224

Windham County VT Houses for Sale

Section Image
  • /59

    $275,000

    • 2 Beds
    • 1 Bath
    • 715 Sq Ft

    81 Parish Hill Rd, Newfane, VT 05345

    Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

    Chad Bruyette Whitetail Properties Real Estate, LLC

    81 Parish Hill Rd, Newfane, VT 05345
  • /30

    $400,000 Open Sat 11AM - 1PM

    • 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. Again in place is easy

    Christine Lewis Brattleboro Area Realty

    1089 Marlboro Rd, Brattleboro, VT 05301
  • /39

    $310,000

    • 2 Beds
    • 1 Bath
    • 1,367 Sq Ft

    672 Huckle Hill Rd, Vernon, VT 05354

    This sweet, well-built home is full of character and curb appeal, thoughtfully updated over the years to blend historic charm with modern convenience. The standing-seam metal roof, an updated 200-amp electric panel should provide peace of mind for years to come. There is fabulous two-story deck with low-maintenance Trex decking, a poured slab, and hookups ready for a hot tub.Inside,

    Kerry Mulverhill

    672 Huckle Hill Rd, Vernon, VT 05354
  • /19

    $84,500

    • 3 Beds
    • 1 Bath
    • 1,490 Sq Ft

    7 Nichols Dr, Guilford, VT 05301

    This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry,

    Derek Greene Derek Greene

    7 Nichols Dr, Guilford, VT 05301
  • /44

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /60

    $495,000

    • 6 Beds
    • 3 Baths
    • 3,954 Sq Ft

    430 Huckle Hill Rd, Vernon, VT 05354

    Perfect EXTENDED FAMILY OR IN-LAW set up!! This spacious and inviting property offers the perfect blend of privacy and comfort. Nestled in a peaceful wooded setting, surrounded by classic stone walls and a year-round stream, it provides the Vermont lifestyle you’ve been dreaming of. Inside, the main level features gleaming hardwood floors with radiant heat and an open-concept layout with vaulted

    Carol Slocum Keller Williams Realty Metro-Keene

    430 Huckle Hill Rd, Vernon, VT 05354
  • /29

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    132 Pratt Bridge Rd, Jamaica, VT 05343

    Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, Jamaica, VT 05343
  • /38

    $395,000

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft

    105 Chestnut St, Brattleboro, VT 05301

    This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining

    Kristen Ziter Taylor Brattleboro Area Realty

    105 Chestnut St, Brattleboro, VT 05301
  • /20

    $469,000

    • 4 Beds
    • 2 Baths
    • 2,219 Sq Ft

    45 Dover Hill Rd, East Dover, VT 05341

    Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Dover Hill Rd, East Dover, VT 05341
  • /24

    $279,000

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    91 Carriage Hill Rd, Brattleboro, VT 05301

    This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level

    Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
  • /36

    $442,500

    • 4 Beds
    • 3.5 Baths
    • 2,794 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    Pleasant and comfortable! This inviting home offers four bedrooms, three and a half bathrooms, a choice of primary bedroom with ensuite bath on the first floor or on the second. Enjoy a pleasant open flow living, kitchen and dining with hard wood floors for entertaining or hosting your next book club. The first floor offers a cheerful step saver kitchen with a pantry, gas range and views to the

    Jim Bellville Bellville Realty

    87 Orchard St, Brattleboro, VT 05301
  • /54

    $335,000

    • 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
  • /51

    $845,000

    • 4 Beds
    • 4 Baths
    • 3,987 Sq Ft

    6235 Grafton Rd, Grafton, VT 05146

    1820 sunny farmhouse on 53 acres with comfortable additions, energy saving updates, and long frontage on Stiles Brook, running through the property. Recent first floor bedroom has handicap accessible adjoining bathroom (walk-in shower and clawfoot tub). Many windows have been replaced and full insulation added. One recent addition is the south-facing "sun room" - warm in the winter with its

    Judy Dickison Barrett & Valley Assoc. Inc

    6235 Grafton Rd, Grafton, VT 05146
  • /44

    $364,900

    • 4 Beds
    • 1.5 Baths
    • 2,316 Sq Ft

    16 Forest St, Bellows Falls, VT 05101

    Welcome to this beautifully maintained 4-bedroom, 2-bath New Englander, perfectly blending timeless character with modern updates. Nestled in the quintessential New England town of Rockingham, this home offers the warmth of history and the comfort of today’s conveniences.Step inside to find a recently painted interior, stunning natural woodwork, and gleaming floors throughout. The updated

    Bruce Murphy Keller Williams Realty Metro-Keene

    16 Forest St, Bellows Falls, VT 05101
  • /35

    $2,197,000

    • 5 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    14 Tarheel Trail, Wilmington, VT 05363

    This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14 Tarheel Trail, Wilmington, VT 05363
  • /32

