Bennington County VT Homes for Sale

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  /58

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  27 Broken Pines Dr, Bennington, VT 05201

  Welcome to your peaceful country retreat just over the Bennington town line in Shaftsbury! This 3BR/2BA ranch offers effortless one-level living on a generous 3.5-acre lot surrounded by nature and abundant wildlife. The heart of the home features a modern eat-in kitchen with granite countertops, freshly painted cabinetry and durable vinyl plank flooring throughout, creating a stylish yet

  Vicki Wilson Maple Leaf Realty

  27 Broken Pines Dr, Bennington, VT 05201
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  /3

  $79,900

  • Land
  • 10.1 Acres
  • $7,911 per Acre

  0 Old County Ln, Readsboro, VT 05350

  Escape to the peaceful countryside of Readsboro with this beautiful 10.10-acre parcel offering privacy and natural charm. The land features a blend of level areas, gentle rolling hills, established orchards, and a scenic brook running through the property.Ideal for a primary residence, vacation home, or private retreat, this property provides the perfect setting to build your Vermont getaway.

  Raelene Robinson-Garrow Real Broker LLC

  0 Old County Ln, Readsboro, VT 05350
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  /14

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

  Maximize your time on the snow in this coveted two-bedroom village watch condo. Featuring a spacious, open layout, the interior boasts a classic wood-burning fireplace and a full kitchen perfect for entertaining. Forget the shuttle; enjoy the seamless convenience of a private ski locker and immediate access to both the lifts and the vibrant resort village. A perfect blend of convenience,

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
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  /8

  $1,900,000

  • Land
  • 199 Acres
  • $9,548 per Acre

  00 Vermont 11, Peru, VT 05152

  199 +/- acre parcel in Peru Vermont bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains. The scale of the land, elevation and orientation provide exceptional privacy, consistent natural light and expansive long range mountain vistas. The property offers a rare combination of direct forest access and proximity to

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /20

  $600,000

  • Land
  • 28 Acres
  • $21,429 per Acre

  00 Vermont 11, Peru, VT 05152

  28 +/- acre parcel in Peru Vermont with views of Stratton Mountain, Bromley Mountain and Magic Mountain. Rare east, south and westerly exposure provides consistent natural light and excellent solar orientation throughout the day. Positioned across from Johnny Seesaw’s and minutes to Bromley Market and Bromley Mountain Ski Resort, the property offers privacy with immediate access to dining, skiing

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /33

  $265,000

  • 2 Beds
  • 1 Bath
  • 1,064 Sq Ft

  1758 East Rd, Bennington, VT 05201

  Welcome to this thoughtfully cared-for 2-bedroom, 1-bath ranch located on desirable East Road in Bennington. Offering easy one-level living and meaningful upgrades, this home delivers both practicality and long-term value. Inside, you’ll find a bright and efficient layout featuring an updated kitchen and refreshed bath, along with a recently updated boiler and new energy-efficient mini-split

  Morriah Adams BHG Masiello Brattleboro

  1758 East Rd, Bennington, VT 05201
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  /13

  $649,900

  • 2 Beds
  • 2 Baths
  • 2,250 Sq Ft

  23 Stonewall Ln, Dorset, VT 05251

  Charming Colonial home set on 1.79 acres in the Vintage Village of Dorset. The home offers two bedrooms and one and three-quarters baths, a large living room, a fireplace, and centrally located kitchen. Easy access to downtown Manchester and surrounding ski areas and hiking trails.

  Diana Lynn Harvey Alison McCullough Real Estate

  23 Stonewall Ln, Dorset, VT 05251
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  /46

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,564 Sq Ft

  112 Norton St, Bennington, VT 05201

  Move-in ready 2BR/1.5BA ranch on a sunny 0.27-acre lot offering comfort, updates, and easy living—ideal for first-time buyers or those looking to downsize. This well-maintained home features efficient mini-split systems for year-round comfort, brand-new vinyl plank flooring, and a new 50-year architectural shingle roof installed in 2024 for long-term peace of mind. The fully insulated attached

  Vicki Wilson Maple Leaf Realty

  112 Norton St, Bennington, VT 05201
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  /46

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 6,129 Sq Ft

  1035 Holy Smoke Rd, Shaftsbury, VT 05262

  Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

  Lori Hurley Four Corner Properties LLC

  1035 Holy Smoke Rd, Shaftsbury, VT 05262
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  /40

  $114,900

  • 4 Beds
  • 1 Bath
  • 1,156 Sq Ft

  130 Lincoln St, Bennington, VT 05201

  Convenient location walking distance to downtown Bennington shops and amenities. Spacious eat-in kitchen, formal dining room, and adjoining porch flow perfectly for entertaining. The rustic living room has a beautiful wood ceiling and plenty of windows letting in copious amounts of natural light. The 198' deep backyard is perfect for tossing a ball and enjoying backyard barbeques. Two porches are

