378

Windham County VT Homes for Sale

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  • /30

    $749,000

    • Land
    • 2.57 Acres
    • $291,440 per Acre

    Lot 3 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 Old Mill Ln, Wilmington, VT 05363
  • /22

    $539,000

    • Land
    • 2.88 Acres
    • $187,153 per Acre

    309 Vermont Route 100, Dover, VT 05356

    Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

    Rich Caplan Deerfield Valley Real Estate

    309 Vermont Route 100, Dover, VT 05356
  • /20

    $995,000

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

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Kim Morgan-Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /5

    $139,000

    • Land
    • 8.52 Acres
    • $16,315 per Acre

    0 Higley Hill, Dover, VT 05356

    Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

    Michael Purcell Berkley & Veller Greenwood/Dover

    0 Higley Hill, Dover, VT 05356
  • /2

    $70,000

    • Land
    • 2.01 Acres
    • $34,826 per Acre

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

    Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails. Enjoy the peace of a quiet country setting where you can listen to

    Kerry Mulverhill

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354
  • /40

    $214,900

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    2139 Vt Route 30, Townshend, VT 05353

    Great days ahead for the buyer of this stately, manor styled home on close to three (3) acres. You have to see the interior to believe it. Dated? Yes, but solid bones. Crazy nice wood floors, classic built-ins & style. So many 'nooks & crannies. Cavernous, dry & clean basement. Exterior: 'challenged', but I have all the bids to bring it to 'good' condition & the techies are ready to complete

    Robert Balewicz Evergreen Realty of Vermont

    2139 Vt Route 30, Townshend, VT 05353
  • /60

    $499,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,312 Sq Ft

    23 Wilsons Woods Rd, Brattleboro, VT 05301

    Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

    Kate Barry EXP Realty

    23 Wilsons Woods Rd, Brattleboro, VT 05301
  • /27

    $425,000

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

    135 Overlook Dr, Londonderry, VT 05148

    Investment opportunity! This beautiful ski country compound offers 3 streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped

    Zachary Zupan EXP Realty

    135 Overlook Dr, Londonderry, VT 05148
  • /9

    $198,000

    • Land
    • 0.73 Acre
    • $271,233 per Acre

    5 Pinnacle View Rd, Dover, VT 05356

    With views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering world-class skiing

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    5 Pinnacle View Rd, Dover, VT 05356
  • /37

    $50,000

    • Land
    • 0.93 Acre
    • $53,763 per Acre

    564 Upper Dam Rd, Wilmington, VT 05363

    Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing,

    Sigrid Pickering Chimney Hill Realty

    564 Upper Dam Rd, Wilmington, VT 05363
  • /31

    $459,000

    • 1 Bed
    • 2.5 Baths
    • 2,076 Sq Ft

    33 W Main St, Wilmington, VT 05363

    Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33 W Main St, Wilmington, VT 05363
  • /58

    $349,900

    • 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
  • /16

    $26,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 8 unit consists of two adjoining units. Studio unit (unit 163) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (165) Two queen beds, Full bathroom and a deck. Units are located the valley side of the hotel. Benefits of Grand Summit ownership include the best ski in/out mountain

    Kelly Agrillo Southern Vermont Realty Group

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /29

    $469,000

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft

    33D White Oaks Loop Unit 38, Dover, VT 05356

    Owners will consider offers. Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and more. The

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33D White Oaks Loop Unit 38, Dover, VT 05356
  • /54

    $2,050,000

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft

    97 N Brookwood Rd, Stratton, VT 05360

    Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
  • /24

    $680,000

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360

    *** Stratton Club *** Stratton Club *** Stratton Club ***Owner will resign from the STRATTON MOUNTAIN CLUB so the buyer can join right away!Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #322 is one of the

    Andrew King Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360
  • /24

    $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
  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /2

    $350,000

    • 2 Beds
    • 1 Bath
    • 3,312 Sq Ft

    573 S Main St, Brattleboro, VT 05301

    Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

    Christine Lewis Brattleboro Area Realty

    573 S Main St, Brattleboro, VT 05301
  • /41

    $3,050,000

    • 6 Beds
    • 3 Baths
    • 3,309 Sq Ft

    36 Woffenden Rd, Wilmington, VT 05363

    Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • /12

    $36,999

    • Land
    • 2 Acres
    • $18,500 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
  • /44

    $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
  • /28

    $269,000 Coming Soon

    • 4 Beds
    • 1 Bath
    • 1,374 Sq Ft

    15 West St, Brattleboro, VT 05301

    Enjoy a spacious kitchen that flows seamlessly into a large living area with open views of Mount Wantastiquet. This single-level ranch offers four generously sized bedrooms and a full bath, making it ideal for those seeking one-floor living and efficient heating. A cozy woodstove in the living area helps offset heating costs while adding warmth and charm. Hardwood flooring, a beautifully tiled

    Liz LaVorgna Brattleboro Area Realty

    15 West St, Brattleboro, VT 05301
  • /8

    $48,000

    • Land
    • 6.1 Acres
    • $7,869 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
  • /12

    $119,000

    • Land
    • 5 Acres
    • $23,800 per Acre

    0 Banning Rd, Putney, VT 05346

    Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

    Bill Hickok Berkley & Veller Greenwood Country

    0 Banning Rd, Putney, VT 05346
  • /26

    $395,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    135 Country Hill, Brattleboro, VT 05301

    Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

    Neil Goldberg Brattleboro Area Realty

    135 Country Hill, Brattleboro, VT 05301
  • /17

    $150,000

    • Land
    • 2.8 Acres
    • $53,571 per Acre

    37 Fred Houghton Rd, Putney, VT 05346

    Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

    Christine Lewis Brattleboro Area Realty

    37 Fred Houghton Rd, Putney, VT 05346
  • /35

    $899,900

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

    12 Encore Place, Dover, VT 05356

    Mountain Modern Living with unmatched ski views of 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 Carinthia. 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 alpine landscape.

