423

Windham County VT Homes for Sale

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  • /43

    $565,000

    • 4 Beds
    • 2.5 Baths
    • 2,149 Sq Ft

    66 Hilltop Rd, Londonderry, VT 05155

    This great home is a must see! Fully renovated in the past 8 months, from floor to ceilings, every inch has been updated. Brand new kitchen and baths, all new fixtures and appliances, this 4 bedroom 3 bath home is waiting for new owners to enjoy it! Great proximity to skiing, recreation, groceries and dining, yet private and set back from the road. Sold furnished with a pleasing neutral palate,

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 553-3290

    66 Hilltop Rd, Londonderry, VT 05155
  • /53

    $1,470,000

    • 5 Beds
    • 4.5 Baths
    • 5,160 Sq Ft

    224 Cobble Ridge Rd, Londonderry, VT 05148

    Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    224 Cobble Ridge Rd, Londonderry, VT 05148
  • /41

    $499,000

    • 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
  • /60

    $750,000

    • 2 Beds
    • 1 Bath
    • 17,000 Sq Ft

    24 Rockingham St, Bellows Falls, VT 05101

    Entrepreneur's Dream! Step into a world of endless potential in the historic Newberry Building. Built in 1938 with robust masonry and steel construction,this one-of-a-kind property offers the ultimate "live, work, and play" lifestyle. Situated in a prime location with excellent visibility, this building is a proven success story, having housed two of the town's most beloved restaurants: The

    Heidi Bernier Berkley & Veller Greenwood Country

    24 Rockingham St, Bellows Falls, VT 05101
  • /20

    $195,000

    • Land
    • 46.2 Acres
    • $4,221 per Acre

    1499 Josh Rd, Halifax, VT 05358

    46 + acres (33 AC in Halifax & 13.20 AC in Guilford) with a modified camper accessed by an existing gravel woods road off Josh Road (class 4) and beautiful pond with dock in a peaceful remote valley surrounded by over 2,000 acres of private land mostly open to recreation with miles of trails and old town roads. Josh Brook is a major trout stream and has waterfalls and deep pools for cooling off.

    Chris Long BHG Masiello Brattleboro

    1499 Josh Rd, Halifax, VT 05358
  • /35

    $579,000

    • 4 Beds
    • 1 Bath
    • 1,560 Sq Ft

    104 Karen Day Rd, Halifax, VT 05342

    1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

    Chris Long BHG Masiello Brattleboro

    104 Karen Day Rd, Halifax, VT 05342
  • /18

    $259,000

    • 3 Beds
    • 1 Bath
    • 1,712 Sq Ft

    48 Legion Rd, Newfane, VT 05345

    Adorable contemporary home nestled in the quaint town of Newfane. A perfect combination of privacy and country. Enjoy the covered porch during those warm summer days or crisp fall mornings. Ample space with the open concept living room and kitchen for endless entertainment. This home still has the rustic charm to make you feel right at home. Plenty of room for gardening and animals. Schedule your

    Katelyn Heaney Greenwald Realty Group

    48 Legion Rd, Newfane, VT 05345
  • /45

    $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
  • /20

    $475,000

    • Land
    • 136.9 Acres
    • $3,470 per Acre

    0 Taft Rd Unit 5064573, Townshend, VT 05353

    In the late 1790's, General Samuel Fletcher gave a large parcel of land to young Benjamin Murdock, whose father had died from smallpox while serving in the Revolutionary War. Benjamin built a cabin and then a house, cleared and plowed the land, and with his wife raised 8 children. That land is now known as Murdock Mountain. Entering the property is like stepping into the past. The deep stone

    Bill Hickok Berkley & Veller Greenwood Country

    0 Taft Rd Unit 5064573, Townshend, VT 05353
  • /37

    $479,000

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

    529 Finkel Rd, Wardsboro, VT 05355

    Sage Hill offers the perfect blend of privacy and convenience, set along a scenic country road yet just minutes to groceries, gas, and skiing. This contemporary home is thoughtfully tucked back into the landscape, framed by classic stonewalls and majestic oak trees. Enter directly from the carport into a tiled mudroom with closet space, ideal for storing all your outdoor gear. The main living

    Monique White Deerfield Valley Real Estate

    529 Finkel Rd, Wardsboro, VT 05355
  • /24

    $849,000

    • 4 Beds
    • 2 Baths
    • 1,638 Sq Ft

    12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

    Unmatched Comfort and Convenience at Stratton's Ober Tal – Walk to LiftDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village.Close enough to swing back for a quick lunch, this condo lets you make

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
  • /49

    $525,000

    • 4 Beds
    • 3.5 Baths
    • 1,913 Sq Ft

    35 Birch Rd, Londonderry, VT 05148

    Nestled in the heart of Vermont’s ski country, this architect-designed home is a striking blend of whimsical artistry and alpine living. A stones throw from Magic Mountains base lodge, skiing and four-season adventure await right outside your door. Designed by a visionary architect with a love for natural light, the residence offers both artistic flair and multiple finished spaces the whole