    $425,000

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

    155 Upper Dummerston Rd, Brattleboro, VT 05301

    Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

    John Hatton Berkley & Veller Greenwood Country

    155 Upper Dummerston Rd, Brattleboro, VT 05301
  • /50

    $680,000

    • 4 Beds
    • 4 Baths
    • 2,590 Sq Ft

    196 Old Sawmill Rd, Londonderry, VT 05148

    Nestled in the Green Mountains just minutes from Magic Mountain Ski Area, this spacious 4-bedroom retreat offers the perfect Vermont lifestyle. Enjoy easy access to beautiful Lowell Lake, while tucked away on a quiet dead-end road with serene mountain views. Inside, the home features 3 private en suite bedrooms, two of which include cozy loft spaces, plus an additional guest room. A warm and

    Lee Brown Four Seasons Sotheby's Int'l Realty

    196 Old Sawmill Rd, Londonderry, VT 05148
  • /19

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,830 Sq Ft

    4850 Vermont Route 100, Wardsboro, VT 05355

    Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4850 Vermont Route 100, Wardsboro, VT 05355
  • /20

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    175 Sherwood Forest, Londonderry, VT 05148

    Nestled in the scenic beauty of Londonderry, Vermont, this delightful 3-bedroom, 2-bathroom home offers the perfect blend of comfort, convenience, and outdoor charm. With a thoughtfully designed layout that includes a bedroom and full bath on the main floor, this home is ideal for aging in place or accommodating guests.The heart of the home boasts an open living, dining, and kitchen area,

    Christiane Carroccio TPW Real Estate

    175 Sherwood Forest, Londonderry, VT 05148
  • /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

    Janet Boyd Boyd Real Estate

    27 Country Ct, Wilmington, VT 05363
  • /33

    $397,777

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    528 Vermont 121, Windham, VT 05155

    Nestled alongside a meandering stream, this perfectly private Cape-style home offers an idyllic setting with over 2 acres of lush land, perfect for play, gardening, or entertaining. Built in the late 80's this home features 3 bedrooms and 2 baths blending timeless appeal with modern conveniences. First floor bedroom and a 2 car garage attached with a practical mudroom offers easy living. 5 new

    Julie Citron RE/MAX Four Seasons

    528 Vermont 121, Windham, VT 05155
  • /29

    $514,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    275 Pams Hill Rd, Wardsboro, VT 05355

    Absolutely meticulous and renovated gambrel chalet with private parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to extensive upgrades throughout making it truly turn key. There is a large great room with expansive windows, natural woodwork, great natural light, and efficient gas stove, a beautiful updated

    Adam Palmiter Berkley & Veller Greenwood/Dover

    275 Pams Hill Rd, Wardsboro, VT 05355
  • /55

    $319,000

    • 3 Beds
    • 2 Baths
    • 2,910 Sq Ft

    597 Gates Pond Rd, Jacksonville, VT 05342

    Classic Greek Revival Expanded in True New England Farmhouse Fashion w/Studios, Timber-Frame Barn, Workshop, & Greenhouse on 3+ surveyed Acres. This 3-bed, 2-bath offers approximately 3,000 square feet of finished living space w/ flowing layout connecting a series of versatile spaces—all under one roof. From the original formal rooms of the farmhouse, step into a sequence of functional bonus

    Jacki Murano Southern Vermont Realty Group

    597 Gates Pond Rd, Jacksonville, VT 05342
  • /20

    $285,000

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    172 Franklin Rd, Vernon, VT 05354

    Fantastic opportunity! This split level has 3 floors to finish for lots of living! Or, choose to begin with the first floor that has living/dining/kitchen/full bath and bedroom. It needs work, but an easy way to get started. 4 Possible bedrooms (town says 3, appraiser says 4), The basics are here, sheetrock up and partially mudded, good sized bedrooms, lots of windows and kitchen has been

    Christine Lewis Brattleboro Area Realty

    172 Franklin Rd, Vernon, VT 05354
  • /37

    $849,000

    • 4 Beds
    • 4 Baths
    • 3,600 Sq Ft

    5 Hillwinds N, Brattleboro, VT 05301

    Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • /44

    $475,000

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

    76 Spruce St, Brattleboro, VT 05301

    Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

    Christine Lewis Brattleboro Area Realty

    76 Spruce St, Brattleboro, VT 05301
  • /39

    $699,000

    • 6 Beds
    • 3 Baths
    • 2,825 Sq Ft

    95 Melendy Hill Rd, Londonderry, VT 05155

    A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

    Jessica Citera Cummings & Co

    95 Melendy Hill Rd, Londonderry, VT 05155
  • /53

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1192 Chapel Hill Rd, Whitingham, VT 05361

    Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

    Cliff Leinonen Four Seasons Sotheby's Int'l Realty

    1192 Chapel Hill Rd, Whitingham, VT 05361
  • /60

    $1,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,900 Sq Ft

    136 Yeaw Rd, Dover, VT 05341

    This is the perfect Vermont getaway, private and secluded, minutes from skiing, restaurants, and all the charm of Southern Vermont. This property is truly special, set on landscaped grounds with rolling meadows, a small, renovated barn with deck, and a 30x40 insulated Q Building with heat, water and 220 amps, as well as a whole house generator.The location is choice: close to world-class

