Windham County VT Houses for Sale

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  /51

  $915,000

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  33 Carinthia Rd, Dover, VT 05356

  LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

  Jacki Murano Southern Vermont Realty Group

  33 Carinthia Rd, Dover, VT 05356
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  /55

  $859,000

  • 6 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  5825 Vermont 30, Townshend, VT 05353

  6+ bed, 5 bath 21± Acre Equestrian Estate in West Townshend VT Distinctive property combines the charm of a private equestrian estate w/tastefully finished and versatile living space & top horse facilities. On ~21 acres, including a 3-bed main home plus attached 1-bed accessory unit—ideal for guests, staff, or flex living. Metal roof, drilled well, whole-house generator. Main Barn: 8 box stalls,

  Jacki Murano Southern Vermont Realty Group

  5825 Vermont 30, Townshend, VT 05353
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  /60

  $429,000

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  26 N Wind Rd, Wilmington, VT 05363

  Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

  Rich Caplan Deerfield Valley Real Estate

  26 N Wind Rd, Wilmington, VT 05363
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  /55

  $699,900

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  300 Route 121 E, Grafton, VT 05146

  Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park-like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll find a spacious eat-in kitchen with abundant counter space and

  Gary Coger Four Seasons Sotheby's Int'l Realty

  300 Route 121 E, Grafton, VT 05146
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  /60

  $749,000

  • 4 Beds
  • 4 Baths
  • 2,964 Sq Ft

  16 Rock Split Way, Wilmington, VT 05363

  Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings,

  Chad Lackey Deerfield Valley Real Estate

  16 Rock Split Way, Wilmington, VT 05363
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  /16

  $1,400,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,844 Sq Ft

  286 Coldbrook Rd, Wilmington, VT 05363

  This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

  Melissa Nebelski Real Broker LLC

  286 Coldbrook Rd, Wilmington, VT 05363
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  /55

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1 Frog Hollow, Wilmington, VT 05363

  Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

  Rich Caplan Deerfield Valley Real Estate

  1 Frog Hollow, Wilmington, VT 05363
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  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
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  /39

  $1,750,000

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
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  /30

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
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  /32

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,326 Sq Ft

  103 Sherwood Cir, West Brattleboro, VT 05301

  Welcome Home!! This sweet little cape is move in ready and is just what you are looking for! Enter into the mudroom with half bath, continue to the bright open kitchen and dining area, living room, and first floor bedroom. Upstairs are two generous bedrooms and a full bath. The walk out basement offers fantastic expansion potential, family room?? Exercise room?? You name it! The back deck is

  Rebecca Seymour Brattleboro Area Realty

  103 Sherwood Cir, West Brattleboro, VT 05301
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  /54

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,666 Sq Ft

  3 Overbrook Dr Unit Outlook, Dover, VT 05356

  STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Set against the backdrop of Mount Snow, this just-completed luxury single-family home offers the perfect blend of modern design and spacious living. Located in the base area of the Mount Snow Resort, The OutLook at Mount Snow offers the perfect mix of mountain modern luxury and the ultimate convenience. This home features an open

  John Redd Skihome Realty

  3 Overbrook Dr Unit Outlook, Dover, VT 05356
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  /33

  $349,000

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

  29 Pikes Falls Rd, Jamaica, VT 05343

  MOTIVATED SELLERS! Bring your offers! Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living.Ideally situated just 15 minutes from Stratton Mountain and 25 minutes

  Carrie Mathews Winhall Real Estate

  29 Pikes Falls Rd, Jamaica, VT 05343
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  /27

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,599 Sq Ft

  175 Sak Rd, Vernon, VT 05354

  This is it!!!! One level living with a bonus room and bath in the lower level for a bit of get away family room living. Perfect for downsizing or just beginning. Professional builder has taken this home to a brand new level, adding a living room with vaulted ceilings, wall of windows and a slider to a lovely back deck. The lot is level and sunny enough for a garden, and crosses the Sak Brook with

  Christine Lewis Brattleboro Area Realty

  175 Sak Rd, Vernon, VT 05354
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  /18

  $220,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  97 Westminster Rd, Putney, VT 05346

  Sought after location in the Southeastern town of Putney, Vermont. This1900's 2 bedroom cape style home on a .91 acre has sidewalk access to the Village and local amenities. With 2 outbuildings for storage, private driveway, mature garden plantings and location, this property is an opportunity.