  Lisa Friedman Great American Dream Realty

  130 Lincoln St, Bennington, VT 05201
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  /35

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  308 Elm St, Bennington, VT 05201

  Vermont charm meets move-in ready comfort on Elm Street! This inviting 3-bedroom, 2.5-bath Cape offers warm, welcoming spaces throughout. The cozy yet spacious living room features a fireplace — perfect for snowy Vermont evenings — while the generously sized dining room is ideal for hosting holidays and gatherings. The beautifully updated kitchen showcases granite countertops and rich cherry

  Kelley Mccarthy Mahar McCarthy Real Estate

  308 Elm St, Bennington, VT 05201
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  /42

  $540,000

  • 3 Beds
  • 2 Baths
  • 3,196 Sq Ft

  1858 King Hill Rd, Readsboro, VT 05350

  Come see this pristine, newly renovated 3 bedroom, 2 bath home set on 7.58 private acres. The current owner has thoughtfully enhanced the property with numerous upgrades, including fresh exterior paint, an oversized wraparound deck, a poured concrete garage floor, new high efficiency water heater, and wood stove inserts in both the main level and lower level fireplaces. Mini splits provide

  Prema Fitzpatrick Real Broker LLC

  1858 King Hill Rd, Readsboro, VT 05350
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  /41

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  4991 Vt Route 313 W, Arlington, VT 05250

  Nestled in the heart of Vermont’s picturesque Battenkill Valley, this charming three-bedroom, two-bath Cape offers the perfect blend of natural beauty and timeless New England character. Framed by sweeping views of the Green Mountains and just a stone’s throw from the renowned fly-fishing waters of the Battenkill River, this property is an idyllic retreat for outdoor enthusiasts and

  

  Margretta Fischer

  Wohler Realty Group

  (802) 416-4131

  4991 Vt Route 313 W, Arlington, VT 05250
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  /16

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

  Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

  Northshire Sales Group Real Broker LLC

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
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  /39

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

  Mike England Michael England Real Estate

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
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  /30

  $225,000

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

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

  2 bedroom, 1 bath townhouse offering a bright open concept layout across two levels. The main level features comfortable living and dining spaces, in-unit laundry, and hardwood flooring. Upstairs you’ll find two nicely sized bedrooms and a full bath. Ideally located in the heart of Manchester Center, just minutes from shopping, dining, schools, and everyday amenities, with easy access to multiple

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 357-7389

  92 Bourn Brook Rd Unit 67, Manchester Center, VT 05255
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  /11

  $2,425,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,536 Sq Ft

  6 Stone Lodge Rd, Winhall, VT 05340

  SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

  Kim Morgan-Wohler Wohler Realty Group

  6 Stone Lodge Rd, Winhall, VT 05340
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  /33

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 2,813 Sq Ft

  264 French Hollow Rd, Bondville, VT 05340

  Step into this newly constructed 2022 residence offering a rare sense of elevation—both literal and figurative—without sacrificing ease of access. While the home feels perched above it all, it is reached via a gentle sloping driveway, providing everyday convenience alongside breathtaking views. Sweeping, uninterrupted vistas are enjoyed from nearly every room, creating a constant connection to

  Kristin Pirie Winhall Real Estate

  264 French Hollow Rd, Bondville, VT 05340
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  /13

  $17,000

  • Land
  • 1 Acre
  • $17,000 per Acre

  326A Bergabhang Dr, Stamford, VT 05352

  Affordable one-acre lot in Alpenwald Village, offering a charming country setting ideal for a primary residence or vacation retreat. With ample space to design and build, this parcel presents a wonderful opportunity to create the home you’ve always envisioned. The Alpenwald Village HOA fee is $450 annually and covers road maintenance; community guidelines include, but are not limited to, a

  Monique White Deerfield Valley Real Estate

  326A Bergabhang Dr, Stamford, VT 05352
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  /54

  $389,900

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  328 Chester Knoll Dr, Bennington, VT 05201

  Well-maintained 2005 tri-level home offering comfortable, easy living in a desirable residential neighborhood. Features include efficient radiant floor heat, mini-split system for added comfort and new vinyl plank flooring on the lower and main levels. The kitchen is outfitted with attractive cherry cabinets and offers a functional layout for everyday living. Located within a PUD, the HOA covers

