Windham County VT Houses for Sale

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  /44

  $1,295,000

  $205K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,099 Sq Ft

  314 Putnam State Forest Rd, Grafton, VT 05146

  Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside.At the heart of the home is

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  314 Putnam State Forest Rd, Grafton, VT 05146
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  /35

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  7 Lightning Ledge Way, Wilmington, VT 05363

  Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  7 Lightning Ledge Way, Wilmington, VT 05363
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  /41

  $1,498,500

  $252K PRICE DROP

  • 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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  /48

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
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  /27

  $289,000

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  45 Kopkind Rd, Guilford, VT 05301

  Tucked into a peaceful, wooded setting on 2.1 acres in Guilford, just over the Massachusetts border, this cozy 2-bedroom, 1-bath home offers simple Vermont living with plenty of charm. Designed for convenient one-level living, the home features a back deck overlooking the yard surrounded by the quiet of the woods. Several recent improvements add to the home’s comfort and practicality, including a

  Neil Goldberg Brattleboro Area Realty

  45 Kopkind Rd, Guilford, VT 05301
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  /14

  $275,000

  • 1,200 Sq Ft

  752 Butternut Rd, Guilford, VT 05301

  A perfect start! Well, power and driveway are all installed & septic design is available. The building constructed on slab, mostly finished surfaces, cathedral ceiling in the "living room". The interior is already sectioned into 4 rooms, waiting for kitchen and bath fixtures. Seller has plans for a one or 2 unit home build out. Sitting near the end of a quiet country road in no zoning Guilford,

  Christine Lewis Brattleboro Area Realty

  752 Butternut Rd, Guilford, VT 05301
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  /31

  $425,000

  $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  53 Sugar House Rd, West Dover, VT 05356

  Just minutes from Mount Snow, this contemporary chalet offers approximately 3,000 square feet of finished living space and easy access to Southern Vermont's year-round recreation.A cathedral ceiling, floor-to-ceiling windows, abundant natural light, hardwood floors, and a wood-burning fireplace create a warm and inviting atmosphere. The flexible floor plan offers ample space for

  Melissa Nebelski Real Broker LLC

  53 Sugar House Rd, West Dover, VT 05356
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  /31

  $319,000

  $20K PRICE DROP

  • 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
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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
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  /59

  $775,000

  $70K PRICE DROP

  • 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
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  /35

  $749,000

  $50K PRICE DROP

  • 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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  /55

  $550,000

  • 3 Beds
  • 5 Baths
  • 5,046 Sq Ft

  13 Brookside Ln, Newfane, VT 05345

  Beautiful Cape style home nestled in a private country setting, surrounded by mature trees in desirable Newfane and just a short drive to skiing, hiking and other outdoor recreation. Offering exceptional flexibility, the property features an in-law apartment in addition to a separate living quarter, both are currently generating rental income, ideal for multigenerational living, extended family,

  Kerry Mulverhill

  13 Brookside Ln, Newfane, VT 05345
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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
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  /45

  $1,625,000

  • 15 Beds
  • 10 Baths
  • 12,845 Sq Ft

  4 Court St, Newfane, VT 05345

  A rare offering on the Newfane village green: a Federal-style inn dating to 1787, set beside the Windham County Courthouse along VT Route 30 in one of New England's most photographed villages. The property combines eight guest accommodations (a mix of multi-room suites and private rooms, each with a private bath) with a three-bedroom, two-bath owner's residence featuring its own full kitchen and

  Eben Viens Berkley & Veller Greenwood Country

  4 Court St, Newfane, VT 05345
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  /33

  $475,000

  $150K 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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  /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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  /25

  $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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  /49

  $399,000

  $96K PRICE DROP

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

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Now Offered at $399,000! 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 Pond,

  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

  $324,000

  New Construction $145K 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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  /41

