Windham County VT Homes for Sale

• 

  

  

  /42

  $675,000

  $20K PRICE DROP

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

  54 Main St, Grafton, VT 05146

  This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept

  Jessica Landers Barrett and Valley Associates Inc.

  54 Main St, Grafton, VT 05146
• 

  

  

  /18

  $90,100

  • Land
  • 21,780 Sq Ft
  • $180,200 per Acre

  LOT 3 158/160 High Peak Way, Wilmington, VT 05363

  A opportunity to own this .50-acre double lot in the High Peak Development, offering a double lot for your Vermont getaway. Ideally situated adjacent to the Haystack Golf Course, this parcel provides the perfect mountain convenience. Just a short drive to Mount Snow**, The Hermitage Club, and all the year-round recreation the Deerfield Valley is known for, this property also offers direct access

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  LOT 3 158/160 High Peak Way, Wilmington, VT 05363
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  /32

  $728,000

  $47K PRICE DROP

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

  15 Bears Den Rd, Dover, VT 05356

  A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living.This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356
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  /33

  $225,000

  $75K PRICE DROP

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

  16 Washington St, Brattleboro, VT 05301

  Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! 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

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  

  /20

  $23,500

  • 1 Bed
  • 2 Baths
  • 846 Sq Ft

  130/132, Qtr 3 89 Grand Summit Way, Dover, VT 05356

  This premier trailside, ski-in/ski-out lockout unit is located at the base of Mount Snow and offers exceptional versatility, comfortably sleeping up to eight people. The unit can be utilized as a full 1 bedroom, two-bath home or separated into individual suites to maximize rental potential. Unit 130 features a kitchenette and a comfortable living area with a sleep sofa, and a Murphy bed, sleep 4.

  Sheila Joyce-Albano Skihome Realty

  130/132, Qtr 3 89 Grand Summit Way, Dover, VT 05356
• 

  

  /43

  $1,392,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations.Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
• 

  

  /20

  $24,900

  • 1 Bed
  • 2 Baths
  • 791 Sq Ft

  249/251, Qtr1 89 Grand Summit Way, Dover, VT 05356

  Own Where You Play in this Mountainview Quarter-Share! Experience the best of Mount Snow with this unique quarter-share ownership at the Grand Summit Resort Hotel. Designed to accommodate up to eight guests comfortably, this two-bath unit offers the flexibility to use, rent, or exchange your ownership for vacation stays worldwide. The main living area features an open-concept kitchen, dining, and

  Patricia Fitzpatrick Skihome Realty

  249/251, Qtr1 89 Grand Summit Way, Dover, VT 05356
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  /4

  $55,000

  • Land
  • 1.05 Acres
  • $52,381 per Acre

  31 Woodsman Rd, West Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. The Woodsman development features large private home sites affording great privacy with thick tree buffers, public sewer hookups, easy access of a paved road nearby and tremendous site potential. This lot has been priced to sell!

  Adam Palmiter Berkley & Veller Greenwood/Dover

  31 Woodsman Rd, West Dover, VT 05356
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  /9

  $198,000

  • Land
  • 3.27 Acres
  • $60,550 per Acre

  0 Pleasant Valley Rd, Brattleboro, VT 05301

  It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

  Christine Lewis Brattleboro Area Realty

  0 Pleasant Valley Rd, Brattleboro, VT 05301
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  /59

  $675,000

  $25K PRICE DROP

  • 6,144 Sq Ft

  2170 N Main St, Londonderry, VT 05148

  For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that

  Jessica Ackley

  2170 N Main St, Londonderry, VT 05148
• 

  

  /23

  $499,000

  $41K PRICE DROP

  • 6,000 Sq Ft

  16 School St, Brattleboro, VT 05301

  Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a

  Kate Barry EXP Realty

  16 School St, Brattleboro, VT 05301
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  /46

  $869,900

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

  45 Sawmill Village Way, Dover, VT 05356

  Experience the perfect blend of Vermont charm and modern comfort in this beautifully crafted custom post-and-beam home with a beautiful view, ideally located in the heart of Dover. Just minutes from Mount Snow, local restaurants, shopping, area amenities, and the scenic Valley Trail, this home offers the perfect balance of convenience and privacy in a peaceful wooded setting. Inside, many windows

