229

Windham County VT Houses for Sale

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  • /50

    $435,000

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    27 Country Ct, Wilmington, VT 05363

    Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use

    Janet Boyd Boyd Real Estate

    27 Country Ct, Wilmington, VT 05363
  • /44

    $450,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,943 Sq Ft

    24 Antler Loop, West Dover, VT 05356

    This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    24 Antler Loop, West Dover, VT 05356
  • /4

    $182,000

    • 3 Beds
    • 1.5 Baths
    • 1,114 Sq Ft

    23 Williams St, Brattleboro, VT 05301

    Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the

    Christine Lewis Brattleboro Area Realty

    23 Williams St, Brattleboro, VT 05301
  • /36

    $469,000

    • 4 Beds
    • 2 Baths
    • 2,515 Sq Ft

    20 Wildwood Acres Rd, Newfane, VT 05345

    Lovely country home conveniently located just up from the Rock River in South Newfane, near the village, elementary school, and a short drive in to Brattleboro. This home is being offered for the first time in 40 years and has been lovingly maintained by the current owners. The 14+ acre parcel features a private setting, extensive stone work and landscaping, and an additional parcel which allows

    Adam Palmiter Berkley & Veller Greenwood/Dover

    20 Wildwood Acres Rd, Newfane, VT 05345
  • /26

    $219,000

    $40K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft

    279 North St, East Dover, VT 05341

    Rustic Hunting Cabin on 1+/- Acres. Spring water supply and a holding tank for septic in place. Several sleeping areas including a loft. One full bathroom. Kitchen with stove, ,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer & dryer. Plan your weekend runaway now!

    Janet Boyd Boyd Real Estate

    279 North St, East Dover, VT 05341
  • /39

    $795,000

    $280K PRICE DROP
    • 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
  • /60

    $535,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,397 Sq Ft

    14 High Top Rd Unit B124, Wilmington, VT 05363

    Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are

    Sigrid Pickering Chimney Hill Realty

    14 High Top Rd Unit B124, Wilmington, VT 05363
  • /60

    $1,160,000

    • 5 Beds
    • 4 Baths
    • 3,664 Sq Ft

    82 N Brookwood Rd, Stratton, VT 05360

    Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

    Kim Morgan-Wohler Wohler Realty Group

    82 N Brookwood Rd, Stratton, VT 05360
  • /52

    $1,450,000

    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /60

    $750,000

    • 6 Beds
    • 4.5 Baths
    • 3,259 Sq Ft

    492 Dover Rd, Newfane, VT 05351

    Own a piece of Vermont history with this charming 1854 home, formerly known as The ThreePenny Lodge and now known as The Cardinal Lodge, nestled in the heart of desirable Newfane near skiing, trails and year-round recreation. Cross a picturesque, covered bridge on your way home and discover a property full of character, currently operating as a successful Airbnb with a live-in caretaker. Whether

    Kerry Mulverhill

    492 Dover Rd, Newfane, VT 05351
  • /35

    $325,000

    New Construction $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    203 Fairview St, Brattleboro, VT 05301

    PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, & year-round comfort. Completed in July 2026 & designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating & cooling.

    Kristen Ziter Taylor Brattleboro Area Realty

    203 Fairview St, Brattleboro, VT 05301
  • /29

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 3,314 Sq Ft

    28 Partridge Run Rd, Dover, VT 05356

    This stunning post and beam home is located just off the Mount Snow golf course, a short drive from the resort, with direct snowmobile trail access right from your home. This home sits on a level lot with nice privacy around the front deck and hot tub, for soaking after a day on the slopes. Inside is a tremendous great room with vaulted ceilings, great natural light, and exposed post and beam

    Adam Palmiter Berkley & Veller Greenwood/Dover

    28 Partridge Run Rd, Dover, VT 05356
  • /59

    $425,000

    • 4 Beds
    • 3 Baths
    • 2,345 Sq Ft

    52 Ruth Way, Wilmington, VT 05363

    Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

    Donna Brown Skihome Realty

    52 Ruth Way, Wilmington, VT 05363
  • /38

    $645,000

    • 4 Beds
    • 3 Baths
    • 2,740 Sq Ft

    1161 Little Pond Rd, Londonderry, VT 05148

    Beautifully renovated 4-bedroom home with a stylish 2-bedroom accessory dwelling, offering the perfect blend of modern comfort, flexibility, and Vermont charm. Whether you're looking for space for extended family, guests, or the potential for rental income, this thoughtfully designed property offers endless possibilities.Step inside to discover contemporary upgrades throughout, where every

