Windham County VT Houses for Sale

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  /60

  $4,950,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
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  /33

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  1829 W Jamaica Rd, Jamaica, VT 05343

  Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms

  

  Alison Cummings

  Cummings & Co

  (802) 471-3958

  1829 W Jamaica Rd, Jamaica, VT 05343
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  /31

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  410 Tallwood Cir, Londonderry, VT 05148

  This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
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  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
• 

  

  

  /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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  /31

  $619,000

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with an attached garage offers over 3,000 square feet of living space and the perfect blend of comfort, style, and refined Vermont living. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /58

  $720,000

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom.Original details are beautifully preserved throughout, including four elegant Regency

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /37

  $795,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /32

  $499,000

  • 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
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  /35

  $425,000

  • 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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  /30

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  313 S Pine Banks Rd, Putney, VT 05346

  Experience the Magic of Putney, Vermont. Discover a private sanctuary in the heart of Vermont’s "Craft Capital." This meticulously maintained ranch offers the perfect blend of secluded country living and proximity to Putney’s vibrant cultural hub. Known for its world-class arts scene, organic farms, Yellow Barn Music, Next Stage Arts, Putney COOP, and iconic institutions like Sandglass Theater

  Thomas Dahlin Berkley & Veller Greenwood Country

  313 S Pine Banks Rd, Putney, VT 05346
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  /41

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,948 Sq Ft

  196 Powder Mill Rd, Londonderry, VT 05148

  Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for

  Katie Ladue Gilbert BHHS Verani Upper Valley

  196 Powder Mill Rd, Londonderry, VT 05148
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  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /60

  $725,000

  • 6 Beds
  • 3 Baths
  • 3,630 Sq Ft

  5 William Mundell Rd, South Newfane, VT 05351

  Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

  The Malley Group KW Vermont

  5 William Mundell Rd, South Newfane, VT 05351
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  /39

  $725,000

  • 5 Beds
  • 4 Baths
  • 2,962 Sq Ft

  250 Valley View Rd, Dover, VT 05356

  Unique, spacious, and just minutes to Mount Snow, this 5-bedroom, 4-bath home with a private pond is the kind of property buyers wait for. Whether for personal use, a vacation getaway, or short-term rental potential, it offers a setting to enjoy every season. Set on a beautiful 2-acre lot, the home features a large open-concept main living area with a cathedral ceiling and oversized windows that

  Melissa Nebelski Real Broker LLC

  250 Valley View Rd, Dover, VT 05356
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  /31

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  459 Silver Ln, Wardsboro, VT 05355

  Come and visit your potential get away in the much sought after development of Snow Mountain Farms in Wardsboro, VT. This community offers an indoor swimming pool, tennis courts and an exercise facility for an extremely modest fee. A three-bedroom, one bonus room home has the perfect balance of Vermont charm and comfort for you and your guests. With recently installed floors and all new

  Peggy O'neill Cummings & Co

  459 Silver Ln, Wardsboro, VT 05355
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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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  /43

  $625,000

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  15 Bills Rd, West Wardsboro, VT 05360

  This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  15 Bills Rd, West Wardsboro, VT 05360
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  /40

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  1355 Whitneyville Rd, Halifax, VT 05301

  Welcome to this charming country log home set on 30.6 private acres at the peaceful end of the road. Thoughtfully positioned to capture its surroundings, the home sits just high enough to enjoy pleasant views and beautiful mountain sunsets, best experienced from the inviting covered porches and open deck. Inside, the open-concept main level features abundant windows and cathedral ceiling creating

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  1355 Whitneyville Rd, Halifax, VT 05301
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  /40

  $4,087,000

  • 6 Beds
  • 7 Baths
  • 7,090 Sq Ft

  22 Stags Leap Ln, Wilmington, VT 05363

  Spectacular custom home at the base of the Hermitage Club in the Stags Leap community, adjacent to the ski trails at the base of Haystack mountain. This is a rare lot overlooking the trails, with direct ski-on/off and lift access, mountain views, and sunsets beyond, unimpeded by any other homes. Featuring 6 bedrooms, 5 and two half baths, with luxurious high ceiling great room with exposed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  22 Stags Leap Ln, Wilmington, VT 05363
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  /60

