Bennington County VT Homes for Sale with Acreage

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  /52

  $725,000

  • 4 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on 50

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8873

  2 Cold Spring Rd, North Bennington, VT 05257
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  /47

  $1,500,000

  • Land
  • 38.57 Acres
  • $38,890 per Acre

  500 Nims Rd, Dorset, VT 05251

  This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 634-4776

  500 Nims Rd, Dorset, VT 05251
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  /38

  $1,200,000

  • 5 Beds
  • 1 Bath
  • 2,228 Sq Ft

  395 King Hill Rd, Readsboro, VT 05350

  Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

  

  Margretta Fischer

  Wohler Realty Group

  (802) 348-2742

  395 King Hill Rd, Readsboro, VT 05350
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  /40

  $1,245,000

  • 4 Beds
  • 6 Baths
  • 4,272 Sq Ft

  1016 West Rd, Manchester Center, VT 05255

  Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 357-7462

  1016 West Rd, Manchester Center, VT 05255
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  /15

  $115,000

  • Land
  • 2.9 Acres
  • $39,655 per Acre

  Lot 3 Route 11 30, Winhall, VT 05340

  Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6197

  Lot 3 Route 11 30, Winhall, VT 05340
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  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 347-9044

  397 Fern Hill, Dorset, VT 05251
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  /35

  $379,900

  • 4 Beds
  • 2.5 Baths
  • 2,530 Sq Ft

  93 Russett Dr, Bennington, VT 05201

  Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 416-3661

  93 Russett Dr, Bennington, VT 05201
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  /40

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,378 Sq Ft

  61 E Branch Farms Unit 1, Manchester Center, VT 05255

  East Branch Farms is in the most convenient location! This 3 bedroom and 2 and a half bath condo is ready for its next owners. Wood floors on the main level and new granite countertops in the kitchen. Full basement with both interior and exterior access for workshop space or extra storage. Located at the edge of lovely Manchester VT it is privately screened from the road with views of soaring

  

  Alison Cummings

  Cummings & Co

  (802) 300-4136

  61 E Branch Farms Unit 1, Manchester Center, VT 05255
• 

  

  /51

  $1,650,000

  • 3 Beds
  • 2.5 Baths
  • 3,368 Sq Ft

  276 Wilcox Hollow Rd, Sandgate, VT 05250

  Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid

  

  Margretta Fischer

  Wohler Realty Group

  (802) 521-2796

  276 Wilcox Hollow Rd, Sandgate, VT 05250
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  /42

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

  

  Wendy Larson

  Hooscik Realty

  (802) 526-6197

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
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  /36

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  682 E Manchester Rd, Manchester Center, VT 05255

  Welcome to a private Vermont retreat that blends rustic post-and-beam charm with modern versatility. Nestled above the serene Bourne Brook, this property offers the perfect balance of privacy, natural beauty and convenience. The main house exudes warmth and craftmanship, and is complemented by an income producing apartment above the 2 car garage, adding flexibility for extra guests, long term

  

  Christopher Cummings

  Cummings & Co

  (802) 441-7038

  682 E Manchester Rd, Manchester Center, VT 05255
• 

  

  /56

  $1,750,000

  • 6 Beds
  • 3 Baths
  • 3,340 Sq Ft

  215 & 221 Vt Route 30, Dorset, VT 05251

  Two homes, multiple barns and outbuildings on 60 +/- incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain

  

  Margretta Fischer

  Wohler Realty Group

  (802) 944-4482

  215 & 221 Vt Route 30, Dorset, VT 05251
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  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  

  Margretta Fischer

  Wohler Realty Group

  (802) 481-3493

  935 Old Manchester Rd, Peru, VT 05152
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  /43

  $2,300,000

  • Land
  • 60 Acres
  • $38,333 per Acre

  215 Vermont 30, Dorset, VT 05251

  Opportunities are Knocking! Welcome to an extraordinary 60 +/- acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta—location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont’s

  

