Windham County VT Homes for Sale

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  /13

  $980,000

  • Land
  • 43.67 Acres
  • $22,441 per Acre

  Lot 10 & 16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 44 acres of land including approximately 0.7 miles of private trails for hiking, ATV, snowmobiling and indirect connection to the VAST trails via Bluebrook Rd. The home site features full panoramic 180-degree mountain and woodland views to the north, east and south,

  Patricia Fitzpatrick Skihome Realty

  Lot 10 & 16 Overlook Dr, Dover, VT 05356
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  /38

  $35,000

  • 1 Bed
  • 2 Baths
  • 846 Sq Ft

  103/05 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 (105) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (103) Two queen beds and full bathroom. Units are located the mountain side of the hotel just above from a beautiful brook and just down the hallway from the Spa, ski locker,

  Kelly Agrillo Southern Vermont Realty Group

  103/05 Qtr.1,89 Grand Summit Way, Dover, VT 05356
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  /13

  $150,000

  • Land
  • 4.68 Acres
  • $32,051 per Acre

  8559 Vt Route 30, Jamaica, VT 05343

  Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

  TG Glazer Winhall Real Estate

  8559 Vt Route 30, Jamaica, VT 05343
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  /9

  $225,000

  • Land
  • 0.73 Acre
  • $308,219 per Acre

  5 Pinnacle View Rd, Dover, VT 05356

  With breathtaking 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

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  5 Pinnacle View Rd, Dover, VT 05356
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  /45

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,341 Sq Ft

  49 High Point Dr Unit A122, Stratton, VT 05360

  Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living

  Mike England Michael England Real Estate

  49 High Point Dr Unit A122, Stratton, VT 05360
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  /31

  $525,000

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

  19A Kingswood Rd, Dover, VT 05356

  Enjoy the best of Vermont in this bright and welcoming three bedroom plus den townhome. Featuring three full bathrooms, vaulted ceilings, an open concept living and dining area, wood burning fireplace and a private deck with a hot tub, this home offers the perfect balance of comfort and charm. The Kingswood Community center is just a short walk away and includes wonderful amenities such as an

  Melissa Ellis Southern Vermont Realty Group

  19A Kingswood Rd, Dover, VT 05356
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  /36

  $98,000

  • Land
  • 10 Acres
  • $9,800 per Acre

  1105 S Hill Rd, Jamaica, VT 05343

  Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

  Curtis Trousdale

  1105 S Hill Rd, Jamaica, VT 05343
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  /26

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Owner will consider offers. Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
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  /21

  $609,000

  • 2 Beds
  • 2 Baths
  • 916 Sq Ft

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

  771 Stratton Mountain Access Rd, Stratton, VT 05155Long 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 #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common.

  Andrew King Stratton Real Estate

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
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  /24

  $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
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  /26

  $749,000

  • Land
  • 1.22 Acres
  • $613,934 per Acre

  Lot 2 Old Mill Ln, Wilmington, VT 05363

  Bring your own builder and discover an exceptional opportunity to own a 1.22-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 2 Old Mill Ln, Wilmington, VT 05363
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  /36

  $998,500

  • 4 Beds
  • 3.5 Baths
  • 2,070 Sq Ft

  32 Shattarack Rd Unit B5, Stratton, VT 05360

  They say beauty is only skin deep, but not in the case of this meticulously renovated Slopeside residence, which offers a rare combination of quality, comfort, and location. With more than $500,000 invested, this home delivers far more than surface-level appeal — the kind of work that is not always seen but is most certainly felt. Every system and surface has been thoughtfully addressed. Unlike

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  32 Shattarack Rd Unit B5, Stratton, VT 05360
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  /24

  $774,000

  • Land
  • 3.6 Acres
  • $215,000 per Acre

  Lot 5 Old Mill Ln, Wilmington, VT 05363

  Bring. your own builder and discover an exceptional opportunity to own a 3.6 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 with your own builder or to be crafted by the Wadsworth Design Build..

