Windham County VT Houses for Sale

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  /42

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency.This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
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  /59

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  732 Under the Mountain Rd, South Londonderry, VT 05155

  Welcome to "Fairmount," a beautiful historic home with unrivaled panoramic views and an extraordinary blend of history, grace, and quintessential Vermont living on 42 acres. Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse seamlessly merges historic charm with modern sensibility. Exposed beams, wide plank floors, and architectural character remain, while the thoughtful

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
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  /53

  $1,550,000

  • 4 Beds
  • 4.5 Baths
  • 4,241 Sq Ft

  207 Boynton Rd, Londonderry, VT 05148

  Perched on 12.70 pristine acres, this exceptional residence offers the perfect blend of refined comfort & serene seclusion. Set on a private rise w/ sweeping views, the property captures the quiet majesty of all four seasons. A tranquil pond reflects the ever-changing sky, inviting quiet mornings on the expansive deck, a coffee in hand or peaceful evenings listening to nature under the stars.

  Kim Morgan-Wohler Wohler Realty Group

  207 Boynton Rd, Londonderry, VT 05148
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  /37

  $739,000

  • 3 Beds
  • 4 Baths
  • 3,352 Sq Ft

  183 Vacation Lodge Rd, Londonderry, VT 05148

  Welcome to your mountain oasis tucked away in the scenic hills of Londonderry, Vermont. This contemporary 3-bedroom, 4-bathroom home is designed for comfort, entertaining, and enjoying every season. Whether you're looking for a relaxing retreat, a rental income opportunity, or a full-time family compound, this property offers something special for everyone.Step into a space that blends

  Brian Hill Remax Summit

  183 Vacation Lodge Rd, Londonderry, VT 05148
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  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,551 Sq Ft

  1247 Cole Pond Rd, Jamaica, VT 05343

  A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1247 Cole Pond Rd, Jamaica, VT 05343
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  /53

  $989,000

  • 5 Beds
  • 6 Baths
  • 5,600 Sq Ft

  10 & 14 Wiswall Hill Rd, Newfane, VT 05345

  Welcome to 2 exceptional homes set on 8 acres of meadows w/ stone walls, woodland, and frontage on the Smith Brook. The contemporary barn conversion was architect designed & boasts an impressive Great Room with soaring ceilings, exposed post & beams, and gas fireplace. Patio doors open onto a huge deck, offering views of the in-ground pool and serene surroundings. The dining room, crafted from

  Robert Doyle Berkley & Veller Greenwood Country

  10 & 14 Wiswall Hill Rd, Newfane, VT 05345
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  /41

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 4,219 Sq Ft

  5 N Main St, Wilmington, VT 05363

  Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

  Morriah Adams BHG Masiello Brattleboro

  5 N Main St, Wilmington, VT 05363
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  /59

  $529,000

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

  30 Big Bend Loop, Wilmington, VT 05363

  Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

  Chad Lackey Deerfield Valley Real Estate

  30 Big Bend Loop, Wilmington, VT 05363
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  /41

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,612 Sq Ft

  178 Parsons Rd, Wilmington, VT 05363

  Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  178 Parsons Rd, Wilmington, VT 05363
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  /38

  $520,000

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft

  829 Pennel Hill Rd, Halifax, VT 05342

  Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

  Megan Quinn Southern Vermont Realty Group

  829 Pennel Hill Rd, Halifax, VT 05342
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  /9

  $430,000

  • 7 Beds
  • 4 Baths
  • 3,551 Sq Ft

  1950 N Main St, Londonderry, VT 05148

  PRICE REDUCTION! IT IS possible to Live rent or mortgage free!!! And HERE it is.This is a 3 unit multi-family, fully rented/money making property now..Live in one and let the other two pay your bills.. Or, use your imagination, create your vision of what this premier location could be. Zoned BOTH commercial AND residential.. this property could be a fabulous restaurant with rivers edge al fresco

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
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  /45

  $265,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  121 Happy Haven Rd, Wilmington, VT 05363

  This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  121 Happy Haven Rd, Wilmington, VT 05363
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  /47

  $899,000

  • 2 Beds
  • 4 Baths
  • 4,210 Sq Ft

  13 Kimball Hill, Putney, VT 05346

  Bring Your Business Home. This beautifully restored former 1859 Masons Hall has been carefully transformed into a gracious home. Soaring ceilings, period correct 6ft 6/6 windows and original architectural detail attest to the early Italianate Period and the heyday of the ever-so-quaint village of Putney. The current owner has transformed the 1,880sf first floor into a Pilates studio, kitchen and

