Windham County VT Homes for Sale

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  /36

  $799,000

  • 4 Beds
  • 4 Baths
  • 3,691 Sq Ft

  42 Airport Rd, Shaftsbury, VT 05262

  Set just minutes from world class skiing at Mount Snow, this inviting timber frame home offers comfort, convenience, and year-round adventure right outside your door. Located just off the Mount Snow Golf course and with direct access to VAST snowmobile trails, this property is perfectly positioned for ski weekends, snowmobiling adventures, summer hiking, and everything in between. Inside, you’ll

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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  /26

  $550,000

  • 8 Beds
  • 4 Baths
  • 6,466 Sq Ft

  72 Landmark Hill Dr, Brattleboro, VT 05301

  What will the next life be for this iconic property? From popular and innovative hair salon to successful dental practice to a 4 unit family complex....pick your use!!! Owner occupied business...roomy apartments...small business complex...this multi use property has been renovated in the last few years with nice kitchens and baths..and has been used essentially as a single family with a huge

  Christine Lewis Brattleboro Area Realty

  72 Landmark Hill Dr, Brattleboro, VT 05301
• 

  

  

  /29

  $569,000

  • 4 Beds
  • 3 Baths
  • 2,050 Sq Ft

  39B Kingswood Rd, Dover, VT 05356

  An impeccably maintained, beautifully furnished, and recently painted Kingswood townhome is conveniently located just minutes from Mount Snow and the Hermitage Club. This townhome features four bedrooms; an open-concept living area on the main level; a kitchen with a large island, granite countertops, and a vaulted ceiling; a wood-burning fireplace; and sliding doors leading to a private deck

  Patricia Fitzpatrick Skihome Realty

  39B Kingswood Rd, Dover, VT 05356
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  /28

  $235,000

  • 2 Beds
  • 1 Bath
  • 970 Sq Ft

  3153 Vermont Route 100, Wardsboro, VT 05355

  Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard—perfect for easy outdoor

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  3153 Vermont Route 100, Wardsboro, VT 05355
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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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  /5

  $55,000

  • Land
  • 1 Acre
  • $55,000 per Acre

  000F-320 Bourbon Run Rd, Jamaica, VT 05343

  This 1-acre wooded lot in Jamaica, Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and Mount Snow, ideal for

  Mike England Michael England Real Estate

  000F-320 Bourbon Run Rd, Jamaica, VT 05343
• 

  

  /31

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  72A Kingswood Rd, Dover, VT 05356

  Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned on the lower side of the development, offering greater separation between units, easy trail access, and a more usable private rear yard. The home features an open-concept living space with vaulted ceilings, a

  Adam Palmiter Berkley & Veller Greenwood/Dover

  72A Kingswood Rd, Dover, VT 05356
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  /60

  $8,200,000

  • 6 Beds
  • 10 Baths
  • 10,763 Sq Ft

  557 Trager Rd, Jamaica, VT 05343

  Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

  Kim Morgan-Wohler Wohler Realty Group

  557 Trager Rd, Jamaica, VT 05343
• 

  

  /35

  $34,500

  • 2 Beds
  • 3 Baths
  • 1,026 Sq Ft

  316/318, QTR 1 89 Grand Summit Way, Dover, VT 05356

  The best ski-on/ski-off location in Mount Snow! This two-bedroom, three-bathroom loft unit, which sleeps 8, features both valley vista views from the living room and deck, and mountain views from the loft bedroom. Enjoy your own little piece of Vermont with family and friends. You own 13 weeks of vacation to use, rent, or trade! Year-round use of the Grand Summit amenities includes valet parking,

  Patricia Fitzpatrick Skihome Realty

  316/318, QTR 1 89 Grand Summit Way, Dover, VT 05356
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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
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  /60

  $549,000

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

  35 Upper Bartonsville Rd, Chester, VT 05143

  Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

  Erin Kendall EXP Realty

  35 Upper Bartonsville Rd, Chester, VT 05143
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  /38

  $1,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,965 Sq Ft

  26 Springhill Rd, Dover, VT 05301

  This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Springhill Rd, Dover, VT 05301
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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /46

  $898,000

  • 4 Beds
  • 3.5 Baths
  • 3,420 Sq Ft

  41 Two Brook Dr, Wilmington, VT 05363

  Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all.Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  41 Two Brook Dr, Wilmington, VT 05363
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  /27

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,306 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  32 Old Town Rd, Dover, VT 05356
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  /16

  $353,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
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  /39

  $295,000

  • 4 Beds
  • 1 Bath
  • 1,248 Sq Ft

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301

  Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

  Steve Schoppmeyer BHG Masiello Brattleboro

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301
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  /34

  $459,900

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  Conveniently located in Brattleboro Center, this historic three-family home offers the perfect blend of Historic charm, and modern convenience. It is an ideal opportunity for an investor seeking profitable rental income or an owner-occupant looking to live on the main level while offsetting their mortgage with two additional rental units. The first-floor unit features high ceilings, French doors,

  Matt Waddington Hoffman Real Estate

  176 High St, Brattleboro, VT 05301
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  /60

  $429,000

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  26 N Wind Rd, Wilmington, VT 05363

  Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

  Rich Caplan Deerfield Valley Real Estate

  26 N Wind Rd, Wilmington, VT 05363
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  /48

  $294,000

  • 5 Beds
  • 3 Baths
  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

  Kate Barry EXP Realty

  5 Reynolds Dr, 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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  /6

  $475,000

  • Land
  • 188.9 Acres
  • $2,515 per Acre

  1301 Brockway Mills Rd, Bellows Falls, VT 05101

  Prime forested investment opportunity encompasses 190 acres, situated in the Northeast corner of Windham County. The property offers significant timber value and solar potential, making it attractive for both resource management and sustainable energy endeavors. The land borders Springfield and is conveniently located within easy reach of I-91, exit 6. It is also close to the villages of Chester

