21,045

Bennington County, VT Homes

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  • /54

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,064 Sq Ft

    48 Canal Dr, Readsboro, VT 05350

    What an opportunity! This versatile property offers an affordable buy-in with multiple possibilities. Just removed from the heart of Readsboro, the home is privately tucked away with a peaceful yard perched above the Deerfield River.The upper level features an inviting open-concept living area filled with natural light. Sliding glass doors open to a spacious deck — the perfect spot to relax

    Flex Realty Group Flex Realty

    48 Canal Dr, Readsboro, VT 05350
  • /50

    $419,000 Sold Oct 16, 2025

    • 1,941 Sq Ft
    • $216/SF
    • 85 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1872

    97 Buck Hill Rd, Shaftsbury, VT 05262

    Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    97 Buck Hill Rd, Shaftsbury, VT 05262
    • /33

      Est $667,922 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,145 Sq Ft

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262
  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /21

    $300,000 Sold Oct 16, 2025

    • 1,365 Sq Ft
    • $220/SF
    • 77 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    339 Chester Knoll Dr, Bennington, VT 05201

    A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

    Lori Hurley Four Corner Properties LLC

    339 Chester Knoll Dr, Bennington, VT 05201
    • /32

      Est $324,246 Not Listed For Sale

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

      317 Trumbull Hill Rd, Shaftsbury, VT 05262

      317 Trumbull Hill Rd, Shaftsbury, VT 05262
  • /3

    $109,000

    • Land
    • 17 Acres
    • $6,412 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Escape to the Green Mountains with this beautiful 17-acre parcel located at the end of a town-maintained road in scenic Readsboro, Vermont. This private property offers the perfect mix of seclusion and convenience, surrounded by nature and outdoor recreation opportunities. At the rear of the property, you’ll find a serene beaver pond that attracts moose, birds, and other local wildlife—an ideal

    Samantha Decker Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /15

    $380,000 Sold Oct 15, 2025

    • Land
    • 16 Acres
    • $23,750 per Acre
    • 0 Days On Market

    0 Tower Rd Unit 28, Dorset, VT 05251

    Very Private Wooded Parcel off of Tower Road sharing a drive with the neighbor... Mountain Views... borders Green Mountain National Forrest...a great 16 acre residential parcel that supports quiet enjoyment of Dorset's quiet end of the Dorset Hollow Location. The 4 BR VT WW permit is in place. A well exists on the property... rough drive in place. Woods roads and an easement exists on

    Laura Beckwith Josiah Allen Real Estate, Inc.

    0 Tower Rd Unit 28, Dorset, VT 05251
    • /40

      Est $523,783 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262
  • /24

    $471,000

    • 3 Beds
    • 2 Baths
    • 1,357 Sq Ft

    102 Mccormick Ln, Sunderland, VT 05250

    Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

    Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

    102 Mccormick Ln, Sunderland, VT 05250
  • /30

    $400,000 Sold Oct 15, 2025

    • 1,616 Sq Ft
    • $248/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1952

    38 Spruce Ln, Arlington, VT 05250

    Discover this updated 3-bedroom, 2-bath home in the heart of Arlington, Vermont. The main level features a newly added primary suite with its own full bath. Recent upgrades include new windows in all three bedrooms, living room, and dining room, enhancing both comfort and energy efficiency.Outside, a brand-new 24x24 two-car garage provides ample space for vehicles and features a second-story

    Lori Hurley Four Corner Properties LLC

    38 Spruce Ln, Arlington, VT 05250
    • /40

      Est $851,957 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,096 Sq Ft

      1279 W Mountain Rd, Shaftsbury, VT 05262

      1279 W Mountain Rd, Shaftsbury, VT 05262
  • /9

    $60,000

    536 Mill Rd, Stamford, VT 05352

    This house had a house fire a little less than 2 years ago. The structure there can possibly be rebuilt. Buyer would need to check with the town of Stamford about a new build. Buyers agent to verify all information. The barn is still standing and there is a shed across the street.

    Regina Perrotto Skihome Realty

    536 Mill Rd, Stamford, VT 05352
  • /47

    $455,555 Sold Oct 15, 2025

    • 3,024 Sq Ft
    • $151/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    380 Suncrest Rd, Rupert, VT 05776

    Property is HUD owned. CASE# 531-029113. Located in a picturesque yet rural location sits this large home on large 10 acre lot with barns and detached garage. Room to roam, have animals, a garden; so many possibilities. 3+ bedroom, 3 bathroom 2 story home!