  Vicki Wilson Maple Leaf Realty

  328 Chester Knoll Dr, Bennington, VT 05201
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  /38

  $1,095,000

  • 4 Beds
  • 3 Baths
  • 3,252 Sq Ft

  E1 Rock Ridge Rd, Winhall, VT 05155

  Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

  Christine Chovan

  E1 Rock Ridge Rd, Winhall, VT 05155
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  /52

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 4,650 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome to Bromley Village. This spacious 5 bedroom, 5 bath house offers everything you need to ensure the comfort of your group whether it’s large or small. The heart of this home is the magnificent great room with 20 foot ceilings, wood burning fireplace, slate floors, dining area and corner bar. The gourmet kitchen with red cabinets, soapstone counters, and top of the line appliances (Sub

  David Citron RE/MAX Four Seasons

  20 Blackberry Ln, Peru, VT 05152
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  /2

  $125,000

  • Land
  • 1.45 Acres
  • $86,207 per Acre

  L/O River Rd, Winhall, VT 05340

  This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

  Cheyanne Pugliese

  L/O River Rd, Winhall, VT 05340
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  /45

  $1,075,000

  • 13 Beds
  • 12 Baths
  • 8,594 Sq Ft

  2759 Vt Route 11, Peru, VT 05152

  Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2759 Vt Route 11, Peru, VT 05152
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  /60

  $5,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,674 Sq Ft

  1060 Upper Hollow Rd, Dorset, VT 05251

  'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy

  Sunny Breen Josiah Allen Real Estate, Inc.

  1060 Upper Hollow Rd, Dorset, VT 05251
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  /16

  $215,000

  • 1 Bed
  • 1 Bath
  • 616 Sq Ft

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255

  Modern In-Town Living and Fully Renovated Bourn Brook Condo. Experience the best of Manchester Center in this meticulously renovated end-unit at Bourn Brook. Whether you are looking for an affordable primary residence or a sleek "lock-and-leave" weekend getaway, this condo delivers modern style in a prime, walkable location.Interior HighlightsNo detail was spared in this top-to-bottom

  Robin Apps Four Seasons Sotheby's Int'l Realty

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255
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  /23

  $120,000

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  818 Old Depot Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway, vacation rental, or full-time home. While the house is a fixer upper, it has some nice features

  Lisa Friedman Great American Dream Realty

  818 Old Depot Rd, Shaftsbury, VT 05262
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  /37

  $849,000

  • 4 Beds
  • 3 Baths
  • 2,797 Sq Ft

  13 Betty Johnson Ln, Bondville, VT 05340

  Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  13 Betty Johnson Ln, Bondville, VT 05340
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  /31

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
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  /15

  $500,000

  • Land
  • 21.2 Acres
  • $23,585 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  /49

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2092 N Bennington Rd, North Bennington, VT 05257
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  /58

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, 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
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  /50

  $750,000

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

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340

  WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340
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  /49

  $510,000

  • 4 Beds
  • 3 Baths
  • 1,680 Sq Ft

  7 Stratton West Rd Unit 7, Winhall, VT 05340

  This recently renovated 4/5 bedroom Stratton West home is located minutes to Stratton Resort for skiing, golf, and all your recreation activities. The new, custom-built kitchen offers an open layout with beautiful granite countertops. Front and back decks provides places to grill and relax on warm summer nights, or you can cozy up with the Harman pellet stove in the winter months. The first level

  Mike England Michael England Real Estate

  7 Stratton West Rd Unit 7, Winhall, VT 05340
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  /51

  $1,875,000

  • 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
• 

  

  /30

  $349,000

  • 2 Beds
  • 1 Bath
  • 1,845 Sq Ft

  1450 Vermont 8, Readsboro, VT 05350

  Charming Adirondack-style home set on 2.5 private acres, offering a warm, rustic aesthetic with thoughtful updates throughout. The main level features wood floors, an open cathedral ceiling with exposed beams, and a cozy woodstove anchoring the living space. The kitchen is ideal for entertaining with a large bar area, live-edge countertops, and an inviting open layout. An updated bathroom with a

  Kelley Mccarthy Mahar McCarthy Real Estate

  1450 Vermont 8, Readsboro, VT 05350
• 

  

  /25

  $98,999 New Construction

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft

  78 Ethans Way, Bennington, VT 05201

  Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  78 Ethans Way, Bennington, VT 05201
• 

  

  /38

  $375,000

  • Land
  • 1.23 Acres
  • $304,878 per Acre

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

  Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

  Kim Morgan-Wohler Wohler Realty Group

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
• 

  

  /12

  $450,000

  • Land
  • 10.26 Acres
  • $43,860 per Acre

  4.1 Pearl Buck Dr, Winhall, VT 05340

  One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

  Kim Morgan-Wohler Wohler Realty Group

  4.1 Pearl Buck Dr, Winhall, VT 05340

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