Bennington, VT Homes

• 

  

  

  /60

  $875,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,168 Sq Ft

  368 Bowen Dr, Readsboro, VT 05350

  Discover a rare Vermont retreat offering 83 acres of open fields, sugar maples, stone walls, and total privacy. This modern timber-frame homestead blends character and sustainability: a grid-tied 4kW solar array, gravity-fed spring water, high-speed fiber internet, and 23 raised garden beds with berries and fruit trees. Step inside to wide-plank pine floors, a kitchen with a cast iron porcelain

  Nick Sicard EXP Realty

  368 Bowen Dr, Readsboro, VT 05350
• 

  

  

  /30

  $160,000 Sold Jul 09, 2025

  • 1,056 Sq Ft
  • $152/SF
  • 49 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1875

  195 Tunnel St, Readsboro, VT 05350

  This picturesque riverfront home offers a blend of natural beauty and rustic charm! Perfectly situated along the popular Deerfield River, the property boasts stunning water views, direct access for fishing or kayaking, and peaceful sounds of flowing water right outside your window. This two bedroom, 1 and a half bath home is located outside of flood zone territory, has low maintenance vinyl

  Casey Scott Southern Vermont Realty Group

  195 Tunnel St, Readsboro, VT 05350
• 

  

  

  /27

  Est $261,686 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,941 Sq Ft

  239 Breezy Acres Dr, Vernon, VT 05354

  239 Breezy Acres Dr, Vernon, VT 05354
• 

  

  

  /10

  $20,000

  • Land
  • 1.20 Acres
  • $16,667 per Acre

  0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350

  1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

  Community Lands

  0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350
• 

  

  

  /49

  $525,000 Sold Jun 06, 2025

  • 3,104 Sq Ft
  • $169/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  1450 King Hill Rd, Readsboro, VT 05350

  This warm, inviting home has so much to offer—vaulted ceilings, exposed hand-hewn beams, and tons of natural light that fills the open living space. The recently renovated kitchen is a standout, with bright granite counters and sleek cabinetry that flows beautifully into the dining and living areas. Whether you’re hosting friends or enjoying a quiet night by the wood-burning fireplace, this home

  Melissa Nebelski Skihome Realty

  1450 King Hill Rd, Readsboro, VT 05350
• 

  

  /13

  Est $260,601 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,612 Sq Ft

  390 Tunnel St, Readsboro, VT 05350

  390 Tunnel St, Readsboro, VT 05350
• 

  

  /28

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  139 Bergwelt Ln, Readsboro, VT 05350

  Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  139 Bergwelt Ln, Readsboro, VT 05350
• 

  

  /60

  $235,000 Sold May 20, 2025

  • Land
  • 5.00 Acres
  • $47,000 per Acre

  • 88 Days On Market

  1304 Vermont Route 100, Readsboro, VT 05350

  Spectacular hillside lot with expansive 180 degree mountain views bordering the Green Mountain National Forest! Enjoy direct access to the VAST and VASA trail networks to horseback ride, snowmobile, ATV, snowshoe, cross country ski, mountain bike, and hike. There are seemingly endless trails to explore and wildlife galore! This 5 acre lot is build ready. All of the major legwork has been done. 3

  Lisa Friedman Great American Dream Realty

  1304 Vermont Route 100, Readsboro, VT 05350
• 

  

  /38

  Est $161,783 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,809 Sq Ft

  56 Jarvis Hill Rd, Readsboro, VT 05350

  56 Jarvis Hill Rd, Readsboro, VT 05350
• 

  

  /44

  $499,000 Open Sun 2PM - 4PM

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

  144 Oberdorf Rd, Readsboro, VT 05350

  Open House 8/10/2025 2pm-4pm 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

  Evan Russell Real Broker LLC

  144 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /7

  $75,000 Sold May 20, 2025

  • Land
  • 31 Acres
  • $2,419 per Acre

  • 261 Days On Market

  00 Vermont 8, Readsboro, VT 05350

  Discover 31 stunning acres in Southern Vermont, ideally situated just 10 minutes from the Massachusetts border. Enjoy the convenience to Williams College, MASS MoCA in North Adams, and Berkshire East Mountain Resort all less than 30 minutes away. For outdoor enthusiasts, Harriman Reservoir in Wilmington, VT, is just down the road, offering endless opportunities for boating, kayaking, and fishing.

