471

Windham County VT Homes for Sale

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  • /20

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,401 Sq Ft

    783 Wilmington Cross Rd, Whitingham, VT 05361

    Private 72 acre playground with 3 bedrooms, 3 bath log cabin. Lots of room to play, including a VAST trail in the rear. A great covered porch makes for enjoying the privacy just out side to large kitchen/living/dining room, or downstairs outside the equally large family room. Plenty of room for guests and a large barn or outbuildings for all your Vt outdoor stuff. Lake Whitingham is minutes down

    Michael Purcell Berkley & Veller Greenwood/Dover

    783 Wilmington Cross Rd, Whitingham, VT 05361
  • /2

    $125,000

    • 4 Beds
    • 2 Baths
    • 2,644 Sq Ft

    54 Williams St Unit 56, Bellows Falls, VT 05101

    Offering over 2,500 square feet of potential. The 2.5-story layout with porches offers a project for buyers seeking sweat equity, rental income potential, or a large single-family home tailored to their needs. Located within walking distance of downtown Bellows Falls, you'll be close to shops, restaurants, the Connecticut River, and all the character this historic village has to offer. Please

    Shawna Fox BHHS Verani Upper Valley

    54 Williams St Unit 56, Bellows Falls, VT 05101
  • /39

    $520,342

    • 3 Beds
    • 3 Baths
    • 1,521 Sq Ft

    34 Rock Split Way, Wilmington, VT 05363

    Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, flows seamlessly into

    Megan Quinn Southern Vermont Realty Group

    34 Rock Split Way, Wilmington, VT 05363
  • /27

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,530 Sq Ft

    72 Green Meadow Rd, West Brattleboro, VT 05301

    Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck

    Thomas Dahlin Berkley & Veller Greenwood Country

    72 Green Meadow Rd, West Brattleboro, VT 05301
  • /59

    $354,900

    • 3 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    21 Big Bend Loop, Wilmington, VT 05363

    Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas. Step inside through the spacious

    Kelsey Malloy Keller Williams Realty Metro-Keene

    21 Big Bend Loop, Wilmington, VT 05363
  • /60

    $995,000

    • 4 Beds
    • 3 Baths
    • 2,821 Sq Ft

    179 Reed Rd, Athens, VT 05143

    Custom Swedish Cope Log Home on 14 plus acres in Southern Vermont.Hidden among the hills, this custom log home combines rugged craftsmanship with warm, open living spaces. Oversized timbers transported from Idaho were assembled in the Swedish Cope style, featuring traditional saddle notched logs that give the home its distinctive character.A cathedral style entry leads into a dramatic

    Julie Lowe Lowe's Real Estate, LLC

    179 Reed Rd, Athens, VT 05143
  • /12

    $67,500

    • Land
    • 3.5 Acres
    • $19,286 per Acre

    0 Dover Rd Unit 5102886, Newfane, VT 05345

    Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    0 Dover Rd Unit 5102886, Newfane, VT 05345
  • /10

    $499,000

    • Land
    • 2 Acres
    • $249,500 per Acre

    70 Overlook Dr, Dover, VT 05356

    Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

    Adam Palmiter Berkley & Veller Greenwood/Dover

    70 Overlook Dr, Dover, VT 05356
  • /9

    $198,000

    • Land
    • 3.27 Acres
    • $60,550 per Acre

    0 Pleasant Valley Rd, Brattleboro, VT 05301

    It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

    Christine Lewis Brattleboro Area Realty

    0 Pleasant Valley Rd, Brattleboro, VT 05301
  • /56

    $624,900

    • 4 Beds
    • 2.5 Baths
    • 2,904 Sq Ft

    37 Stowe Hill Rd, Wilmington, VT 05363

    Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm.

    Monique White Deerfield Valley Real Estate

    37 Stowe Hill Rd, Wilmington, VT 05363
  • /45

    $1,625,000

    • 15 Beds
    • 10 Baths
    • 12,845 Sq Ft

    4 Court St, Newfane, VT 05345

    A rare offering on the Newfane village green: a Federal-style inn dating to 1787, set beside the Windham County Courthouse along VT Route 30 in one of New England's most photographed villages. The property combines eight guest accommodations (a mix of multi-room suites and private rooms, each with a private bath) with a three-bedroom, two-bath owner's residence featuring its own full kitchen and

    Eben Viens Berkley & Veller Greenwood Country

    4 Court St, Newfane, VT 05345
  • /8

    $585,000

    • Land
    • 91.6 Acres
    • $6,386 per Acre

    0 Water St Unit 5102573, Jamaica, VT 05343

    A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events.The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surroundings.