  Rich Caplan Deerfield Valley Real Estate

  45 Sawmill Village Way, Dover, VT 05356
• 

  /2

  $150,000

  • Land
  • 2.05 Acres
  • $73,171 per Acre

  00 Fort Dummer Heights, Brattleboro, VT 05301

  Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  00 Fort Dummer Heights, Brattleboro, VT 05301
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  /58

  $549,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  3148 Route 11, Londonderry, VT 05148

  More than a Vermont home, this is a property built for the way you want to live here.Set on 14 acres in Londonderry, this versatile Southern Vermont property combines a 3-bedroom, 2-bath home with something increasingly difficult to find near the mountains: acreage, substantial storage, multiple outbuildings and room for all the gear that comes with the Vermont lifestyle.The

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
• 

  

  /5

  $380,000

  • 3,264 Sq Ft

  25 Cottage St, Brattleboro, VT 05301

  Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

  Christine Lewis Brattleboro Area Realty

  25 Cottage St, Brattleboro, VT 05301
• 

  

  /19

  $249,000

  • 3 Beds
  • 1 Bath
  • 775 Sq Ft

  5 Oregon Falls Rd, Newfane, VT 05345

  Welcome to your serene escape nestled in nature’s embrace. This secluded riverside retreat offers stunning river frontage and panoramic views of the majestic Green Mountains, creating a peaceful sanctuary for relaxation and rejuvenation.Despite its tranquil setting, this home is conveniently located just 20 minutes from the vibrant slopes of Mt. Snow, perfect for winter sports

  Colt Hazell Flex Realty

  5 Oregon Falls Rd, Newfane, VT 05345
• 

  

  /27

  $68,500

  $7K PRICE DROP

  • Land
  • 1 Acre
  • $68,500 per Acre

  170 Maple Dr, Wardsboro, VT 05355

  This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this lot provides both easy access and privacy. Driveway is in, lot is

  Chris Lowe Lowe's Real Estate, LLC

  170 Maple Dr, Wardsboro, VT 05355
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  /22

  $18,000

  • 1 Bath
  • 407 Sq Ft

  217, QTR 2 89 Grand Summit Way, Dover, VT 05356

  This sleep-four studio features one full bath, an open-concept kitchen and dining area, and a spacious living room with both a queen-size sleeper sofa and queen Murphy bed. Whether you’re looking for a convenient mountain getaway, a rental opportunity, or additional vacation flexibility, this property offers plenty of options: Use it, Rent it, or Trade it!Grand Summit ownership includes

  Patricia Fitzpatrick Skihome Realty

  217, QTR 2 89 Grand Summit Way, Dover, VT 05356
• 

  

  /27

  $230,000

  $20K PRICE DROP

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

  11 Evergreen Ln, Brattleboro, VT 05301

  This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

  Janet Lucier Barrett & Valley Assoc. Inc

  11 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /32

  $375,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,502 Sq Ft

  715 Chase Rd, West Townshend, VT 05359

  In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for

  Christine Lewis Brattleboro Area Realty

  715 Chase Rd, West Townshend, VT 05359
• 

  

  /4

  $18,500

  $17K PRICE DROP

  • Land
  • 10,890 Sq Ft
  • $74,000 per Acre

  2 Brook Ln, Wilmington, VT 05363

  Nice building lot located in the Two Brook community, conveniently situated near Haystack Golf Course and just minutes from skiing, golf, lakes, and snowmobiling. This attractive parcel offers a peaceful setting with common land bordering the rear of the property and a stream flowing through the lot, adding to its natural appeal. Power, public water, and public sewer infrastructure are available

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  2 Brook Ln, Wilmington, VT 05363
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  /41

  $825,000

  $50K PRICE DROP

  • 7 Beds
  • 6.5 Baths
  • 1,152 Sq Ft

  136 Vermont Route 100, Dover, VT 05356

  Residential Property with Income Potential Near Mount Snow Discover a rare opportunity to own a versatile residential property with multiple income streams, located just minutes from the village of West Dover and the Mount Snow Resort area. Whether used as a primary residence, second home, or investment property, this offering provides exceptional flexibility. The main residence features a