  Kim Meeker Southern Vermont Realty Group

  00 Vermont 8, Readsboro, VT 05350
• 

  

  /39

  Est $264,576 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,837 Sq Ft

  93 Depot St, Readsboro, VT 05350

  93 Depot St, Readsboro, VT 05350
• 

  

  /42

  $439,000

  • 4 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  639 Wiley Mountain Rd, Readsboro, VT 05350

  Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

  Melissa Nebelski Skihome Realty

  639 Wiley Mountain Rd, Readsboro, VT 05350
• 

  

  /31

  $316,999 Sold Apr 28, 2025

  • 1,000 Sq Ft
  • $317/SF
  • 58 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  713 Shippee Rd, Readsboro, VT 05350

  Lovely 2 story home with a great deck. Open concept living/dinning room. Convenient 1st floor laundry. Good sized kitchen with plenty of cabinets. The two bedrooms on the 2nd floor are good sized. The charming home has fresh paint throughout, new flooring, new bath fixtures, new kitchen counter top and sink. The basement is full walk out for additional space. Great country location with decent

  Susan Bellville Bellville Realty

  713 Shippee Rd, Readsboro, VT 05350
• 

  

  /18

  Est $104,378 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,024 Sq Ft

  78 Canal Dr, Readsboro, VT 05350

  78 Canal Dr, Readsboro, VT 05350
• 

  

  /34

  $499,000

  • 3 Beds
  • 3 Baths
  • 1,696 Sq Ft

  104 Johnny Cake Hill Ln, Readsboro, VT 05350

  If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 22 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.This serene retreat offers the best of nature — birdsong in the morning, occasional

  Monica Sumner BHG Masiello Brattleboro

  104 Johnny Cake Hill Ln, Readsboro, VT 05350
• 

  

  /23

  $160,740 Sold Feb 07, 2025

  • 2,504 Sq Ft
  • $64/SF
  • 82 Days On Market

  • 6 Beds
  • 2.5 Baths
  • Built 1890

  22 Tunnel St, Readsboro, VT 05350

  Accepting back up offers. Discover the charm of this up-and-down duplex, nestled in the heart of Readsboro, Vermont! Formerly Colo's General store this property offers abundant storage and flexible living arrangements, and presents a fantastic opportunity for owner-occupancy or rental income. The home has been lovingly held by the same family for years and is now ready for new owners to make it

  Morriah Adams BHG Masiello Brattleboro

  22 Tunnel St, Readsboro, VT 05350
• 

  

  /40

  Est $606,809 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,263 Sq Ft

  1456 Branch Hill Rd, Readsboro, VT 05350

  1456 Branch Hill Rd, Readsboro, VT 05350
• 

  

  /37

  $599,999

  • 4 Beds
  • 3 Baths
  • 3,504 Sq Ft

  636 Tunnel St, Readsboro, VT 05350

  Almost there! This owner has taken a traditional farmhouse and transformed it into an amazing home full of style and grace. There are many ways to consider this home...over 3500 square feet of single family living with 4 bedrooms (or even 5) and 3 baths...live on one floor, AIR B&B all or part of the other floor....rent both levels and use as a vacation home on off seasons. The kitchen is

  Christine Lewis Brattleboro Area Realty

  636 Tunnel St, Readsboro, VT 05350
• 

  

  /59

  $178,500 Sold Feb 03, 2025

  • 598 Sq Ft
  • $298/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  30 Lee Rd, Readsboro, VT 05350

