21,045

Bennington County, VT Homes

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  • /8

    $71,200 Sold Oct 09, 2025

    • Land
    • 7.12 Acres
    • $10,000 per Acre
    • 58 Days On Market

    272 Twenty Acre Wood Rd, Arlington, VT 05250

    Enjoy views all around on this ready to build on lot of over 7 acres. The views are 180 degrees , but you don't have to drive up a steep hill to get to them. Land has been surveyed house site cleared and septic permit in place.

    Andy Reed Four Seasons Sotheby's Int'l Realty

    272 Twenty Acre Wood Rd, Arlington, VT 05250
    • /12

      Est $207,023 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 920 Sq Ft

      816 Shaftsbury Hollow Rd, North Bennington, VT 05257

      816 Shaftsbury Hollow Rd, North Bennington, VT 05257
  • /45

    $1,195,000

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

    9 Lower Taylor Hill Rd, Winhall, VT 05340

    Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

    Timothy Mich Doddridge Stratton Real Estate

    9 Lower Taylor Hill Rd, Winhall, VT 05340
  • /48

    $550,000 Sold Oct 09, 2025

    • 2,524 Sq Ft
    • $218/SF
    • 31 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2006

    441 Woodcock Rd, Arlington, VT 05250

    First time on the market! This unique Earth-Sheltered home in quiet Sandgate, VT (pop. ~500) offers sustainable living on 10 private acres with apple & pear trees, a small greenhouse, and garden space. Built into the landscape for natural insulation, it provides year-round comfort and exceptional energy efficiency - can be heated with less than 6 cords of wood/year. The main level features 9'

    Faith Rhodes Maple Leaf Realty

    441 Woodcock Rd, Arlington, VT 05250
    • /40

      Est $901,273 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,239 Sq Ft

      16 Glastenbury Rd, Shaftsbury, VT 05262

      16 Glastenbury Rd, Shaftsbury, VT 05262
  • /58

    $294,500

    • 3 Beds
    • 1.5 Baths
    • 1,934 Sq Ft

    508 Barney Rd, Bennington, VT 05201

    WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.

    Dan Mason Perrott Realty

    508 Barney Rd, Bennington, VT 05201
  • /37

    $775,000 Sold Oct 09, 2025

    • 3,609 Sq Ft
    • $215/SF
    • 68 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1843

    3357 Main St, Manchester, VT 05254

    Situated along one of Manchester Village’s most iconic, tree-lined streets, this impeccably restored mid-19th century Colonial blends timeless charm with modern comfort. Surrounded by marble sidewalks and classic lantern lighting, this exceptional property offers the rare opportunity to live in a storybook setting with walkability to dining, shopping, hiking, and year-round recreational

    Annette Gallo Real Broker LLC

    3357 Main St, Manchester, VT 05254
    • /38

      Est $378,423 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,588 Sq Ft

      726 Old Depot Rd, Shaftsbury, VT 05262

      726 Old Depot Rd, Shaftsbury, VT 05262
  • /56

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 3,059 Sq Ft

    466 3 Maple Dr, Manchester, VT 05254

    Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views.This home features three spacious bedroom

    David Shehadi Josiah Allen Real Estate, Inc.

    466 3 Maple Dr, Manchester, VT 05254
  • /39

    $550,000 Sold Oct 09, 2025

    • 1,982 Sq Ft
    • $277/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1920

    556 Mann Hill Rd S, Pownal, VT 05261

    76 Acres of Southern Vermont Living - The simple two-story Vermont farmhouse with its two original barns enjoys views, privacy, serenity, and all the outdoor space one could need to enjoy farming on a small scale or to allow the adjacent farmer to continue haying the large fields. There majority of the land is wooded and offers all sorts of options from leaving nature alone, to trails, to

    Paul Harsch HARSCH ASSOCIATES

    556 Mann Hill Rd S, Pownal, VT 05261
    • /38

      Est $394,682 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft

      1139 Old Depot Rd, Shaftsbury, VT 05262

      1139 Old Depot Rd, Shaftsbury, VT 05262
  • /45

    $450,000

    • 4 Beds
    • 3 Baths
    • 2,030 Sq Ft

    848 Coleville Rd, Bennington, VT 05201

    The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways,

    Beatrice O'Connell Maple Leaf Realty

    848 Coleville Rd, Bennington, VT 05201
  • /23

    $125,000 Sold Oct 07, 2025

    • 2,206 Sq Ft
    • $57/SF
    • 6 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1976

