191

Windham County VT Homes for Sale with Acreage

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  • /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
  • /39

    $585,000

    • Land
    • 67.63 Acres
    • $8,650 per Acre

    932 Middle Rd, Dummerston, VT 05301

    Discover the perfect blend of peace, privacy, and potential on this 67.63-acre privately owned parcel of land. Nestled in a scenic and serene setting, this expansive property is a rare opportunity to build your dream home, estate, or getaway retreat. Two picturesque ponds – ideal for fishing, wildlife watching, or just enjoying the view. The main home site has amazing mountain views and sits atop

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    932 Middle Rd, Dummerston, VT 05301
  • /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 southern

    Rich Caplan Deerfield Valley Real Estate

    32 Steep Hill Rd, Wilmington, VT 05363
  • /15

    $67,500

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

    0 Dover Rd Unit 5054979, 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 5054979, Newfane, VT 05345
  • /37

    $690,000

    • 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
  • /60

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,978 Sq Ft

    23 Brook Rd, Saxtons River, VT 05154

    Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

    Isabella Luhrs BHG Masiello Keene

    23 Brook Rd, Saxtons River, VT 05154
  • /60

    $775,000

    • 2 Beds
    • 2 Baths
    • 2,190 Sq Ft

    85 Browns Rd, Newfane, VT 05345

    Timeless 1780 Colonial on 80 Acres with Modern Sustainability- A Rare Historic Gem! Own a piece of American history with this stunning circa 1780 Colonial home, set on 80 serene acres of meadows and forest. Featuring 2 bedrooms plus a dedicated bedroom/office ,2 full bathrooms, and over two centuries of character, this historic property offers unmatched charm- now enhanced with energy-efficient

    Janet Lucier Barrett & Valley Assoc. Inc

    85 Browns Rd, Newfane, VT 05345
  • /24

    $499,000

    • 7 Beds
    • 2 Baths
    • 2,038 Sq Ft

    45 Blue Brook Rd, Dover, VT 05356

    A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple miles to the Mount Snow

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Blue Brook Rd, Dover, VT 05356
  • /55

    $869,000

    • 6 Beds
    • 4.5 Baths
    • 3,500 Sq Ft

    5825 Vermont 30, Townshend, VT 05353

    6+ bed, 5 bath 21± Acre Equestrian Estate in West Townshend VT Distinctive property combines the charm of a private equestrian estate w/tastefully finished and versatile living space & top horse facilities. On ~21 acres, including a 3-bed main home plus attached 1-bed accessory unit—ideal for guests, staff, or flex living. Metal roof, drilled well, whole-house generator. Main Barn: 8 box stalls,

    Jacki Murano Southern Vermont Realty Group

    5825 Vermont 30, Townshend, VT 05353
  • /16

    $259,900

    • Land
    • 29.2 Acres
    • $8,901 per Acre

    1270 Melendy Hill Rd, Guilford, VT 05301

    A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is a

    Christine Lewis Brattleboro Area Realty

    1270 Melendy Hill Rd, Guilford, VT 05301
  • /12

    $235,000

    • Land
    • 18.93 Acres
    • $12,414 per Acre

    0 Forest Heights Rd, West Dover, VT 05356

    Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

    Michelle O'Neil Deerfield Valley Real Estate

    0 Forest Heights Rd, West Dover, VT 05356
  • /40

    $1,695,000

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

    251 Pratt Bridge Rd, Jamaica, VT 05343

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

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /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

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,957 Sq Ft

    256 Potter Rd, Wardsboro, VT 05355

    Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    256 Potter Rd, Wardsboro, VT 05355
  • /34

    $125,000

    • Land
    • 1.31 Acres
    • $95,420 per Acre

    118 Chimney Hill Rd, Wilmington, VT 05363

    Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

    Sigrid Pickering Chimney Hill Realty

    118 Chimney Hill Rd, Wilmington, VT 05363
  • /34

    $699,000

    • 3 Beds
    • 4 Baths
    • 3,796 Sq Ft

    233 Poverty Row, Whitingham, VT 05361

    What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

    Adam Palmiter Berkley & Veller Greenwood/Dover

    233 Poverty Row, Whitingham, VT 05361
  • /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
  • /8

    $119,000

    • Land
    • 14.91 Acres
    • $7,981 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
  • /10

    $179,000

    • Land
    • 9.45 Acres
    • $18,942 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
  • /58

