Windham County VT Houses for Sale

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  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  2117 Pine Banks Rd, Putney, VT 05346

  Set off a country road, this renovated home offers a contemporary interior featuring an open concept kitchen, dining, and living spaces. All of these spaces are bright and welcoming and have engineered hardwood floors. The kitchen is well thought out with multiple workstations and plenty of cabinets and countertop space. The bedrooms have new carpeting and ample closet space. You'll be warm in

  Bill Hickok Berkley & Veller Greenwood Country

  2117 Pine Banks Rd, Putney, VT 05346
• 

  

  

  /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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  /54

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 3,654 Sq Ft

  201 Chester Rd, Grafton, VT 05146

  Meticulously maintained and thoughtfully designed, this three-bedroom, three-bath home offers the perfect balance of comfort, functionality, and classic Vermont charm. Set on a picturesque parcel with stunning long-range views, the property is surrounded by mature trees, a small pond, established gardens, and simple, easy-to-maintain landscaping that enhances the natural beauty of the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  201 Chester Rd, Grafton, VT 05146
• 

  

  

  /59

  $845,000

  • 4 Beds
  • 2 Baths
  • 2,613 Sq Ft

  170 Townshend Rd, Grafton, VT 05146

  This handsome turn-key property is available sooner than one might expect! Due to changing life developments, the owners are offering their beloved Vermont home for sale. Not long ago, the 19th century Chapman House underwent a full renovation, including a stunning new kitchen and updated baths. The kitchen features marble countertops, glass-front backlit cabinetry, a deep farmhouse sink,

  Jessica Landers Barrett and Valley Associates Inc.

  170 Townshend Rd, Grafton, VT 05146
• 

  

  

  /46

  $774,000

  • 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
• 

  

  /35

  $799,000

  • 5 Beds
  • 3 Baths
  • 2,070 Sq Ft

  24 Snow Vidda Loop, Dover, VT 05356

  Mount Snow Retreat – Walk to the Slopes!Experience the ultimate Vermont mountain getaway in this spacious, fully furnished home, ideally located within walking distance to the Mount Snow slopes. Perfect for large families, groups, or as a vacation retreat, this inviting property features 5 bedrooms and 3 bathrooms, offering plenty of space for everyone.The open-concept living and dining

  Lisa Mirando Deerfield Valley Real Estate

  24 Snow Vidda Loop, Dover, VT 05356
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  /60

  $455,000

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  2 Wood Lot Ln Unit C-215, Wilmington, VT 05363

  Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More

  Sigrid Pickering Chimney Hill Realty

  2 Wood Lot Ln Unit C-215, Wilmington, VT 05363
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  /51

  $1,990,000

  $109K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 7,190 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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  /44

  $1,475,000

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  691 Black Bear Rd, Jamaica, VT 05343

  A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying

  Carrie Mathews Winhall Real Estate

  691 Black Bear Rd, Jamaica, VT 05343
• 

  

  /40

  $199,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  253 Farnsworth Cir, Putney, VT 05346

  Welcome to 253 Farnsworth Circle in Westminster, VT—a property with beautiful views and plenty of potential to make it your own. The home has already seen several meaningful updates, including a newer metal roof, a refreshed kitchen with new cabinets and countertops, and newer appliances, giving you a great head start on improvements. Step outside onto the spacious deck, the perfect place to

  Kelsey Malloy Keller Williams Realty Metro-Keene

  253 Farnsworth Cir, Putney, VT 05346
• 

  

  /60

  $344,900

  $4K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft

  90 Wilsons Woods Rd, Brattleboro, VT 05301

  Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient

  Sally Fegley BHG Masiello Brattleboro

  90 Wilsons Woods Rd, Brattleboro, VT 05301
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  /33

  $599,000

  $26K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355
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  /16

  $260,000

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  319 River Rd S, Putney, VT 05346

  Looking for the simple life in tiny home living, or maybe just a good basecamp to explore the outdoors? Look no further! This unique property is conveniently located just a couple miles outside the bucolic village of Putney off a main road, with easy access to I-91. With 33 acres of rolling woods and local valley views there's plenty of land to explore and play with, while the cozy little home

  Courtney Doubleday EXP Realty

  319 River Rd S, Putney, VT 05346
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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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  /36

  $325,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,216 Sq Ft

  6 Sycamore St, Brattleboro, VT 05301

  Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  6 Sycamore St, Brattleboro, VT 05301
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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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  /30

  $334,000

  $65K PRICE DROP

  • 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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  /59

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,245 Sq Ft

  442 Josh Rd, Brattleboro, VT 05301

  These spectacular 64 acres are located in one of the area's most romantically pastoral settings with open fields offering a mesmerizing view of Mount Monadnock, all of which is protected by a view easement. Set back at the end of a quiet dirt road and lined by stone walls, with boundary points marked by white quartz boulders, this renovated 1825 post-and-beam farmhouse combines classic

  Neil Goldberg Brattleboro Area Realty

  442 Josh Rd, Brattleboro, VT 05301
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  /44

  $429,000

  $66K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Now Offered at $429,000 – Exceptional Value Near Mount Snow & Stratton. Classic Vermont Home with Stunning Hilltop Views – Minutes from Mount Snow & Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout

