Bennington County VT Houses for Sale

• 

  

  

  /60

  $1,495,000

  $300K PRICE DROP

  • 17 Beds
  • 20 Baths
  • 14,861 Sq Ft

  3888 Vermont Route 7a, Shaftsbury, VT 05262

  The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

  Vicki Wilson Maple Leaf Real Estate

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /17

  $469,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

  Lori Hurley Four Corner Properties LLC

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
• 

  

  

  /50

  $489,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,144 Sq Ft

  5131 Main Rd, Stamford, VT 05352

  Set on 2.85 acres with beautiful mountain views, this 4-bedroom, 2-bath Colonial offers space, comfort, and classic Vermont charm in the heart of Stamford. The home features 2,144 finished square feet with a welcoming layout that includes a bright living room, family room, dining area, and a spacious kitchen with warm cabinetry, an arched window, and great flow for everyday living or

  Colt Hazell Flex Realty

  5131 Main Rd, Stamford, VT 05352
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  /37

  $1,600,000

  • 5 Beds
  • 5 Baths
  • 4,700 Sq Ft

  212 Taconic Rd, Manchester, VT 05255

  Set on coveted Taconic Road in the heart of Manchester Village, this beautifully renovated five-bedroom home seamlessly blends timeless Vermont charm with modern comfort. Thoughtfully reimagined from top to bottom, every detail has been carefully considered, resulting in a home that is both inviting and functional.Filled with natural light, the spacious floor plan centers around a beautifully

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

  212 Taconic Rd, Manchester, VT 05255
• 

  

  

  /20

  $475,000

  $24K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
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  /48

  $450,000

  $100K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 3,105 Sq Ft

  193 Finley Dr, Bennington, VT 05201

  Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

  Jenifer Prouty Hoffman Hoffman Real Estate

  193 Finley Dr, Bennington, VT 05201
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  /60

  $3,500,000

  • 6 Beds
  • 5.5 Baths
  • 3,690 Sq Ft

  123 Nichols Rd, Landgrove, VT 05148

  HIGH-QUALITY NEW CONSTRUCTION | 123 Nichols Hill Road, Peru, VermontRarely does an opportunity like this come to market in Peru, Vermont, a brand new, high-quality, luxury residence offering the perfect combination of refined construction, privacy, expansive mountain views, a private pond, and a beautifully renovated guest house. The main residence was thoughtfully designed for both

  Britt Wohler

  123 Nichols Rd, Landgrove, VT 05148
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  /85

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  1996 N Pownal Rd, Pownal, VT 05261

  Uncommonly Superb View -- A Vermont Meadow RetreatTucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival,

  Paul Harsch HARSCH ASSOCIATES

  1996 N Pownal Rd, Pownal, VT 05261
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  /53

  $949,000

  • 3 Beds
  • 3 Baths
  • 1,823 Sq Ft

  40 Kelleher Rd, Dorset, VT 05251

  Where Vermont Living Feels EffortlessDorset Home, Guest Cottage, Pond & Mountain ViewsSettle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy space,

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  40 Kelleher Rd, Dorset, VT 05251
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  /57

  $2,275,000

  $25K PRICE DROP

  • 9 Beds
  • 8 Baths
  • 5,512 Sq Ft

  288 Cedar Ln, Peru, VT 05152

  Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /39

  $1,450,000

  $125K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 4,530 Sq Ft

  527 Sleighbell Ln, Manchester Center, VT 05255

  Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home

  David Halligan Four Seasons Sotheby's Int'l Realty

  527 Sleighbell Ln, Manchester Center, VT 05255
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  /60

  $4,995,000

  • 5 Beds
  • 6.5 Baths
  • 7,455 Sq Ft

  440 Marcia Ln, Dorset, VT 05251

  A rare opportunity awaits at this exceptional Dorset Hollow estate, privately situated at the end of exclusive Marcia Lane. Perched high on Dorset Mountain across 16.74 acres, the property captures breathtaking long-range views of Owls Head, Equinox Mountain, and beyond.Built in 2005 by renowned craftspeople, this 7,451-square-foot, five-bedroom, seven-bath estate has undergone a