    Carrie Mathews Winhall Real Estate

    0 Water St Unit 5102573, Jamaica, VT 05343
  • /28

    $25,000

    • 1 Bed
    • 2 Baths
    • 846 Sq Ft

    103/105, QTR 1 89 Grand Summit Way, Dover, VT 05356

    Own Where You Play!Enjoy effortless mountain living with this turnkey, fully furnished quartershare that comfortably sleeps up to eight and offers beautiful views of Mount Snow from the Grand Summit Resort Hotel. This spacious condo provides exceptional flexibility, making it ideal for personal use, rental income, or vacation exchanges.Designed with convenience in mind, the unit features

    Patricia Fitzpatrick Skihome Realty

    103/105, QTR 1 89 Grand Summit Way, Dover, VT 05356
  • /15

    $57,000

    • Land
    • 2 Acres
    • $28,500 per Acre

    56 & 57 Boardman Loop, Wardsboro, VT 05355

    Located in the Snow Mountain Farms West community, this wooded two acre lot offers the perfect setting and privacy for your Vermont home. Positioned strategically between Stratton and Mount Snow, the property serves as an ideal base camp for winter sports enthusiasts and summer adventurers alike. Also close by is the Green Mountain National Forest, and the VAST snowmobile trails. Successful

    Prema Fitzpatrick Real Broker LLC

    56 & 57 Boardman Loop, Wardsboro, VT 05355
  • /36

    $22,500

    • 1 Bed
    • 1 Bath
    • 671 Sq Ft

    308 Qtr.4, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

    Kelly Agrillo Southern Vermont Realty Group

    308 Qtr.4, 89 Grand Summit Way, Dover, VT 05356
  • /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
  • /60

    $1,600,000

    • 5 Beds
    • 5 Baths
    • 6,118 Sq Ft

    3 Eldredge Rd, Chester, VT 05143

    A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    3 Eldredge Rd, Chester, VT 05143
  • /4

    $45,000

    • Land
    • 30 Acres
    • $1,500 per Acre

    00 Kidder Hill Rd, Grafton, VT 05146

    Invest in Vermont's forests and wildlife. This 30 acre wooded lot now available in Grafton. Entirety of parcel is enrolled in the Vermont Land Use program for forest management. Last cut was in 2020, plan update is required in 2028 with a projected next cut in approximately 2030. Topography does not offer typical residential building potential.

    Jessica Landers Barrett and Valley Associates Inc.

    00 Kidder Hill Rd, Grafton, VT 05146
  • /51

    $5,100,000

    • 10 Beds
    • 9.5 Baths
    • 6,648 Sq Ft

    15 Sawmill Rd, Stratton, VT 05155

    Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

    Kim Morgan-Wohler Wohler Realty Group

    15 Sawmill Rd, Stratton, VT 05155
  • /14

    $249,999

    • Land
    • 29 Acres
    • $8,621 per Acre

    0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301

    Here's your chance to own 29 acres of wooded Vermont countryside with frontage on both Stickney Brook Road and Hopkins Road, offering flexible access and endless possibilities. Set along one of Dummerston's most picturesque country roads this unique parcel offers privacy, potential and the perfect setting for a private retreat, camp or future homesite. A mix of timber and classic New England

    Lily Gautot Greenwald Realty Group

    0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301
  • /4

    $28,000

    $7K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $112,000 per Acre

    2 Brook Ln, Wilmington, VT 05363

    Nice building lot located in the Two Brook community, conveniently situated near Haystack Golf Course and just minutes from skiing, golf, lakes, and snowmobiling. This attractive parcel offers a peaceful setting with common land bordering the rear of the property and a stream flowing through the lot, adding to its natural appeal. Power, public water, and public sewer infrastructure are available

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    2 Brook Ln, Wilmington, VT 05363
  • /40

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /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
  • /27

    $519,000

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft

    56 Park Laughton Rd, East Dummerston, VT 05346

    A wonderful Colonial home in Dummerston Village Vermont. Classic layout with a huge primary bedroom with double closets, 2 additional generouslysized bedrooms and a full bath on the second floor. The first floor has a large family room, dining room, a full bath with laundry, and a lovely 1/2 bath. Freshly updated with a new roof, new Anderson windows, new high efficiency furnace, whole house

    Derek Greene Derek Greene

    56 Park Laughton Rd, East Dummerston, VT 05346
  • /44

    $136,000

    • Land
    • 14 Acres
    • $9,714 per Acre

    182 Partridge Ln, Jamaica, VT 05343

    Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a

    Jessica Landers Barrett and Valley Associates Inc.

    182 Partridge Ln, Jamaica, VT 05343
  • /60

    $690,000

    • 5 Beds
    • 4 Baths
    • 2,642 Sq Ft

    57 Castle Hill Rd, Wilmington, VT 05363

    Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while

    Donna Brown Skihome Realty

    57 Castle Hill Rd, Wilmington, VT 05363
  • /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
  • /21

    $290,000

    • Land
    • 289.12 Acres
    • $1,003 per Acre

    0 Black Bear Rd Unit 5101033, Jamaica, VT 05343

    Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

    Thom Milke Fountains Land Inc.