  Donald Koelsch Deerfield Valley Real Estate

  137 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /36

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,427 Sq Ft

  95 Hemlock Dr, Londonderry, VT 05148

  The smell of woodsmoke on a crisp alpine afternoon, the quiet crunch of fresh powder underfoot, and the sense that the rest of the world has dropped away—this is the reality waiting at the top of Powder Mill Ridge. Tucked into three acres of private Vermont forest, this contemporary retreat is designed less like a standard house and more like a basecamp for a life well-lived.Winters mean

  Robin Apps Four Seasons Sotheby's Int'l Realty

  95 Hemlock Dr, Londonderry, VT 05148
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  /12

  $349,000

  New Construction $120K PRICE DROP

  • 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

  $25K PRICE DROP

  • 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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  /60

  $2,290,000

  • 5 Beds
  • 9 Baths
  • 4,400 Sq Ft

  634 Lower Dover Rd, Marlboro, VT 05301

  Discover a once-in-a-generation opportunity to own an extraordinary 745± acre estate in the heart of Southern Vermont. Steeped in centuries of history yet thoughtfully updated for modern living, this remarkable property combines unmatched natural beauty, recreational opportunities, and agricultural potential. The diverse landscape features expansive open fields, mature woodlands, pristine

  Michael Purcell Berkley & Veller Greenwood/Dover

  634 Lower Dover Rd, Marlboro, VT 05301
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  /20

  $330,000

  $120K PRICE DROP

  • 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

  $6,898,000

  New Construction

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

  88 Mann Rd, Wilmington, VT 05363

  A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At

  Rich Caplan Deerfield Valley Real Estate

  88 Mann Rd, Wilmington, VT 05363
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  /11

  $149,000

  • 1 Bed
  • 1 Bath
  • 128 Sq Ft

  1 N Ridge Rd, Town of Rockingham, VT 05101

  Tiny home living in a big way! Enjoy the conveniences of public sewer and water on a quiet plot of land close to I-91 and five minutes to the Amtrack station. This property is well cared for and maintained. All you need to do is either move in or start renting it out for extra income. This adorable home generates over $20,000 per year as an Airbnb, or you can get up to $1500/mo in long term

  Amanda Cota The Thomas Group of Northern New England, LLC

  1 N Ridge Rd, Town of Rockingham, VT 05101
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  /32

  $469,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  /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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  /33

  $1,650,000

  • 5 Beds
  • 2.5 Baths
  • 4,443 Sq Ft

  874 Middletown Rd, Grafton, VT 05146

  Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions.

  Story Jenks LandVest, Inc/Woodstock

  874 Middletown Rd, Grafton, VT 05146
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  /48

  $629,000

  $15K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /40

  $419,000

  • 3 Beds
  • 1.5 Baths
  • 1,908 Sq Ft

  1408 Hatch School Rd, Brattleboro, VT 05301

  This lovely New England cape is situated on 11 acres, surrounded by beautiful, level land and abundant wildlife. A charming wildlife pond is tucked behind the home, accompanied by a clearing for breathtaking nature scenes. The home has been lovingly cared for by the same family since it was built. Boasting granite countertops and spacious cabinets, the kitchen is well equipped. Two eating areas

  Monica Sumner BHG Masiello Brattleboro

  1408 Hatch School Rd, Brattleboro, VT 05301
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  /41

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft

  200 Riverdale Rd, Townshend, VT 05353

  This classic Federal-style brick home blends historic character with thoughtful modern updates, offering a lifestyle that feels both grounded and effortlessly comfortable. Set on a dead-end road, the property enjoys the rare balance of peaceful country living and everyday convenience, all within moments of the local store, hospital, pharmacy, bank, and neighboring homes. Inside, you will be

  Lee Brown Four Seasons Sotheby's Int'l Realty

  200 Riverdale Rd, Townshend, VT 05353
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  /37

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
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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
• 

  

  /28

  $325,000

  $60K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft

  1644 Upper Dummerston Rd, Dummerston, VT 05301

  Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern with lots of counter top for the bakers and cookie makers, The laundry lives next to the kitchen and there is a second bath for visitors and guests. The sweet spot is the huge living room with a wood stove insert in the lovely fireplace. Mini-splits are already up and running for help with both heating and

  Christine Lewis Brattleboro Area Realty

  1644 Upper Dummerston Rd, Dummerston, VT 05301
• 

  

  /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
• 

  

  /29

  $349,000

  $31K PRICE DROP

  • 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
• 

  

  /55

  $399,000

  $19K PRICE DROP

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

  6 Outer Limits Ln, Wilmington, VT 05363

  Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home

  Donna Brown Skihome Realty

  6 Outer Limits Ln, Wilmington, VT 05363
• 

  

  /49

  $575,000

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

  8 Deer Run, Wilmington, VT 05363

  Located in the desirable Chimney Hill community, this beautifully maintained 4 bedroom, 4 bath home offers the perfect combination of comfort, convenience, and year-round recreation. Designed for gathering and relaxing, the open-concept floor plan features vaulted ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas. A cozy gas fireplace creates a warm

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  8 Deer Run, Wilmington, VT 05363

Showing Results 161 - 200, Page 5 of 6