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 5 Old Mill Ln, Wilmington, VT 05363
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  /43

  $2,000,000

  • 6 Beds
  • 4.5 Baths
  • 4,950 Sq Ft

  43 Upton Rd, Dover, VT 05356

  The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43 Upton Rd, Dover, VT 05356
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  /44

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  24 Antler Loop, West Dover, VT 05356

  This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  24 Antler Loop, West Dover, VT 05356
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  /22

  $275,000

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
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  /22

  $275,000

  • 4 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
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  /9

  $40,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  189 Shady Pines Park, Westminster, VT 05158

  1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

  John Hatton Berkley & Veller Greenwood Country

  189 Shady Pines Park, Westminster, VT 05158
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  /10

  $199,000

  • Land
  • 23.1 Acres
  • $8,615 per Acre

  184 Dupre Dr, Guilford, VT 05301

  Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301
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  /38

  $85,000

  • Land
  • 1.09 Acres
  • $77,982 per Acre

  95 Chimney Hill Rd, Wilmington, VT 05363

  Triple Merged Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! Right off the pavement about halfway up the Hill on the plateau. If you've been thinking of building your Dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season

  Sigrid Pickering Chimney Hill Realty

  95 Chimney Hill Rd, Wilmington, VT 05363
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  /10

  $299,000

  • Land
  • 7.08 Acres
  • $42,232 per Acre

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

  Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

  Heidi Bernier Berkley & Veller Greenwood Country

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101
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  /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
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  /30

  $50,000

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

  566 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 getaway 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

  566 Upper Dam Rd, Wilmington, VT 05363
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  /30

  $25,000

  • Land
  • 0.53 Acre
  • $47,170 per Acre

  452 2 Wall Way, Wilmington, VT 05363

  Single Lot on top of the Hill! Walk to the clubhouse from your very own vacation home, designed by you. Survey required and septic design. Lot is unimproved but has had recent favorable soil tests. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking, biking, snowmobiling, and more on our

  Sigrid Pickering Chimney Hill Realty

  452 2 Wall Way, Wilmington, VT 05363
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  /58

  $764,900

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  Step back in time without sacrificing comfort at the Woolley House, an exquisite 1818 Brick Federal style home nestled in the postcard-perfect village of Grafton, Vermont. This rare property seamlessly blends early 19th-century craftsmanship with thoughtful modern upgrades. Original details are beautifully preserved throughout, including four elegant Regency fireplaces, a central cooking hearth

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /49

  $999,800

  • 4 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  60 Forest Heights Rd, Stratton, VT 05360

  Spectacular Soaring Post and Beam located on the Dover/Stratton town line. This fabulous home boasts soaring vaulted ceilings in the living room with a wall of windows bringing the view into your home complete with a cozy brick fireplace that sets the perfect ambiance. The kitchen is a chef’s delight, featuring granite countertops with eat in dining, a center island, half bath and easy access to

  Rich Caplan Deerfield Valley Real Estate

  60 Forest Heights Rd, Stratton, VT 05360
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  /49

  $369,000

  • 4 Beds
  • 2 Baths
  • 2,202 Sq Ft

  20 Newell Hill Rd, Wardsboro, VT 05355

  Now offering multiple buyer credits, including a $10,000 credit at closing—ask your agent for full details. Enter through the oversized mudroom, which once served as the town post office, from the attached three-bay garage with automatic doors. This home features generous rooms throughout, starting with a large kitchen and dining area, a living room, two main-level bedrooms, and a full bath.

