Windham County VT Houses for Sale

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  /34

  $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
• 

  

  

  /35

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  /44

  $429,900

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft

  1909 Davidson Hill Rd, Westminster, VT 05158

  This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

  Steve Schoppmeyer BHG Masiello Brattleboro

  1909 Davidson Hill Rd, Westminster, VT 05158
• 

  

  

  /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
• 

  

  

  /30

  $449,000

  • 2 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  6 Gates Lake Raponda Ln, Wilmington, VT 05363

  Welcome to your idyllic escape with private dock on the shores of beautiful Lake Raponda. This cozy 2 bedroom 1.5 bath house offers the perfect blend of rustic charm and modern comfort, nestled in a peaceful wooded setting minutes from downtown Wilmington and a short walk to your waterfront dock!Step inside to discover warm wood accents, open concept living and dining area on the main level

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  6 Gates Lake Raponda Ln, Wilmington, VT 05363
• 

  

  /40

  $214,900

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

  2139 Vt Route 30, Townshend, VT 05353

  Great days ahead for the buyer of this stately, plantation styled home on close to three (3) acres. You have to see the interior to believe it. Dated? Yes, but solid bones. Crazy nice wood floors, classic built-ins & style. So many 'nooks & crannies. Cavernous, dry & clean basement. Exterior: 'challenged', but I have all the bids to bring it to 'good' condition & the techies are ready to complete

  Robert Balewicz Evergreen Realty of Vermont

  2139 Vt Route 30, Townshend, VT 05353
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  /51

  $585,000

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

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /27

  $425,000

  • 5 Beds
  • 3 Baths
  • 1,440 Sq Ft

  135 Overlook Dr, Londonderry, VT 05148

  Investment opportunity! This beautiful ski country compound offers 3 streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped

  Zachary Zupan EXP Realty

  135 Overlook Dr, Londonderry, VT 05148
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  /52

  $1,150,000

  • 8 Beds
  • 4 Baths
  • 4,828 Sq Ft

  5 Tannery Rd, West Dover, VT 05356

  Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

  Michelle O'Neil Deerfield Valley Real Estate

  5 Tannery Rd, West Dover, VT 05356
• 

  

  /31

  $435,000

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

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  /58

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  1192 Chapel Hill Rd, Whitingham, VT 05361

  Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

  Cliff Leinonen Four Seasons Sotheby's Int'l Realty

  1192 Chapel Hill Rd, Whitingham, VT 05361
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  /43

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  58 Buckboard Dr, Dover, VT 05356

  58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  58 Buckboard Dr, Dover, VT 05356
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  /45

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  210 Burrington Hill Rd, Whitingham, VT 05361

  Impeccably maintained 2007 residence in like-new condition, offering quality construction and thoughtful design throughout. The home features vinyl siding and a full concrete walk-out basement with high ceilings—an outstanding opportunity for adding 1000+ future finished living space customized to your needs. The main level showcases an open-concept living, kitchen, and dining area with natural

  Jacki Murano Southern Vermont Realty Group

  210 Burrington Hill Rd, Whitingham, VT 05361
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  /54

  $2,050,000

  • 4 Beds
  • 4.5 Baths
  • 2,486 Sq Ft

  97 N Brookwood Rd, Stratton, VT 05360

  Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  97 N Brookwood Rd, Stratton, VT 05360
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  /35

  $620,000

  • 6 Beds
  • 4 Baths
  • 3,592 Sq Ft

  1375 Sheldon Hill Rd, Wardsboro, VT 05355

  Stunning unique 2024 renovated chalet with rare 2+ acre parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to a large open concept great room with vaulted ceilings, natural woodwork, and great natural light throughout thanks to large windows and transoms. There is a gas fireplace with stone hearth, upscale custom

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1375 Sheldon Hill Rd, Wardsboro, VT 05355
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  /19

  $399,000

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  4850 Vermont Route 100, Wardsboro, VT 05355

  Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4850 Vermont Route 100, Wardsboro, VT 05355
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  /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
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  /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
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  /40

  $3,050,000

  • 6 Beds
  • 3 Baths
  • 3,309 Sq Ft

  36 Woffenden Rd, Wilmington, VT 05363

  Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

  Melissa Ellis Southern Vermont Realty Group

  36 Woffenden Rd, Wilmington, VT 05363
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  /26

  $649,000

  • 3 Beds
  • 3 Baths
  • 2,170 Sq Ft

  14 Johnson Hill Rd, Dover, VT 05356

  Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Johnson Hill Rd, Dover, VT 05356
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  /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
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  /21