    0 Black Bear Rd Unit 5101033, Jamaica, VT 05343
  • /21

    $290,000

    • Land
    • 289.12 Acres
    • $1,003 per Acre

    2817 Lt 22, Jamaica, VT 05343

    Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

    Zach Jaminet Fountains Land

    2817 Lt 22, Jamaica, VT 05343
  • /42

    $479,999

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    7 High Top Unit B117, Wilmington, VT 05363

    Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and

    Sigrid Pickering Chimney Hill Realty

    7 High Top Unit B117, Wilmington, VT 05363
  • /36

    $319,000

    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    12 Par Dr Unit 12, Wilmington, VT 05363

    Enjoy year-round Vermont living in this classic Spyglass townhome that is located right on the 10th fairway of the Haystack Golf course. Offering 3 bedrooms plus a sleeping loft and 3.5 baths. Designed for comfort and convenience, the main level features a mudroom, an open-concept living and dining area with vaulted ceilings, a fully equipped kitchen, and a cozy wood-burning fieldstone fireplace.

    Rich Caplan Deerfield Valley Real Estate

    12 Par Dr Unit 12, Wilmington, VT 05363
  • /55

    $550,000

    • 3 Beds
    • 5 Baths
    • 5,046 Sq Ft

    13 Brookside Ln, Newfane, VT 05345

    Beautiful Cape style home nestled in a private country setting, surrounded by mature trees in desirable Newfane and just a short drive to skiing, hiking and other outdoor recreation. Offering exceptional flexibility, the property features an in-law apartment in addition to a separate living quarter, both are currently generating rental income, ideal for multigenerational living, extended family,

    Kerry Mulverhill

    13 Brookside Ln, Newfane, VT 05345
  • /26

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    Beautiful three story Powderhorn townhome on the slopes of Haystack Mountain at the exclusive Hermitage Club Ski Resort - a true four-season retreat with thoughtful upgrades that set it apart from anything else in the development. Wake up to sunrise winter views over the mountains through expansive windows thanks to the end unit location. Enjoy woodsy scenery over your private deck and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /54

    $579,000

    • 4 Beds
    • 2 Baths
    • 1,723 Sq Ft

    66 Upper Oak Hill Rd, Newfane, VT 05345

    180 +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation that define this special corner

    Jacki Murano Southern Vermont Realty Group

    66 Upper Oak Hill Rd, Newfane, VT 05345
  • /60

    $945,000

    • 2 Beds
    • 1.5 Baths
    • 2,721 Sq Ft

    51 Dusty Ridge Rd, Putney, VT 05346

    Nestled along one of Putney's most scenic country roads, this private 18.3 acre property offers the perfect balance of wooded privacy, open space, and classic Vermont charm. Stone walls, mature perennial gardens, walking trails, and a meandering stream create a peaceful setting. The thoughtfully designed home offers 2,721 square feet of living space with 2 bedrooms and 2 bathrooms. A soaring

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    51 Dusty Ridge Rd, Putney, VT 05346
  • /20

    $24,500

    • 1 Bath
    • 673 Sq Ft

    224 Qtr. 2, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? One bedroom, sleeps 6, single-le unit. Close to the elevator, the Owners Lounge, and the library. King bed, Queen sleeper sofa, Queen Murphy bed. One bathroom. Use it, rent it, trade it! Does having 13 weeks of vacation a year sound appealing? This one-bedroom unit accommodates up to six people and is conveniently located on

    Kelly Agrillo Southern Vermont Realty Group

    224 Qtr. 2, 89 Grand Summit Way, Dover, VT 05356
  • /42

    $340,000

    $10K PRICE DROP
    • 2,745 Sq Ft

    120 Western Ave, Brattleboro, VT 05301

    Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    120 Western Ave, Brattleboro, VT 05301
  • /41

    $529,000

    • 3 Beds
    • 3 Baths
    • 1,688 Sq Ft

    190 Route 11 Unit 2, Peru, VT 05152

    Escape to the heart of Southern Vermont in this recently renovated chalet-style mountain home, where timeless charm meets four-season recreation. Being sold fully furnished. Ideally located under 25 minutes from four premier ski resorts - Bromley, Stratton, Magic, and Okemo - this inviting retreat offers the perfect balance of adventure and relaxation. Set against a backdrop of breathtaking

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    190 Route 11 Unit 2, Peru, VT 05152
  • /7

    $135,000

    • Land
    • 4.5 Acres
    • $30,000 per Acre

    0 Route 100 Unit 5100378, Dover, VT 05356

    Nestled just half a mile from the renowned Mount Snow Resort, this exquisite 4.50-acre property offers a remarkable opportunity to create your dream home in a prime location. With a cleared driveway and an essential permit already secured (Waste Water Permit for a mound wastewater disposal system and a Potable Water Permit for a drilled bedrock water supply), this lot is ready for development.

    Donna Brown Skihome Realty

    0 Route 100 Unit 5100378, Dover, VT 05356
  • /41

    $999,000

    • 4 Beds
    • 4.5 Baths
    • 5,050 Sq Ft

    3 Shannon Ridge Rd, Dover, VT 05356

    Some homes are renovated. Others are carefully crafted. 3 Shannon Ridge Road is unmistakably the latter.At first glance, the home feels elegant. Spend time inside, however, & its character begins to emerge: 16-ft.-long wide pine floors secured w/ traditional square nails, remarkably high ceilings, beautifully composed architecture, expansive windows, live-edge wood, a kitchen for entertaining and

    Jacki Murano Southern Vermont Realty Group

    3 Shannon Ridge Rd, Dover, VT 05356

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