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    12 Encore Place, Dover, VT 05356
  • /39

    $499,000

    • Land
    • 80.11 Acres
    • $6,229 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /21

    $24,000

    • 1 Bed
    • 1 Bath
    • 673 Sq Ft

    222 Q1, 89 Grand Summit Way, Dover, VT 05356

    An opportunity to own at the beautiful and conveniently located trailside, Grand Summit Hotel. Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities, directly at the base of Mount Snow! This valley facing, sleep 6 unit is perfect for family, guests or great rental options. The unit features a fully-equipped kitchen, dining area and living room with a queen

    Prema Fitzpatrick Real Broker LLC

    222 Q1, 89 Grand Summit Way, Dover, VT 05356
  • /35

    $350,000

    • 4 Beds
    • 3 Baths
    • 2,460 Sq Ft

    6795 Vt Route 100, Londonderry, VT 05148

    Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    6795 Vt Route 100, Londonderry, VT 05148
  • /36

    $499,000

    • Land
    • 41 Acres
    • $12,171 per Acre

    706 Vt Route 100, Stratton, VT 05360

    Exceptional New Offering! Rare 41± acres in Stratton with extraordinary 180 +/- long-range mountain views, improvements, base camp, driveway, clearings, trails, wildlife, and a substantial WOW factor. All for approx. $12,000/acre. A short drive in from paved Route 100, before the land rises further in elevation, sits the rustic 1-bed base camp overlooking open field and multiple ski

    Jacki Murano Southern Vermont Realty Group

    706 Vt Route 100, Stratton, VT 05360
  • /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
  • /28

    $1,395,000

    • 4 Beds
    • 4.5 Baths
    • 3,476 Sq Ft

    3B Freestyle Cir, Dover, VT 05356

    Trailside luxury at the base of the Mount Snow ski resort just off the Snowdance ski trail. This spectacular 2016 unit is just about as close and turn key as you can find. Amazing convenience to the mountain thanks to direct ski trail access, affording the ability to stop by to warm up or get a bite, yet with easterly views and a size usually only found in off mountain properties. The large

    Adam Palmiter Berkley & Veller Greenwood/Dover

    3B Freestyle Cir, Dover, VT 05356
  • /37

    $730,000

    • 5 Beds
    • 3 Baths
    • 2,635 Sq Ft

    341 Under the Mountain Rd, Londonderry, VT 05148

    Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

    Andy Reed Four Seasons Sotheby's Int'l Realty

    341 Under the Mountain Rd, Londonderry, VT 05148
  • /29

    $425,000

    • 4 Beds
    • 1 Bath
    • 1,730 Sq Ft

    83 Depot St, Jamaica, VT 05343

    Step back in time while enjoying modern comforts in this lovingly restored 1800s farmhouse with attached barn, set in the heart of Southern Vermont. Rich with historic character, the home features original wide pine floors, plaster walls, a slate roof, and classic architectural lines that reflect Vermont’s timeless heritage.The private backyard offers a peaceful setting to relax, gather

    Carrie Mathews Winhall Real Estate

    83 Depot St, Jamaica, VT 05343
  • /54

    $695,000

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

    1161 Little Pond Rd, Londonderry, VT 05148

    Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    1161 Little Pond Rd, Londonderry, VT 05148
  • /17

    $449,000

    • 3 Beds
    • 3 Baths
    • 1,726 Sq Ft

    4A Suntec Loop Unit 4A, Dover, VT 05356

    Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick hearth, rustic wood

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4A Suntec Loop Unit 4A, Dover, VT 05356
  • /33

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    662 Vt Route 30, Newfane, VT 05345

    Whether you’re just starting out with your first home or looking to downsize and simplify, this sweet home is just the right size. It features two bedrooms plus bonus room upstairs, with a full bathroom conveniently located on the first floor. The kitchen is charming, complete with a dishwasher, newer refrigerator and stove, opens to a dining area, and a spacious living room with beautiful wood

    Rebecca Seymour Brattleboro Area Realty

    662 Vt Route 30, Newfane, VT 05345
  • /17

    $459,000

    • 5 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    46 Town Farm Rd, Wilmington, VT 05363

    3 Story home with 1 car attached garage....new vinyl siding, windows and roofing installed in 2021 along with exterior foamboard insulation.FIRST FLOOR- Open concept entirely remodeled in 2022; mudroom, kitchen, 1/2 bath, and family/dining room. Vinyl plank flooring throughout, white shiplap walls and natural tongue & groove ceilings. Vermont castings wood burning stove.SECOND

    David White OwnerEntry.com

    46 Town Farm Rd, Wilmington, VT 05363

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