424

Windham County VT Homes for Sale

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  • /3

    $60,000

    • Land
    • 1.1 Acres
    • $54,545 per Acre

    63 Villager Loop, Dover, VT 05356

    Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    63 Villager Loop, Dover, VT 05356
  • /40

    $389,000

    • 3 Beds
    • 2.5 Baths
    • 2,146 Sq Ft

    49 Whitetail Dr, Vernon, VT 05354

    Welcome to this very special neighborhood and home, still owned and loved by the original owners. Enter through an oversized two-car garage into a lovely tile foyer and a half bath. The open concept is warm and inviting with an efficient pellet stove. The Dining area has a slider out to an impressive 12x32-foot deck overlooking a nice combination of a level lawn and woods. For the past 20 years

    Kristen Ziter Taylor Brattleboro Area Realty

    49 Whitetail Dr, Vernon, VT 05354
  • /37

    $874,000

    • 6 Beds
    • 3 Baths
    • 2,900 Sq Ft

    261 Handle Rd, Dover, VT 05356

    Slopeside 6 Bedroom Ski Chalet at Carinthia Base, Mount Snow This ski chalet is perfectly positioned at the base of Carinthia, offering true slopeside access and unmatched convenience. Step out your door and onto the trails, with the Carinthia Base Lodge, terrain parks, lifts, and all the action of the mountain just steps away. Inside, the home blends classic chalet character with thoughtful

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    261 Handle Rd, Dover, VT 05356
  • /25

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft

    337 Handle Rd Unit Pines K, West Dover, VT 05356

    Welcome to this beautifully updated two bedroom, two-bathroom condo in the desirable upper Snow Tree community. The home is perfectly positioned to capture incredible mountain views and the true essence of Mount Snow base area living. Step inside to find a bright, inviting interior featuring new efficient windows, a cozy gas fireplace, and beautiful cathedral ceiling that enhances the spacious

    Melissa Ellis Southern Vermont Realty Group

    337 Handle Rd Unit Pines K, West Dover, VT 05356
  • /38

    $475,000

    • Land
    • 133.1 Acres
    • $3,569 per Acre

    40 E Putney Brook Rd, Putney, VT 05346

    Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

    Geralyn Donohue Engel & Völkers Okemo

    40 E Putney Brook Rd, Putney, VT 05346
  • /4

    $160,000

    • Land
    • 9.3 Acres
    • $17,204 per Acre

    00 E Putney Brook Rd, Putney, VT 05346

    Located on E. Putney Brook Rd., approx. 2.5 miles from Putney Village, this beautiful, wooded 9+ ac property offers a desirable place to build. Bring your own building plans, power is nearby, and septic design is available. Clear a prime building site on level plateau and surround your home with mature woodlands. This county location offers easy access to orchards, farmstands for local produce,

    Heidi Bernier Berkley & Veller Greenwood Country

    00 E Putney Brook Rd, Putney, VT 05346
  • /25

    $239,000

    • 4 Beds
    • 1.5 Baths
    • 1,690 Sq Ft

    7511 Westminster West Rd, Putney, VT 05346

    This property has so much potential! Located just 3 minutes from the village of Saxtons River home to the Vermont Academy School this property finds itself nestled in the countryside. The Home has some great features like a finished basement, a screened in porch plus a large deck, a primary bedroom with a bathroom and so much more! There is some TLC needed but the potential is endless. The

    Thaddeus Abare Barrett and Valley Associates Inc.

    7511 Westminster West Rd, Putney, VT 05346
  • /56

    $1,345,000

    • 3 Beds
    • 2 Baths
    • 2,546 Sq Ft

    135 Fred Houghton Rd, Putney, VT 05346

    This one-of-a-kind Vermont property offers three dwellings on 5.6 acres - each blending elevated aesthetics, thoughtful design, and a true connection to nature. The 2011 main house features an open layout and handcrafted finishes throughout. The kitchen boasts soapstone countertops and custom cherry cabinetry. A very special wood-fired masonry heater anchors the living space and a spacious

    Benjamin Cote EXP Realty

    135 Fred Houghton Rd, Putney, VT 05346
  • /42

    $574,900

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    555 Vermont 9, Wilmington, VT 05363

    Welcome to your dream home in the heart of Southern Vermont. This brand-new construction 3-bedroom, 2-bath residence seamlessly blends modern comfort with classic Vermont charm, perfect for year-round living or a weekend escape. Enjoy a spacious, open-concept layout filled with natural light, enhanced by high-quality Anderson windows and doors. The kitchen boasts brand new appliances, while the

    Flex Realty Group Flex Realty

    555 Vermont 9, Wilmington, VT 05363
  • /55

    $329,000

    • 6 Beds
    • 2 Baths
    • 2,656 Sq Ft

    24 South St, Bellows Falls, VT 05101

    Unique in-village Victorian home offers so many possibilities: a large 6 bedroom home, as a primary with a large in-law suite, or as a duplex multifamily with possible 3rd or 4th rental units Both units on the 1st and 2nd floor feature high quality construction and finishes with many thoughtful touches. Both units are move in ready. Each floor has 3 bedrooms, newer quality kitchens, dining room,

