Windham County VT Homes for Sale

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  /46

  $485,000

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

  4027 Route 100 Hwy, Wardsboro, VT 05360

  Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you’ll find soaring cathedral ceilings in the living

  Steve Goldfarb Deerfield Valley Real Estate

  4027 Route 100 Hwy, Wardsboro, VT 05360
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  /53

  $4,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,700 Sq Ft

  24 Sawmill Rd, Stratton, VT 05360

  Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

  Carrie Mathews Winhall Real Estate

  24 Sawmill Rd, Stratton, VT 05360
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  /44

  $1,475,000

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  691 Black Bear Rd, Jamaica, VT 05343

  A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying

  Carrie Mathews Winhall Real Estate

  691 Black Bear Rd, Jamaica, VT 05343
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  /52

  $1,400,000

  • 4 Beds
  • 3.5 Baths
  • 3,536 Sq Ft

  1845 Hatch School Rd, Brattleboro, VT 05301

  Thoughtfully constructed in 2016 with efficiency, durability, and longevity in mind, this modern farmhouse offers 3,536 square feet of open, light-filled living space on nearly 100 private acres, just 0.8 miles from the Wilmington town line. Built with double-wall construction, a high-performance building envelope, and imported European triple-pane windows, the home reflects a deliberate

  Melissa Nebelski Real Broker LLC

  1845 Hatch School Rd, Brattleboro, VT 05301
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  /43

  $1,392,000

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

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations.Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  /18

  $535,000

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  12 Ober Tal Dr Unit C14, Stratton, VT 05360

  Opportunity awaits in this trailside condominium at Stratton Mountain Resort. Ideally positioned for convenient access to the Tamarack Chairlift and Stratton Village, this residence offers the mountain lifestyle buyers seek with direct access to skiing, dining, shopping, and year-round resort amenities. Inside, a wood-burning fireplace anchors the living area, creating an inviting space to gather

  Timothy Mich Doddridge Stratton Real Estate

  12 Ober Tal Dr Unit C14, Stratton, VT 05360
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  /23

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Mill Rd, West Dover, VT 05356

  When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 3 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large vaulted living room and wood burning fireplace on brick hearth,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  7 Mill Rd, West Dover, VT 05356
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  /37

  $369,000

  • 4 Beds
  • 1.5 Baths
  • 1,882 Sq Ft

  120 Carriage Hill Rd, Brattleboro, VT 05301

  MAKE YOUR APPOINTMENT TODAY!A very sweet house in a desired West Brattleboro neighborhood on nice corner lot. Pull your car right into the 2-car oversized garage and enter through the enclosed porch which makes an excellent mudroom. First floor: beautifully updated kitchen with quartz countertops and cherry cabinets, a dining area that adjoins the light-filled large living room with lovely

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  120 Carriage Hill Rd, Brattleboro, VT 05301
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  /33

  $2,100,000

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

  121 Fannie Hill Rd, 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 Rd, Wilmington, VT 05363
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  /30

  $649,000

  • 5 Beds
  • 3 Baths
  • 2,830 Sq Ft

  36 Bears Den Rd, West Dover, VT 05356

  Lovely ski home home in an ideal location, offering the privacy of a single-family residence with the convenience of a groomed ski-home trail and direct shuttle service just steps from your front door. Nestled on a well-positioned lot in the desirable Bears Crossing community, the home backs directly to the ski-home trail with a bridge to cross right to your deck on your way home and offers ample

  Adam Palmiter Berkley & Veller Greenwood/Dover

  36 Bears Den Rd, West Dover, VT 05356
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  /43

  $774,000

  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
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  /42

  $959,900

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

  598 Hubbard Hill Rd, Halifax, VT 05342

  Set on 65± acres, this four-bedroom, three-bath home offers the privacy, views, and outdoor lifestyle that so many buyers seek in Southern Vermont. Perched to capture sweeping mountain views and spectacular sunsets, the home welcomes you with a covered front porch where you can relax and take in the ever-changing landscape.Inside, the spacious floor plan is designed for comfortable year-round

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  598 Hubbard Hill Rd, Halifax, VT 05342
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  /31

  $1,050,000

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

  1C Ego Aly, Dover, VT 05356

  Breathtaking, direct Mount Snow views from this spectacular Outlook Townhome, perched just above the base area at Mount Snow Ski Resort. With rustic natural wood finishes, soaring vaulted spaces, and sweeping slopeside exposure, this five-bedroom, four-bath townhome strikes a rare balance of warmth and luxury. A timber-framed covered porch wraps around to the rear, opening up to west and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1C Ego Aly, Dover, VT 05356
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  /59

  $3,495,000

  • 9 Beds
  • 11 Baths
  • 6,726 Sq Ft

  238 Stowe Hill Rd, Wilmington, VT 05363

  Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  238 Stowe Hill Rd, Wilmington, VT 05363
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  /49

  $259,000

  • 3 Beds
  • 1.5 Baths
  • 1,655 Sq Ft

  373 Vt Route 30, Newfane, VT 05345

  A great fixer-upper find! Solid feeling cape home set on 2 level acres just outside the village of Newfane with long frontage on the Smith Brook. Once a loved local primary home - now it's your opportunity. If you are handy and have cash or pre-qualified for a construction loan this may be your chance to break into the Newfane area at a fraction of what a renovated home will cost. Seller has

  Jessica Landers Barrett and Valley Associates Inc.