  Dan Normandeau Berkley & Veller Greenwood Country

  13 Kimball Hill, Putney, VT 05346
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  /28

  $520,000

  • 6 Beds
  • 3.5 Baths
  • 2,766 Sq Ft

  624 Boyd Hill Rd, Wilmington, VT 05363

  Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s

  Jason Saphire www.HomeZu.com

  624 Boyd Hill Rd, Wilmington, VT 05363
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  /59

  $675,000

  • 4 Beds
  • 2 Baths
  • 2,540 Sq Ft

  42 View Rd, Wilmington, VT 05363

  Welcome to your turnkey Vermont chalet in the heart of Chimney Hill. Situated on a rare double lot, this spacious 6-bedroom, 3-bath mountain home offers approximately 2700 square feet* of finished living space including a heated oversized garage with a fully finished bonus level ideal for guests, hobbies, or remote work. Vaulted pine ceilings, a central skylight, and a wood-burning brick

  Nick Sicard EXP Realty

  42 View Rd, Wilmington, VT 05363
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  /33

  $425,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360

  Excellent opportunity to be close to everything Vermont has to offer and still feel secluded. This off grid efficient home is so easy to live in, get to and enjoy. IF you'd like to be on grid you're only about 7 power poles away. This offering is for currently combined 2 buildable lots which were subdivided many years ago. There is wonderful access to the woods for all activities. You can

  Steve Goldfarb Deerfield Valley Real Estate

  6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
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  /23

  $349,000

  • 2 Beds
  • 1 Bath
  • 941 Sq Ft

  57 Hartley Hill Rd S, Putney, VT 05346

  NEW ROOF! This charmingly restored 1820's brick, former one-room schoolhouse has been meticulously expanded to include two bedrooms, a kitchen and full bathroom, and sits on a tranquil 5-acre lot with a mostly open, old pasture. The property retains its historical charm with exposed hand-hewn beams in the former schoolhouse that now serves as the living/dining area. Ideal for a cozy primary

  Dan Normandeau Berkley & Veller Greenwood Country

  57 Hartley Hill Rd S, Putney, VT 05346
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  /20

  $350,000

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  3730 Route 100, Wardsboro, VT 05355

  Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers.

  Ginny Read Read Realty LTD

  3730 Route 100, Wardsboro, VT 05355
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  /60

  $639,000

  • 5 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  673 Route 121 E, Grafton, VT 05146

  Step into a classic Vermont farmhouse from the 1830s, built by a successful mill owner and loved by its current stewards for over fifty years. Minutes from the center of charming Grafton and only thirty minutes from Okemo, this beautiful property offers wide, level lawns and sits on 45 acres of untouched woodland in the hills behind—never logged and fully unencumbered. Inside, the original

  Keri Cole Williamson Group Sothebys Intl. Realty

  673 Route 121 E, Grafton, VT 05146
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  /34

  $189,900

  • 3 Beds
  • 1 Bath
  • 1,824 Sq Ft

  14 Cherry Hill St, Bellows Falls, VT 05101

  Located in the heart of Bellows Falls, Vermont, this charming 1880's home showcases classic 19th-century architecture. Set on a 0.30+/-acre lot, the property includes three bedrooms and one full bathroom. The open concept living and dining areas provide a welcoming space for gatherings, while the adjoining family room offers extra room for an office or flexible use. The full bathroom is

  Rob Weltz Barrett & Valley Assoc. Inc

  14 Cherry Hill St, Bellows Falls, VT 05101
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  /18

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  3 Mill Rd, West Dover, VT 05356

  When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 4 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large living room and updated gas fireplace on brick hearth, direct views of

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3 Mill Rd, West Dover, VT 05356
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  /58

  $586,000

  • 4 Beds
  • 2 Baths
  • 3,090 Sq Ft

  301 Maple St, Brattleboro, VT 05301

  This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home,

  Christine Lewis Brattleboro Area Realty

  301 Maple St, Brattleboro, VT 05301
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  /31

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,338 Sq Ft

  2779 Pikes Falls Rd, Jamaica, VT 05343

  Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

  Carrie Mathews Winhall Real Estate

  2779 Pikes Falls Rd, Jamaica, VT 05343
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  /39

  $415,000

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  6795 Vt Route 100, Londonderry, VT 05148

  Charming Property with Endless Possibilities in Southern VermontNestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful Quilt Shop, this property presents an exceptional opportunity for a variety of uses – whether you’re looking to return it to a spacious home with

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  6795 Vt Route 100, Londonderry, VT 05148
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  /47

  $999,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  151 Holland Rd, Dover, VT 05341

