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Windham County VT Homes 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

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 317-7158

    1950 Collins Rd, Brattleboro, VT 05301
  • /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

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 392-0721

    410 Tallwood Cir, Londonderry, VT 05148
  • /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 sunny

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 424-8491

    111 Gib Lockerby Rd, Grafton, VT 05146
  • /33

    $1,760,000

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

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

    Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

    Edwin Kevil Stratton Real Estate

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
  • /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
  • /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
  • /12

    $999,000

    • Land
    • 12.2 Acres
    • $81,885 per Acre

    Higley Hill Rd, Wilmington, VT 05363

    Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

    Community Lands Community Lands

    Higley Hill Rd, Wilmington, VT 05363
  • /26

    $599,000

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

    10 Grouse Ln Unit 10A, Dover, VT 05356

    Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    10 Grouse Ln Unit 10A, Dover, VT 05356
  • /51

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1886 Winhall Hollow Rd, South Londonderry, VT 05155

    Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or

    Kim Morgan-Wohler Wohler Realty Group

    1886 Winhall Hollow Rd, South Londonderry, VT 05155
  • /41

    $899,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    9 Windham Way, Dover, VT 05356

    This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9 Windham Way, Dover, VT 05356
  • /32

    $949,000 New Construction

    • 3 Beds
    • 4.5 Baths
    • 2,800 Sq Ft

    49 Joan's Ridge Rd, Dover, VT 05356

    Gorgeous new construction home just completed and ready for immediate use this season. This lovely home looks out to the ski trails at Mount Snow yet is in the heart of Dover with very easy access off a paved road. The interior features gorgeous natural light and exposed natural woodwork throughout, 3/4 inch solid red oak flooring, oversized windows, a bright living area with gas fireplace off

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 Joan's Ridge Rd, Dover, VT 05356
  • /35

    $899,900

    • 4 Beds
    • 3.5 Baths
    • 2,272 Sq Ft

    12 Encore Place, Dover, VT 05356

    Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    12 Encore Place, Dover, VT 05356
  • /37

    $690,000

    • 5 Beds
    • 3 Baths
    • 2,635 Sq Ft

    341 Under the Mountain Rd, Londonderry, VT 05148

    Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

    Andy Reed Four Seasons Sotheby's Int'l Realty

    341 Under the Mountain Rd, Londonderry, VT 05148
  • /54

    $695,000

    • 6 Beds
    • 3 Baths
    • 2,740 Sq Ft

    1161 Little Pond Rd, Londonderry, VT 05148

    Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    1161 Little Pond Rd, Londonderry, VT 05148
  • /60

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,978 Sq Ft

    23 Brook Rd, Saxtons River, VT 05154

    Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

    Isabella Luhrs BHG Masiello Keene

    23 Brook Rd, Saxtons River, VT 05154
  • /60

    $549,000

    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /29

    $569,000

    • 4 Beds
    • 3 Baths
    • 2,050 Sq Ft

    39B Kingswood Rd, Dover, VT 05356

    An impeccably maintained, beautifully furnished, and recently painted Kingswood townhome is conveniently located just minutes from Mount Snow and the Hermitage Club. This townhome features four bedrooms; an open-concept living area on the main level; a kitchen with a large island, granite countertops, and a vaulted ceiling; a wood-burning fireplace; and sliding doors leading to a private deck

    Patricia Fitzpatrick Skihome Realty

    39B Kingswood Rd, Dover, VT 05356
  • /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

    Tamara Purcell Berkley & Veller Greenwood Country

    12 Three Streams Way, Wilmington, VT 05363
  • /27

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

    There are only 2 townhomes of this style at the desirable Snowtree development, and this particular 3 bedroom, 3 bath has been completely renovated. Walk out your private entry to the base area at Mount Snow via the convenient stream crossing bridge to access the magic carpet and tubing area, ideal for the ski season, but also any summer festivals. If someone doesn't ski they can still easily

    Adam Palmiter Berkley & Veller Greenwood/Dover

    16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356
  • /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
  • /50

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    3148 Route 11, Londonderry, VT 05148

    Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on

    Erin Kendall EXP Realty

    3148 Route 11, Londonderry, VT 05148
  • /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
  • /26

    $625,000

    • 3 Beds
    • 2 Baths
    • 2,360 Sq Ft

    68 Ellis Brook Rd, Dover, VT 05341

    Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    68 Ellis Brook Rd, Dover, VT 05341
  • /31

    $539,000

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

    72A Kingswood Rd, Dover, VT 05356

    Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned on the lower side of the development, offering greater separation between units, easy trail access, and a more usable private rear yard. The home features an open-concept living space with vaulted ceilings, a

    Adam Palmiter Berkley & Veller Greenwood/Dover

    72A Kingswood Rd, Dover, VT 05356
  • /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
  • /60

    $599,000

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    673 Vermont 121, Grafton, VT 05146

    Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

    Janet Lucier Barrett & Valley Assoc. Inc

    673 Vermont 121, Grafton, VT 05146
  • /23

    $649,000

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

    457 Ray Hill Rd, Wilmington, VT 05363

    Owners will consider reasonable offers. Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous

    Adam Palmiter Berkley & Veller Greenwood/Dover

    457 Ray Hill Rd, Wilmington, VT 05363
  • /33

    $599,000

    • 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
  • /39

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,957 Sq Ft

    256 Potter Rd, Wardsboro, VT 05355

    Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    256 Potter Rd, Wardsboro, VT 05355
  • /32

    $559,000

    • 3 Beds
    • 3 Baths
    • 2,080 Sq Ft

    9 Greer Ct, Wilmington, VT 05363

    Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9 Greer Ct, Wilmington, VT 05363
  • /60

    $549,000

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

    35 Upper Bartonsville Rd, Chester, VT 05143

    Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

    Erin Kendall EXP Realty

    35 Upper Bartonsville Rd, Chester, VT 05143
  • /48

    $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
  • /21

    $489,000

    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    12 Lilla Ln, Wilmington, VT 05363

    Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Lilla Ln, Wilmington, VT 05363
  • /31

    $1,750,000

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

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

    148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

    Andrew King Stratton Real Estate

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
  • /15

    $67,500

    • Land
    • 3.5 Acres
    • $19,286 per Acre

    0 Dover Rd Unit 5054979, Newfane, VT 05345

    Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    0 Dover Rd Unit 5054979, Newfane, VT 05345
  • /30

    $749,000

    • Land
    • 2.57 Acres
    • $291,440 per Acre

    Lot 3 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 Old Mill Ln, Wilmington, VT 05363
  • /22

    $539,000

    • Land
    • 2.88 Acres
    • $187,153 per Acre

    309 Vermont Route 100, Dover, VT 05356

    Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

    Rich Caplan Deerfield Valley Real Estate

    309 Vermont Route 100, Dover, VT 05356
  • /20

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Kim Morgan-Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /5

    $139,000

    • Land
    • 8.52 Acres
    • $16,315 per Acre

    0 Higley Hill, Dover, VT 05356

    Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

    Michael Purcell Berkley & Veller Greenwood/Dover

    0 Higley Hill, Dover, VT 05356
  • /2

    $70,000

    • Land
    • 2.01 Acres
    • $34,826 per Acre

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

    Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails. Enjoy the peace of a quiet country setting where you can listen to

    Kerry Mulverhill

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

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