  David Halligan Four Seasons Sotheby's Int'l Realty

  440 Marcia Ln, Dorset, VT 05251
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  /30

  $209,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,127 Sq Ft

  20 Sage St, North Bennington, VT 05257

  Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an

  Abi Gregorio

  20 Sage St, North Bennington, VT 05257
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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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  /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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  /59

  $1,150,000

  Coming Soon

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

  11 Spruce High Rd, Winhall, VT 05340

  Discover this truly exceptional Vermont Mountain Retreat just seven miles from Stratton Mountain, perfectly located for four-season living! Boasting an inviting open layout great for spending time together, southern exposure and an abundance of natural light this beautifully renovated home has been updated in a sophisticated Vermont rustic style with all the comforts. Enjoy the Luxurious primary

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  11 Spruce High Rd, Winhall, VT 05340
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  /44

  $1,375,000

  • 3 Beds
  • 3 Baths
  • 2,457 Sq Ft

  1474 Dorset West Rd, Dorset, VT 05251

  "Spring Meadow" is textured with history and offers 10 acres of idyllic landscaping featuring the Ethan Allen Spring, a refreshing brook, perennial and vegetable gardens, wild flower meadow, orchard trees, trails throughout 10 acres, and a house that was moved to the site in the 1920's and lovingly added onto creating 2457 SF of one floor living with a separate guest cottage that is privately set

  Laura Beckwith Josiah Allen Real Estate, Inc.

  1474 Dorset West 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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  /39

  $189,900

  • 2 Beds
  • 1 Bath
  • 462 Sq Ft

  301 Beech St, Bennington, VT 05201

  Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with

  Floyd Amidon Maple Leaf Real Estate

  301 Beech St, Bennington, VT 05201
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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

  $190,000

  $20K PRICE DROP

  • 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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  /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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  /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
• 

  

  /20

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  327 Vt Route 313 W, Arlington, VT 05250

  I ain’t your father’s farmhouse (or your great-great-grandfather’s as the case may be!). Yes, I’ve been here since James Madison was President, and I’ve seen a LOT. But the thing I’m looking forward to most is you making your memories here. My 3 bedrooms and 2 updated baths have been lovingly cared for, and I await your personal touch. I also have a good sized eat-in kitchen with plenty of

  TG Glazer Winhall Real Estate

  327 Vt Route 313 W, Arlington, VT 05250
• 

  

  /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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  /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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  /60

  $4,200,000

  • 4 Beds
  • 6 Baths
  • 7,833 Sq Ft

  325 Twin Willows Ln, Dorset, VT 05251

  "Twin Willows... A private Architectural Gem with captivating vistas amidst the pines." Timeless elegance and modern comfort blend to perfection in this handsomely designed home, thoughtfully nestled on a private 18 acre estate. Every detail reflects consummate care and superb craftsmanship! No expense has been spared creating this serene retreat where luxury meets nature! Surrounded by dramatic

  Sunny Breen Josiah Allen Real Estate, Inc.

  325 Twin Willows Ln, Dorset, VT 05251
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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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  /37

  $379,000

  $51K 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
• 

  

  /46

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  735 Granger Hollow Rd, North Bennington, VT 05257

  Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also

  Vicki Wilson Maple Leaf Real Estate

  735 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /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
• 

  

  /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
• 

  

  /35

  $495,000

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft

  66 Crosier Rd, Shaftsbury, VT 05262

  Set on 3 beautiful acres with fabulous views in every direction, this spacious and inviting home offers a wonderful blend of comfort, character, and versatility. The main level features a private primary bedroom, a large kitchen, and a welcoming living room with hardwood floors and a fireplace with woodstove insert. A generously sized office with built-ins provides the perfect space for working

  Kelley Mccarthy Mahar McCarthy Real Estate

  66 Crosier Rd, Shaftsbury, VT 05262
• 

  

  /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

Showing Results 121 - 160, Page 4 of 5