    5089 Vt Route 7a, Arlington, VT 05250

    Great use of space upstairs 3 bedrooms, 2 bathrooms, center island kitchen and living/dining with 2 sliding glass doors access the back deck. Spacious guest quarters with private entry on ground level with kitchen and living room. Wood stove or pellet stove hook up 2 bedrooms and full bath. Oversized 2 car garage with a work bench and great storage. Commercially zoned. Enjoy views of the

    Susan Bellville Bellville Realty

    5089 Vt Route 7a, Arlington, VT 05250
    • /40

      Est $960,000 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft

      498 Birch Hill Rd, Shaftsbury, VT 05262

      498 Birch Hill Rd, Shaftsbury, VT 05262
  • /33

    $815,000

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft

    158 Upland Downs Rd, Manchester Center, VT 05255

    This well-maintained home is nestled on an open, sunny lot with mountain views, offering a serene and picturesque setting. The property is in move-in condition and boasts one of Manchester's best locations, providing convenient access to the town, schools, and shops, all just minutes away. It is set back from the road, surrounded by beautifully landscaped lawn, gardens, and a spacious

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    158 Upland Downs Rd, Manchester Center, VT 05255
  • /4

    $45,000 Sold Oct 06, 2025

    • 1,142 Sq Ft
    • $39/SF
    • 7 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1948

    45 Shady Ln, Bennington, VT 05201

    This property presents a rare opportunity for the right buyer to restore or redevelop a home on a quiet lot at the end of a dead-end street. Tucked away in a peaceful setting with a small stream nearby, the lot offers a sense of privacy while still being within town limits. The structure needs a new roof and there is active water damage and mold. Power and water have been turned off. The house

    Erika Floriani Hoffman Real Estate

    45 Shady Ln, Bennington, VT 05201
    • /39

      Est $502,941 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,128 Sq Ft

      127 Birch Hill Rd, Shaftsbury, VT 05262

      127 Birch Hill Rd, Shaftsbury, VT 05262
  • /40

    $875,000

    • 6 Beds
    • 5 Baths
    • 5,689 Sq Ft

    2677 Route 30, Dorset, VT 05251

    Dorset Historic six-bedroom farmhouse with an apartment above a garage on 1.79 acres with view. This charming home blends Vermont rustic appeal with modern family living.Upon entering, you'll find a brightly lit mudroom with wide board flooring, built-in shelving, and ample space for all seasons. This leads into a large breakfast room that adjoins the kitchen and family rooms. The first

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    2677 Route 30, Dorset, VT 05251
  • /34

    $399,900 Sold Oct 06, 2025

    • 1,700 Sq Ft
    • $235/SF
    • 8 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1996

    43 Spur Rd, Bennington, VT 05201

    Private and gorgeous home situated on 3.54 acres in Shaftsbury. Offering 2 bedrooms with a full primary suite (large primary bathroom and walk in closet), 3 total bathrooms and modern design. Enjoy the large airy and open living room with fireplace, modern kitchen with plenty of cupboards and marble counter top and dining area with slider to the private backyard and multi-level deck. Many

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    43 Spur Rd, Bennington, VT 05201
    • /39

      Est $760,571 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,206 Sq Ft

      192 Old Depot Rd, Shaftsbury, VT 05262

      192 Old Depot Rd, Shaftsbury, VT 05262
  • /7

    $29,000

    • Land
    • 1.2 Acres
    • $24,167 per Acre

    00 Oberdorf Rd, Stamford, VT 05350

    This 1.2 acre rectangular lot is located in Alpenwald Village! The village roads are community-maintained, have electricity service through Green Mountain Power Company and is loaded with recreational perks! 1.4 miles to hiking/ biking trails on the Dutch Hill Backcountry Area of the Green Mountain National Forest. 1.9 miles to an ATV & snowmobile trailhead in Heartwellville. Situated in the town