  $999,000

  • 4 Beds
  • 4.5 Baths
  • 5,050 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  Some homes are renovated. Others are carefully crafted. 3 Shannon Ridge Road is unmistakably the latter.At first glance, the home feels elegant. Spend time inside, however, & its character begins to emerge: 16-ft.-long wide pine floors secured w/ traditional square nails, remarkably high ceilings, beautifully composed architecture, expansive windows, live-edge wood, a kitchen for entertaining and

  Jacki Murano Southern Vermont Realty Group

  3 Shannon Ridge Rd, Dover, VT 05356
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  /21

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  354 Orchard St, Brattleboro, VT 05301

  You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a

  Christine Lewis Brattleboro Area Realty

  354 Orchard St, Brattleboro, VT 05301
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  /60

  $690,000

  • 5 Beds
  • 4 Baths
  • 2,642 Sq Ft

  57 Castle Hill Rd, Wilmington, VT 05363

  Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while

  Donna Brown Skihome Realty

  57 Castle Hill Rd, Wilmington, VT 05363
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  /51

  $5,100,000

  • 10 Beds
  • 9.5 Baths
  • 6,648 Sq Ft

  15 Sawmill Rd, Stratton, VT 05155

  Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

  Kim Morgan-Wohler Wohler Realty Group

  15 Sawmill Rd, Stratton, VT 05155
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  /60

  $6,898,000

  New Construction

  • 5 Beds
  • 8 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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  /50

  $699,000

  $70K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 629 Sq Ft

  1100 Houghtonville Rd, Grafton, VT 05146

  Write your Vermont story at this extraordinary 38-acre retreat just one mile from Grafton Village, set along the peaceful Saxtons River. Built in 2007, the seasonal one bedroom cottage with loft blends beautifully into the natural landscape and captures the very best of indoor and outdoor living. Perched above the water’s edge, the cottage offers a screened porch, two sliding doors from the main

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  1100 Houghtonville Rd, Grafton, VT 05146
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  /11

  $139,000

  $10K PRICE DROP

  • 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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  /56

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  7 Cross St, Newfane, VT 05345

  This is your chance to be part of the historic and lively community in the center of Newfane.This home underwent a complete overhaul in the early 2000s, including a new slate roof, a relocated fireplace for a more practical layout, a reinforced stone foundation with a poured concrete floor, new windows, boiler, cement clapboard, and new kitchen countertops. The main level features radiant

  Victoria Woods Brattleboro Area Realty

  7 Cross St, Newfane, VT 05345
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  /33

  $249,000

  • 1 Bed
  • 468 Sq Ft

  246 Mann Rd, Wilmington, VT 05363

  Location, location, location! This rare opportunity is surrounded by the beautiful Haystack Golf Course, offering an unbeatable setting in one of southern Vermont's premier resort destinations. The property currently features a camp and a one-car garage, allowing you to enjoy the land immediately while planning your dream home or future getaway. Just minutes from Mount Snow, The Hermitage Club,

  Jeffrey Brisson Cohn & Company

  246 Mann Rd, Wilmington, VT 05363
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  /24

  $299,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  1329 Newfane Rd, Wardsboro, VT 05355

  Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retreat, privately set on a secluded 1-acre lot surrounded by woods and nature. Tucked away in a peaceful setting, this inviting home offers warmth, character, and the simple beauty of country living. The first floor features an open floor plan with hardwood floors and natural woodwork throughout, a cozy

  Matt Waddington Hoffman Real Estate

  1329 Newfane Rd, Wardsboro, VT 05355
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  /33

  $499,000

  • 2 Beds
  • 2 Baths
  • 3,320 Sq Ft

  5855 Windham Hill Rd, West Townshend, VT 05359

  Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting.Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  5855 Windham Hill Rd, West Townshend, VT 05359
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  /33

  $1,450,000

  $200K PRICE DROP

  • 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

  $599,000

  $45K 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

  $250,000

  $10K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /37

  $285,000

  $14K PRICE DROP

  • 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

Showing Results 161 - 200, Page 5 of 6