Bennington County VT Homes for Sale

• 

  

  

  /19

  $224,000

  • 3 Beds
  • 2 Baths
  • 1,718 Sq Ft

  7066 Main St, Readsboro, VT 05350

  So many possibilities await at this recently renovated and affordable 3-bedroom, 2-bath home, featuring two full kitchens, one up and one down. Whether you're envisioning multigenerational living, a home-based business, or simply want to be close to skiing and outdoor adventure, this versatile layout adapts to fit your life. Recent renovations touch nearly every corner of the home, including both

  Pam Tworig BISHOP WEST REAL ESTATE

  7066 Main St, Readsboro, VT 05350
• 

  

  

  /39

  $59,900

  • Land
  • 40,075 Sq Ft
  • $65,109 per Acre

  14 The Ln, Stamford, VT 05352

  Escape to the beauty of VT with this unique shed/cabin in charming Stamford VT. This is a beautiful almost 1 acre lot that has direct frontage on the North Branch of the Hoosic River. It is mostly cleared & level & has a quaint pathway leading down to the river, to enjoy nature. The property includes a cozy shed/cabin with solar powered lights, with 2 batteries for storage. A rustic sink, ( bring

  Susan Colvin MONARCH REALTY, INC.

  14 The Ln, Stamford, VT 05352
• 

  

  

  /59

  $210,000

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

  118 Foster Dr, Bennington, VT 05201

  Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
• 

  

  

  /53

  $205,000

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

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
• 

  

  

  /38

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Bondville, VT 05340

  Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Bondville, VT 05340
• 

  

  /60

  $1,495,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 5 Baths
  • 5,029 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous

  Dylan Gage Bromley Real Estate

  20 Blackberry Ln, Peru, VT 05152
• 

  

  /6

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  631 Oberdorf Rd, Readsboro, VT 05350

  Bring your vision and transform this 3-bedroom, 2-bathroom home into the Vermont getaway you've always wanted. Located in the private Alpenwald Village community, this fixer-upper offers a fantastic opportunity for investors, vacation home buyers, or anyone looking to build equity in a scenic mountain setting.Surrounded by the Green Mountain National Forest, the property provides direct

  Kristen Breeden Southern Vermont Realty Group

  631 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /13

  $229,000

  • Land
  • 0 Sq Ft

  468 Skyboro Rd, Pownal, VT 05261

  Beautiful property featuring an impressive 835.9 feet of road frontage and over 10 partially cleared acres of private land in Pownal, Vermont. This land is situated on a private road with rolling woods, making it an ideal location to build a dream home or a vacation getaway. It offers easy access to Route 7, providing a quick drive north to the Bennington, Vermont area and local ski resorts.

  

  Sheryl Morehouse

  BISHOP WEST REAL ESTATE

  468 Skyboro Rd, Pownal, VT 05261
• 

  

  /48

  $230,000

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft

  104 Short St, Bennington, VT 05201

  Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

  Lindsey Martin Maple Leaf Real Estate

  104 Short St, Bennington, VT 05201
• 

  

  /43

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  96 Twitchell Hill Rd, Shaftsbury, VT 05262

  Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home

  Daire Gibney Barrett and Valley Associates Inc.

  96 Twitchell Hill Rd, Shaftsbury, VT 05262
• 

  

  /15

  $125,000

  • Land
  • 1.18 Acres
  • $105,932 per Acre

  510 Center St, Pownal, VT 05261

  Discover the potential of this scenic 1.18 acre parcel situated on a quiet street directly across from the town offices. Offering beautiful views and the convenience of town sewer, this property presents an excellent opportunity to build the home you've been dreaming of. Whether you're planning a year-round residence or a peaceful retreat, the generous lot provides plenty of space to create your

  Angela Bevin Maple Leaf Real Estate

  510 Center St, Pownal, VT 05261
• 

  

  /21

  $750,000

  • 3,216 Sq Ft

  198 Elm St, Manchester Center, VT 05255

  Rare opportunity to own a well-maintained 4-unit property in the heart of Manchester, one of Southern Vermont’s most sought-after destinations. Offered at an attractive 8% cap rate, this unique investment features a charming 2-bedroom, 2-bath carriage house, two 2-bedroom, 1-bath units, and a 1-bedroom, 1-bath apartment, providing an appealing mix for a variety of tenants. Recent updates include

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  198 Elm St, Manchester Center, VT 05255
• 

  

  /22

  $499,000

  • 3,648 Sq Ft

  938 Vt Route 7a, Shaftsbury, VT 05262

  Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. Offered at an attractive 10% cap rate, the building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  938 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /8