    Dick Thackston R.H. Thackston & Company

    380 Suncrest Rd, Rupert, VT 05776
    • /40

      Est $541,145 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,396 Sq Ft

      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      349 Blueberry Hill Rd, Shaftsbury, VT 05262
  • /10

    $14,999

    • Land
    • 1 Acre
    • $14,999 per Acre

    0 Oberhugel Rd, Readsboro, VT 05350

    1-acre generally flat and densely wooded building lot in Alpenwald Village in Stamford, VT. This is a very well maintained district with lots of privacy and the neighbors widely spread out on their own acreage, yet there's still a friendly neighborhood feel. Speaking of privacy, the rear boundary is the large southern portion of the 420,000-acre Green Mountain National Forest. Stare off your back

    David White OwnerEntry.com

    0 Oberhugel Rd, Readsboro, VT 05350
  • /49

    $929,500 Sold Oct 15, 2025

    • 3,400 Sq Ft
    • $273/SF
    • 14 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    681 Powderhorn Rd, Manchester Center, VT 05255

    Enjoy privacy and convenience in this charming New England country home, just minutes from town. An open floor plan connects the updated country kitchen to the dining area and living room which features a fireplace and beamed cathedral ceiling. A large mud room with built in storage benches and a farmhouse sink has doors to the stone patio. In the living room, french doors open to a screened

    Christiane Carroccio TPW Real Estate

    681 Powderhorn Rd, Manchester Center, VT 05255
    • /40

      Est $374,427 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,632 Sq Ft

      60 Cedar Cir, Shaftsbury, VT 05262

      60 Cedar Cir, Shaftsbury, VT 05262
  • /25

    $385,000

    • Land
    • 41.1 Acres
    • $9,367 per Acre

    00 Ross Rd, Winhall, VT 05340

    Welcome to 41.1 acres of quintessential Vermont beauty, ideally located between downtown Manchester (11 minutes), Bromley Mountain (6 minutes), and Stratton Mountain (15 mins). This property offers the best of both worlds—easy access to town, ski mountains, and year-round recreation, yet a peaceful and private setting surrounded by nature. The land features a meandering stream, a mix of mature

    David Shehadi Josiah Allen Real Estate, Inc.

    00 Ross Rd, Winhall, VT 05340
  • /47

    $406,000 Sold Oct 15, 2025

    • 1,490 Sq Ft
    • $272/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1973

    231 Tudor Rd, Arlington, VT 05250

    Perfect weekend getaway or full time home. Private cape cod 1.5 story home with three bedrooms on 8.10 acres, offers mountain views, privacy, and is in excellent condition. Recent Improvements include: thermopane windows and doors, replacement of furnace & hot water heater, kitchen appliances, and added exterior water shut off valves. The home has forced hot air heating (oil), a drilled well,

    David Halligan Four Seasons Sotheby's Int'l Realty

    231 Tudor Rd, Arlington, VT 05250
    • /40

      Est $239,105 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,006 Sq Ft

      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262

      214 Valley View Rd Unit PVT, Shaftsbury, VT 05262
  • /17

    $65,000

    • Land
    • 2.38 Acres
    • $27,311 per Acre

    0 Sunset Hill Rd Unit B, Pownal, VT 05261

    Motivated sellers welcome you to this gorgeous 2.38+/- acre lot in Pownal, Vermont! Located on a dead end, private road, this lot is nestled on the right hand side when pulling into Sunset Hill Road. Recently flagged for easy access. Mostly level with some vegetation in a quiet neighborhood. Are you dreaming of building your own home or investing in VT real estate? You won’t want to miss this

    Terri Edgerley Edge Realty Vermont

    0 Sunset Hill Rd Unit B, Pownal, VT 05261
  • /60

    $194,900 Sold Oct 15, 2025

    • 1,056 Sq Ft
    • $185/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    233 Hollow Hideaway, Shaftsbury, VT 05262

    Escape to your own private Vermont camp retreat in Shaftsbury VT. Nestled on four acres, this property blends comfort, charm, and natural beauty with a large private pond just off the expansive 12' x 30' covered deck, alive with sunfish and wildlife, and framed by landscaped grounds, footbridges, and outdoor living spaces including an outdoor kitchen gazebo and outdoor propane heated shower —

    Jeffrey Dorman

    233 Hollow Hideaway, Shaftsbury, VT 05262
    • /39

      Est $766,895 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,312 Sq Ft

      3842 Vt Route 7a, Shaftsbury, VT 05262

      3842 Vt Route 7a, Shaftsbury, VT 05262
  • /22

    $249,900

    • 4 Beds
    • 2 Baths
    • 1,702 Sq Ft

    107 Coolidge Ave, Bennington, VT 05201

    Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball

    Matt Waddington Hoffman Real Estate

    107 Coolidge Ave, Bennington, VT 05201
  • /39

    $250,000 Sold Oct 14, 2025

    • 1,264 Sq Ft
    • $198/SF
    • 25 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1920

