Windham County VT Houses for Sale

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  /15

  $529,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  117 Ray Hill Rd, Wilmington, VT 05363

  This wonderful home boast 10.5 +/- acres, plenty of room for gardening, a pond and is only moments to the village center! Beautiful hard wood floors throughout, Livingroom with gas fireplace a a beautiful view, dining area and kitchen, 3 bedrooms, 2 bathrooms, 2 decks and a simple 1 car garage. The lower level boasts a walk- out, is completely dry and waiting to be finished!

  Janet Boyd Boyd Real Estate

  117 Ray Hill Rd, Wilmington, VT 05363
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  /39

  $459,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /27

  $950,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,564 Sq Ft

  4 Breezy Way, West Dover, VT 05356

  Brand new construction ski home just south of the Mount Snow ski resort recently finished for immediate use. This convenient location has MOOver shuttle service at the end of the street to and from the mountain, easy access to great restaurants and coffee shops, and direct snowmobile trail access, in addition to ample parking and privacy. The home was just finished by the developer and is ready

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4 Breezy Way, West Dover, VT 05356
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  /31

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  68 E Brook Crossing, Wilmington, VT 05363

  Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 E Brook Crossing, Wilmington, VT 05363
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  /39

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The Hermitage Club Experience the perfect fusion of luxury, privacy, and adventure in this beautifully renovated 4,950 sq ft home set on 1.62 acres of tranquil Vermont countryside. Ideally positioned between Mount Snow and the private Hermitage Club, this home offers a rare opportunity for refined mountain living

  Derek Greene Derek Greene

  3 Shannon Ridge Rd, Dover, VT 05356
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  /50

  $495,000

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

  26 Babbitt Rd, Bellows Falls, VT 05101

  Begin your journey by crossing a classic covered bridge and traveling along a quiet country road, leading you to this secluded hilltop retreat. Nestled on 37 acres of pristine woodlands with trails, the property offers a striking combination of natural beauty and privacy. The residence seamlessly blends contemporary design with country charm. A welcoming screened porch opens into a spacious,

  Heidi Bernier Berkley & Veller Greenwood Country

  26 Babbitt Rd, Bellows Falls, VT 05101
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  /16

  $353,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
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  /40

  $1,800,000

  • 9 Beds
  • 9 Baths
  • 8,054 Sq Ft

  207 Brooks Ln, Londonderry, VT 05148

  This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  207 Brooks Ln, Londonderry, VT 05148
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  /51

  $949,000

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

  33 Carinthia Rd, Dover, VT 05356

  LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

  Jacki Murano Southern Vermont Realty Group

  33 Carinthia Rd, Dover, VT 05356
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  /60

  $2,150,000

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

  18 New England Power Rd, Wilmington, VT 05363

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

  Samantha Decker Deerfield Valley Real Estate

  18 New England Power Rd, Wilmington, VT 05363
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  /55

  $899,000

  • 6 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  5825 Vermont 30, Townshend, VT 05353

  6+ bed, 5 bath 21± Acre Equestrian Estate in West Townshend VT Distinctive property combines the charm of a private equestrian estate w/tastefully finished and versatile living space & top horse facilities. On ~21 acres, including a 3-bed main home plus attached 1-bed accessory unit—ideal for guests, staff, or flex living. Metal roof, drilled well, whole-house generator. Main Barn: 8 box stalls,

  Jacki Murano Southern Vermont Realty Group

  5825 Vermont 30, Townshend, VT 05353
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  /35

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,480 Sq Ft

  24 Laurel St, Brattleboro, VT 05301

  OPEN HOUSE SUNDAY January 18th 12-2 PM This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and