  $250,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /15

  $169,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  415 County St, Bennington, VT 05201

  STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

  Lori Hurley Four Corner Properties LLC

  415 County St, Bennington, VT 05201
• 

  

  /50

  $160,000

  • 5 Beds
  • 2 Baths
  • 1,575 Sq Ft

  127 Dewey St, Bennington, VT 05201

  Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single-family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
• 

  /2

  $4,979,900

  • 33,801 Sq Ft

  1000 Investors Ln, Manchester, VT 05255

  Exceptional opportunity to acquire a well-established Vermont investment portfolio consisting of 10 properties inclusive of 35 residential units and 5 commercial units located across the desirable communities of Brattleboro, Ludlow, Manchester, Cavendish, Shaftsbury, Proctorsville, and Chester. This diverse portfolio has been thoughtfully maintained and professionally managed, with many long-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  1000 Investors Ln, Manchester, VT 05255
• 

  

  /26

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  777 McCooey Dr, Manchester Center, VT 05255

  Set back from a quiet country road in Manchester, Vermont, this spaciousFederal farmhouse style home offers a wonderful blend of comfort, privacyand Vermont charm. The classic white exterior with its attached red barncreates a welcoming first impression, while the home’s thoughtful designprovides plenty of space for everyday living, entertaining and enjoying thepeaceful

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

  777 McCooey Dr, Manchester Center, VT 05255
• 

  

  /21

  $210,000

  • Land
  • 4.51 Acres
  • $46,563 per Acre

  2740 Sandgate Rd, Arlington, VT 05250

  Set on 4.51 picturesque acres with an impressive 932 feet of frontage along the coveted Green River, this exceptional property is truly a fisherman's dream and a nature lover's paradise. Open meadows, mature trees, and beautifully maintained grounds create a peaceful setting that showcases the best of Vermont's natural beauty. A winding wooded walking path invites you to explore the landscape

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  2740 Sandgate Rd, Arlington, VT 05250
• 

  

  /6

  $22,000

  • Land
  • 1.13 Acres
  • $19,469 per Acre

  0 Rue Madeline Rd Unit 8, Readsboro, VT 05350

  1.1 acre lot conveniently located off Vermont Route 100 in Readsboro. Approximately half the property is cleared, offering a great start for a future homesite or recreational retreat. Enjoy easy access to the VAST trail system. With selective tree clearing, the property may offer scenic mountain views. Pictures show both the current state and what's under it before it got a little over grown.

  Erica Hale Ridgeline Real Estate

  0 Rue Madeline Rd Unit 8, Readsboro, VT 05350
• 

  

  /14

  $139,900

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit C10, Bennington, VT 05201

  Townhouse style condo on the north side of Nathaniel court. Living room, kitchen, and half bath downstairs. Upstairs is the full bath with laundry and 2 bedrooms. No pets allowed.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit C10, Bennington, VT 05201
• 

  

  /28

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  107 Jefferson Ave, Bennington, VT 05201

  Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Jefferson Ave, Bennington, VT 05201
• 

  

  /49

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,204 Sq Ft

  11 Stratton View Rd, Bondville, VT 05340

  This is not your average chalet. Tucked in the quiet Stratton View neighborhood, just 1 mile from the base of the Stratton Access Road, this 3-bedroom, 2-bath home offers the warmth and character of a classic Vermont chalet with updated systems, thoughtful improvements, and the things you have been looking for but can’t seem to find: two living spaces and a garage — actually, two garages. Offered

  Cheyanne Pugliese

  11 Stratton View Rd, Bondville, VT 05340
• 

  

  /4

  $80,000

  • 2 Beds
  • 2 Baths
  • 1,465 Sq Ft

  107 Lyons St, Bennington, VT 05201

  Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Lyons St, Bennington, VT 05201
• 

  

  /34

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  2436 Mad Tom Rd, East Dorset, VT 05253

  Picture yourself on 12 private wooded acres along one of Vermont's most scenic country roads in a classic 4-bedroom, 3-bath Colonial offering the perfect blend of comfort, character, and outdoor adventure. Built in 1977 and thoughtfully maintained, the home welcomes you with warm hardwood floors, a beautifully renovated kitchen featuring soapstone countertops, abundant cabinetry, and a sunny

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2436 Mad Tom Rd, East Dorset, VT 05253
• 

  

  /60

  $2,275,000

  $196K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 3,504 Sq Ft

  59 Barrows Heights, Dorset, VT 05251

  Unmatched Dorset village Charm!!...In the heart of Historic Dorset, just steps away from all village amenities. Leave the car in the garage and stroll to your morning coffee at the Dorset Bakery, pick up groceries at the Union Store or meet friends for dinner at the beloved Barrows House or the historic Dorset Inn after a round of golf at the Field Club or post-theater at the Playhouse. This is a

  Sunny Breen Josiah Allen Real Estate, Inc.

