Bennington County VT Homes for Sale

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  /40

  $1,200,000

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  81 Fern Hill, Dorset, VT 05251

  Nestled in one of Dorset’s most desirable private settings, this enchanting storybook Cape is a rare offering that beautifully blends timeless New England character with the relaxed elegance of Vermont living. Set amid seven picturesque acres, the property is surrounded by lush perennial gardens, magnificent specimen maples, and an extraordinary acre of mature pachysandra, creating a remarkable

  Elena Atwill Four Seasons Sotheby's Int'l Realty

  81 Fern Hill, Dorset, VT 05251
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  /40

  $989,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  3542 North Rd, Arlington, VT 05250

  Modern Four-Season Home with Exceptional Views & Workshop Space.Built in 2022, this modern home offers easy one-floor living, beautiful four-season views, and a convenient location close to Manchester’s amenities.The bright, open and airy main level features 3 bedrooms and 2 bathrooms, with comfortable living spaces designed to take full advantage of the surrounding views. The

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  3542 North Rd, Arlington, VT 05250
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  /49

  $1,100,000

  • 4 Beds
  • 4 Baths
  • 5,164 Sq Ft

  78 Bonnet St, Manchester Center, VT 05255

  Built in 1905, when Manchester was emerging as one of Vermont's most desirable summer destinations, this stately Queen Anne residence on Bonnet Street reflects an era of exceptional craftsmanship and enduring quality. Offered for sale for the first time since 1974, the property has been lovingly maintained by its longtime owner, preserving much of its original character and architectural detail

  Christiane Carroccio TPW Real Estate

  78 Bonnet St, Manchester Center, VT 05255
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  /59

  $2,350,000

  • 5 Beds
  • 3.5 Baths
  • 4,752 Sq Ft

  6 Sunset Ridge Rd, Winhall, VT 05340

  Set within the exclusive High Meadow community, one of Stratton's most prestigious mountain enclaves, 6 Sunset Ridge is an extraordinary resort residence of post and beam architecture & impeccable craftsmanship. Positioned to capture sweeping views of Stratton Mountain, this exceptional residence offers an unparalleled lifestyle in one of Stratton's most sought-after luxury neighborhoods. From

  Kim Morgan-Wohler Wohler Realty Group

  6 Sunset Ridge Rd, Winhall, VT 05340
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  /30

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,379 Sq Ft

  1278 Harrington Rd, Bennington, VT 05201

  Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and

  Kelley Mccarthy Mahar McCarthy Real Estate

  1278 Harrington Rd, Bennington, VT 05201
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  /30

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, Arlington, VT 05250

  A little bit of Vermont country living, tucked into 3.05 acres in Sunderland! This 4-bedroom, 2.5 bath Colonial offers a great mix of traditional and open concept living, with wood floors, large windows, granite countertops, open kitchen/dining, spacious living room, den/office, mudroom, and first floor laundry. The primary suite features a private bath with soaking tub and walk in closet. Step

  Abi Gregorio

  1180 North Rd, Arlington, VT 05250
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  /2

  $245,000

  • Land
  • 3 Acres
  • $81,667 per Acre

  0 Fox Ln Unit 5105566, Dorset, VT 05251

  The last lot located in a quaint Dorset cul de sac. One of the few building lots left in the most coveted Dorset village, abutting national forest on the marsh. This lot is the only available lot in Dorset Village. Home Owners Association, organized and fully functional by the residents of Fox Lane. Take a walk, create a bench from a fallen tree, in the 18 acre common forested land adjoining the

  Laura Beckwith Josiah Allen Real Estate, Inc.