  Kelly Agrillo Southern Vermont Realty Group

  24 Laurel St, Brattleboro, VT 05301
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  /51

  $699,000

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft

  98 Darby Hill Rd, Bellows Falls, VT 05101

  TOTAL PRIVACY ON 96 ACRES ABUTS THE VILLAGE FOREST & THE LOCATION OF MINARD'S POND. THIS WELL CARED FOR HOME IS CLASSIC COUNTRY THROUGHOUT W/HARD WOOD, WIDE BOARD FLOORS & BEAUTIFULL WOOD CEILINGS, FULLY APPLIANCED KITCHEN & LAUNDRY ROOM, UPDATED BATHS PLUS A REAR DECK W/TREX FLOORING OFF THE FOUR SEASON SUN ROOM. A LARGE 3 BAY BARN, WORKSHOP W/ 2ND FLOOR & ATTACHED CAR PORT W/CEMENT FLOOR. PLUS

  Don Chabot Town and Country Realty

  98 Darby Hill Rd, Bellows Falls, VT 05101
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  /38

  $449,000

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  26 N Wind Rd, Wilmington, VT 05363

  Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

  Rich Caplan Deerfield Valley Real Estate

  26 N Wind Rd, Wilmington, VT 05363
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  /39

  $890,000

  • 5 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /46

  $2,250,000

  • 6 Beds
  • 5.5 Baths
  • 6,995 Sq Ft

  71 Overlook Dr, Dover, VT 05356

  Enjoy stunning views, privacy, and access, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, pickleball courts, game room, on site management company, and direct shuttle service from your

  Adam Palmiter Berkley & Veller Greenwood/Dover

  71 Overlook Dr, Dover, VT 05356
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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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  /26

  $575,000

  • 4 Beds
  • 3 Baths
  • 3,275 Sq Ft

  12 Colonial Ridge Rd, Dover, VT 05356

  This one won't last long! Beautifully maintained chalet in the Dover Hills, on a 2 acre parcel, just a short drive from the Mount Snow ski resort. The current owners have taken care to keep the original charm of this home while updating consistently to allow for minimal maintenance and easy enjoyment. Off easy paved access, this home sits on a level parcel with ample parking, storage shed,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Colonial Ridge Rd, Dover, VT 05356
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  /53

  $284,900

  • 2 Beds
  • 1 Bath
  • 1,062 Sq Ft

  1227 Vermont 30, Townshend, VT 05353

  Discover classic Vermont charm and exceptional versatility at this unique property. Nestled on a picturesque lot, this retreat features a cozy main house with one bedroom, a full bath, and a dedicated office space that is perfect for remote work or creative pursuits. Step inside to enjoy inviting living areas filled with warm natural light, a comfortable bedroom, and a functional kitchen. The

  Flex Realty Group Flex Realty

  1227 Vermont 30, Townshend, VT 05353
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  /56

  $899,000

  • 9 Beds
  • 9 Baths
  • 5,480 Sq Ft

  3732 Vermont 30, Jamaica, VT 05343

  Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take over.This historic property boasts two dwellings and a guest cottage. Looking for a family compound to get away from it all?This is your haven! Plenty of room to have friends and family come and stay! So many options.The Main House features 4 ensuite bedrooms! The living room is a late 1700"s delight, with an

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  3732 Vermont 30, Jamaica, VT 05343
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  /2

  $1,400,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,844 Sq Ft

  286 Coldbrook Rd, Wilmington, VT 05363

  This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

  Melissa Nebelski Real Broker LLC

  286 Coldbrook Rd, Wilmington, VT 05363
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  /20

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1 Frog Hollow, Wilmington, VT 05363

  Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful brick fireplace, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will love the easy access to snowmobile and hiking trails,

  Rich Caplan Deerfield Valley Real Estate

  1 Frog Hollow, Wilmington, VT 05363
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  /54

  $325,000

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

  2015 Vermont 30, Townshend, VT 05353

  Perfectly situated on the scenic road to Stratton Mountain—just 25 minutes from the slopes—this charming turn-of-the-century mixed-use property offers endless potential. Step inside to discover original period woodwork, gleaming hardwood floors, and classic details that give this roomy home its timeless character.The property also boasts a large two-story post-and-beam barn, lovingly restored