    Mendi Michael Engel & Völkers Okemo

    35 Birch Rd, Londonderry, VT 05148
  • /24

    $365,000

    • 5 Beds
    • 3 Baths
    • 2,254 Sq Ft

    85 Stockwell Dr, Brattleboro, VT 05301

    Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

    Christine Lewis Brattleboro Area Realty

    85 Stockwell Dr, Brattleboro, VT 05301
  • /21

    $205,000

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    12 Laurel Ave, Bellows Falls, VT 05101

    Move-in ready and full of charm! This well-maintained, beautifully decorated home offers both comfort and convenience in the heart of Bellows Falls. Set on a corner lot within walking distance to town amenities, it features a generously sized kitchen complete with a beverage station and three upstairs bedrooms, providing plenty of space to fit your needs. The manageable lot requires very little

    Linda Benoit Highland Realty

    12 Laurel Ave, Bellows Falls, VT 05101
  • /60

    $474,000

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    8 Little Bend Unit M-175, Wilmington, VT 05363

    Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

    Sigrid Pickering Chimney Hill Realty

    8 Little Bend Unit M-175, Wilmington, VT 05363
  • /39

    $519,000

    • Land
    • 80.11 Acres
    • $6,479 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await!Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /17

    $459,000

    • 5 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    46 Town Farm Rd, Wilmington, VT 05363

    3 Story home with 1 car attached garage....new vinyl siding, windows and roofing installed in 2021 along with exterior foamboard insulation.FIRST FLOOR- Open concept entirely remodeled in 2022; mudroom, kitchen, 1/2 bath, and family/dining room. Vinyl plank flooring throughout, white shiplap walls and natural tongue & groove ceilings. Vermont castings wood burning stove.SECOND

    David White OwnerEntry.com

    46 Town Farm Rd, Wilmington, VT 05363
  • /12

    $125,000

    • Land
    • 15.6 Acres
    • $8,013 per Acre

    0 Thayer Rd, Westminster, VT 05158

    Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

    Steve Schoppmeyer BHG Masiello Brattleboro

    0 Thayer Rd, Westminster, VT 05158
  • /60

    $645,000

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    38 Greenspring Rd, Dover, VT 05356

    Welcome to Greensprings one of Mount Snow’s most sought-after communities offering the perfect blend of mountain convenience and Vermont charm. This spacious 3 bedroom, 4 bath townhome features stunning mountain views and an inviting open-concept living area with vaulted wood ceilings, a dramatic wall of windows, and a floor-to-ceiling wood-burning fireplace.The main level is ideal for

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    38 Greenspring Rd, Dover, VT 05356
  • /56

    $975,000

    • 9 Beds
    • 9 Baths
    • 5,480 Sq Ft

    3732 Vermont 30, Jamaica, VT 05343

    Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take over.This historic property boasts two dwellings and a guest cottage. Looking for a family compound to get away from it all?This is your haven! Plenty of room to have friends and family come and stay! So many options.The Main House features 4 ensuite bedrooms! The living room is a late 1700"s delight, with an

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    3732 Vermont 30, Jamaica, VT 05343
  • /19

    $65,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    2022 Vermont 30, Jamaica, VT 05343

    Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both!Stratton is just 20

    Carrie Mathews Winhall Real Estate

    2022 Vermont 30, Jamaica, VT 05343
  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /24

    $28,995

    • 2 Beds
    • 2 Baths
    • 745 Sq Ft

    304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units Studio unit (306) Queen murphy bed , kitchenette and full bathroom. Hotel unit (304) Two king beds and full bathroom. Units are located the valley side of the hotel . Lock out units has the benefit of using the unit as a whole or stay in one side and rent the other side out.

    Kelly Agrillo Southern Vermont Realty Group

    304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356
  • /60

    $2,889,000

    • 6 Beds
    • 7 Baths
    • 6,400 Sq Ft

    56 Handle Rd, Dover, VT 05356

    Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler’s panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood

    Rich Caplan Deerfield Valley Real Estate

    56 Handle Rd, Dover, VT 05356
  • /50

    $425,000

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

    715 Chase Rd, West Townshend, VT 05359

    Welcome to 715 Chase Road where you will find peace, tranquility and even convenience. This home offers so much bang for its' buck, you must come see it to believe it. Three bedrooms one full bath and laundry on the main level along with den, breakfast room and inviting living area with wood burning fireplace. The kitchen boasts plenty of counter and cupboard space with newer appliances and a

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    715 Chase Rd, West Townshend, VT 05359
  • /44

    $1,500,000

    • 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
  • /60

    $415,000

    • 6 Beds
    • 2 Baths
    • 2,048 Sq Ft

    58-60 Frost Place, Brattleboro, VT 05301

    OPEN HOUSE 11/13 4-5:30PM This turnkey income generator is now move in ready! One side is vacant and ready for your plans, the other has a successful Airbnb rental history and was completely renovated in 2018. Both have in-unit washer/dryer/ hook up. Enter through the thoughtfully crafted mudroom with generous built-in storage. The open-concept kitchen, dining, and living areas create an inviting

