Bennington County VT Homes for Sale

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  /33

  $975,000

  $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,403 Sq Ft

  99 Holly's Way, Rupert, VT 05776

  Imagine waking to the quiet rhythm of the Vermont countryside, where morning light stretches across open meadows, woodland trails begin just beyond your door, and the pace of life slows to match the landscape. Set on 26 acres in Rupert, this exceptional property offers a rare combination of privacy, craftsmanship, and room to pursue the life you've imagined. The home is designed to feel connected

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  99 Holly's Way, Rupert, VT 05776
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  /60

  $1,195,000

  Open Sat 11AM - 2PM $200K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 3,873 Sq Ft

  181 Route 11, Winhall, VT 05340

  Perched on 6.3 private acres with sweeping views of Mt. Equinox, this custom post-and-beam home offers a rare combination of craftsmanship, energy efficiency, and natural beauty. Bordering the Green Mountain National Forest on two sides and located just minutes from Manchester, Bromley, and Stratton, the property delivers a secluded mountain retreat without sacrificing convenience. Built in 2012,

  Jonathan Minerick

  181 Route 11, Winhall, VT 05340
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  /26

  $825,000

  $25K PRICE DROP

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

  C-4 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

  C-4 Ridge Rd Unit C-4, Winhall, VT 05340
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  /16

  $1,050,000

  • 4 Beds
  • 3.5 Baths
  • 2,256 Sq Ft

  16 Middle Ridge Rd Unit 22, Winhall, VT 05155

  Unique four bedroom three and one half bath townhome, located directly across the street from the Stratton Village and ski area. Built in 1988, Fox Chapel is the second phase of the Village Chalet neighborhood. Only 27 of these properties exist. Although connected by a breezeway to the property next to it, feels very much like a stand alone home. Walking distance to shops, restaurants and all ski

  John Sikes Stratton Real Estate

  16 Middle Ridge Rd Unit 22, Winhall, VT 05155
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  $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
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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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  /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
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  /43

  $499,900

  $50K 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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  /56

  $1,775,000

  $425K PRICE DROP

  • 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

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /22

  $430,000

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  13 Golden Triangle Rd, Winhall, VT 05340

  The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

  Mike England Michael England Real Estate

  13 Golden Triangle Rd, Winhall, VT 05340
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  /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

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1111 Old Depot Rd, Shaftsbury, VT 05262
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  /32

  $595,000

  $55K PRICE DROP

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

  81 Honeysuckle Ln, North Bennington, VT 05257

  Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn’t be better, nestled on 9+ secluded acres in North Bennington.

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
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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
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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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  /9

  $374,900

  • Land
  • 2.31 Acres
  • $162,294 per Acre

  0 Wall St, Winhall, VT 05340

  Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

  Cheyanne Pugliese

  0 Wall St, Winhall, VT 05340
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  /16

  $875,000

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

  447 Rock Bottom Ln, Peru, VT 05152

  Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

  Andy Reed Four Seasons Sotheby's Int'l Realty

  447 Rock Bottom Ln, Peru, VT 05152
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  /24

  $389,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,535 Sq Ft

  515 Buck Hill Rd, Arlington, VT 05250

  Completely renovated from top to bottom, this move-in-ready home perfectly blends modern updates with classic Vermont charm. 3 bedrooms and 1 bathroom with a layout that includes multiple practical options for adding a second bathroom. The layout also includes a unique, unfinished bonus area off the primary bedroom with its own private staircase to the backyard—a blank canvas ideal for an

  Lori Hurley Four Corner Properties LLC

  515 Buck Hill Rd, Arlington, VT 05250
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  /48

  $429,000

  • 2 Beds
  • 2 Baths
  • 7,000 Sq Ft

  3310 Vermont 346, Pownal, VT 05260

  Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

  Paul Harsch HARSCH ASSOCIATES

  3310 Vermont 346, Pownal, VT 05260
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  /13

  $1,295,000

  • Land
  • 52 Acres
  • $24,904 per Acre

  0 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Montgomery Rd, Pownal, VT 05261
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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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  /4

  $1,295,000

  • Land
  • 52.61 Acres
  • $24,615 per Acre

  00 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  00 Montgomery Rd, Pownal, VT 05261
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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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  /17

  $198,900

  • 2 Beds
  • 1 Bath
  • 1,332 Sq Ft

  348 Center St, Pownal, VT 05261

  Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a

  

  Sheryl Morehouse

  Bishop West Real Estate, Inc.

  348 Center St, Pownal, VT 05261
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  /27

  $1,200,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  233 Squires Rd, Manchester Center, VT 05255

  Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

  Mark Triller Real Broker LLC

  233 Squires Rd, Manchester Center, VT 05255
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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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  /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
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  /49

  $1,375,000

  $75K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,376 Sq Ft

  39 Eagle Ridge, Dorset, VT 05251

  5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished

  Laura Beckwith Josiah Allen Real Estate, Inc.

  39 Eagle Ridge, Dorset, VT 05251
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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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  /40

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,453 Sq Ft

  6 Old Ridge Rd, Winhall, VT 05340

  Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering,

  Trent Stephens Wohler Realty Group

  6 Old Ridge Rd, Winhall, VT 05340
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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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  /42

  $499,000

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

  336 Kirby Hollow Rd, Dorset, VT 05251

  Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont.The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an office, three

  Britt Wohler

  336 Kirby Hollow Rd, Dorset, VT 05251
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  /27

  $179,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  432 South St Unit D2, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
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  /52

  $2,285,000

  • 5 Beds
  • 4.5 Baths
  • 4,647 Sq Ft

  543 Lower Hollow Rd, Dorset, VT 05251

  A Serene Dorset Hollow Retreat Along the Mettowee RiverTucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

  Britt Wohler

  543 Lower Hollow Rd, Dorset, VT 05251
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  /32

  $775,000

  • 5 Beds
  • 2 Baths
  • 3,500 Sq Ft

  20 Bishop Rd, Searsburg, VT 05363

  Sweeping long-range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton ridgelines from this stunning 2020 Moosehead log home. Situated on 7+ acres bordering thousands of acres of National Forest, the property offers direct access to VAST snowmobile trails, space to create your own private loops, and exceptional privacy — all while remaining just a short

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Bishop Rd, Searsburg, VT 05363
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  /44

  $2,495,000

  • 4 Beds
  • 5.5 Baths
  • 4,506 Sq Ft

  3039 Vermont 30, Pawlet, VT 05761

  Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

  Carrie Mathews Winhall Real Estate

  3039 Vermont 30, Pawlet, VT 05761
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  /37

  $875,000

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

  155 Brookman Rd, Pownal, VT 05261

  Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  155 Brookman Rd, Pownal, VT 05261
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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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  /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
• 

  

  /45

  $449,000

  $46K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  298 Mad Tom Rd, Dorset, VT 05253

  Set on over half an acre in the heart of East Dorset Village, this newly renovated three-bedroom, two-bath bungalow blends modern upgrades with cozy charm and even includes a peaceful brook running through the property. Recent upgrades include completely new kitchen and bathrooms and fresh interior paint throughout. The open-concept layout creates a bright,connected space that’s perfect for

  David Halligan Four Seasons Sotheby's Int'l Realty

  298 Mad Tom Rd, Dorset, VT 05253
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  /60

  $695,000

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

  Vicki Wilson Maple Leaf Real Estate

  515 Quarry Rd, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 7