  Erica Reynolds Southern Vermont Realty Group

  20 Newell Hill Rd, Wardsboro, VT 05355
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  /31

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

  148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit

  Andrew King Stratton Real Estate

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
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  /52

  $999,000

  • 4 Beds
  • 2 Baths
  • 2,741 Sq Ft

  20 Finkel Rd, Wardsboro, VT 05355

  Nestled on nearly 260 acres, this exquisite 18th-century solid post & beam 4 bedroom 2 bath cape offers a harmonious blend of historic charm and modern convenience. Boasting original features like fireplaces, wood flooring, and exposed beams, the home is filled with character. Spacious rooms create a perfect setting for gatherings. Recent updates include a new roof, windows, furnace & oil tank;

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  20 Finkel Rd, Wardsboro, VT 05355
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  /36

  $449,000

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  44 Villager Loop, Dover, VT 05356

  Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VTVery little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

  Janet Boyd Boyd Real Estate

  44 Villager Loop, Dover, VT 05356
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  /40

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
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  /2

  $80,000

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West Brattleboro, VT 05301
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  /50

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 3,358 Sq Ft

  1917 Stowe Mountain Rd, West Halifax, VT 05358

  Welcome to 1917 Stowe Mountain Rd., a sanctuary of modern elegance nestled in the breathtaking green mountains of Halifax, VT. This luxurious contemporary residence spans 3,358 square feet and seamlessly blends sophisticated design with natural beauty. As you approach this architectural masterpiece, soaring cathedral ceilings create a sense of expansive openness. The glass and Hardie plank

  Monica Sumner BHG Masiello Brattleboro

  1917 Stowe Mountain Rd, West Halifax, VT 05358
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  /28

  $25,000

  • Land
  • 0.6 Acre
  • $41,667 per Acre

  28 Upper Howes Way, Wilmington, VT 05363

  BUILD your dream home in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at

  Sigrid Pickering Chimney Hill Realty

  28 Upper Howes Way, Wilmington, VT 05363
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  /29

  $25,000

  • Land
  • 0.6 Acre
  • $41,667 per Acre

  26 Upper Howes Way, Wilmington, VT 05363

  BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse

  Sigrid Pickering Chimney Hill Realty

  26 Upper Howes Way, Wilmington, VT 05363
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  /32

  $28,500

  • 1 Bed
  • 1 Bath
  • 671 Sq Ft

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

  Kelly Agrillo Southern Vermont Realty Group

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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  /32

  $25,000

  • Land
  • 0.56 Acre
  • $44,643 per Acre

  25 Upper Howes Way, Wilmington, VT 05363

  BUILD your Getaway Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200'

  Sigrid Pickering Chimney Hill Realty

  25 Upper Howes Way, Wilmington, VT 05363
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  /37

  $1,700,000

  • 4 Beds
  • 4.5 Baths
  • 3,808 Sq Ft

  15 Stone Ridge Loop, Dover, VT 05356

  A luxurious mountain property with views and acreage, still with great proximity to Mt Snow. This stunning barn style post and beam is nestled on a private 5.97 acre parcel at the rear of the Village at Sawmill Farms. The siting affords gorgeous pastoral views over the common field of the community, views of the peak of Mount Snow, and mountains beyond, with 180 degree winter views, which could

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Stone Ridge Loop, Dover, VT 05356
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  /8

  $65,000

  • Land
  • 2 Acres
  • $32,500 per Acre

  585 Sawmill Rd, Stratton, VT 05360

  Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway.

  Carrie Mathews Winhall Real Estate

  585 Sawmill Rd, Stratton, VT 05360
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  /6

  $45,000

  • Land
  • 1 Acre
  • $45,000 per Acre

  0 Boardman Loop, Wardsboro, VT 05360

  In the Heart of it all! This affordable acre of land is close to skiing, hiking, ponds and all the good stuff Vermont has to offer. Electric poles are across the street and the neighbors are hooked up. Starlink and Xfinity charts say they service the area for at home work, streaming or game playing. There are Covenants attached for the after midnight reading. There is a small stream on the

  Christine Lewis Brattleboro Area Realty

  0 Boardman Loop, Wardsboro, VT 05360

Showing Results 361 - 400, Page 10 of 11