    Lily Gautot Greenwald Realty Group

    58-60 Frost Place, Brattleboro, VT 05301
  • /2

    $169,900

    • Land
    • 35.4 Acres
    • $4,799 per Acre

    0 Minard Rd, Westminster, VT 05346

    Over 35 wooded acres to call your own. Drive up the winding country road edged with meadows, views and a sense of peace to your own little haven. Spend some time on the land, scouting the views, finding the right site and falling in love with all the potential. Owned by the same family for over 30 years, it has finally come to market in just the right season to experience the golden glow of

    Christine Lewis Brattleboro Area Realty

    0 Minard Rd, Westminster, VT 05346
  • /34

    $499,000

    • 4 Beds
    • 4 Baths
    • 3,152 Sq Ft

    977 Route 121, West Townshend, VT 05359

    Classic 1875 colonial home located on 5 acres in beautiful Windham VT. Home sits well off the road for privacy. Large first floor with kitchen, two living rooms, dining room and half bath with laundry. Second floor has 3 bedrooms and 2 full baths. Detached 2 car garage has a first floor bonus room with 1 bedroom 1 bathroom ADU on the second floor with separate utilities. Great rental

    Eric Scott Barrett & Valley Assoc. Inc

    977 Route 121, West Townshend, VT 05359
  • /18

    $120,000

    • Land
    • 2.84 Acres
    • $42,254 per Acre

    111 Gib Lockerby Rd, Grafton, VT 05146

    Nestled in the rolling hills of southern Vermont, just minutes above the charming center of Grafton, this professionally developed parcel of land beckons you to build your Vermont dream home. This open and sunny lot, complete with its own small apple orchard is surrounded by timeless stone walls and lovely woodlands. Choose the best building site for you; the cleared front acre, formerly a

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 424-8491

    111 Gib Lockerby Rd, Grafton, VT 05146
  • /60

    $5,900,000

    • 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

    1950 Collins Rd, Brattleboro, VT 05301
  • /52

    $1,725,000

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft

    122 Sunbowl Ridge Rd, Stratton, VT 05360

    Solstice has long been considered the very finest townhome development at Stratton Mountain. With an unparalleled slope side location and private amenities such as heated pool and tub , private shuttle service. This four bedroom four bath townhome is the ultimate ski and summer getaway. Beautifully redone. One car heated garage, family room.

    John Sikes Stratton Real Estate

    122 Sunbowl Ridge Rd, Stratton, VT 05360
  • /38

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 3,113 Sq Ft

    1382 Grassy Brook Rd, Brookline, VT 05345

    Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity—ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished

    Thomas Dahlin Berkley & Veller Greenwood Country

    1382 Grassy Brook Rd, Brookline, VT 05345
  • /36

    $479,000

    • 4 Beds
    • 2.5 Baths
    • 1,887 Sq Ft

    230 Western Ave, Brattleboro, VT 05301

    This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect

    John Hatton Berkley & Veller Greenwood Country

    230 Western Ave, Brattleboro, VT 05301
  • /17

    $659,000

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    761 Stratton Mountain Access Rd Unit 130, Stratton, VT 05360

    Location Location Location! A premiere property in the ever popular Long Trail House at Stratton Mountain Resort, Vermont. This two bedroom two bathroom condominium located on the first floor has direct access to the outdoor year round pool and hot tubs. The walkout access includes an open air as well as a covered patio with direct mountain views. The southern exposure provides wonderful natural

    Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 130, Stratton, VT 05360
  • /29

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 2,706 Sq Ft

    916 Wiswall Hill Rd, Townshend, VT 05353

    Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

    Mike Masters Four Seasons Sotheby's Int'l Realty

    916 Wiswall Hill Rd, Townshend, VT 05353
  • /58

    $32,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious mountain-side lockout unit, the closest unit to the back door to the slopes, comfortably sleeps 8. Unit 123 is a hotel room with 2

    Donna Brown Skihome Realty

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356
  • /28

    $399,000

    • 2 Beds
    • 2.5 Baths
    • 1,558 Sq Ft

    339G Handle Rd Unit Elms G, Dover, VT 05356

    This unique two-level condo has been tastefully updated, featuring a 2-bedroom, 2.5-bath condo in the desirable Snow Tree community, which offers the perfect blend of comfort, style, and convenience—just moments from the slopes of Mount Snow!Step inside the entry level and enjoy an open-concept floor plan ideal for entertaining or relaxing after a day on the mountain. The renovated kitchen

    Patricia Fitzpatrick Skihome Realty

    339G Handle Rd Unit Elms G, Dover, VT 05356
  • /46

    $992,000

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

    33 Carinthia Rd, Dover, VT 05356

    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 ceilings and soaring brick fireplace,

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Rd, Dover, VT 05356
  • /20

    $99,500

    • Land
    • 10.27 Acres
    • $9,688 per Acre

    0 Theresa Ln, Wilmington, VT 05363

    This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

    Lisa Mirando Deerfield Valley Real Estate

    0 Theresa Ln, Wilmington, VT 05363

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