  Craig Ruggless EXP Realty

  2015 Vermont 30, Townshend, VT 05353
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  /23

  $649,000

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

  457 Ray Hill Rd, Wilmington, VT 05363

  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 westerly views over Haystack Mountain for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  457 Ray Hill Rd, Wilmington, VT 05363
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  /24

  $225,000

  • 1 Bed
  • 1 Bath
  • 265 Sq Ft

  2053 Pikes Falls Rd, Jamaica, VT 05343

  A unique tiny house offering contemporary, Vermont farmhouse luxury in the Green Mountains. Featured on A & E's Living Smaller!This is tiny house vacation living at its finest. The house offers a full kitchen with four-burner gas stove and oven, farmhouse sink, butcher-block countertops, electric fireplace, AC, 40” Smart TV, Starlink WiFi, small soaking bathtub with shower. The bedroom loft

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  2053 Pikes Falls Rd, Jamaica, VT 05343
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  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
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  /30

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
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  /43

  $599,000

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  883 Smead Rd, Wardsboro, VT 05355

  Enjoy Vermont living in this bright and inviting 3-bedroom, 4-bathroom home, ideally located 7 minutes from Mount Snow and just under 20 minutes from Stratton. The open-concept kitchen (completely renovated in 2021) and dining area are perfect for gatherings, with natural light enhancing the home’s warm and welcoming feel.A new heating system for efficient year-round comfort is complemented by a

  Samantha Decker Deerfield Valley Real Estate

  883 Smead Rd, Wardsboro, VT 05355
• 

  

  /54

  $1,550,000

  • 4 Beds
  • 3.5 Baths
  • 3,666 Sq Ft

  3 Overbrook Dr Unit Outlook, Dover, VT 05356

  STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Set against the backdrop of Mount Snow, this just-completed luxury single-family home offers the perfect blend of modern design and spacious living. Located in the base area of the Mount Snow Resort, The OutLook at Mount Snow offers the perfect mix of mountain modern luxury and the ultimate convenience. This home features an open

  John Redd Skihome Realty

  3 Overbrook Dr Unit Outlook, Dover, VT 05356
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  /60

  $798,000

  • 3 Beds
  • 3 Baths
  • 2,757 Sq Ft

  1909 Pine Banks Rd, Putney, VT 05346

  Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

  Heidi Bernier Berkley & Veller Greenwood Country

  1909 Pine Banks Rd, Putney, VT 05346
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  /41

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 4,219 Sq Ft

  5 N Main St, Wilmington, VT 05363

  Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

  Morriah Adams BHG Masiello Brattleboro

  5 N Main St, Wilmington, VT 05363
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  /24

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  115 Country Hill, Brattleboro, VT 05301

  This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

  Kristen Ziter Taylor Brattleboro Area Realty

  115 Country Hill, Brattleboro, VT 05301
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  /60

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  732 Under the Mountain Rd, South Londonderry, VT 05155

  With 42+ stunning acres and unrivaled panoramic mountain (and sunset) views, this beautiful historic home seamlessly blends an extraordinary sense of history, grace, modern amenities, and will offer you the quintessential Vermont experience! Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse features exposed beams, wide plank wood floors, and architectural character, and

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
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  /49

  $2,099,000

  • 5 Beds
  • 5.5 Baths
  • 5,235 Sq Ft

  6 Trail View Ln, Dover, VT 05356

  Enjoy stunning views, privacy, and luxury, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, tennis courts, game room, on site management company, and direct shuttle service between your

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Trail View Ln, Dover, VT 05356
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  /35

  $749,000

  • 4 Beds
  • 5 Baths
  • 3,129 Sq Ft

  20 Ray Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Ray Hill Rd, Wilmington, VT 05363
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  /45

  $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
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  /55

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
• 

  

  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 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
• 

  

  /31

  $649,000

  • 5 Beds
  • 3.5 Baths
  • 2,706 Sq Ft

  916 Wiswall Hill Rd, Townshend, VT 05353

  Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  916 Wiswall Hill Rd, Townshend, VT 05353

Showing Results 81 - 120, Page 3 of 5