374

Windham County VT Homes for Sale

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  • /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

    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 downtown, to Memorial

    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

    $449,000

    • 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
  • /56

    $899,000

    • 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

    $63,000

    • 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

    $1,400,000

    • 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
  • /48

    $415,000

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

    58-60 Frost Place, Brattleboro, VT 05301

    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. Brand new hot water heater, dishwasher, garbage disposal, and toilet have just been installed. Both have in-unit washer & dryer. Enter through the thoughtfully crafted mudrooms with generous built-in storage. The

    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
  • /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
  • /31

    $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
  • /22

    $199,000

    • Land
    • 3.6 Acres
    • $55,278 per Acre

    00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361

    Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing showing positive results, utilities at the road,

    Chad Lackey Deerfield Valley Real Estate

    00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361
  • /60

    $2,150,000

    • 5 Beds
    • 5 Baths
    • 5,500 Sq Ft

    18 New England Power Rd, Wilmington, VT 05363

    This extraordinary luxury farmhouse has been masterfully remodeled by the current owners, offering a refined retreat abutting Vermont’s Green Mountain Forest. Every inch has been reimagined with high-end finishes, from the new roof to custom details throughout, creating a turnkey sanctuary that blends timeless charm with modern sophistication. A beautiful sunroom invites relaxation with abundant

    Samantha Decker Deerfield Valley Real Estate

    18 New England Power Rd, Wilmington, VT 05363
  • /38

    $1,075,000

    • 5 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    3715 Route 11, Londonderry, VT 05148

    Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

    Cheyanne Pugliese

    3715 Route 11, Londonderry, VT 05148
  • /3

    $275,000

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

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361
  • /35

    $34,900

    • 1 Bed
    • 2 Baths
    • 745 Sq Ft

    341/43 Qtr.4,89 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 (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

    Kelly Agrillo Southern Vermont Realty Group

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
  • /6

    $49,000

    • Land
    • 10.2 Acres
    • $4,804 per Acre

    0 Kurn Hattin Rd, Putney, VT 05346

    Discover the potential of this 10.2 acre lot nestled in the scenic hills of Westminster. With road frontage on a paved, town maintained road and easy access to I-91, this property offers both privacy and convenience. Located in an accessible area with a peaceful, wooded setting, it’s an ideal opportunity to own a piece of Vermont’s natural beauty.

    Rebecca Hiam Southern Vermont Realty Group

    0 Kurn Hattin Rd, Putney, VT 05346
  • /79

    $275,000

    • Land
    • 22.32 Acres
    • $12,321 per Acre

    81 Parish Hill Rd Unit 26, Newfane, VT 05345

    Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

    Chad Bruyette Whitetail Properties Real Estate

    81 Parish Hill Rd Unit 26, Newfane, VT 05345
  • /39

    $849,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,020 Sq Ft

    101 North Rd, Wilmington, VT 05363

    Stunning new construction in the Chimney Hill community just outside the village of Wilmington, and a short drive to both the Mount Snow ski resort, Hermitage Club, and Lake Whitingham. Located on an easily accessible corner lot in the desirable B section at the bottom of the hill with unique double lot size allowing for tremendous expansion potential . This home was built sparing no expense and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    101 North Rd, Wilmington, VT 05363
  • /31

    $33,500

    • 1 Bed
    • 2 Baths
    • 709 Sq Ft

    145/47 Qtr.1,89 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 (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

    Kelly Agrillo Southern Vermont Realty Group

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /43

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    1587 Upper Holbrook Rd, Whitingham, VT 05361

    Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1587 Upper Holbrook Rd, Whitingham, VT 05361
  • /32

    $560,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    162 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

    162 Buttonwood Dr, Brattleboro, VT 05301
  • /32

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,216 Sq Ft

    12 Three Streams Way, Wilmington, VT 05363

    Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Three Streams Way, Wilmington, VT 05363
  • /28

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    49 West Rd, Wilmington, VT 05363

    Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 West Rd, Wilmington, VT 05363
  • /36

    $529,000

    • 3 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /32

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    161 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

    161 Buttonwood Dr, Brattleboro, VT 05301

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