  $725,000

  • 5 Beds
  • 3.5 Baths
  • 2,696 Sq Ft

  145 Shearer Hill Rd, Wilmington, VT 05363

  Beautiful 2010 post and beam home just a short drive from the Mount Snow Ski Resort and village of Wilmington. This meticulous turn key home was built with quality in mind, is very energy efficient and sits on a on a private 5+ acre parcel abutting a stream just up from Spruce Lake. Inside is a gorgeous great room space with vaulted ceilings and exposed natural woodwork, great natural light

  Adam Palmiter Berkley & Veller Greenwood/Dover

  145 Shearer Hill Rd, Wilmington, VT 05363
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  /41

  $539,000

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

  196 Powder Mill Rd, Londonderry, VT 05148

  Falling Leaves and PRICES! Buy now before the ski season begins!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

  Katie Ladue Gilbert KW Vermont Woodstock

  196 Powder Mill Rd, Londonderry, VT 05148
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  /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
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  /2

  $199,000

  • 2 Beds
  • 2,710 Sq Ft

  29 Stable Rd, Wilmington, VT 05363

  The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

  Mark Yule BHG Masiello Brattleboro

  29 Stable Rd, Wilmington, VT 05363
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  /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
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  /37

  $730,000

  • 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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  /60

  $650,000

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

  23 Brook Rd, Saxtons River, VT 05154

  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 quartz countertops —all overlooking

  Isabella Luhrs BHG Masiello Keene

  23 Brook Rd, Saxtons River, VT 05154
• 

  

  /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
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  /31

  $2,100,000

  • 7 Beds
  • 4 Baths
  • 4,256 Sq Ft

  121 Fannie Hill Dr, Wilmington, VT 05363

  Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Dr, Wilmington, VT 05363
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  /26

  $497,500

  • 4 Beds
  • 3 Baths
  • 1,776 Sq Ft

  28 Country Club Rd, Dover, VT 05356

  Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Country Club Rd, Dover, VT 05356
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  /26

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  48 Villager Loop, West Dover, VT 05356

  What a find! This well-maintained 3-bedroom plus den home in the Dover Hills is the perfect year-round Vermont getaway. Just 10 minutes to Mount Snow, you’ll have easy access to world-class skiing and riding in winter and scenic lift-served mountain biking in summer. With a first-floor bedroom and laundry, it’s designed for ease and convenience. Stay cozy with the pellet stove in winter, and cool

  Patrice Schneider Southern Vermont Realty Group

  48 Villager Loop, West Dover, VT 05356
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  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
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  /51

  $899,800

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /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
• 

  

  /60

  $1,255,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  This is the perfect Vermont getaway, private and secluded, minutes from skiing, restaurants, and all the charm of Southern Vermont. This property is truly special, set on landscaped grounds with rolling meadows, a small, renovated barn with deck, and a 30x40 insulated Q Building with heat, water and 220 amps, as well as a whole house generator.The location is choice: close to world-class

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
• 

  

  /20

  $469,000

  • 4 Beds
  • 2 Baths
  • 2,219 Sq Ft

  45 Dover Hill Rd, East Dover, VT 05341

  Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Dover Hill Rd, East Dover, VT 05341
• 

  

  /42

  $559,990

  • 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

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  /3

  $625,000

  • 4 Beds
  • 1.5 Baths
  • 2,764 Sq Ft

  768 Vt Route 30, Jamaica, VT 05343

  Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

  Julie Lowe Lowe's Real Estate, LLC

  768 Vt Route 30, Jamaica, VT 05343
• 

  

  /37

  $874,000

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  261 Handle Rd, Dover, VT 05356

  Slopeside 6 Bedroom Ski Chalet at Carinthia Base, Mount Snow This ski chalet is perfectly positioned at the base of Carinthia, offering true slopeside access and unmatched convenience. Step out your door and onto the trails, with the Carinthia Base Lodge, terrain parks, lifts, and all the action of the mountain just steps away. Inside, the home blends classic chalet character with thoughtful

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  261 Handle Rd, Dover, VT 05356

Showing Results 1 - 40, Page 1 of 5