    Carrie Mathews Winhall Real Estate

    1161 Little Pond Rd, Londonderry, VT 05148
  • /45

    $399,000

    $60K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    60 E Brook Crossing, Wilmington, VT 05363

    Tucked among mature trees in the desirable lower section of Chimney Hill, this charming home offers comfort, character, and easy living. A gently sloping gravel driveway and attached converted garage provide year-round convenience, while beautifully established perennial gardens and a gently sloping yard create an inviting outdoor setting rarely found in the area. Inside, the home exudes warmth

    Erica Reynolds Southern Vermont Realty Group

    60 E Brook Crossing, Wilmington, VT 05363
  • /37

    $679,000

    • 3 Beds
    • 3.5 Baths
    • 2,476 Sq Ft

    15 Skyline Dr, Vernon, VT 05354

    Open House 8/2, 1:00–3:00 PM Nestled on approximately 4 private acres, this custom-built timber frame home offers an exceptional blend of craftsmanship, comfort, and privacy. Tucked away on a quiet, dead-end road, this is one of only four sites, providing a peaceful setting with the perfect balance of seclusion and convenience. Inside, exposed timber framing, soaring vaulted ceilings, and walls

    Morriah Adams BHG Masiello Brattleboro

    15 Skyline Dr, Vernon, VT 05354
  • /40

    $1,500,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /20

    $320,000

    $34K PRICE DROP
    • 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
  • /60

    $700,000

    $25K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,630 Sq Ft

    5 William Mundell Rd, South Newfane, VT 05351

    Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

    The Malley Group KW Vermont

    5 William Mundell Rd, South Newfane, VT 05351
  • /59

    $715,000

    $5K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,379 Sq Ft

    587 Vermont 121, Grafton, VT 05146

    Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details

    Mendi Michael Engel & Völkers Okemo

    587 Vermont 121, Grafton, VT 05146
  • /13

    $249,000

    • 1 Bed
    • 1 Bath
    • 480 Sq Ft

    1970 S Wardsboro Rd, Wardsboro, VT 05355

    Charming one bedroom cottage just outside the village of Wardsboro in Southern Vermont. This home away from home is being offered for sale for the first time by the original owners that built it. Up a private drive with easy access off a paved road sits this charming cottage, overlooking a river and short range mountain view across the way. There is a lovely open lawn space which is a small

    Adam Palmiter Berkley & Veller Greenwood/Dover

    1970 S Wardsboro Rd, Wardsboro, VT 05355
  • /55

    $649,500

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    800 Hubbard Hill Rd, Jacksonville, VT 05342

    This stately Colonial Revival style home is situated privately on nearly 10 acres with its awesome 3 story 30' X 40' barn accessed by a long winding driveway. The main level features include large spacious rooms with wainscoting and natural woodwork, an open kitchen/dining/living floor plan, half bath/laundry and a pantry off kitchen, proper foyer, living room with a grand fireplace, wide

    Chris Long BHG Masiello Brattleboro

    800 Hubbard Hill Rd, Jacksonville, VT 05342
  • /24

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,036 Sq Ft

    456 Route 100, Wilmington, VT 05363

    Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or

    Patrice Schneider Southern Vermont Realty Group

    456 Route 100, Wilmington, VT 05363
  • /40

    $489,000

    $36K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,320 Sq Ft

    5735 Vt Route 11, Londonderry, VT 05148

    What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Sellers are motivated due to having already relocated for work!

    Zachary Zupan EXP Realty

    5735 Vt Route 11, Londonderry, VT 05148
  • /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
  • /45

    $629,000

    • 5 Beds
    • 3 Baths
    • 2,430 Sq Ft

    13 Circle View Dr, Dover, VT 05356

    Perfectly positioned for enjoying all that the Mount Snow area has to offer, this beautifully updated home is located just 1.5 miles from Mount Snow Ski Resort and approximately 1 mile from the Mount Snow Golf Course.Step inside to a bright and inviting interior featuring vaulted ceilings, beautiful wood floors, mini-splits for year-round comfort, and a cozy woodstove the perfect place to