  0 Fox Ln Unit 5105566, Dorset, VT 05251
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  /39

  $1,185,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  133 Kent Hill Rd, Dorset, VT 05251

  The moment you step through the front door of Kent Hill Cottage, your shoulders drop, and you immediately exhale. Nestled along a quiet, tree-lined road at 133 Kent Hill Road in Dorset, Vermont, this home is a true sanctuary designed for peaceful living. It strikes an effortless balance between cozy comfort and stylish design, welcoming you with authentic warmth from the very first step

  Tim Post LandVest, Inc/Woodstock

  133 Kent Hill Rd, Dorset, VT 05251
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  /37

  $539,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  811 Middle Pownal Rd, Bennington, VT 05201

  Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

  Jeffrey Dorman

  811 Middle Pownal Rd, Bennington, VT 05201
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  /14

  $104,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  William Paquin Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201
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  /20

  $495,000

  $105K PRICE DROP

  • Land
  • 28 Acres
  • $17,679 per Acre

  00 Vermont 11, Peru, VT 05152

  Sweeping views of Stratton, Bromley, and Magic Mountains define this 28 +/- acre offering in Peru, Vermont, where rare east, south, and westerly exposure provides exceptional natural light and solar orientation throughout the day. The surrounding landscape combines open mountain vistas, varied terrain, and connection to the Green Mountains in a setting shaped by Southern Vermont’s four-season

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /38

  $1,795,000

  $80K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,370 Sq Ft

  1310 Dorset Hill Rd, East Dorset, VT 05253

  Perched on the side of Mount Aeolus and conveniently located near Manchester, this exceptional 4-bedroom, 3-bath contemporary retreat offers privacy, sophistication, and year-round natural beauty across 21 picturesque acres. Thoughtfully designed to embrace its surroundings, the property features rolling meadows, mature woodland, vibrant perennial gardens, and sweeping views of the Green

  Annette Gallo Real Broker LLC

  1310 Dorset Hill Rd, East Dorset, VT 05253
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  /59

  $210,000

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

  118 Foster Dr, Bennington, VT 05201

  Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities.The main residence features

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
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  /21

  $150,000

  • 4 Beds
  • 1 Bath
  • 1,536 Sq Ft

  207 Sycamore Rd, Woodford, VT 05201

  Rehabbers rejoice! This 4-bedroom lakehouse has been in the family since it was built in the late 1980s, and is now available on the cheap for you to restore and enjoy! A short stroll from Big Pond and backing up to a tremendous amount of National Forest, this property puts you near the water for summer enjoyment and near VAST trails for the winter. Enjoy the amenities of neighboring Bennington

  Zachary Zupan EXP Realty

  207 Sycamore Rd, Woodford, VT 05201
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  /25

  $1,997,000

  • 4 Beds
  • 2.5 Baths
  • 4,125 Sq Ft

  655 Squirrel Hollow Rd, East Dorset, VT 05253

  This contemporary residence by acclaimed architect Jeff Barnes offers a versatile floor plan with abundant living options, set on 23 private acres that balance tranquility with equal proximity to Manchester Center and Dorset Village. A quick trip to Bromley Mountain and Stratton, the home is set amidst professional landscaping with sweeping Green Mountain views. The main level is designed for

  Laura Kottler LandVest, Inc/Woodstock

  655 Squirrel Hollow Rd, East Dorset, VT 05253
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  /5

  $375,000

  $90K PRICE DROP

  • Land
  • 5.54 Acres
  • $67,690 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
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  /52

  $84,500

  $15K PRICE DROP

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  Wonderful little getaway for some ''EZ'' living. Be one with nature with all the essentials in place! It’s common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you’ll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a

  Dan Mason Perrott Realty

  845 Bailey Hill Rd, Readsboro, VT 05350
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  /36

  $399,000

  $31K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,768 Sq Ft

  253 Perkins Rd, Rupert, VT 05776

  INTERIOR PHOTOS NOW ADDED. Tucked away on a quiet, town-maintained dead-end dirt road, this inviting Rupert, Vermont property offers the kind of peaceful country setting that's becoming increasingly hard to find. Set on 6.79± acres, it's a place where morning walks, afternoon bike rides, and evenings under the stars can become part of everyday life.At the heart of the property is a circa 1850

