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

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
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  /45

  $789,000

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  15 Sawmill Village Way, Dover, VT 05356

  If you are looking for a quality-built, well-maintained home with modern updates and built-in property maintenance near Mt. Snow, this Village at Sawmill Farms home checks all the boxes. Located just up the hill from the businesses and services of West Dover, near the Mt. Snow golf course, recreational trails, and 2.5 miles from the ski resort, this home is situated perfectly to enjoy the area's

  

  Beth Vickers

  Vermont Real Estate Company

  (802) 341-9969

  15 Sawmill Village Way, Dover, VT 05356
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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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  /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
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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
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  /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
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  /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
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  /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
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  /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
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  /48

  $510,000

  • 3 Beds
  • 3 Baths
  • 3,420 Sq Ft

  27 Ray Hill Rd, Wilmington, VT 05363

  Located in a desirable setting that offers both privacy and the convenience of walking to the quaint village of downtown Wilmington, this spacious country home is full of potential. The home features a large, light-filled kitchen with plenty of space for cooking and gathering. The original post-and-beam barn, which was moved to the property, has been converted into a generous living and dining

  Monica Sumner BHG Masiello Brattleboro

  27 Ray Hill Rd, Wilmington, VT 05363
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  /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
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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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  /60

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,408 Sq Ft

  75 Westminster Rd, Putney, VT 05346

  This charming historic Colonial just moments from Putney Village, blends timeless character with thoughtful updates. This 4-bedroom, 3-bath home features a spacious, open kitchen highlighted by an antique brick hearth, perfect for gathering and entertaining. The flexible floor plan includes a first-floor bedroom with an ensuite full bath and its own separate entrance, offering excellent potential

  Rebecca Hiam Southern Vermont Realty Group

  75 Westminster Rd, Putney, VT 05346
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  /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
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  /40

  $675,000

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

  47 Oak Hill Dr, Dummerston, VT 05301

  Tucked away on a private road, this impeccably maintained 3-bedroom, 2-bathroom home sits on a serene 6-acre lot, offering the perfect blend of privacy and comfort. Set well back from the road, the property provides a peaceful retreat surrounded by nature. Inside, you’ll find a bright and inviting open-concept layout designed for both everyday living and entertaining. The spacious living and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  47 Oak Hill Dr, Dummerston, VT 05301
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  /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
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  /32

  $595,000

  • 5 Beds
  • 2 Baths
  • 2,892 Sq Ft

  238 Hemlock Hill Rd, Wardsboro, VT 05355

  This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the

  Jeffrey Sheehan Cummings & Co

  238 Hemlock Hill Rd, Wardsboro, VT 05355
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  /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
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  /42

  $499,990

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
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  /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
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  /46

  $625,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  143 Hillwinds Rd, Brattleboro, VT 05301

  Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden

  Christine Lewis Brattleboro Area Realty

  143 Hillwinds Rd, Brattleboro, VT 05301
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  /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
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  /34

  $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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  /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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  /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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  /44

  $525,888

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  37B Kingswood Rd, Dover, VT 05356

  Refined mountain luxury meets effortless four-season living in this impeccable Kingswood townhome, offering direct snowmobile trail access and private shuttle service to Mount Snow. Ideally positioned on the level portion of the development, this exceptional four-bedroom residence enjoys convenient trail access and a more expansive, usable, level rear yard—a rare and highly sought-after offering

  Michelle O'Neil Deerfield Valley Real Estate

  37B Kingswood Rd, Dover, VT 05356
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  /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
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  /27

  $495,000

  • 3 Beds
  • 3 Baths
  • 1,246 Sq Ft

  81 Chapin St, Brattleboro, VT 05301

  Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a

  John Hatton Berkley & Veller Greenwood Country

  81 Chapin St, Brattleboro, VT 05301
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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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  /60

  $525,000 Open Sat 9AM - 5PM

  • 2 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  4 Newfane Cir Unit 4B, Dover, VT 05356

  LOCATION LOCATION LOCATION!!! Directly across the street from Mt. Show ski resort with shuttle service to and from the mountain. Avoid parking fees and be chauffeured back and forth. Located in the prestigious Greenspring Community, with year round activities. Ski at Mt. Snow, Vermont's closest mountain to NYC, golf in the summer (located with 6 miles of 2 beautiful golf courses, Mt. Snow Golf

  Jason Saphire www.HomeZu.com

  4 Newfane Cir Unit 4B, Dover, VT 05356
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  /26

  $579,000

  • 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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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

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