  Cyd Scott Cohn & Company

  136 Vermont Route 100, Dover, VT 05356
• 

  

  /30

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,406 Sq Ft

  36 Pine St, Brattleboro, VT 05301

  In the heart of it all! Just minutes to everything Brattleboro...Day or night, there is something fun to do....movies, eats, hiking and so may other choices....3 generations have lived in and loved this home, gardening, sipping on the back deck, saying hello on the Vermont front porch. An era when homes were built with good bones, craftsmanship and quality hard to afford today. A pretty face to

  Christine Lewis Brattleboro Area Realty

  36 Pine St, Brattleboro, VT 05301
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  /11

  $149,000

  • 2 Beds
  • 1 Bath
  • 744 Sq Ft

  1530 Somerset Rd, Somerset, VT 05363

  Have you ever wanted to live in the middle of the Nation Forest? Look no further, this 2-bedroom property with room to expand on the second floor with off grid power bank and generator to keep the lights on and the dish network so you don’t miss all your favorite tv show or sporting events. All the outdoor experiences you could ever dream of right outside your front door. Just a short drive to

  Dan Mason Perrott Realty

  1530 Somerset Rd, Somerset, VT 05363
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  /38

  $388,000

  $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  8 Deer Creek Unit E, Dover, VT 05356

  Located at the base of Mount Snow, Deer Creek offers a prime setting just an easy walk across Handle Road to the Sundance Base Lodge, home to two new chairlifts—including a high-speed detachable 6-pack. Recently painted, this 2-bedroom plus loft, 2-bath condo features all-new flooring, a convenient ski locker one floor down from the unit, and an in-home washer and dryer. The open-concept living,

  Donna Brown Skihome Realty

  8 Deer Creek Unit E, Dover, VT 05356
• 

  

  /17

  $95,000

  $20K PRICE DROP

  • Land
  • 4 Acres
  • $23,750 per Acre

  00 S Ryder Pond Rd, Whitingham, VT 05361

  Discover the perfect setting for your Vermont getaway or future home on this beautiful 4-acre lot located at the end of a quiet dead-end road with direct access to a private pond. The gently sloping, wooded landscape offers privacy, natural beauty, and an ideal mix of mature trees and usable terrain for your vision. A Vermont wastewater permit is already in place, making it even easier to start

  Patrice Schneider Southern Vermont Realty Group

  00 S Ryder Pond Rd, Whitingham, VT 05361
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  /15

  $450,000

  $80K PRICE DROP

  • Land
  • 30 Acres
  • $15,000 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
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  /36

  $675,000

  • 4 Beds
  • 3 Baths
  • 2,565 Sq Ft

  451 N Main St, Londonderry, VT 05148

  Custom designed and built by original owner, architect and builder Stuart MacDonald, this four bedroom, three bath South Londonderry home combines distinctive Vermont character with thoughtful design on 4.8 acres. The approximately 2,565 square foot home features a ground floor primary suite, living room with fireplace, an inviting sitting area off the kitchen with woodstove, and flexible living

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  451 N Main St, Londonderry, VT 05148
• 

  

  /33

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  8 Beech Tree Ln, Newfane, VT 05345

  This is just the cutest little cottage you ever did see! It is just the right size not too big, not too small. This charming country cottage would be a wonderful small footprint primary home or would make an ideal weekend getaway! The first floor living space is open with lovely wood floors and a wood stove perfect for those crisp country evenings, tastefully updated kitchen, dining area, and

  Rebecca Seymour Brattleboro Area Realty

  8 Beech Tree Ln, Newfane, VT 05345
• 

  

  /27

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  10 Grouse Ln Unit 10A, Dover, VT 05356

  Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  10 Grouse Ln Unit 10A, Dover, VT 05356
• 

  

  /57

  $465,000

  • 4 Beds
  • 3 Baths
  • 3,268 Sq Ft

  2855 Thompsonburg Rd, South Londonderry, VT 05155

  This spacious Londonderry contemporary house sits on a sunny, level one-acre lot and is conveniently located at the base of Glebe Mountain and mere minutes from Magic Mountain for snow sports and Lowell Lake for summer hikes, kayaking and keeping an eye on the native loons that nest there. The layout offers three levels of bright and roomy living spaces with a comfortable floorplan and lots of