    Steve Schoppmeyer BHG Masiello Brattleboro

    24 South St, Bellows Falls, VT 05101
  • /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
  • /28

    $285,000

    • 2 Beds
    • 1 Bath
    • 903 Sq Ft

    1555 W River Rd, Dummerston, VT 05301

    Open House 11/15 - 12pm-2pm Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot

    Morriah Adams BHG Masiello Brattleboro

    1555 W River Rd, Dummerston, VT 05301
  • /43

    $299,000

    • 6 Beds
    • 5 Baths
    • 3,942 Sq Ft

    2072 N Main St, Londonderry, VT 05148

    This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths

    Catherine Cairns Maple Leaf Realty

    2072 N Main St, Londonderry, VT 05148
  • /32

    $295,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    70 Overlook Dr, Londonderry, VT 05148

    Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice one-level layout

    Claudia Harris Mary Mitchell Miller Real Estate

    70 Overlook Dr, Londonderry, VT 05148
  • /8

    $52,000

    • Land
    • 6.1 Acres
    • $8,525 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • /23

    $3,500,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 7,000 Sq Ft

    29 Mountain Ridge Dr, Wilmington, VT 05363

    The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already

    Adam Palmiter Berkley & Veller Greenwood/Dover

    29 Mountain Ridge Dr, Wilmington, VT 05363
  • /12

    $249,000

    • Land
    • 19.6 Acres
    • $12,704 per Acre

    227 Gault Rd, Wardsboro, VT 05355

    This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

    Victoria Woods Brattleboro Area Realty

    227 Gault Rd, Wardsboro, VT 05355
  • /15

    $20,000

    • 1 Bath
    • 407 Sq Ft

    152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356

    Quarter share (deeded interval 3) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 152) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356
  • /12

    $175,000

    • Land
    • 16.48 Acres
    • $10,619 per Acre

    1854 Vermont 9, Marlboro, VT 05344

    Escape to Nature – 16.48-Acre Glampsite with Cozy Cabins and Endless Potential Discover your private retreat on 16.48 serene wooded acres featuring two comfortably appointed sleeping cabins, each offering electricity, electric fireplaces for year-round comfort, and the possibility of internet. Enjoy modern convenience in a natural setting, with facilities for cooking and showering already onsite.

    Kristen Breeden Southern Vermont Realty Group

    1854 Vermont 9, Marlboro, VT 05344
  • /43

    $619,900

    • 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
  • /18

    $199,000

    • 2,139 Sq Ft

    34 Williams St, Bellows Falls, VT 05101

    Discover a superb investment or owner-occupant opportunity in the heart of downtown Bellows Falls, Vermont. This well-maintained two-story multi-family building offers two separate units, each featuring two bedrooms and one full bathroom. The property is dressed in durable vinyl siding for low-maintenance appeal and is fully insulated in the basement, exterior walls, and attic—enhancing energy

    Rob Weltz Barrett and Valley Associates Inc.

    34 Williams St, Bellows Falls, VT 05101
  • /41

    $799,000

    • 5 Beds
    • 3 Baths
    • 3,091 Sq Ft

    798 Vermont Route 100, Wilmington, VT 05363

    Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    798 Vermont Route 100, Wilmington, VT 05363
  • /18

    $55,000

    • 3 Beds
    • 1.5 Baths
    • 924 Sq Ft

    78 Shady Pines Park, Westminster, VT 05158

    Looking for an affordable place to call home? This could be the place for you! This 1989 Mobile Home currently sits on a large, rented lot in the conveniently located Shady Pines Park in Westminster VT, close to I-91, and many surrounding towns like Bellows Falls, Saxtons River, and Walpole. The home features a large eat-in kitchen, 3 bedrooms, one and a half bathrooms, and the addition of a

    Chelsea Richardson Barrett and Valley Associates Inc.

    78 Shady Pines Park, Westminster, VT 05158
  • /40

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    166 Taylor Ln, Whitingham, VT 05361

    Nestled in the scenic hills of Whitingham, this beautifully updated Vermont retreat offers the perfect blend of comfort, privacy, and breathtaking natural surroundings. Enjoy stunning views overlooking Lake Sadawga and the surrounding mountain landscape, creating a peaceful setting ideal for year-round living or a seasonal getaway. The home features new siding and a new roof, ensuring long-term

    Flex Realty Group Flex Realty

    166 Taylor Ln, Whitingham, VT 05361
  • /56

    $475,000

    • 3,954 Sq Ft

    430 Hucklehill Rd, Vernon, VT 05354

    NEW PRICE!! LOTS OF OPTIONS!! This quality built home can be enjoyed as spacious one floor living. There is a full finished walkout basement expanding your living space. A second full kitchen with granite counter tops, large family room, 3 bedrooms, bath, and laundry area, . Double doors open to a private patio, making this level ideal for an in-law suite, extended family, guests, or rental.