  59 Barrows Heights, Dorset, VT 05251
• 

  

  /54

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /50

  $775,000

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  392 Powderhorn Rd, Manchester Center, VT 05255

  Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial balances privacy and convenience with easy access to both Manchester and Dorset. Wide-plank pine floors, abundant natural light, and inviting living spaces define the interiors. The main level features a spacious living room anchored by a stone fireplace, a formal dining room, and an

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /56

  $995,000

  • 5 Beds
  • 5 Baths
  • 4,126 Sq Ft

  238 Seminary Ave, Manchester, VT 05254

  Manchester Village LivingExperience the charm of village life in this expansive Victorian home and guest cottage, ideally located in the heart of Manchester Village. Rich in character and architectural detail, the home features original woodwork, soaring ceilings, generously sized rooms, and timeless New England appeal—enhanced by a new roof, windows and heating system.The spacious main

  

  Margretta Fischer

  Wohler Realty Group

  238 Seminary Ave, Manchester, VT 05254
• 

  

  /38

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /52

  $285,000

  $4K PRICE DROP

  • 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
• 

  

  /26

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,598 Sq Ft

  46 Ridge Rd Unit C-4, Winhall, VT 05340

  Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  46 Ridge Rd Unit C-4, Winhall, VT 05340
• 

  

  /34

  $850,000

  • 2,060 Sq Ft

  609 Depot St, Manchester Center, VT 05255

  Rare opportunity to own TWO prime town center buildings in the heart of the Manchester Depot. This unique offering includes a charming multi unit front home with two well maintained apartments and a separate commercial building currently occupied by a successful well established business! The current business/owner would like to continue operating the business and remain as a tenant, thus

  Sunny Breen Josiah Allen Real Estate, Inc.

  609 Depot St, Manchester Center, VT 05255
• 

  

  /22

  $1,425,000

  • Land
  • 38 Acres
  • $37,500 per Acre

  B Prospect St, Manchester, VT 05254

  A rare opportunity to own 38 stunning acres in the heart of Manchester Village, offering the perfect balance of seclusion, natural beauty, and convenience. A long, winding serpentine driveway gracefully leads to a beautifully manicured and ready-to-build homesite, creating a dramatic and private approach. Thoughtfully improved with underground power brought directly to the building site, a well,

  Sunny Breen Josiah Allen Real Estate, Inc.

  B Prospect St, Manchester, VT 05254
• 

  

  /38

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft

  1 Beaver St, Bondville, VT 05340

  Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

  Carrie Mathews Winhall Real Estate

  1 Beaver St, Bondville, VT 05340
• 

  

  /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
• 

  

  /56

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  312 Beartown Rd, Manchester Center, VT 05255

  Set on 24 private acres with sweeping mountain views, 312 Beartown Road offers a sense of complete escape while remaining moments from Manchester.Filled with natural light, the four-bedroom residence is thoughtfully designed to capture its extraordinary setting. Every room is oriented to the outdoors, with expansive windows that keep the Vermont landscape always in view. The chef's kitchen

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /10

  $125,000

  • Land
  • 5.77 Acres
  • $21,664 per Acre

  0 East Rd, Shaftsbury, VT 05262

  Set along scenic East Road in Shaftsbury, this 5.77-acre wooded parcel offers a beautiful opportunity to create a private Vermont homesite in one of the area’s most appealing rural settings. The land is currently wooded, allowing the next owner to decide how much to clear for a driveway, yard, gardens, or building site, with potential for a mountain view to the north with selective clearing.

  Jenifer Prouty Hoffman Hoffman Real Estate

  0 East Rd, Shaftsbury, VT 05262
• 

  

  /60

  $395,000

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  1111 Old Depot Rd, Shaftsbury, VT 05262

  Welcome to 1111 Old Depot Road in Shaftsbury, Vermont, where country living and natural beauty come together on approximately four scenic acres. This inviting four-bedroom, two-full-bath ranch-style home offers a rare opportunity to enjoy privacy, natural beauty, and convenient access to one of Southern Vermont's most beloved recreational destinations. Set on a spacious parcel with room to relax,

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1111 Old Depot Rd, Shaftsbury, VT 05262
• 

  

  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 5,524 Sq Ft

  81 Honeysuckle Ln, North Bennington, VT 05257

  Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257

Showing Results 1 - 40, Page 1 of 5