    139 Mckinley St, Bennington, VT 05201

    Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

    Brooke Thomson Drew Mahar McCarthy Real Estate

    139 Mckinley St, Bennington, VT 05201
    • /39

      Est $536,823 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft

      541 Blueberry Hill Rd, Shaftsbury, VT 05262

      541 Blueberry Hill Rd, Shaftsbury, VT 05262
  • /60

    $579,900

    • 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
  • /44

    $2,200,000 Sold Oct 14, 2025

    • 7,625 Sq Ft
    • $289/SF
    • 190 Days On Market
    • 5 Beds
    • 7 Baths
    • Built 2000

    19 Old Town Rd, Bondville, VT 05340

    Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

    Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340
    • /45

      Est $431,509 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,573 Sq Ft

      294 Tinkham Rd, North Bennington, VT 05257

      294 Tinkham Rd, North Bennington, VT 05257
  • /26

    $165,000

    • Land
    • 10 Acres
    • $16,500 per Acre

    777 Butternut Gutter, Arlington, VT 05250

    ''DIVIDED SKY, A RIVER SIDE RETREAT WITH PREMIER BROWN TROUT FISHING''! Nestled in the heart of Arlington, this breathtaking 10 acre lot offers unparalleled natural beauty, complete with sweeping mountain views and pristine surroundings! Perfect for outdoor enthusiasts, the lot features access to exceptional Brown Trout fishing waters, making it an Angler's Paradise! Whether you are

    Sunny Breen Josiah Allen Real Estate, Inc.

    777 Butternut Gutter, Arlington, VT 05250
  • /3

    $18,000 Sold Oct 14, 2025

    • Land
    • 1.66 Acres
    • $10,843 per Acre
    • 123 Days On Market

    lot 92 Alpendorf Ave, Readsboro, VT 05350

    Discover your own piece of Vermont paradise in this picturesque building lot. Surrounded by the scenic Green Mountains with stunning views, this peaceful setting is perfect for your dream home or getaway. Located near top ski areas and just a short drive to North Adams, MA, enjoy easy access to cultural attraction like MASS MoCA. Embrace the tranquility of nature while staying close to outdoor

    Christine Girard STEEPLEVIEW REALTY - N. ADAMS

    lot 92 Alpendorf Ave, Readsboro, VT 05350
    • /29

      Est $387,801 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 2,400 Sq Ft

      604 Tinkham Rd, North Bennington, VT 05257

      604 Tinkham Rd, North Bennington, VT 05257
  • /30

    $735,000

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

    This gorgeous Stratton area townhome is designed for comfort and style, featuring three spacious bedrooms, three baths plus an open loft. Being a Highgate model, it offers a second family room with ample space for relaxation and entertainment, making it perfect for holiday gatherings. The interior of this special home has been freshly painted in October '25 and stunning wide-board pine floors

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
  • /49

    $435,000 Sold Oct 10, 2025

    • 3,040 Sq Ft
    • $143/SF
    • 7 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2007

    458 Fox Hill Rd, Bennington, VT 05201

    Beautiful Colonial-style home with an oversized two-car attached garage, set in one of Bennington’s most desirable neighborhoods. This inviting home features an open kitchen and family room, a bright sunroom, formal living and dining rooms, and 2.5 baths. The primary suite is complemented by three additional bedrooms, offering plenty of space for family and guests. A versatile, walkout finished

    Kelley Mccarthy Mahar McCarthy Real Estate

    458 Fox Hill Rd, Bennington, VT 05201
    • /52

      Est $415,548 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,535 Sq Ft

      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262

      489 Ridge Rd Unit PVT, Shaftsbury, VT 05262
  • /34

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    114 Colebrook Rd, East Arlington, VT 05252

    This is an unfinished home that needs the right owner to complete it to its fullcapacity.Set off on a private road this home is set on a beautiful, secluded, wooded lot.Access to major highways and schools

    David White OwnerEntry.com

    114 Colebrook Rd, East Arlington, VT 05252
  • /24

    $1,025,000 Sold Oct 10, 2025

    • 2,160 Sq Ft
    • $475/SF
    • 5 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1988

    10 Middle Ridge Rd, Winhall, VT 05155

    Fox Chapel luxury townhome at Stratton. This four bedroom, four bathroom home is offered with the ability to skip the wait list at the Stratton Mountain Club. Renovated bathrooms and air conditioning make this the year round place to be. Prime location next to the ‘Chapel of the Snows’ and the Commons, walk to the Stratton village for ski access, dining, shopping, and resort amenities. Watch the

    Christiane Carroccio TPW Real Estate

    10 Middle Ridge Rd, Winhall, VT 05155
    • /24

      Est $439,333 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,065 Sq Ft

      318 Eleanors Way, North Bennington, VT 05257

      318 Eleanors Way, North Bennington, VT 05257
  • /2

    $74,900

    • Land
    • 5.3 Acres
    • $14,132 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 5-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

    Flex Realty Group Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350

Showing Results 281 - 320, Page 8 of 18

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