    $865,000

    • 3 Beds
    • 4.5 Baths
    • 3,318 Sq Ft

    42 Sugar House Rd, West Dover, VT 05356

    Furnished mountain home in Mount Snow, Vermont.This custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    42 Sugar House Rd, West Dover, VT 05356
  • /11

    $250,000

    • Land
    • 18 Acres
    • $13,889 per Acre

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

    Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

    Christine Lewis Brattleboro Area Realty

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
  • /10

    $24,999

    • Land
    • 1.1 Acres
    • $22,726 per Acre

    4 Antler Loop, Dover, VT 05356

    Wooded Acre Close to Skiing at Mount Snow Beautiful wooded parcel less than ten minutes from skiing at Mount Snow and all the attractions in downtown Dover. While the property's address is technically 4 Antler Loop, it's much easier to access off the end of Timberview Road, which is one street up the hill. After passing by a gorgeous home at 15 Timberview, the road swaps over from gravel to

    David White OwnerEntry.com

    4 Antler Loop, Dover, VT 05356
  • /51

    $899,800

    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /6

    $229,000

    • Land
    • 1.57 Acres
    • $145,860 per Acre

    2 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Find

    Andrew King Stratton Real Estate

    2 Gold Medal Cir, Stratton, VT 05343
  • /30

    $139,000

    • Land
    • 20.1 Acres
    • $6,915 per Acre

    251 Phillips Hill Rd, West Halifax, VT 05358

    Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage of

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    251 Phillips Hill Rd, West Halifax, VT 05358
  • /48

    $380,000 Open House 4/18

    • 3 Beds
    • 1.5 Baths
    • 2,433 Sq Ft

    183 Bear Hill Rd, Dummerston, VT 05301

    Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency. This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

    Kate Barry EXP Realty

    183 Bear Hill Rd, Dummerston, VT 05301
  • /4

    $132,500

    • Land
    • 1.3 Acres
    • $101,923 per Acre

    00 Creamery Rd, Guilford, VT 05301

    Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get

    Christine Lewis Brattleboro Area Realty

    00 Creamery Rd, Guilford, 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
  • /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
  • /13

    $69,000

    • Land
    • 3.69 Acres
    • $18,699 per Acre

    0 Honeycomb Hill, Marlboro, VT 05301

    On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

    Laura D'Angelo Berkley & Veller Greenwood Country

    0 Honeycomb Hill, Marlboro, VT 05301
  • /19

    $194,000

    • Land
    • 20.09 Acres
    • $9,657 per Acre

    189 North St, Dover, VT 05356

    Discover the perfect Vermont retreat on this 20.09 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    189 North St, Dover, VT 05356
  • /10

    $88,000

    • Land
    • 10.05 Acres
    • $8,756 per Acre

    Lot 3 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 3 North St, Dover, VT 05431
  • /38

    $499,000

    • 3 Beds
    • 3 Baths
    • 2,040 Sq Ft

    829 Pennel Hill Rd, Halifax, VT 05342

    Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

    Megan Quinn Southern Vermont Realty Group

    829 Pennel Hill Rd, Halifax, VT 05342
  • /9

    $118,000

    • Land
    • 10.04 Acres
    • $11,753 per Acre

    Lot 2 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 2 North St, Dover, VT 05431
  • /11

    $75,000

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    L40 Boardman Loop, Wardsboro, VT 05360

    Nestled in the desirable Snow Mountain Farms West community, this 1.8-acre wooded lot offers the perfect setting to build your Vermont dream home or getaway. Gently sloping and bordered by the serene Wardsboro Brook (outside the FEMA flood zone), the property combines natural beauty with practical readiness. A state-issued wastewater permit for a 3 bedroom single family home and an individual

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    L40 Boardman Loop, Wardsboro, VT 05360
  • /7

    $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
  • /20

    $330,000

    • 4 Beds
    • 3.5 Baths
    • 2,575 Sq Ft

    3730 Route 100, Wardsboro, VT 05355

    Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax

    Ginny Read Read Realty LTD

    3730 Route 100, Wardsboro, VT 05355
  • /33

    $85,000

    • Land
    • 1.04 Acres
    • $81,731 per Acre

    402 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

    Sigrid Pickering Chimney Hill Realty

    402 Fox Mountain Rd, Wilmington, VT 05363
  • /28

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 2,240 Sq Ft

    47 Ives Rd, Wilmington, VT 05363

    Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

    Adam Palmiter Berkley & Veller Greenwood/Dover

    47 Ives Rd, Wilmington, VT 05363
  • /60

    $3,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343

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