Windham County VT Homes for Sale

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  $89,900

  • 4 Beds
  • 2 Baths
  • 1,902 Sq Ft

  203 Smith Rd, Jamaica, VT 05343

  Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

  Christine Lewis Brattleboro Area Realty

  203 Smith Rd, Jamaica, VT 05343
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  /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
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  /49

  $425,000

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

  1993 U S 5, Putney, VT 05346

  Captivating easterly views of the Connecticut River, this home immediately captured the heart of its current owner. The property has been thoughtfully maintained and features numerous upgrades, ensuring comfort and appeal throughout. The attached garage provides convenient access to the first floor, where you will find a spacious family room perfect for gatherings or relaxation. This level also

  Heidi Bernier Berkley & Veller Greenwood Country

  1993 U S 5, Putney, VT 05346
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  /40

  $214,900

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

  2139 Vt Route 30, Townshend, VT 05353

  This is on Auction.com until 4/21, all offers through them. 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

  Robert Balewicz Evergreen Realty of Vermont

  2139 Vt Route 30, Townshend, VT 05353
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  /28

  $52,000

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  274/76Qtr. 4 Grand Summit Way, Dover, VT 05356

  Wake up to the Grand Summit Express and the Bluebird lifts right outside your room. Sleep 10 condo comprises two units. Unit 276 has a private bedroom with a queen bed, a queen sleeper sofa, and a queen Murphy bed in the living area, a kitchenette, and a full bath with an extra-large covered balcony. The adjoining room, 274, has 2 king beds and a full bath. Units are located on the base area side

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 4 Grand Summit Way, Dover, VT 05356
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  /59

  $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
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  /9

  $198,000

  • Land
  • 31,798 Sq Ft
  • $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
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  /52

  $1,150,000

  • 8 Beds
  • 4 Baths
  • 4,828 Sq Ft

  5 Tannery Rd, West Dover, VT 05356

  Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

  Michelle O'Neil Deerfield Valley Real Estate

  5 Tannery Rd, West Dover, VT 05356
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  /37

  $50,000

  • Land
  • 40,510 Sq Ft
  • $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, hiking,

  Sigrid Pickering Chimney Hill Realty

  564 Upper Dam Rd, Wilmington, VT 05363
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  /23

  $159,000

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /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
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  /37

  $489,000

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356

  Meticulously maintained and updated, rare to come on the market, top-floor 2-bedroom, 2-bath condo located in the Seasons on Mount Snow trailside community! A two-level unit featuring a primary ensuite on the main level and a bedroom with an ensuite on the second level. Newer appliances, granite kitchen counters, a tastefully renovated primary ensuite bathroom, and plush carpeting are some of the

  Patricia Fitzpatrick Skihome Realty

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356
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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
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  /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
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  /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
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  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
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  /8

  $480,000

  • Land
  • 5.08 Acres
  • $94,488 per Acre

  10 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

  Patricia Fitzpatrick Skihome Realty

  10 Overlook Dr, Dover, VT 05356
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  /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
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  /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
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  $2,999,000

  • 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
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  /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
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  /44

  $384,000

  • 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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  /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
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  /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
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  /2

  $25,000

  • Land
  • 26,136 Sq Ft
  • $41,667 per Acre

  28 Upper Howes Way, Wilmington, VT 05363

  Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

  Sigrid Pickering Chimney Hill Realty

  28 Upper Howes Way, Wilmington, VT 05363
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  /2

  $55,000

  • Land
  • 21,780 Sq Ft
  • $110,000 per Acre

  404 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

  Sigrid Pickering Chimney Hill Realty

  404 Fox Mountain Rd, Wilmington, VT 05363
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  /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
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  /21

  $19,000

  • 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
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  /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
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  /36

  $489,000

  • Land
  • 41 Acres
  • $11,927 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
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  /2

  $174,900

  • 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, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. 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
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  /60

  $479,000

  • 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 Chimney

  Sigrid Pickering Chimney Hill Realty

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363
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  /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
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  /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 the development having 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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4A Suntec Loop Unit 4A, Dover, VT 05356
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  /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
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  /8

  $74,900

  • Land
  • 1.1 Acres
  • $68,091 per Acre

  2 Johnson Hill, Dover, VT 05356

  Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

  Janet Boyd Boyd Real Estate

  2 Johnson Hill, Dover, VT 05356
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  /4

  $59,000

  • Land
  • 3.3 Acres
  • $17,879 per Acre

  0 Hunt Rd, Wardsboro, VT 05355

  Discover the perfect canvas for your Vermont dream home on this newly created 3.3-acre parcel in Wardsboro. Tucked away in a peaceful, private setting, you’ll enjoy the quiet beauty of the surrounding woods while still being within easy reach of some of Southern Vermont’s most sought-after destinations. Spend your winters skiing at Mount Snow or Stratton Mountain Resort, and take advantage of

  Mike Masters Four Seasons Sotheby's Int'l Realty

  0 Hunt Rd, Wardsboro, VT 05355
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  /17

  $2,495,000

  • Land
  • 2.36 Acres
  • $1,057,203 per Acre

  4 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. Lot #4

  Andrew King Stratton Real Estate

  4 Gold Medal Cir, Stratton, VT 05343
• 

  

  /23

  $474,900

  • 3 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  28 Lightning Ledge Way, Wilmington, VT 05363

  Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Lightning Ledge Way, Wilmington, VT 05363
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  /33

  $19,500

  • 1 Bed
  • 1 Bath
  • 589 Sq Ft

  102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

  Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, end-unit, slopeside 1-bedroom, 1 full bath unit has sleeping space for 4, and looks out over the Sundance Base Lodge and the Sundance Express, the new 6-person chairlift. Open-concept kitchen/dining room, and a

  Donna Brown Skihome Realty

  102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

Showing Results 41 - 80, Page 2 of 9