Bennington County VT Homes for Sale

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  /38

  $775,000

  • 4 Beds
  • 4 Baths
  • 3,520 Sq Ft

  12 Stratton Ridge Rd, Winhall, VT 05340

  First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

  Carrie Mathews Winhall Real Estate

  12 Stratton Ridge Rd, Winhall, VT 05340
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  /22

  $595,000

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

  111 Harmony Ln, Manchester Center, VT 05255

  Exceptional opportunity to own a versatile mixed-use property located in one of Dorset's designated planned areas, where residential and commercial uses can coexist. Recently utilized as a professional office and later as a residential rental, this flexible property offers endless possibilities for an owner-occupant, investor, or business owner.The main level features four bedrooms, two full

  Andy Reed Four Seasons Sotheby's Int'l Realty

  111 Harmony Ln, Manchester Center, VT 05255
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  /50

  $160,000

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

  127 Dewey St, Bennington, VT 05201

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

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
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  /2

  $4,979,900

  • 33,801 Sq Ft

  1000 Investors Ln, Manchester, VT 05255

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

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  1000 Investors Ln, Manchester, VT 05255
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  /26

  $1,575,000

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

  777 McCooey Dr, Manchester Center, VT 05255

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

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

  777 McCooey Dr, Manchester Center, VT 05255
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  /21

  $210,000

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

  2740 Sandgate Rd, Arlington, VT 05250

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

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  2740 Sandgate Rd, Arlington, VT 05250
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  /6

  $22,000

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

  0 Rue Madeline Rd Unit 8, Readsboro, VT 05350

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

  Erica Hale Ridgeline Real Estate

  0 Rue Madeline Rd Unit 8, Readsboro, VT 05350
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  /14

  $139,900

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit C10, Bennington, VT 05201

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

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit C10, Bennington, VT 05201
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  /37

  $269,900

  $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
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  /28

  $225,000

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

  107 Jefferson Ave, Bennington, VT 05201

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

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Jefferson Ave, Bennington, VT 05201
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  /49

  $675,000

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

  11 Stratton View Rd, Bondville, VT 05340

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

  Cheyanne Pugliese

  11 Stratton View Rd, Bondville, VT 05340
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  /37

  $189,000

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  209 Depot St, Bennington, VT 05201

  This well-maintained New Englander offers the perfect balance of classic character and comfortable living. Featuring four bedrooms and two updated bathrooms. The home provides spacious, comfortable living throughout.The recently renovated kitchen is both stylish and functional, while the updated bathrooms add contemporary appeal. Large rooms and a thoughtful layout create a welcoming

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  209 Depot St, Bennington, VT 05201
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  /42

  $3,900,000

  • 5 Beds
  • 7 Baths
  • 11,736 Sq Ft

  2236 River Rd, Manchester, VT 05254

  Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

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

  2236 River Rd, Manchester, VT 05254
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  /4

  $80,000

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

  107 Lyons St, Bennington, VT 05201

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

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Lyons St, Bennington, VT 05201
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  /34

  $875,000

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

  2436 Mad Tom Rd, East Dorset, VT 05253

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

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2436 Mad Tom Rd, East Dorset, VT 05253
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  /60

  $2,275,000

  $196K PRICE INCREASE

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

  59 Barrows Heights, Dorset, VT 05251

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

  Sunny Breen Josiah Allen Real Estate, Inc.

  59 Barrows Heights, Dorset, VT 05251
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  /54

  $495,000

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

  498 Townline Rd, Bennington, VT 05201

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

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
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  /23

  $279,000

  $10K PRICE DROP

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

  1806 Bosley Hill Rd, Readsboro, VT 05350

  This Contemporary Chalet sit on a quiet rural town maintained road.The property is a tasteful blend of woodland and grassy yard with gardens. You can enter from the garage ,above ground , and walk up an interior staircase to the the next level. There is also a half bath and laundry room and plenty of room for side-by-sides, snowmobiles and seasonal gear!On the second level there is a very

  Janet Boyd Boyd Real Estate

  1806 Bosley Hill Rd, Readsboro, VT 05350
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  /50

  $775,000

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

  392 Powderhorn Rd, Manchester Center, VT 05255

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

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
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  /56

  $995,000

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

  238 Seminary Ave, Manchester, VT 05254

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

  

  Margretta Fischer

  Wohler Realty Group

  238 Seminary Ave, Manchester, VT 05254
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  /38

  $325,000

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

  89 Merson St, Woodford, VT 05201

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

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
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  /52

  $285,000

  $4K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
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  /33

  $1,100,000

  • 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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  /25

  $620,000

  • 4 Beds
  • 3 Baths
  • 1,768 Sq Ft

  35 Valley Pass St, Manchester, VT 05255

  Move right into this turnkey Cape offering 4 bedrooms and 3 bathrooms with extensive recent updates throughout. Combining classic New England charm with modern conveniences, this thoughtfully renovated home is designed for comfortable everyday living and effortless entertaining. The main level features a bright, open concept floor plan centered around a beautifully updated kitchen with quartz

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  35 Valley Pass St, Manchester, VT 05255
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  /60

  $1,395,000

  • 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

  $850,000

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

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

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

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  46 Ridge Rd Unit C-4, Winhall, VT 05340
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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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  /34

  $850,000

  • 2,060 Sq Ft

  609 Depot St, Manchester Center, VT 05255

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

  Sunny Breen Josiah Allen Real Estate, Inc.

  609 Depot St, Manchester Center, VT 05255
• 

  

  /22

  $1,425,000

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

  B Prospect St, Manchester, VT 05254

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

  Sunny Breen Josiah Allen Real Estate, Inc.

  B Prospect St, Manchester, VT 05254
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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

  $550,000

  • 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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  /15

  $389,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,516 Sq Ft

  319 Chester Knoll Dr, Bennington, VT 05201

  Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

  Lilli West Maple Leaf Real Estate

  319 Chester Knoll Dr, Bennington, VT 05201
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  /56

  $2,200,000

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

  312 Beartown Rd, Manchester Center, VT 05255

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

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /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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  /10

  $125,000

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

  0 East Rd, Shaftsbury, VT 05262

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

  Jenifer Prouty Hoffman Hoffman Real Estate

  0 East Rd, Shaftsbury, VT 05262
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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 relax,

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1111 Old Depot Rd, Shaftsbury, VT 05262
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  /49

  $650,000

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

  81 Honeysuckle Ln, North Bennington, VT 05257

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

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
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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
• 

  

  /25

  $1,997,000

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

  655 Squirrel Hollow Rd, East Dorset, VT 05253

  Set on 23 private acres with sweeping Green Mountain views, this contemporary residence by acclaimed architect Jeff Barnes is thoughtfully composed to engage its landscape at every turn. Walls of glass, soaring ceilings, exposed timber trusses, and stone fireplaces bring scale and warmth to the interiors, while broad windows draw in light and long views from nearly every principal room.

  Laura Kottler LandVest, Inc/Woodstock

  655 Squirrel Hollow Rd, East Dorset, VT 05253
• 

  

  /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

Showing Results 41 - 80, Page 2 of 7