  Jody Graves Berkley & Veller Greenwood Country

  97 Westminster Rd, Putney, VT 05346
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  /17

  $339,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  274 Vermont Route 100, Dover, VT 05356

  This storybook log cabin is the kind of place you picture when you think "perfect Vermont getaway." Tucked in the middle of town, everything you want is right here, and Mount Snow resort is just over a mile away. Whether you’re chasing powder days, snowmobile/summer trails, or just a cozy escape, this spot makes it easy to do it ALL. On the MOOver public transportation route to get you around

  Prema Fitzpatrick Real Broker LLC

  274 Vermont Route 100, Dover, VT 05356
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  /41

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
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  /21

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  28 Summit Meadows Cir, Dover, VT 05356

  Lovely updated contemporary chalet nestled at the base of the Dover Hills in the village of Dover, just a short drive from the Mount Snow ski resort. This convenient location affords the privacy of a home, but much easier access, and proximity to amenities, dining, shopping, and more. At the end of a loop, this home sits on a private and quiet parcel with a nice buffer of trees, level lawn, stone

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Summit Meadows Cir, Dover, VT 05356
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  /50

  $2,099,000

  • 5 Beds
  • 5.5 Baths
  • 5,235 Sq Ft

  6 Trail View Ln, Dover, VT 05356

  Enjoy stunning views, privacy, and luxury, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, tennis courts, game room, on site management company, and direct shuttle service between your

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Trail View Ln, Dover, VT 05356
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  /54

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
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  /30

  $399,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation—from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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  /12

  $399,000 New Construction

  • 4 Beds
  • 2 Baths
  • 3,700 Sq Ft

  442 Mcmillan Rd, Whitingham, VT 05342

  New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels.

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
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  /35

  $399,900

  • 4 Beds
  • 3 Baths
  • 4,488 Sq Ft

  35 School St, Bellows Falls, VT 05101

  This single-family Victorian home located in the village of Bellows Falls has lots of space for family and friends! Four bedrooms, three full baths, a second-floor laundry room, two kitchens, two living rooms, three bonus rooms, and even an area for a potential apartment above the one-car garage! The open-concept updated kitchen/living room offer plenty of storage and seating for everyone and

  Heather Gleim CENTURY 21 North East

  35 School St, Bellows Falls, VT 05101
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  /20

  $345,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  5 Vancor Dr, Town of Rockingham, VT 05154

  Excellent! Light, Bright, Tidy! This home has it all rolled up in one nice package. Located on the outskirts (strolling distance) of the very cool village of Saxton's River, with Vermont Academy, dining, village market and, of course, the Saxton's river! Besides, the very special, level lot with a sweet view, you have curb appeal you will want to come home to! The hang out, living area is

  Christine Lewis Brattleboro Area Realty

  5 Vancor Dr, Town of Rockingham, VT 05154
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  /20

  $330,000

  • 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. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax

  Ginny Read Read Realty LTD

  3730 Route 100, Wardsboro, VT 05355
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  /60

  $549,000

  • 2 Beds
  • 2 Baths
  • 2,016 Sq Ft

  35 Upper Bartonsville Rd, Chester, VT 05143

  Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

  Erin Kendall EXP Realty

  35 Upper Bartonsville Rd, Chester, VT 05143
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  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
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  /39

  $295,000

  • 4 Beds
  • 1 Bath
  • 1,248 Sq Ft

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301

  Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

  Steve Schoppmeyer BHG Masiello Brattleboro

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301
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  /48

  $644,000

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  774 Stratton Arlington Rd, Stratton, VT 05360

  Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  774 Stratton Arlington Rd, Stratton, VT 05360
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  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345
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  /38

  $499,000

  • 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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  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /23

  $3,500,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 7,000 Sq Ft

  29 Mountain Ridge Dr, Wilmington, VT 05363

  The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29 Mountain Ridge Dr, Wilmington, VT 05363
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  /27

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,306 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  32 Old Town Rd, Dover, VT 05356
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  /54

  $999,000

  • 4 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, rolling meadows, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes to town,

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
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  /36

  $382,000

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
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  /27

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  34 Main St, Wardsboro, VT 05355

  Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  34 Main St, Wardsboro, VT 05355
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  /44

  $279,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  10 King St, Bellows Falls, VT 05101

  Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

  Floyd Amidon Maple Leaf Realty

  10 King St, Bellows Falls, VT 05101

Showing Results 81 - 120, Page 3 of 4