Bennington County VT Homes for Sale

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  /52

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
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  /37

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  291 Springhill Rd, Bennington, VT 05201

  Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons.

  Faith Rhodes Maple Leaf Real Estate

  291 Springhill Rd, Bennington, VT 05201
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  /32

  $239,900

  • 4 Beds
  • 1.5 Baths
  • 2,104 Sq Ft

  1955 Vt Route 100, Readsboro, VT 05350

  Open House: Saturday, August 15th from 10 am to 12 pm. Welcome to 1955 Vermont Route 100, a character-filled 1870 farmhouse offering 4 bedrooms, 2 bathrooms, and 2,104 square feet of finished living space on a half-acre country lot in Readsboro. Abutting Vermont National Forest and close to VASA and Vast Trails. Inside, warm wood details and inviting living spaces create a classic Vermont feel.

  Colt Hazell Flex Realty

  1955 Vt Route 100, Readsboro, VT 05350
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  /49

  $675,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  40 Jameson Flats, Manchester, VT 05255

  NEW CONSTRUCTION | EXCEPTIONAL CRAFTSMANSHIP | PRIME MANCHESTER LOCATIONThis exceptional new-construction 3-bedroom, 2.5-bath duplex has been thoughtfully designed and built to an exceptionally high standard, combining refined finishes, impressive craftsmanship, and highly efficient modern systems just steps from the heart of Manchester.The open-concept main level is designed for both

  Britt Wohler

  40 Jameson Flats, Manchester, VT 05255
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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
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  /60

  $5,575,000

  • 7 Beds
  • 9.5 Baths
  • 9,915 Sq Ft

  159 Winhall Hollow Rd, Bondville, VT 05340

  Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

  Kim Morgan-Wohler Wohler Realty Group

  159 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /15

  $115,000

  • Land
  • 1 Acre
  • $115,000 per Acre

  75 Sylvan Ridge Rd, Winhall, VT 05340

  Your Vermont adventure starts here. This 0.90 - acre parcel offers a fantastic location between Stratton, Bromley, and Magic Mountains, with easy access to the year round recreation, dining, and shopping of Manchester. The current owner cleared and leveled the building site and excavated and built a driveway. There is a Waste Water Permit for a 4 bedroom home in place. Electric service is readily

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  75 Sylvan Ridge Rd, Winhall, VT 05340
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  /58

  $1,599,000

  • 4 Beds
  • 2.5 Baths
  • 5,403 Sq Ft

  525 Andrea Dr, Stamford, VT 05352

  The Ultimate Vermont Mountain Sanctuary: Discover total serenity at the end of a winding gravel road. Encircled by 37 acres of pristine woods, a natural pond, and sprawling lawns, this impeccably maintained contemporary estate offers complete isolation from the outside world. Located in peaceful Stamford, you are just minutes from Premier Vermont skiing boating, and hiking, as well as the

  Paul Harsch Harsch Associates

  525 Andrea Dr, Stamford, VT 05352
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  /24

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,035 Sq Ft

  84 Overlook Rd, East Dorset, VT 05253

  Commanding panoramic mountain views define this exceptional Dorset Overlook residence, where every room is designed to capture the beauty of Southern Vermont's ever-changing landscape. Bathed in natural light, the home's open floor plan creates an effortless flow between living, dining, and entertaining spaces, making everyday living as enjoyable as hosting family and friends.The thoughtfully

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

  84 Overlook Rd, East Dorset, VT 05253
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  /23

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  37 Brookside Rd, Manchester Center, VT 05255

  Tucked away on a quiet residential street, just moments from the heart of Manchester Center, 37 Brookside Road offers a rare balance of privacy and connection. Start the morning with coffee in the three-season sunporch, enjoy the changing seasons from the back deck, and settle into the evening warmth of the wood stove. Here, the rhythm of village life is close at hand, yet home feels comfortably

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  37 Brookside Rd, Manchester Center, VT 05255
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  /25

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft

  1625 Barnumville Rd, Manchester Center, VT 05255

  Offered for the first time in almost 40 years, this charming farmhouse is set on a picturesque 1.7-acre parcel of open land in Manchester, Vermont. Ideally located directly across from East of Equinox horse farm, the property offers a country setting just minutes from town. The main level features tall ceilings, a spacious kitchen with an adjoining dining area, and a generous living room centered

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  1625 Barnumville Rd, Manchester Center, VT 05255
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  /35

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,580 Sq Ft

  134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262

  Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262
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  /25