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  253 Perkins Rd, Rupert, VT 05776
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  /55

  $895,000

  $100K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 4,502 Sq Ft

  3373 Main St, Manchester, VT 05254

  In the heart of Manchester Village, this four-bedroom, six-bath colonial blends classic New England charm with the kind of space and flexibility that fits modern living. Set on a level 0.85-acre lot with mountain views, the property offers both privacy and easy access to everything the village has to offer. Inside, you'll find character you can't replicate - spruce and pine floors, exposed beams,

  David Halligan Four Seasons Sotheby's Int'l Realty

  3373 Main St, Manchester, VT 05254
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  /59

  $949,000

  $30K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,248 Sq Ft

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  This is the ultimate modern Alpine chalet -- with the rare opportunity to also have a separate guest house on the property for income or guests! Both buildings are fully renovated, yet boast the classic detailing of mountain homes in the Alps. In the 4BR/3.5BA main house, three expansive floors offer sunny, well-appointed space for everyone. Head upstairs to join your friends and family in the

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340
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  /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
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  /60

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,023 Sq Ft

  1268 Myers Rd, Shaftsbury, VT 05262

  Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's

  Laura Beckwith Josiah Allen Real Estate, Inc.

  1268 Myers Rd, Shaftsbury, VT 05262
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  /6

  $395,000

  $100K PRICE DROP

  • Land
  • 6.93 Acres
  • $56,999 per Acre

  lot#2 Margeaux Ln, Stratton, VT 05155

  This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  lot#2 Margeaux Ln, Stratton, VT 05155
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  /15

  $85,000

  $15K PRICE DROP

  • Land
  • 1.2 Acres
  • $70,833 per Acre

  23 Moose Hollow Rd, Winhall, VT 05340

  Beautiful parcel located in a highly desirable Winhall neighborhood, just minutes to Bromley and Stratton Mountains, and a short drive to Manchester’s shops and dining. This property offers a State of Vermont potable water supply and wastewater permit in place for a 4-bedroom home. The lot is cleared and ready for construction; an ideal opportunity to build your Vermont retreat.

  Carrie Mathews Winhall Real Estate

  23 Moose Hollow Rd, Winhall, VT 05340
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  /20

  $535,000

  • 4 Beds
  • 3 Baths
  • 1,974 Sq Ft

  286 Green Mountain Rd, Manchester Center, VT 05255

  Discover comfort, style, and mountain views at Green Mountain Estates. This meticulously maintained split-level ranch offers four bedrooms, three bathrooms, and a flexible floor plan designed for everyday living. The bright upper level features 3 bedrooms an open-concept kitchen with new appliances and dining area that flows seamlessly into a cozy living room. Sliding door lead to a spacious and

  Andy Reed Four Seasons Sotheby's Int'l Realty

  286 Green Mountain Rd, Manchester Center, VT 05255
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  /6

  $39,500

  • Land
  • 2.1 Acres
  • $18,810 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /14

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

  Imagine Friday evening: you pull through the private gate, the tires of your car crunching over the paved lot, and you find that perfect spot right near the entrance. As you turn off the engine, a quiet stillness settles in. You won’t be reaching for those keys again until Monday.Welcome to your retreat at Village Watch. The ArrivalStep inside the dedicated mudroom, where there’s a place

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
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  /52

  $5,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,674 Sq Ft

  1060 Upper Hollow Rd, Dorset, VT 05251

  'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy

  Sunny Breen Josiah Allen Real Estate, Inc.