  373 Vt Route 30, Newfane, VT 05345
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  /12

  $269,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  333 US Route 5, Westminster, VT 05158

  Nestled on approximately nine plus acres in Westminster, Vermont, this charming three-bedroom, two-bathroom ranch-style home offers the perfect blend of privacy, comfort, and country living. Set back from Route 5, the property provides a peaceful retreat while remaining conveniently accessible. The expansive grounds feature mature fruit trees, open space for recreation or gardening, and

  Kassie Rubico Berkley & Veller Greenwood Country

  333 US Route 5, Westminster, VT 05158
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  /21

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  243 Newton Rd, Vernon, VT 05354

  Vernon! Affordable! School choice! Summer at the pool! This is it! One level living for those who want to age in place, have challenges with stairs, or just want to move up from an apartment....The best floor plan with open concept common space and bedrooms at the ends, for privacy and best use of space. With a sunny, level, with much of the yard fenced, there is lots of play space, gardening and

  Christine Lewis Brattleboro Area Realty

  243 Newton Rd, Vernon, VT 05354
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  /2

  $50,000

  • Land
  • 28 Acres
  • $1,786 per Acre

  non Pikes Falls Rd, Jamaica, VT 05343

  This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5%

  Carrie Mathews Winhall Real Estate

  non Pikes Falls Rd, Jamaica, VT 05343
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  /26

  $299,000

  New Construction $41K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft

  333 Poverty Row, Whitingham, VT 05361

  Escape to the beauty of Southern Vermont with this newly built chalet, offering comfort, flexibility, and year-round recreation. Situated just minutes from Lake Sadawga and Town Hill Park, this property is ideal as a full-time residence, vacation home, or investment getaway.The well and septic system were installed in Spring 2026, providing peace of mind and a strong foundation for future

  Kristen Breeden Southern Vermont Realty Group

  333 Poverty Row, Whitingham, VT 05361
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  /28

  $562,500

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

  29A 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 centrally in the development, offering greater separation between units, great parking, and yet easy clubhouse access. The home features an open-concept living space with vaulted ceilings, a wood-burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29A Kingswood Rd, Dover, VT 05356
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  /33

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft

  231B Route 100 Unit 23B, Dover, VT 05356

  Just 1.5 miles from the slopes of Mount Snow, this bright and inviting 2.5-story townhome offers the perfect blend of convenience and comfort—with a shuttle to the mountain and easy access to nearby dining and shops. Thoughtfully updated, and with a new roof, the home features a welcoming entry with plenty of storage for all your outdoor gear.The renovated kitchen shines with quartz

  Carrie Mathews Winhall Real Estate

  231B Route 100 Unit 23B, Dover, VT 05356
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  /46

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft

  16 A Snowtree Ln, Dover, VT 05356

  This exceptional townhouse in the sought-after SnowTree development offers a unique opportunity for homeownership in a community with a reliable HOA management company. Spread across three meticulously updated levels, the townhouse welcomes you with a spacious, sun-filled living room featuring a wood-burning fireplace and large windows that offer winter mountain views and allow natural light to

  Sheila Joyce-Albano Skihome Realty

  16 A Snowtree Ln, Dover, VT 05356
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  /23

  $78,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  4 Reservoir Rd, Brattleboro, VT 05301

  In a very private area of the Park. Right out your door is the walking path to Pleasant Valley Reservoir! This 2 bedroom home has an updated bathroom. There's a concrete grilling/patio pad, lovely flower beds line the front yard and the front and back entryway are covered.*Back on the market because previous buyer could not secure cash.

  Victoria Woods Brattleboro Area Realty

  4 Reservoir Rd, Brattleboro, VT 05301
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  /37

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
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  /47

  $545,000

  • 2 Beds
  • 1 Bath
  • 1,576 Sq Ft

  211 Pleasant Valley Rd, Brattleboro, VT 05301

  Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural

  Chris Long BHG Masiello Brattleboro

  211 Pleasant Valley Rd, Brattleboro, VT 05301
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  /39

  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,824 Sq Ft

  9 Mountain Reach Mews Rd Unit 9, Stratton, VT 05155

  Experience Stratton at its absolute finest from one of the mountain's most coveted locations. Perfectly positioned just behind Stratton Village, this exceptional ski-in/ski-out residence offers the rare combination of effortless slope access and a short stroll to the Village's vibrant shops, restaurants, cafés, and year-round activities. Leave the car behind and enjoy the ultimate mountain

  Carrie Mathews Winhall Real Estate

  9 Mountain Reach Mews Rd Unit 9, Stratton, VT 05155
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  /3

  $749,000

  • 6 Beds
  • 3 Baths
  • 3,362 Sq Ft

  106 Town Farm Rd, Wilmington, VT 05363

  Town listed acreage of 14.5 GIS 15.27. Located at the end of Town Farm Road with views of Lake Whitingham. The setting is private as well as the driveway. The kitchen, dining and sunken living room are all open for ease of entertaining. The kitchen has maple cabinets and a pantry. There is a formal dining room partially open to the dining room. The first floor has a laundry/mudroom and the

