy Mahar McCarthy Real Estate

    509 Thompson Pond Rd, Pownal, VT 05261
  • /36

    $350,000 Sold Jun 02, 2025

    • 1,275 Sq Ft
    • $275/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    21 Birches Way, Peru, VT 05152

    The Birches is a condo complex in Bromley Village, offering ski in ski out access to the slopes This unit features 3 bedrooms, with the primary bedroom located on the upper level. The lower level includes two bedrooms and a full bath. The main level consists of a kitchen/dining area, along with a large living room featuring vaulted ceilings and a cozy wood-burning fireplace.Bromley Village is a

    Moira Spivey Four Seasons Sotheby's Int'l Realty

    21 Birches Way, Peru, VT 05152
    • /20

      Est $356,934 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,256 Sq Ft

      136 Grove Rd, Shaftsbury, VT 05262

      136 Grove Rd, Shaftsbury, VT 05262
  • /7

    $259,500

    • Land
    • 18 Acres
    • $14,744 per Acre

    188 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

    188 Cedar Ln, Peru, VT 05152
  • /43

    $1,500,000 Sold Jun 02, 2025

    • 3,990 Sq Ft
    • $376/SF
    • 397 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1810

    164 Landmark Ln, Manchester Center, VT 05255

    Surrounded by breathtaking mountain views, this historic property named “The Landmark” was originally built on Main Street in Manchester. To avoid demolition in 1964, The Landmark was moved by the Dyer family to other lands they owned off Barnumville Road. The current owners bought the property in 1970 and has been thoroughly enjoyed by the family of 7 children. Today this magnificent home, on 5

    Donna Murray Varick Associates Ltd

    164 Landmark Ln, Manchester Center, VT 05255
    • /36

      Est $372,554 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,330 Sq Ft

      374 North Rd, Shaftsbury, VT 05262

      374 North Rd, Shaftsbury, VT 05262
  • /18

    $155,000

    • 2 Beds
    • 1.5 Baths
    • 852 Sq Ft

    432 South St Unit C6, Bennington, VT 05201

    A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

    Angela Bevin Maple Leaf Realty

    432 South St Unit C6, Bennington, VT 05201
  • /38

    $193,800 Sold May 30, 2025

    • 1,008 Sq Ft
    • $192/SF
    • 31 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1915

    134 Imperial Ave, Bennington, VT 05201

    Perched high on Imperial Avenue, this delightful Cape-style home is brimming with character, charm, and endless potential. Gorgeous wood floors and abundant natural light set the tone for a warm, inviting space that’s ready for your personal touch. The main level offers a comfortable flow between the living room, dining area, and kitchen—all boasting sweeping views of downtown Bennington and the

    Angela Bevin Maple Leaf Realty

    134 Imperial Ave, Bennington, VT 05201
    • /2

      Est $509,093 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,529 Sq Ft

      126 Simeon Dean Rd, Shaftsbury, VT 05262

      126 Simeon Dean Rd, Shaftsbury, VT 05262
  • /21

    $249,000

    • Land
    • 3.42 Acres
    • $72,807 per Acre

    0 Havoc Hill, Dorset, VT 05253

    Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its rugged beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    0 Havoc Hill, Dorset, VT 05253
  • /33

    $875,000 Sold May 30, 2025

    • 4,046 Sq Ft
    • $216/SF
    • 15 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    401 South Hill, Manchester, VT 05255

    Nestled on 4.44 acres of breathtaking land, this exceptional contemporary home presents panoramic westerly views of Mount Equinox & majestic Taconic Mountain Range from nearly every room. With nearly 4,000 square feet of meticulously designed living space, this 3-bedroom home includes a spacious bonus room/office upstairs, a generously sized family room above the garage, & a fully finished

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    401 South Hill, Manchester, VT 05255
    • /27

      Est $276,258 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft

      338 Twitchell Hill Rd, Shaftsbury, VT 05262

      338 Twitchell Hill Rd, Shaftsbury, VT 05262
  • /37

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 3,252 Sq Ft

    115 Benson Fuller Dr, Jamaica, VT 05343

    Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

    Carrie Mathews Winhall Real Estate

    115 Benson Fuller Dr, Jamaica, VT 05343
  • /28

    $213,200 Sold May 30, 2025

    • 1,872 Sq Ft
    • $114/SF
    • 50 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1920

    1004 Main St, Bennington, VT 05201

    Triplex located downtown. Barney brook runs through the property, land includes yard across the brook from the property. Property is located in a flood zone. Flood map shows only one corner of the building in flood zone. There is no indication that the property has flooded in the past. Listing agent is related to the seller.

    Erica Hale Ridgeline Real Estate

    1004 Main St, Bennington, VT 05201
    • /39

      Est $605,527 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,418 Sq Ft

      553 Daniels Rd, Shaftsbury, VT 05262

      553 Daniels Rd, Shaftsbury, VT 05262

Showing Results 281 - 320, Page 8 of 18

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