  An outdoor enthusiast’s dream retreat! This breathtaking 92.6-acre Vermont sanctuary is a paradise for nature lovers, equestrians, and adventurers alike. The property features rambling stone walls, lush gardens, cherry trees, blueberry bushes, rolling pastures, woodlands, babbling brooks, a serene pond, and miles of scenic trails. The charming, open-concept, four-bedroom Cape includes a

  Patrice Schneider Southern Vermont Realty Group

  151 Holland Rd, Dover, VT 05341
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  /32

  $499,000

  • 7 Beds
  • 5 Baths
  • 3,518 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  This spacious home is located near Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers Four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
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  /28

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  47 Ives Rd, Wilmington, VT 05363

  Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

  Adam Palmiter Berkley & Veller Greenwood/Dover

  47 Ives Rd, Wilmington, VT 05363
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  /48

  $899,000

  • 4 Beds
  • 4 Baths
  • 3,691 Sq Ft

  42 Airport Rd, Shaftsbury, VT 05262

  Welcome to this exquisite post and beam timber frame home, nestled in a prime location just moments from the Mount Snow Ski Resort and Mount Snow Golf Course. This remarkable 4-bedroom, 4-bathroom home blends rustic charm with modern luxury, offering an unparalleled mountain retreat perfect for both relaxation and adventure. As you step inside, you’ll be greeted by soaring ceilings and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
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  /51

  $879,900

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  7 Yodeling Ln, West Dover, VT 05356

  Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

  Richard Caplan Deerfield Valley Real Estate

  7 Yodeling Ln, West Dover, VT 05356
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  /60

  $4,495,500

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
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  /34

  $374,000

  • 5 Beds
  • 2 Baths
  • 2,736 Sq Ft

  5100 Vermont Route 100, Wardsboro, VT 05355

  Nestled between the renowned Mount Snow and Stratton Mountain, this completely remodeled late 19th-century Colonial offers the perfect blend of historic charm and modern comfort. Meticulously renovated, the home has been torn down to the studs and reimagined with no detail overlooked. With all new windows, insulation, electrical, and plumbing, every inch of this home has been looked after with

  Mike Masters Four Seasons Sotheby's Int'l Realty

  5100 Vermont Route 100, Wardsboro, VT 05355
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  /55

  $589,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,438 Sq Ft

  456 Poverty Row, Whitingham, VT 05361

  Lovely country setting on Poverty Row, a road name steeped in history, this builder’s home showcases quality craftsmanship and thoughtful design throughout. Set on 2.66 beautifully manicured acres with wild blueberry bushes and apple trees. Located on a paved public road, this property is less than five minutes from Lake Sadawga and Harriman Reservoir—perfect for boating, kayaking, and swimming.

  Erica Reynolds Southern Vermont Realty Group

  456 Poverty Row, Whitingham, VT 05361
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  /26

  $650,000

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Owner will consider offers. Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
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  /60

  $1,195,000

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

  1845 Hatch School Rd, Brattleboro, VT 05301

  Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

  Richard Caplan Deerfield Valley Real Estate

  1845 Hatch School Rd, Brattleboro, VT 05301
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  /37

  $1,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,965 Sq Ft

  26 Springhill Rd, Dover, VT 05301

  This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Springhill Rd, Dover, VT 05301
• 

  

  /28

  $895,000

  • 4 Beds
  • 3 Baths
  • 2,546 Sq Ft

  19 Village Rd E, Wilmington, VT 05363

  Here is a chance to own a home directly across the street from the private Hermitage Ski Club with easy access to the resort, snowmobile trails, the Mount Snow ski resort, nearby country villages for shopping and dining, and gorgeous area lakes. This lovely renovated chalet sits on a level with ample parking thanks to a circular driveway, winter exposure to Haystack Mountain Peak, a shed for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  19 Village Rd E, Wilmington, VT 05363
• 

  

  /24

  $570,000

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  15 Mill Rd, Dover, VT 05356

  What a location! MOOver shuttle service to the ski mountain yet a nice private home with a backyard and private deck, as well as views of the mountain. Direct snowmobile access and a drive out shed as well. Inside you are treated to a vaulted great room with wood burning brick fireplace and custom glass and metal screen, large newly replaced windows throughout with tremendous natural light, a

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Mill Rd, Dover, VT 05356
• 

  

  /43

  $2,000,000

  • 6 Beds
  • 4.5 Baths
  • 4,950 Sq Ft

  43 Upton Rd, Dover, VT 05356

  The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43 Upton Rd, Dover, VT 05356
• 

  

  /20

  $215,000

  • 3 Beds
  • 1 Bath
  • 636 Sq Ft

  30 Water St, Jamaica, VT 05343

  Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a

  Daire Gibney Barrett and Valley Associates Inc.

  30 Water St, Jamaica, VT 05343

Showing Results 161 - 200, Page 5 of 6