  Tucked away on a private dead-end dirt road, this property offers a peaceful retreat surrounded by natural beauty. The highlight of the property is a gently flowing stream that runs behind the house from which you hear the relaxing sound of flowing water. The living room is warm and inviting, featuring a wood-burning stove that seamlessly connects to the kitchen. Embrace the comfort of

  Monique White Deerfield Valley Real Estate

  30 Lee Rd, Readsboro, VT 05350
• 

  

  /40

  Est $378,310 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,259 Sq Ft

  1693 Branch Hill Rd, Readsboro, VT 05350

  1693 Branch Hill Rd, Readsboro, VT 05350
• 

  

  /8

  $16,000

  • Land
  • 1.20 Acres
  • $13,333 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.

  David White OwnerEntry.com

  0 Alpendorf Ave, Readsboro, VT 05350
• 

  

  /9

  $8,000 Sold Dec 13, 2024

  • Land
  • 1.10 Acres
  • $7,273 per Acre

  • 167 Days On Market

  78 Heartwellville View Rd, Readsboro, VT 05350

  Escape to serenity with this exceptional 1.1-acre residential lot in the enchanting Alpenwald Village, nestled in the heart of Southern Vermont. Priced at just $10,000, this opportunity is not just about land—it's about embracing a lifestyle of safety, privacy, and natural beauty. Your Private Retreat: Experience peace and tranquility in a secure, family-friendly community with annual HOA dues of

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  78 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /25

  Est $95,378 Not Listed For Sale

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  845 Bailey Hill Rd, Readsboro, VT 05350
• 

  

  /60

  $369,900

  • 0.5 Baths
  • 2,320 Sq Ft

  6828 Main St, Readsboro, VT 05350

  Don’t miss your chance to own a piece of Vermont history in the heart of Readsboro. The iconic Readsboro General Store is now available and ready for your vision. Perfectly positioned on Main Street, just steps from the town green, this high-visibility property has long been a favorite stop for locals, visitors, and nearby trail users alike. Currently configured for mixed-use, the building

  Flex Realty Group Flex Realty

  6828 Main St, Readsboro, VT 05350
• 

  

  /8

  $8,000 Sold Dec 13, 2024

  • Land
  • 1.00 Acre
  • $8,000 per Acre

  • 167 Days On Market

  79 Heartwellville View Rd, Readsboro, VT 05350

  Escape to serenity with this exceptional 1.1-acre residential lot in the enchanting Alpenwald Village, nestled in the heart of Southern Vermont. Priced at just $10,000, this opportunity is not just about land—it's about embracing a lifestyle of safety, privacy, and natural beauty. Your Private Retreat: Experience peace and tranquility in a secure, family-friendly community with annual HOA dues of

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  79 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /15

  Est $469,340 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  833 Freezing Hole Dr, Readsboro, VT 05350

  833 Freezing Hole Dr, Readsboro, VT 05350
• 

  

  /38

  $1,200,000

  • 5 Beds
  • 1 Bath
  • 2,228 Sq Ft

  395 King Hill Rd, Readsboro, VT 05350

  Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

  Margretta Fischer Wohler Realty Group

  395 King Hill Rd, Readsboro, VT 05350
• 

  

  /18

  $60,500 Sold Nov 08, 2024

  • 512 Sq Ft
  • $118/SF
  • 7 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1962

  359 Case Ln, Readsboro, VT 05350

  Built back in the 60's by the same family who has enjoyed it ever since, this camp is finally ready for its next owners. Bring your creative visions or keep it a rustic basecamp. Great spot for hiking, mountain biking, snowmobiles and four wheelers. Access to seemingly endless trails and the VAST network is just down the road along with the Green Mountain National Forest. The camp needs some TLC.