  $1,200,000

  • 6 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property can be sold furnished or unfurnished with closing before the ski season is here. 6 bedrooms and 3.5 bathrooms to accommodate your family and guests. Enjoy 2 primary suites with attached baths and one is on the main floor. Walk in

  Derek Greene Derek Greene

  11 Founders Hill Rd, Winhall, VT 05360
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  /4

  $349,000

  • 3,637 Sq Ft

  710 Main St, Bennington, VT 05201

  Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and

  Dan Mason Perrott Realty

  710 Main St, 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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  /32

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,878 Sq Ft

  32 Benson Fuller Dr, Bondville, VT 05340

  Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  32 Benson Fuller Dr, Bondville, VT 05340
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  /2

  $75,000

  • Land
  • 11.2 Acres
  • $6,696 per Acre

  0 Mount Anthony Rd, Bennington, VT 05201

  A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont-11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds. Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building a camp

  Kelley Mccarthy Mahar McCarthy Real Estate

  0 Mount Anthony Rd, 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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  /41

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,760 Sq Ft

  87 B Hill Rd, Pownal, VT 05261

  Welcome to your own private Vermont retreat. Nestled on 3.2 acres in the mountains of Pownal, this Adirondack-style home offers the perfect blend of rustic charm, thoughtful craftsmanship, and everyday comfort.Surrounded by walking trails, blueberry and raspberry bushes, fruit trees, and abundant wildlife, the property is designed for those who appreciate the outdoors. Enjoy mountain views

  Lilli West Maple Leaf Real Estate

  87 B Hill Rd, Pownal, VT 05261
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  /15

  $162,500

  $7K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit A11, Bennington, VT 05201

  Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add

  Colt Hazell Flex Realty

  432 South St Unit A11, Bennington, VT 05201
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  /12

  $49,000

  • Land
  • 9,147 Sq Ft
  • $233,333 per Acre

  2 Belvedere St, Bennington, VT 05201

  Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and

  Dan Mason Perrott Realty

  2 Belvedere St, Bennington, VT 05201
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  /52

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 2,399 Sq Ft

  1131 Route 30, Dorset, VT 05251

  Making its first appearance on the market in generations, this beloved circa-1850 New Englander is filled with warmth, character, and endless potential. Situated on 1.5 picturesque acres along Route 30, midway between the charming villages of Dorset and Manchester, the property offers an exceptional setting with easy access to local shops, restaurants, hiking trails, skiing, and all the amenities

  David Shehadi Josiah Allen Real Estate, Inc.

  1131 Route 30, Dorset, VT 05251
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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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  /32

  $350,000

  • 2,586 Sq Ft

  110 Short St, Bennington, VT 05201

  Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth.

  William Paquin Maple Leaf Real Estate

  110 Short St, Bennington, VT 05201
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  /60

  $1,125,000

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  3269 Route 30, Dorset, VT 05251

  Historic District, Dorset Village 4 Bedroom Colonial Farmhouse located with both residential and commercial zoning walk to every village amenity such as the Dorset Inn, Barrows House and Pool, Dorset Bakery, The Union Store, The Field Club, Dorset Library, Theater, Historic Society, and the Pinnacle walking trail. Recently restored this residence lives comfortably with extensive rear yard gardens

  Laura Beckwith Josiah Allen Real Estate, Inc.

  3269 Route 30, Dorset, VT 05251
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  /47

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  87 Grinka Farm Dr, Readsboro, VT 05350

  Set on 5 acres in the scenic hills of Readsboro, this spacious 4-bedroom, 2.5-bath farmhouse offers privacy, mountain views, and plenty of room to enjoy Vermont’s natural beauty. The 2,120-square-foot interior features warm wood flooring, abundant natural light, and a welcoming layout designed for everyday living and entertaining. The kitchen offers generous cabinetry, ample workspace, and an

  Colt Hazell Flex Realty

  87 Grinka Farm Dr, Readsboro, VT 05350
• 

  

  /21

  $132,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  60 Tori Ln, Bennington, VT 05201

  Very well kept single-wide mobile home on it's own land. Cozy 2 bedroom, 1 bathroom home with single level living. Living room, kitchen with dining area, main level laundry and more. Has 2 enclosed porches. The smaller one is used as a pantry and the larger one is heated. Outside 2 sheds and the sounds of the nearby babbling brook. Also has RV electric hook up.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  60 Tori Ln, Bennington, VT 05201
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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
• 

  

