Windham County VT Houses for Sale

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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /39

  $925,000

  • 5 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3715 Route 11, Londonderry, VT 05148

  Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

  Cheyanne Pugliese

  3715 Route 11, Londonderry, VT 05148
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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 2,470 Sq Ft

  1153 Rockingham Rd, Town of Rockingham, VT 05101

  Calling all investors and handy people! This is your opportunity to bring a classic property back to its former glory. Set on approximately 8.67 acres with frontage along the Williams River and Route 103, the location offers endless potential for a variety of uses. The spacious home appears to have solid bones but will require rehabilitation to restore its charm. A concrete slab is already in

  Chelsea Richardson Barrett and Valley Associates Inc.

  1153 Rockingham Rd, Town of Rockingham, VT 05101
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  /59

  $2,398,000

  • 4 Beds
  • 4 Baths
  • 3,585 Sq Ft

  127 Fannie Hill Dr, Wilmington, VT 05363

  Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  127 Fannie Hill Dr, Wilmington, VT 05363
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  /50

  $950,000

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

  1 Tom's Cabin Rd, Dover, VT 05356

  Tucked away on 6 private acres in Dover, Vermont, this beautifully crafted 4-bedroom, 4-bath home offers the perfect blend of rustic charm, comfort, and space for year-round enjoyment. A dramatic great room with soaring ceilings, exposed timber framing, a stone fireplace, and a wall of windows creates a warm and inviting gathering space filled with natural light and woodland views.The

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1 Tom's Cabin Rd, Dover, VT 05356
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  /38

  $749,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  717 Horsenail Hill Rd, Chester, VT 05143

  Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

  Robin Apps Four Seasons Sotheby's Int'l Realty

  717 Horsenail Hill Rd, Chester, VT 05143
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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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  /20

  $179,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  7139 Vermont Route 100, Whitingham, VT 05361

  This cozy two bedroom, one bath cottage with vaulted wood ceilings is just steps away from Lake Whitingham! Enjoy a low maintenance get-away with an inviting living room and kitchen. This charming property offers the perfect escape for summer and winter enjoyment! The heart of the home is open and inviting where cold winter nights are made comfortable with an efficient propane heater. The simple,

  Casey Scott Southern Vermont Realty Group

  7139 Vermont Route 100, Whitingham, VT 05361
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  /27

  $899,000 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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  /26

  $625,000

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

  68 Ellis Brook Rd, Dover, VT 05341

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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 Ellis Brook Rd, Dover, VT 05341
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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 Open Sun 12PM - 3PM

  • 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 SATURDAY FEBRUARY 7th 10 AM- 1 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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  /60

  $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 Open Sat 2PM - 4PM

  • 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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  /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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  /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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  /55

  $389,000

  • 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 Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

  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
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  /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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  /34

  $539,000

  • 4 Beds
  • 3 Baths
  • 3,081 Sq Ft

  3996 Vermont 30, Jamaica, VT 05343

  Village charm meets mountain lifestyle in this beautifully updated home in the heart of Jamaica. Set above the road for added privacy, the property captures lovely winter views of the surrounding mountains and river while remaining just a short stroll to local shops and village conveniences.Inside, you’ll find generous living space with warm wood floors and a flowing, open layout designed for

  Carrie Mathews Winhall Real Estate

  3996 Vermont 30, Jamaica, VT 05343
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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
• 

  

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 5