  Ginny Read Read Realty LTD

  106 Town Farm Rd, Wilmington, VT 05363
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  /52

  $460,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  720 Pine Banks Rd, Putney, VT 05346

  This is a rare turnkey quality home that's been completely refurbished since 2018. The immense list of upgrades includes: completely new paint inside and out, electric overhaul, heat pump hot water heater, bulkhead and exterior foundation waterproofing, fully remodeled bathrooms, all new windows and doors, new lighting throughout, wainscotting, new septic tank and the list goes on.There are 2

  Victoria Woods Brattleboro Area Realty

  720 Pine Banks Rd, Putney, VT 05346
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  /22

  $670,000

  • Land
  • 67 Acres
  • $10,000 per Acre

  00 S Pine Banks Rd, Putney, VT 05346

  Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

  

  Ross Doody

  Century 21 Highview Realty

  00 S Pine Banks Rd, Putney, VT 05346
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  /33

  $1,650,000

  • 5 Beds
  • 2.5 Baths
  • 4,443 Sq Ft

  874 Middletown Rd, Grafton, VT 05146

  Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions.

  Story Jenks LandVest, Inc/Woodstock

  874 Middletown Rd, Grafton, VT 05146
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  /60

  $885,000

  • 4 Beds
  • 3.5 Baths
  • 3,154 Sq Ft

  157 Old Sawmill Rd, Londonderry, VT 05148

  Nestled in a peaceful Londonderry setting, 157 Old Sawmill Road offers the perfect blend of Vermont charm, comfort, and outdoor recreation. Originally built in 1971 and extensively renovated and expanded in 1992, this inviting home features nearly 3,200 square feet of living space designed for year-round enjoyment. Surrounded by nature, the property enjoys direct access to trails leading to

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  157 Old Sawmill Rd, Londonderry, VT 05148
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  /24

  $140,000

  • Land
  • 1.4 Acres
  • $100,000 per Acre

  0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363

  Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful

  Grayson VanHendrick Flex Realty

  0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
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  /36

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 2,678 Sq Ft

  177 Alwin Ln, Jamaica, VT 05343

  Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living.The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and

  Helen Nault

  177 Alwin Ln, Jamaica, VT 05343
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  /43

  $1,975,000

  • 5 Beds
  • 4.5 Baths
  • 5,063 Sq Ft

  183 Old Mill Ln, Wilmington, VT 05363

  Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby

  Adam Palmiter Berkley & Veller Greenwood/Dover

  183 Old Mill Ln, Wilmington, VT 05363
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  /30

  $315,000

  • 2 Beds
  • 2.5 Baths
  • 1,607 Sq Ft

  136 Morningside Dr, Brattleboro, VT 05301

  Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

  Desiree Stango Berkley & Veller Greenwood Country

  136 Morningside Dr, Brattleboro, VT 05301
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  /49

  $575,000

  • 4 Beds
  • 3.5 Baths
  • 2,964 Sq Ft

  8 Deer Run, Wilmington, VT 05363

  Located in the desirable Chimney Hill community, this beautifully maintained 4 bedroom, 4 bath home offers the perfect combination of comfort, convenience, and year-round recreation. Designed for gathering and relaxing, the open-concept floor plan features vaulted ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas. A cozy gas fireplace creates a warm

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  8 Deer Run, Wilmington, VT 05363
• 

  

  /20

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  8F Dover Green Loop Unit 8F, Dover, VT 05356

  Spacious townhome at an incredible price in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This private end unit sits nestled towards the top of the development with great privacy and parking, and has had numerous recent upgrades to the roof, foundation, paint, siding, and whole house water filtration. The interior boasts a vaulted great room, wood

  Adam Palmiter Berkley & Veller Greenwood/Dover

  8F Dover Green Loop Unit 8F, Dover, VT 05356
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  /52

  $629,900

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

  187 Poverty Row, Whitingham, VT 05361

  Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room.The custom maple

  Pauline Green

  187 Poverty Row, Whitingham, VT 05361
• 

  

  /55

  $795,000

  $54K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 3,877 Sq Ft

  2435 Stage Rd, Guilford, VT 05301

  Only a fortunate few have the privilege of calling Green River Village home—a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built in

  John Mcpherson Berkley & Veller Greenwood Country

  2435 Stage Rd, Guilford, VT 05301
• 

  

  /27

  $559,000

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

  39 B Kingswood Rd, Dover, VT 05356

  Experience turnkey mountain living in this impeccably maintained and beautifully furnished Kingswood townhome, ideally situated just minutes from Mount Snow and the Hermitage Club. Recently painted and offered fully furnished, this move-in-ready retreat seamlessly blends comfort, convenience, and year-round recreation. Designed for both relaxation and entertaining, the spacious floor plan

  Patricia Fitzpatrick Skihome Realty

  39 B Kingswood Rd, Dover, VT 05356

Showing Results 81 - 120, Page 3 of 12