  /60

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,420 Sq Ft

  2734 Mad Tom Rd, East Dorset, VT 05253

  Vermont's rustic charm will welcome you in a warm embrace every time you enter this custom built post and beam home on 37.5 private acres. The home features 2 bedrooms plus loft and 2 baths with tons of natural woodwork. The property also includes a detached post and beam garage with additional space above, perfect for an art studio, writer's workshop or plenty of extra storage. The property

  David Citron RE/MAX Four Seasons

  2734 Mad Tom Rd, East Dorset, VT 05253
• 

  

  /40

  $579,900

  $15K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  1649 E Manchester Rd, Manchester Center, VT 05255

  5 bedroom, 2 bath Manchester home in a highly functional ski location: about 8 minutes to Bromley and under 25 minutes to both Magic and Stratton, plus roughly 2 minutes to downtown Manchester and 1 minute to Route 7 for straightforward access in all conditions. The setting supports frequent winter use and works equally well for year-round occupancy. The house underwent a full gut renovation in

  Jonathan Minerick

  1649 E Manchester Rd, Manchester Center, VT 05255
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  /15

  $65,000

  • Land
  • 17.3 Acres
  • $3,757 per Acre

  18 Hidden Valley Rd, Shaftsbury, VT 05262

  Ready to build 2.5 acre building lot with an aditional 14 acres of riding trails with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site and the trails on the lot make it a great opportunity for a horse paddock.

  Dan Mason Perrott Realty

  18 Hidden Valley Rd, Shaftsbury, VT 05262
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  /40

  $1,699,000

  • 4 Beds
  • 4 Baths
  • 2,951 Sq Ft

  1949 South Rd, Peru, VT 05152

  Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

  Helen Nault

  1949 South Rd, Peru, VT 05152
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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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  /55

  $1,475,000

  • 5 Beds
  • 4 Baths
  • 4,491 Sq Ft

  866 E Manchester Rd, Manchester Center, VT 05255

  If you are looking for a property with both mountain and water views, this exceptional five-bedroom Manchester home is a must-see.Set on a remarkable lot featuring breathtaking vistas and approximately 400 feet of frontage along Bromley Brook, this home offers a rare combination of privacy, natural beauty, and convenience. Located just minutes from the center of Manchester and near the

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  866 E Manchester Rd, Manchester Center, VT 05255
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  /56

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 3,394 Sq Ft

  1039 Berwal Rd, Arlington, VT 05250

  Set on over 5 picturesque acres in a peaceful country setting with beautiful Green Mountain views, this spacious 4 bedroom, 3 bath home offers the perfect blend of comfort, flexibility, and Vermont charm. Nestled just south of Manchester, the property provides an ideal balance of rural tranquility and convenient access to shopping, dining, recreation, and year-round attractions. Inside, you'll

  

  Margretta Fischer

  Wohler Realty Group

  1039 Berwal Rd, Arlington, VT 05250
• 

  

  /10

  $105,000

  $4K PRICE DROP

  • Land
  • 30.8 Acres
  • $3,409 per Acre

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262

  30 acres of Vermont Heaven located on a private road just 20 minutes from the center of Shaftsbury . There is a mix of hardwoods, evergreens and wet lands around the pond. this is suitable for a dry camp. A slice paradise to get away to in the Green Mountains just steps away from the National Forest.

  Dan Mason Perrott Realty

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262
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  /11

  $260,000

  • Land
  • 3.3 Acres
  • $78,788 per Acre

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340

  The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportunity for prospective homeowners. This exceptional site boasts views of Stratton Mountain Resort, allowing residents to monitor the mountain's snow conditions from the comfort of their own home each morning, as well as enjoy views

  Mike England Michael England Real Estate

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340
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  /33

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,504 Sq Ft

  252 Tudor Rd, Arlington, VT 05250

  Got a toolbelt, a dangerous amount of Pinterest boards, and an active imagination? It’s your time to shine! Tucked away on 3.52 blissfully serene, wooded acres in beautiful Sandgate, this rural retreat is the dictionary definition of a "diamond in the rough" just waiting for your grand vision! Born in 1983 and being sold "as-is", this ranch has fantastic bones. The main house is completely

  TG Glazer Winhall Real Estate

  252 Tudor Rd, Arlington, VT 05250
• 

  

  /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
• 

  

  /26

  $2,300,000

  • 5 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  241 High Hill Rd, Manchester Center, VT 05255

  Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

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

  241 High Hill Rd, Manchester Center, VT 05255

Showing Results 41 - 80, Page 2 of 7