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,723 Sq Ft

  405 Main St, Wardsboro, VT 05355

  Lovingly shaped over generations of ownership, this is one of those special properties where the setting, charm, and character come together in a way that simply cannot be replicated. Set on 1.10 acres along a woodland creek, this property shines with natural beauty and Vermont charm. A stream-fed pond adds to the tranquil setting, while old stone walls, mature trees, butterfly gardens, and

  Rachel Febbie EXP Realty

  405 Main St, Wardsboro, VT 05355
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  /16

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  10 Riverfront Dr, Bellows Falls, VT 05101

  This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

  Gale Alger

  10 Riverfront Dr, Bellows Falls, VT 05101
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  /60

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3185 Higley Hill Rd, West Marlboro, VT 05363

  Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

  Flex Realty Group Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363
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  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
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  /38

  $329,000

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

  527 Route 121, Bellows Falls, VT 05101

  Move-in ready gutted and renovated home on 1.5 acres. New roof and new propane baseboard furnace and hot water system. New appliances. Insulated two-car garage. Beautiful mountain views.

  David White OwnerEntry.com

  527 Route 121, Bellows Falls, VT 05101
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  /43

  $1,300,000

  • 3 Beds
  • 4 Baths
  • 2,944 Sq Ft

  156 W Lake Rd, Wilmington, VT 05363

  A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an

  Jillian Wimmelman Deerfield Valley Real Estate

  156 W Lake Rd, 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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  /33

  $349,000

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

  29 Pikes Falls Rd, Jamaica, VT 05343

  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 to Mount Snow, the location balances

  Carrie Mathews Winhall Real Estate

  29 Pikes Falls Rd, Jamaica, VT 05343
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  /32

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  13 Yodeling Ln, Dover, VT 05356

  Tremendous opportunity to own an updated A-frame chalet at the base of Mount Snow ski resort and the Carinthia Freestyle Terrain Park. This lovely Vermont home sits nestled on a quiet loop just south of the mountain, with direct walking and hiking trail access.The open floor plan features an updated kitchen with stainless appliances, copper counters, and a vent hood, along with a living room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  13 Yodeling Ln, Dover, VT 05356
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  /49

  $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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  /37

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  239 Valley View Rd, Dover, VT 05356

  This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  239 Valley View Rd, Dover, VT 05356
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  /58

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,772 Sq Ft

  7 Grassy Brook Rd, Brookline, VT 05345

  Incredible Opportunity! This fully renovated, move-in ready retreat is perfectly situated on the picturesque West River. Enjoy your own private beach and waterfront lifestyle at its finest. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully

  Flex Realty Group Flex Realty

  7 Grassy Brook Rd, Brookline, VT 05345
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  /26

  $395,000

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

  135 Country Hill, Brattleboro, VT 05301

  Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

  Neil Goldberg Brattleboro Area Realty

  135 Country Hill, Brattleboro, VT 05301
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  /60

  $489,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,312 Sq Ft

  23 Wilsons Woods Rd, Brattleboro, VT 05301

  Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

  Kate Barry EXP Realty

  23 Wilsons Woods Rd, Brattleboro, VT 05301
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  /43

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  1 Lower Highlands Rd, West Dover, VT 05356

  Custom-built 4-bedroom, 2.5-bath home ideally located less than a mile from Mount Snow. The main level welcomes you with an inviting foyer off the covered front porch and offers a well-designed layout featuring a spacious living room, formal dining room, comfortable family room, versatile den, and a well-appointed kitchen. Additional conveniences include a half bath, dedicated laundry area, and a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1 Lower Highlands Rd, West Dover, VT 05356
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  /29

  $699,995

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

  152 Main St, Grafton, VT 05146

  Newly renovated home located in the heart of Grafton Village! This home features 4 spacious bedrooms, and 2 full baths. Large primary bedroom suite located on the first floor of the home with working fireplace and private bathroom. Brand new kitchen with all new cabinetry, quartz countertops and stainless steel appliances. Original hardwood floors, moldings and original doors. All brand new

  Derek Greene Derek Greene

  152 Main St, Grafton, VT 05146
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  /35

  $350,000

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

  6795 Vt Route 100, Londonderry, VT 05148

  Charming Property with Endless Possibilities in Southern Vermont Nestled 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 business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  6795 Vt Route 100, Londonderry, VT 05148
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  /20

  $400,000

  • 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
• 

  

  /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
• 

  

  /32

  $775,000

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

  15 Bears Den Rd, Dover, VT 05356

  A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356

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