    Rich Caplan Deerfield Valley Real Estate

    13 Circle View Dr, Dover, VT 05356
  • /34

    $799,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,550 Sq Ft

    25 Yeaw Rd, Dover, VT 05341

    Enjoy year-round living in this handsome contemporary home set on over 12 acres of picturesque land, featuring open meadows, a gentle stream, a large pond, mixed woodland, and beautifully maintained gardens. Bright and inviting, the home offers a spacious layout designed for both comfort and entertaining. There is an attached 3 bay garage above which is a huge heated bonus room with storage

    Robert Doyle Berkley & Veller Greenwood Country

    25 Yeaw Rd, Dover, VT 05341
  • /42

    $795,000

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    6694 Route 11, Londonderry, VT 05148

    Pride of ownership is evident throughout this exceptionally well cared for four-bedroom home, beautifully situated on more than four acres in desirable Londonderry. A long, welcoming driveway and a stately row of mature pines create a wonderful sense of arrival while providing year-round privacy. Offering an ideal blend of comfort, seclusion, and convenience, this inviting property is equally

    Carrie Mathews Winhall Real Estate

    6694 Route 11, Londonderry, VT 05148
  • /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
  • /45

    $1,475,000

    • 7 Beds
    • 6 Baths
    • 6,292 Sq Ft

    53 Hickory Ridge Rd, Putney, VT 05346

    Hickory Ridge House is a Federal masterpiece: a definitive piece of Vermont history. Elegant and expansive, the home’s soul is rooted in the 19th century, while its heart beats with 21st-century innovation. The interiors are a masterclass in "refined rustic" design, with original features such as antique wood floors, 12-over-12 windows, crown moldings, and wood-burning fireplaces throughout the

    Thomas Dahlin Berkley & Veller Greenwood Country

    53 Hickory Ridge Rd, Putney, VT 05346
  • /31

    $565,000

    • 5 Beds
    • 3 Baths
    • 2,768 Sq Ft

    77 Villager Loop, Dover, VT 05356

    This one won't last long! Beautifully maintained and updated chalet in the Dover Hills, 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 adding rustic features and recent updates to allow for turn key enjoyment. Off the side of a private paved loop, this home sits on a level parcel with ample parking, spacious

    Adam Palmiter Berkley & Veller Greenwood/Dover

    77 Villager Loop, Dover, VT 05356
  • /38

    $1,850,000

    • 6 Beds
    • 6 Baths
    • 4,154 Sq Ft

    3 Slopeside Rd, West Dover, VT 05356

    Trailside luxury in a class of its own. This stunning home was taken down to the frame and should be considered new construction — positioned immediately trailside at Mount Snow with a private ski trail connecting directly to the magic carpet at Carinthia for full-season ski access. Ski to and from your mudroom door and never worry about shuttles or parking again.Professionally designed and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    3 Slopeside Rd, West Dover, VT 05356
  • /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
  • /29

    $849,000

    • 4 Beds
    • 3.5 Baths
    • 2,272 Sq Ft

    12 Encore Place, Dover, VT 05356

    Mountain Modern Living with unmatched trail views of Carinthia at 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 the Mountain. 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

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    12 Encore Place, Dover, VT 05356
  • /58

    $549,000

    $50K PRICE DROP
    • 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
  • /50

    $619,900

    $80K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,450 Sq Ft

    300 Route 121 E, Grafton, VT 05146

    Nestled in a postcard perfect riverfront setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Property is being offered furnished and turn key! Set on over two park like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll

    Gary Coger Four Seasons Sotheby's Int'l Realty

    300 Route 121 E, Grafton, VT 05146
  • /31

    $260,000

    • 4 Beds
    • 2.5 Baths
    • 2,572 Sq Ft

    106 Coolidge Hwy Unit 6-276, Guilford, VT 05301

    Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment

    John Mcpherson Berkley & Veller Greenwood Country

    106 Coolidge Hwy Unit 6-276, Guilford, VT 05301
  • /44

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    85 Browns Rd, Newfane, VT 05345

    Steeped in Vermont history and surrounded by more than 80 acres of fields, woods, and walking trails, this beautifully preserved Newfane farmhouse offers the rare opportunity to own a property where timeless character and modern comfort come together. Whether you're looking for a full-time residence, country retreat, or recreational property, this is a place to slow down and enjoy the beauty of

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    85 Browns Rd, Newfane, VT 05345
  • /39

    $349,000

    $50K PRICE DROP
    • 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
  • /2

    $350,000

    $50K PRICE INCREASE
    • 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 to

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301

Showing Results 121 - 160, Page 4 of 6

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