    Amy Carson Lowe's Real Estate, LLC

    136 Yeaw Rd, Dover, VT 05341
  • /22

    $349,000

    • 4 Beds
    • 1.5 Baths
    • 1,404 Sq Ft

    696 S Wardsboro Rd, Wardsboro, VT 05355

    Priced to Sell. Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski areas! You'll have Wardsboro Brook in your back yard & Grout pond down the street as well as hiking trails, Vast Appalachian Trail (AT) and long Trails. Plenty of back country outdoor experiences available all year round. They say Location is everything, this property has everything and More. Family room

    Kimberly Dubois Matson Keller Williams Realty

    696 S Wardsboro Rd, Wardsboro, VT 05355
  • /31

    $2,100,000

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

    121 Fannie Hill Dr, 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 Dr, Wilmington, VT 05363
  • /37

    $925,000

    • 7 Beds
    • 7.5 Baths
    • 6,046 Sq Ft

    214 Whites Rd, Wilmington, VT 05363

    Experience a rare combination of proximity, privacy, and exposure, from this spectacular 1900s farmhouse nestled on 10+ private pastoral acres off the beautiful Whites Road, just outside the country village of Wilmington, and a short drive to the Mount Snow and Hermitage ski resorts. This home sits at the end of a private drive, with sunny exposure, horse pasture, rolling lawn space, and tennis

    Adam Palmiter Berkley & Veller Greenwood/Dover

    214 Whites Rd, Wilmington, VT 05363
  • /26

    $740,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    8 Grouse Ln, Dover, VT 05356

    Escape to 8A Grouse Lane at Mount Snow, where timeless post-and-beam character meets modern comfort in a setting designed for all four seasons. This beautifully reimagined end-unit townhome was thoughtfully redesigned to create an open, inviting living space, complete with a striking wood-burning fireplace—the perfect spot to gather after a day on the mountain.Wake up to ridge-line views,

    Wilkie Bushby TPW Real Estate

    8 Grouse Ln, Dover, VT 05356
  • /59

    $2,899,000

    • 5 Beds
    • 5.5 Baths
    • 5,413 Sq Ft

    1 Sundance Village, Dover, VT 05356

    Welcome to your dream home, a striking 5-bedroom, 6-bathroom Mountain Modern home nestled within the exclusive Sundance Village! A unique opportunity awaits to own a stand-alone house, with direct access to the slopes at Mount Snow and the freshly-upgraded amenities of Seasons on Mount Snow. Imagine walking out your door, steps from the ski trail, coming back for a leisurely lunch, and at day's

    Patricia Fitzpatrick Skihome Realty

    1 Sundance Village, Dover, VT 05356
  • /54

    $699,000

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    87 Townshend Rd, Grafton, VT 05146

    Welcome home to The Woodard House, a light-filled, historic home in the heart of beautiful Grafton, Vermont. Just a stroll from the Grafton Inn, Phelps Barn Pub, Nature Museum, dining options, and recreation, the spacious, historic home offers exceptional appeal for personal use or as a proven short-term rental. Available fully furnished for a seamless transition, it’s ready to welcome guests or

    Erin McCormick KW Vermont

    87 Townshend Rd, Grafton, VT 05146
  • /60

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 6,232 Sq Ft

    4 Signal Pine Rd, Putney, VT 05346

    Don’t miss this once-in-a-lifetime opportunity!The historic former Putney High School is ready for its next chapter—yours. This beautiful three-story brick building, complete with a full walk-out basement, offers so much. Step inside and be wowed by soaring ceilings and oversized windows, which flood the space with natural light. The first floor includes four large rooms, and is perfect for a

    Marie Potter EXP Realty

    4 Signal Pine Rd, Putney, VT 05346
  • /60

    $499,999

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363

    On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities

    Sigrid Pickering Chimney Hill Realty

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363
  • /30

    $475,000

    • 2 Beds
    • 1.5 Baths
    • 1,416 Sq Ft

    6 Gates Ln, Wilmington, VT 05363

    Welcome to your idyllic escape with private dock on the shores of beautiful Lake Raponda. This cozy 2 bedroom 1.5 bath house offers the perfect blend of rustic charm and modern comfort, nestled in a peaceful wooded setting minutes from downtown Wilmington and a short walk to your waterfront dock!Step inside to discover warm wood accents, open concept living and dining area on the main level

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    6 Gates Ln, Wilmington, VT 05363
  • /59

    $1,000,000

    • 3 Beds
    • 2 Baths
    • 2,700 Sq Ft

    580 Cross Rd, South Londonderry, VT 05155

    Tucked away in a tranquil setting, this newly constructed 3-bedroom, 2-bath barn-style residence is a masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody

    Loana Sargent Wohler Realty Group

    580 Cross Rd, South Londonderry, VT 05155
  • /60

    $2,195,000

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

    32 Steep Hill Rd, Wilmington, VT 05363

    Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont’s Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the

    Richard Caplan Deerfield Valley Real Estate

    32 Steep Hill Rd, Wilmington, VT 05363

Showing Results 41 - 80, Page 2 of 6

How to Buy a Home How to Finance a Home How to Sell a Home