    Casey Scott Southern Vermont Realty Group

    00 Oberdorf Rd, Stamford, VT 05350
  • /6

    $9,000 Sold Oct 03, 2025

    • Land
    • 1 Acre
    • $9,000 per Acre
    • 76 Days On Market

    lot 305 Lebenschauung Cir, Stamford, VT 05352

    Top-of-the-World Views Await - One Acre in Southern VermontDiscover your own slice of paradise with this beautiful one-acre wooded lot nestled in Southern Vermont. The current owner hand-picked this lot for its ''top of the world'' feel--and with a little clearing, the panoramic views will be nothing short of breathtaking.This is your chance to escape the hustle and build your dream retreat.

    Christine Girard STEEPLEVIEW REALTY - N. ADAMS

    lot 305 Lebenschauung Cir, Stamford, VT 05352
    • /32

      Est $336,056 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft

      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

      1041 Shaftsbury Hollow Rd, North Bennington, VT 05257
  • /33

    $2,295,000

    • 4 Beds
    • 5.5 Baths
    • 4,506 Sq Ft

    3039 Vermont 30, Pawlet, VT 05761

    Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

    Carrie Mathews Winhall Real Estate

    3039 Vermont 30, Pawlet, VT 05761
  • /28

    $80,000 Sold Oct 03, 2025

    • Land
    • 3.75 Acres
    • $21,333 per Acre
    • 7 Days On Market

    0 High Pine Dr Unit 6 5054642, Arlington, VT 05250

    Just a short walk to the Battenkill River and a stone's throw to the Village of Arlington, this 3.75 acre lot is already permitted for a 5BR house! Partial clearing has already been done and with some additional select clearing you can have lovely views while retaining privacy. A wonderful place for your primary residence or your Vermont getaway!

    Vicki Wilson Maple Leaf Realty

    0 High Pine Dr Unit 6 5054642, Arlington, VT 05250
    • /38

      Est $732,380 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,560 Sq Ft

      1058 Granger Hollow Rd, North Bennington, VT 05257

      1058 Granger Hollow Rd, North Bennington, VT 05257
  • /43

    $1,895,000

    • 6 Beds
    • 5.5 Baths
    • 5,178 Sq Ft

    144 Taconic Rd, Manchester, VT 05255

    “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

    Tom Deck Josiah Allen Real Estate, Manchester Branch Office

    144 Taconic Rd, Manchester, VT 05255
  • /5

    $9,000 Sold Oct 03, 2025

    • Land
    • 1 Acre
    • $9,000 per Acre
    • 67 Days On Market

    0 Lebenschauung Cir Unit 305, Stamford, VT 05352

    Top-of-the-World Views Await - One Acre in Southern Vermont Discover your own slice of paradise with this beautiful one-acre wooded lot nestled in Southern Vermont. The current owner hand-picked this lot for its ''top of the world'' feel—and with a little clearing, the panoramic views will be nothing short of breathtaking. This is your chance to escape the hustle and build your dream retreat.

    Christine Girard Steepleview Realty

    0 Lebenschauung Cir Unit 305, Stamford, VT 05352
    • /39

      Est $145,000 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft

      1618 W Sandgate Rd, Arlington, VT 05250

      1618 W Sandgate Rd, Arlington, VT 05250
  • /43

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft

    21 County Rd, Pownal, VT 05261

    Step into the warmth and character of this spacious 4-bedroom, 2-bath farmhouse set on 16 picturesque acres. A classic center hall with a beautiful wooden staircase welcomes you inside, where hardwood floors, exposed beams, and three cozy wood stoves create a timeless, inviting feel throughout.The large country kitchen opens directly to a fenced-in backyard, perfect for pets or simply

    Julie Glover Mahar McCarthy Real Estate

    21 County Rd, Pownal, VT 05261
  • /27

    $440,000 Sold Oct 03, 2025

    • 1,400 Sq Ft
    • $314/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    6 Moose Maple Rd, Winhall, VT 05340