  Margretta Fischer

  Wohler Realty Group

  (802) 300-4271

  215 Vermont 30, Dorset, VT 05251
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  /60

  $220,000

  • Land
  • 54 Acres
  • $4,074 per Acre

  399 Bard Rd, Bennington, VT 05201

  Escape to your own private sanctuary on this sprawling 54+/- acre wooded retreat in beautiful Bennington, VT. Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond situated entirely within its southeastern boundary, perfect as a future homestead centerpiece. Enjoy easy access via a paved, town-maintained road leading to level

  Curtis Trousdale Preferred Properties

  399 Bard Rd, Bennington, VT 05201
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  /10

  $20,000

  • Land
  • 1.2 Acres
  • $16,667 per Acre

  0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350

  1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

  Community Lands Community Lands

  0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350
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  /38

  $4,975,000

  • 5 Beds
  • 4 Baths
  • 6,998 Sq Ft

  527 Benson Rd, Manchester Center, VT 05255

  Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

  Story Jenks LandVest, Inc/Woodstock

  527 Benson Rd, Manchester Center, VT 05255
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  /59

  $3,475,000

  • 5 Beds
  • 6 Baths
  • 5,905 Sq Ft

  220 Camptown Rd, Manchester Center, VT 05255

  Set high on a hillside overlooking a picturesque horse farm, this exceptional Manchester property captures far-reaching mountain views and covetous privacy. Nearly 39 acres of sweeping lawn and open meadow transition into wooded terrain, with direct access to over 1,000 acres of conserved land leading to Mount Equinox and Myrick Mountain in the Equinox Highlands. Trails on the property and

  Christiane Carroccio TPW Real Estate

  220 Camptown Rd, Manchester Center, VT 05255
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  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard S, East Dorset, VT 05253

  Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

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

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /40

  $795,000

  • 6 Beds
  • 5 Baths
  • 5,689 Sq Ft

  2677 Route 30, Dorset, VT 05251

  Step into the timeless charm of this beautifully preserved Dorset farmhouse, where historic character meets the ease of modern living. Set on 1.79 scenic acres with sweeping mountain views, this inviting six-bedroom home with additional apartment offers space, flexibility, and classic Vermont appeal.A bright and welcoming mudroom greets you upon entry, featuring wide-plank original flooring,

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  2677 Route 30, Dorset, VT 05251
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  /29

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /45

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,575 Sq Ft

  146 Clover Ln, Manchester Center, VT 05255

  Come take a look at this charming Cape-style home set on nearly 4 acres, offering river frontage and beautiful mountain views. Bring your fishing pole or a canoe and head down to the river or relax and enjoy the sunshine on your own private beach as the water flows by.Inside, the home features an open-concept living and dining area, along with a first-floor primary suite for added

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  146 Clover Ln, Manchester Center, VT 05255
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  /41

  $394,000

  • 3 Beds
  • 3 Baths
  • 2,038 Sq Ft

  43 Bergblume Cir, Readsboro, VT 05350

  Outdoor Enthusiasts’ Paradise!Tucked into the hills of southern Vermont, this newer updated, and well-maintained home is built for the buyer who lives for the outdoors and wants space for toys and more. Access to major snowmobiling and ATV trails puts you at the trailhead before your coffee gets cold, while skiing, kayaking, boating, fishing, and hiking are all just minutes away. Deer, bear,

  Pam Tworig Bishop West Real Estate, Inc.

  43 Bergblume Cir, Readsboro, VT 05350
• 

  

  /12

  $865,000

  • 12 Beds
  • 8 Baths
  • 5,568 Sq Ft

  1931 Vermont Route 67 E, Shaftsbury, VT 05262

  Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

  Julie Glover Mahar McCarthy Real Estate

  1931 Vermont Route 67 E, Shaftsbury, VT 05262
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  /42

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,886 Sq Ft

  384 Alden Rd, Arlington, VT 05250

  Are you looking for the perfect home that captures the timeless look and feel of old Vermont—without the wear and tear? This beautifully built retreat offers classic rustic charm with modern construction and comforts throughout.Set against scenic views, this inviting home features cathedral ceilings in the main living area, creating an open and airy atmosphere filled with natural light. The