    Carol Slocum Keller Williams Realty Metro-Keene

    430 Hucklehill Rd, Vernon, VT 05354
  • /16

    $19,900

    • Land
    • 0.46 Acre
    • $43,261 per Acre

    00 Country Ct Unit 693, Wilmington, VT 05363

    Attention skiers, golfers, hikers, boaters, VAST lovers, and more! Discover the perfect blend of a country setting, amenities, and convenience with this exceptional land opportunity! This nearly half-acre lot is admirably located within Chimney Hill’s 1,200-acre private resort community with access to a wide range of recreational amenities for both summer and winter enjoyment. Located at the

    Casey Scott Southern Vermont Realty Group

    00 Country Ct Unit 693, Wilmington, VT 05363
  • /36

    $382,000

    • 6 Beds
    • 2.5 Baths
    • 3,590 Sq Ft

    88 Westminster St, Town of Rockingham, VT 05101

    Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 6 bedrooms and 3 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period details remain throughout,

    Jamie Watson BHG Masiello Keene

    88 Westminster St, Town of Rockingham, VT 05101
  • /33

    $390,000

    • 3 Beds
    • 1.5 Baths
    • 2,208 Sq Ft

    440 Stratton Arlington Rd, Stratton, VT 05360

    Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

    Mike England Michael England Real Estate

    440 Stratton Arlington Rd, Stratton, VT 05360
  • /39

    $312,000

    • 2 Beds
    • 2 Baths
    • 860 Sq Ft

    15 Mountain Village Unit 234, West Dover, VT 05356

    Welcome to your mountain getaway! This 2-bedroom, 2-bath condo is perfectly situated at the base of Mount Snow. Enjoy your morning coffee or après-ski beverage on the private balcony while taking in the mountain air and breath taking views. Cozy up by the wood-burning fireplace, perfect for relaxing after a day on the mountain. Recent updates include new windows, slider doors, balcony, flooring

    Jillian Wimmelman Deerfield Valley Real Estate

    15 Mountain Village Unit 234, West Dover, VT 05356
  • /22

    $365,000

    • 4 Beds
    • 2 Baths
    • 1,742 Sq Ft

    801 Newton Rd, Vernon, VT 05354

    Charming renovated split level chalet located conveniently in the heart of Vernon. This lovely spot has a large yard space with ample privacy, and easy nearby access to the Vernon community park. Inside you are treated to a vaulted great room with exposed beams and brick hearth for wood stove, with great natural light. There is a new kitchen with the same vaulted ceilings and slider out to the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    801 Newton Rd, Vernon, VT 05354
  • /34

    $365,000

    • 1 Bed
    • 1 Bath
    • 861 Sq Ft

    12 Cross St, Newfane, VT 05345

    Can you imagine the cutest cottage, on an acre of open, rolling meadow in the center of one of the area's most photographed towns? You walk around the corner to the picture perfect Newfane Common to...maybe a summer concert or the Heritage Festival and, come back home to sit on your cozy front porch or relax by the fireplace on the back patio...either way ...WELCOME TO HISTORIC NEWFANE! .just big

    Christine Lewis Brattleboro Area Realty

    12 Cross St, Newfane, VT 05345
  • /21

    $249,000

    • Land
    • 48.5 Acres
    • $5,134 per Acre

    590 Howard Hill Rd, Landgrove, VT 05148

    Discover the perfect blend of privacy, recreation, and natural beauty with this exceptional 48+ acre parcel located in the desirable Powder Mill development. Set at the end of a quiet, dead-end road, this property offers peace and seclusion while being part of a community known for its extensive network of trails, ideal for year-round enjoyment — hike, cross-country ski, snowshoe, or snowmobile

    Carrie Mathews Winhall Real Estate

    590 Howard Hill Rd, Landgrove, VT 05148
  • /2

    $199,000

    • 2 Beds
    • 2,710 Sq Ft

    29 Stable Rd, Wilmington, VT 05363

    The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

    Mark Yule BHG Masiello Brattleboro

    29 Stable Rd, Wilmington, VT 05363
  • /31

    $735,000

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

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

    Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

    Timothy Mich Doddridge Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
  • /23

    $500,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    137 Pleasant Valley Rd, Brattleboro, VT 05301

    This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

    Christine Lewis Brattleboro Area Realty

    137 Pleasant Valley Rd, Brattleboro, VT 05301
  • /12

    $39,999

    • Land
    • 2 Acres
    • $20,000 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /19

    $190,000

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    39 Brookside Dr Unit 3, Brattleboro, VT 05301

    Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new bathroom

    Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 3, Brattleboro, VT 05301
  • /24

    $29,900

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    97 Glen St, Brattleboro, VT 05301

    Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

    Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
  • /44

    $429,900

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    1909 Davidson Hill Rd, Westminster, VT 05158

    This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

    Steve Schoppmeyer BHG Masiello Brattleboro

    1909 Davidson Hill Rd, Westminster, VT 05158
  • /41

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356

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