    Located in the desirable Moose Maple section of Birch Hill, this well-maintained 3-bedroom, 2-bath Co-Op offers some of the best direct views of Stratton Mountain, along with the convenience of a community shuttle and close proximity to the newly rebuilt seasonal pool. Freshly painted and thoughtfully updated, the condo features flexible living spaces including a lower-level bedroom with a custom

    Andy Reed Four Seasons Sotheby's Int'l Realty

    6 Moose Maple Rd, Winhall, VT 05340
    • /40

      Est $97,358 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 664 Sq Ft

      4355 Sandgate Rd, Arlington, VT 05250

      4355 Sandgate Rd, Arlington, VT 05250
  • /52

    $2,300,000

    • 6 Beds
    • 3 Baths
    • 3,340 Sq Ft

    215 & 221 Vt Route 30, Dorset, VT 05251

    Two homes, multiple barns and outbuildings on 69 incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain views. A

    Margretta Fischer Wohler Realty Group

    215 & 221 Vt Route 30, Dorset, VT 05251
  • /40

    $1,500,000 Sold Oct 01, 2025

    • 3,436 Sq Ft
    • $437/SF
    • 116 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1850

    59 Church St, Dorset, VT 05251

    Exceptional Dorset Church St. offering. Spacious c 1850s Italianate with Greek Revival features in remarkable condition with new roof, windows, refinished floors, A/C. Spacious, bright eat-in kitchen large parlor living room with fireplace, dining room. First floor master suite, bright well-appointed eat-in kitchen and updated bathrooms. 4-5 bedrooms, Large level yard, stone walled terraces

    R. Diedrich August

    59 Church St, Dorset, VT 05251
    • /31

      Est $415,172 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 1,088 Sq Ft

      1388 Pawlet Mountain Rd, Pawlet, VT 05761

      1388 Pawlet Mountain Rd, Pawlet, VT 05761
  • /44

    $375,000

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

    2842 Vermont Route 7a, Shaftsbury, VT 05262

    Spacious split level on 1.16 acres with spectacular views. Surrounded by Grateful Morning Farm, the simple beauty and peaceful landscape is breathtaking. Enjoy your coffee while watching sunrises from the rear stone patio or breakfast nook, both overlooking the big backyard with mountain backdrop. In summertime, the mini split and ceiling fans will keep you cool, and in Vermont's magical winter

    Jenifer Prouty Hoffman Hoffman Real Estate

    2842 Vermont Route 7a, Shaftsbury, VT 05262
  • /6

    $262,500 Sold Sep 30, 2025

    • Land
    • 8.32 Acres
    • $31,550 per Acre
    • 88 Days On Market

    X Mount Aeolus Rd, Manchester, VT 05255

    Time to build your dream home ... 8.32+/- acre lot in prime Manchester location with over 1300 feet of Battenkill River frontage; West Branch. Open meadow with mountain views, wastewater permit in place for a four-bedroom home on 6.34 acres (Parcel B) of total acreage and a second 2+/- acre lot, with 3 bedroom permit (Parcel A) for future expansion. Parcels A & B are naturally divided by the

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

    X Mount Aeolus Rd, Manchester, VT 05255
    • /30

      Est $404,481 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,764 Sq Ft

      513 Sykes Hollow Rd, Pawlet, VT 05761

      513 Sykes Hollow Rd, Pawlet, VT 05761
  • /32

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,696 Sq Ft

    130 Ipan Rd, North Bennington, VT 05257

    Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

    Kelley Mccarthy Mahar McCarthy Real Estate

    130 Ipan Rd, North Bennington, VT 05257
  • /23

    $235,000 Sold Sep 30, 2025

    • 976 Sq Ft
    • $241/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    87 Birch Rd, Woodford, VT 05201

    This charming two-bedroom cabin at Woodford Lake is the ideal retreat for outdoor enthusiasts. Just a short walk from the lake and beachhead, and with the VAST snowmobile trail right outside your door, you’ll enjoy four seasons of adventure, relaxation, and natural beauty. Whether you’re swimming, kayaking, hiking, or snowmobiling, this location puts year-round recreation at your fingertips.

    Patrice Schneider Southern Vermont Realty Group

    87 Birch Rd, Woodford, VT 05201

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