  Mike Masters Four Seasons Sotheby's Int'l Realty

  359 Case Ln, Readsboro, VT 05350
• 

  

  /40

  Est $403,077 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,040 Sq Ft

  470 Freezing Hole Dr, Readsboro, VT 05350

  470 Freezing Hole Dr, Readsboro, VT 05350
• 

  

  /3

  $19,000

  • Land
  • 1.66 Acres
  • $11,446 per Acre

  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
• 

  

  /4

  $50,000 Sold Nov 08, 2024

  • Land
  • 5 Acres
  • $9,259 per Acre

  • 112 Days On Market

  879 Bergrucken Ln, Readsboro, VT 05350

  5.4 acres of easy living in Alpenwald Village. Beautiful vistas with abundant wildlife. Moments from snowmobile trails and all the outdoor recreation Southern Vermont has to offer. A short drive to MASS MoCA in North Adams or Williams College and the Clark Art in Williamstown. Septic plans in place and a driveway has been cut in. Come make an offer!

  Sean Taylor Moresi Real Estate Partners

  879 Bergrucken Ln, Readsboro, VT 05350
• 

  

  /19

  Est $470,260 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,196 Sq Ft

  1858 King Hill Rd, Readsboro, VT 05350

  1858 King Hill Rd, Readsboro, VT 05350
• 

  

  /42

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  516 Oberdorf Rd, Readsboro, VT 05350

  Outdoor lover’s paradise in Alpenwald Village! This beautifully updated 2-bedroom, 2-bath home sits on an ample 2.5 acres and abuts National Forest land—perfect for year-round adventure. Step inside to your open kitchen and a bright family room with cathedral ceilings and a sliding door that opens to a peaceful back porch with stunning mountain views. The spacious mudroom offers plenty of room

  Lindsey Martin Maple Leaf Realty

  516 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /60

  $392,000 Sold Nov 04, 2024

  • 1,440 Sq Ft
  • $272/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  931 Oberdorf Rd, Readsboro, VT 05350

  Impeccably constructed, this custom timber frame home boasts 3 bedrooms, 2 baths, with locally sourced hardwood flooring and pegged beams. Step in from the covered front porch into a tiled mudroom entry. The kitchen is equipped with a gas range, farmhouse sink, center island, and stylish open shelving. The dining area and living room exude coziness with the warmth from a pellet stove, vaulted

  Monique White Deerfield Valley Real Estate

  931 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /20

  Est $373,155 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,156 Sq Ft

  603 Wiley Mountain Dr, Readsboro, VT 05350

  603 Wiley Mountain Dr, Readsboro, VT 05350
• 

  /2

  $44,900

  • Land
  • 1.00 Acre
  • $44,900 per Acre

  270 Bergabhang Dr, Readsboro, VT 05350

  Come and build on this beautiful lot in Alpenwald Village - lot is cleared and is an approved and engineered building lot

  Sean Taylor Moresi Real Estate Partners

  270 Bergabhang Dr, Readsboro, VT 05350
• 

  

  /38

  $415,000 Sold Nov 04, 2024

  • 1,008 Sq Ft
  • $412/SF
  • 10 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2008

  639 Shippee Rd, Readsboro, VT 05350

  This charming cottage is nestled in a serene mountain setting, offering privacy and picturesque views. Off a quiet dirt road you are welcomed onto a deep front porch designed for relaxation. Inside, you will find an open kitchen, dining and living room with a fieldstone hearth, cozy wood stove and wood cathedral ceilings. There are two bedrooms and a full bathroom on the main floor. From the

  Monique White Deerfield Valley Real Estate

  639 Shippee Rd, Readsboro, VT 05350
• 

  

  /58

  Est $279,357 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  1806 Bosley Hill Rd, Readsboro, VT 05350

  1806 Bosley Hill Rd, Readsboro, VT 05350
• 

  /2

  $25,000

  • Land
  • 1.00 Acre
  • $25,000 per Acre

  0 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

  0 Alpendorf Ave, Readsboro, VT 05350

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