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  384 Alden Rd, Arlington, VT 05250
• 

  

  /12

  $244,995

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  240 Church St, Shaftsbury, VT 05262

  Ready for its next owner! This charming home offers a great opportunity for anyone looking to put their personal touch on a property with tons of potential. Sitting on an acre-sized lot, there’s plenty of room to expand. Inside, the home needs some TLC—but that’s where the value lies. With the right updates, you can truly bring your vision to life. The layout also provides potential for an in-law

  Derek Greene Derek Greene

  240 Church St, Shaftsbury, VT 05262
• 

  

  /23

  $349,900

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
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  /4

  $18,000

  • Land
  • 1.1 Acres
  • $16,364 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /33

  $1,399,999

  • 6 Beds
  • 4 Baths
  • 3,800 Sq Ft

  121 High Meadow Rd, Winhall, VT 05340

  Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

  Ralph Harvey Listwithfreedom.com

  121 High Meadow Rd, Winhall, VT 05340
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  /17

  $65,000

  • Land
  • 5.6 Acres
  • $11,607 per Acre

  80 Crossover Rd, Bennington, VT 05201

  This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

  Dan Mason Perrott Realty

  80 Crossover Rd, Bennington, VT 05201
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  /8

  $65,000

  • Land
  • 1.24 Acres
  • $52,419 per Acre

  2041 East Rd, Bennington, VT 05201

  Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /60

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  358 Birch Grove, Arlington, VT 05250

  Have you dreamed of a home on a quiet cul-de-sac with over an acre of land and seasonal mountain views? Look no further! Situated on a wooded lot in a very desirable neighborhood, this spacious home has all you need. Flooded with natural light, the large living room includes a gas fireplace, cozy reading nook, and cute sunroom that is perfect for plants. It leads to a wraparound deck, also

  Justine Curry Maple Leaf Realty

  358 Birch Grove, Arlington, VT 05250
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  /39

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1153 King Hill Rd, Readsboro, VT 05350

  This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

  Casey Scott Southern Vermont Realty Group

  1153 King Hill Rd, Readsboro, VT 05350
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  /34

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  760 W Mountain Rd, Shaftsbury, VT 05262

  Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

  Kelley Mccarthy Mahar McCarthy Real Estate

  760 W Mountain Rd, Shaftsbury, VT 05262
• 

  

  /36

  $539,000

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft

  262 Dwyers Camp Rd, Shaftsbury, VT 05262

  Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  262 Dwyers Camp Rd, Shaftsbury, VT 05262
• 

  

  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
• 

  

  /32

  $695,000

  • 5 Beds
  • 3.5 Baths
  • 2,888 Sq Ft

  22 Sylvan Ridge Rd, Winhall, VT 05340

  Renovated Manchester Mountain VT Retreat, located just minutes from Bromley, Stratton and Manchester, your perfect year-round Vermont vacation home awaits. With 3 levels and an entertain room on each, this home is extremely comfortable for large groups to gather and enjoy. The kitchen, dining room, primary en-suite bedroom, and powder room and rear deck are all located on the main level

  Jason Saphire www.HomeZu.com

  22 Sylvan Ridge Rd, Winhall, VT 05340
• 

  

  /45

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  145 Oberdorf Rd, Readsboro, VT 05350

  Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4-bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

  Evan Russell Real Broker LLC

  145 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /31

  $235,000

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  67 Bourn Brook Rd Unit 53, Manchester Center, VT 05255

  Ideally located in the heart of Manchester Vermont, this 2 Bedroom, 1 Bath townhouse is just minutes from Shopping, Dining, Schools, the Town Recreation area which features Walking Paths, Community Pool, Tennis, Pickle Ball, Basketball, and Athletic Fields. On the main level is a very comfortable living area, dining space, and the kitchen, all with hardwood floors. The kitchen has updated

  Robert Sabol Wohler Realty Group

  67 Bourn Brook Rd Unit 53, Manchester Center, VT 05255

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