  1060 Upper Hollow Rd, Dorset, VT 05251
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  /37

  $385,000

  $10K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 2,067 Sq Ft

  258 Harvest Hills Dr, North Bennington, VT 05257

  Welcome to easy Vermont living in this beautifully maintained ranch-style home offering more than 2,000 finished square feet in one of North Bennington’s most desirable neighborhoods. Set on a quiet cul-de-sac with lovely mountain views, Harvest Hills offers a wonderful sense of community, including a large neighborhood pond for residents to enjoy. The location is equally appealing; close to the

  Mary Beth French Hoffman Real Estate

  258 Harvest Hills Dr, North Bennington, VT 05257
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  /10

  $169,000

  $31K PRICE DROP

  • 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
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  /50

  $745,000

  $30K PRICE DROP

  • 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

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
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  /12

  $90,000

  $5K PRICE DROP

  • Land
  • 1 Acre
  • $90,000 per Acre

  41 Moose Hollow Rd, Winhall, VT 05340

  Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope, power at the road, a nearby stream, and a state-issued 4-bedroom septic permit already in place. The setting provides a peaceful, natural feel while keeping you close to the best of Southern Vermont. Bromley Mountain is about

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  41 Moose Hollow Rd, Winhall, VT 05340
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  /37

  $399,000

  $31K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,663 Sq Ft

  446 Highland Ave, Manchester Center, VT 05255

  Looking for a unique opportunity for equity growth? This is it! Location, location, location. Highly desirable Highland Avenue is one of those rare streets with character homes that is literally only a few walking blocks to town. If you are lucky enough to own this charming 3- bedroom home offering 1,663 sq ft of living space, you will enjoy easy access to the library, local shops, coffee spots,

  Sunny Breen Josiah Allen Real Estate, Inc.

  446 Highland Ave, Manchester Center, VT 05255
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  /54

  $1,990,000

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

  Jamie Wylie Stratton Real Estate

  27 Mountain View Rd, Winhall, VT 05360
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  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
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  /47

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 3,357 Sq Ft

  153 High Meadow Rd, Winhall, VT 05340

  Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace.Recent

  Britt Wohler

  153 High Meadow Rd, Winhall, VT 05340
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  /41

  $429,000

  • 2 Beds
  • 2 Baths
  • 6,686 Sq Ft

  3310 Vt Route 346, Pownal, VT 05261

  Paul Harsch Harsch Associates

  3310 Vt Route 346, Pownal, VT 05261
• 

  

  /53

  $825,000

  $74K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,112 Sq Ft

  2572 Morse Hill Rd, Dorset, VT 05251

  Some properties announce everything at once. Others reward the buyer w/ discernment to see what is quietly waiting to be realized. Set along the rise of Morse Hill Road, this Dorset home is a rare opportunity: a substantial residence on 10 acres where value extends beyond what exists today into what the land could become. Beyond a beautiful Vermont home, there is potential to shape an

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

  2572 Morse Hill Rd, Dorset, VT 05251
• 

  

  /9

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,593 Sq Ft

  493 Main Rd, Stamford, VT 05352

  Bring your imagination to this over 1500 sq. ft. New England farmhouse and let it go wild! Level one acre lot with easy main route access, close to downtown and Stamford Elementary school. Stamford Golf & Country Club is around the corner, and skiing is a short drive away! Just 10 minutes to North Adams, and under 30 minutes to Whitingham, VT. Perfect location, and perfect price to turn this into

  Pauline Green Lamacchia Realty, Inc. - Adams

  493 Main Rd, Stamford, VT 05352
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  /48

  $449,000

  • 4 Beds
  • 2 Baths
  • 3,096 Sq Ft

  928 Main Rd, Stamford, VT 05352

  Welcome to the heart of Stamford, Vermont, where small-town charm meets endless opportunity. Set on 3.99 level acres with beautiful mountain views, this former historic general store has been transformed into a spacious 3,096 sq. ft. residence designed for today's flexible lifestyle. The main home offers 3 bedrooms, open living spaces, and room for everyone, while the separate second-floor

  Christine Girard

  928 Main Rd, Stamford, VT 05352

Showing Results 201 - 240, Page 6 of 7