  Claudia Harris Mary Mitchell Miller Real Estate

  2855 Thompsonburg Rd, South Londonderry, VT 05155
• 

  

  /30

  $137,000

  $2K PRICE DROP

  • Land
  • 20.1 Acres
  • $6,816 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
• 

  

  /38

  $798,000

  • 4 Beds
  • 4.5 Baths
  • 2,858 Sq Ft

  38D Greenspring Rd, Dover, VT 05356

  Enjoy the best of Southern Vermont mountain living in this spacious four-bedroom, four-bath townhome at Greensprings, ideally located just minutes from Mount Snow. With beautiful views of the mountain, this townhome offers the perfect combination of comfort, convenience, and year-round recreation. The generous four-bedroom layout provides plenty of room for family and guests, with four full baths

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  38D Greenspring Rd, Dover, VT 05356
• 

  

  /16

  $336,000

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

  12A Dover Green Loop, Dover, VT 05356

  Move right in and get ready to enjoy the upcoming ski season. This mostly updated 3 bed 2 bath condo at Dover Green is ready for its next owners. With the newly updated kitchen and recently updated bathrooms you can enjoy your time on the mountain before returning to your warm and cozy getaway just a few minutes away. There's a wood burning fireplace anchoring the large living room with high

  Mike Masters Four Seasons Sotheby's Int'l Realty

  12A Dover Green Loop, Dover, VT 05356
• 

  

  /17

  $59,000

  • Land
  • 5.66 Acres
  • $10,424 per Acre

  4 Murdock Ln, Whitingham, VT 05361

  Warranty Deed, 4 Bedroom Septic Permit, Roughed-in Drive, Great location!! Build your dream home on this surveyed 5.66 acre lot with deeded rights to Ryder Pond! A great location for primary or vacation living, situated between down town Wilmington VT and Greenfield MA with easy access to scenic Rt 100. Lakes, ski resorts and out door recreation abound with Mount Snow Resort, Lake Whitingham,

  Jacki Murano Southern Vermont Realty Group

  4 Murdock Ln, Whitingham, VT 05361
• 

  

  /47

  $449,000

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

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363

  Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready!Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse

  Sigrid Pickering Chimney Hill Realty

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363
• 

  

  /60

  $2,895,000

  • 6 Beds
  • 4 Baths
  • 3,946 Sq Ft

  2060 Townshend Rd, Grafton, VT 05146

  A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse,

  Erin McCormick KW Vermont

  2060 Townshend Rd, Grafton, VT 05146
• 

  

  /33

  $865,000

  • 4 Beds
  • 3.5 Baths
  • 2,133 Sq Ft

  6 High Point Dr Unit 401, Stratton, VT 05360

  This tastefully renovated 4-bedroom, 4-bathroom townhome is the mountain getaway you’ve been waiting for. The coveted end unit boasts an open, airy layout and new oversized windows in the kitchen and living room. The result is a space flooded with natural light, offering private, wooded views right from the couch. Just one mile from the Village, you can skip the parking hassle with the convenient

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  6 High Point Dr Unit 401, Stratton, VT 05360
• 

  

  /26

  $329,000

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

  61 E Country Club Rd, Dover, VT 05356

  Charming 3-Bedroom Condo Just Minutes from Mount Snow! Open House Monday Sept. 7, 10 - 12!! Welcome to your perfect Vermont getaway! This beautifully maintained 3-bedroom, 2.5-bath condo is ideally located in Southern Vermont, just minutes from the renowned Mount Snow Ski Resort and the Mount SnowGolf Course. Whether you're an outdoor enthusiast or seeking a peaceful retreat, this property offers

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  61 E Country Club Rd, Dover, VT 05356
• 

  /2

  $45,000

  • Land
  • 10,890 Sq Ft
  • $180,000 per Acre

  45 Mowing Way, Wilmington, VT 05363

  Level building lot with public sewer and water at the street. Across from the Haystack Golf Course for easy year round enjoyment. Direct snowmobile access from the lot. A short drive to the public boat launch at Lake Whitingham or Mount Snow ski resort.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Mowing Way, Wilmington, VT 05363

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