  Heidi Bernier Berkley & Veller Greenwood Country

  1301 Brockway Mills Rd, Bellows Falls, VT 05101
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  /32

  $27,000

  • 1 Bed
  • 2 Baths
  • 791 Sq Ft

  208/210 qtr2 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. Unit 208 boasts a living dining area with a sleep sofa and a Murphy bed There is a full kitchenette including a stove, microwave, dishwasher and refrigerator. Unit 210 includes 2 queen size beds, minifridge and a deck. Use of the Grand

  Sheila Joyce-Albano Skihome Realty

  208/210 qtr2 89 Grand Summit Way, Dover, VT 05356
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  /60

  $599,000

  • 5 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  673 Vermont 121, Grafton, VT 05146

  Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

  Janet Lucier Barrett & Valley Assoc. Inc

  673 Vermont 121, Grafton, VT 05146
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  /41

  $529,000

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

  19B Kingswood Rd, Dover, VT 05356

  Beautiful 3-bedroom, 3 bath Kingswood townhouse ideally located between Mount Snow and Hermitage Club. This Kingswood townhouse offers the perfect mountain getaway. Enjoy the well-appointed kitchen with a center island, a bright dining area, and a living area with a vaulted ceiling and a stunning 3 sided wood-burning fireplace, creating a warm, inviting atmosphere. Step outside onto a private

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  19B Kingswood Rd, Dover, VT 05356
• 

  /2

  $129,900

  • Land
  • 3 Acres
  • $43,300 per Acre

  57 Cheney Brook Loop, Dover, VT 05356

  Rare 3 acre south facing parcel in an area of fine homes, an incredibly short distance from West Dover center dining, shopping, and golf & skiing. Yet, it is just off the paved main artery that provides access to Dover Hills. Plenty of room to provide buffering, a truly unusual offering that shouldn't be missed if you're interested in constructing what you can't find in a limited inventory

  Michael Purcell Berkley & Veller Greenwood/Dover

  57 Cheney Brook Loop, Dover, VT 05356
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  /21

  $379,000

  • Land
  • 12.05 Acres
  • $31,452 per Acre

  101 Catherine Rd, Jamaica, VT 05343

  Discover 12 scenic acres close to Stratton Mountain Resort with sweeping mountain views and endless potential. This unique property features a charming small treehouse and two Jamaica cottage structures set on permanent foundations ready to be finished. Cabin would be perfect for income producing tiny homes, storage, creative space, or future development. An active septic permit is already in

  Jamie Wylie Stratton Real Estate

  101 Catherine Rd, Jamaica, VT 05343
• 

  

  /50

  $565,000

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

  3148 Route 11, Londonderry, VT 05148

  Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
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  /38

  $18,000

  • 1 Bath
  • 407 Sq Ft

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

  Mountain View Sleeps Four Studio, located slopeside at the Mount Snow Ski Resort! 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 slope-side studio unit with 1 full bath has sleeping space for 4, an open-concept kitchen/dining room, and a large living room with a queen sleep sofa and

  Patricia Fitzpatrick Skihome Realty

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

  

  /23

  $679,000

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

  14A Grouse Ln Unit 14A, Dover, VT 05356

  Gorgeous Post and Beam style townhome overlooking spectacular views of the Hermitage Club ski trails and sunsets over the ridgeline. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, easy nearby access to the Mount Snow ski resort, hiking and biking trails in the summer, and nearby convenience to the area's numerous lakes, dining and shopping.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14A Grouse Ln Unit 14A, Dover, VT 05356
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  /31

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  68 E Brook Crossing, Wilmington, VT 05363

  Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 E Brook Crossing, Wilmington, VT 05363
• 

  

  /21

  $849,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,564 Sq Ft

  4 Breezy Way, West Dover, VT 05356

  Brand new construction ski home just south of the Mount Snow ski resort recently finished for immediate use. This convenient location has MOOver shuttle service at the end of the street to and from the mountain, easy access to great restaurants and coffee shops, and direct snowmobile trail access, in addition to ample parking and privacy. The home was just finished by the developer and is ready

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4 Breezy Way, West Dover, VT 05356
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  /54

  $695,000

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

  1161 Little Pond Rd, Londonderry, VT 05148

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

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1161 Little Pond Rd, Londonderry, VT 05148
• 

  

  /20

  $199,595

  • Land
  • 4.2 Acres
  • $47,523 per Acre

  19 Stone Ridge Loop, Dover, VT 05356

  Located within the prestigious Village at Sawmill Farm, this exceptional homesite presents a rare opportunity to own in one of the Mount Snow Valley’s most sought-after communities. The extremely private property enjoys desirable southeasterly exposure with potential views of surrounding ridgelines, beautifully framed by timeless stone walls and majestic pines. A gentle slope makes it ideally

  Monique White Deerfield Valley Real Estate

  19 Stone Ridge Loop, Dover, VT 05356
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  /26

  $179,000

  • 4 Beds
  • 2 Baths
  • 2,470 Sq Ft

  1153 Rockingham Rd, Town of Rockingham, VT 05101

  Calling all investors and handy people! This is your opportunity to bring a classic property back to its former glory. Set on approximately 8.67 acres with frontage along the Williams River and Route 103, the location offers endless potential for a variety of uses. The spacious home appears to have solid bones but will require rehabilitation to restore its charm. A concrete slab is already in

  Chelsea Richardson Barrett and Valley Associates Inc.

  1153 Rockingham Rd, Town of Rockingham, VT 05101
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  /55

  $389,000

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

  1 Frog Hollow, Wilmington, VT 05363

  Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

  Rich Caplan Deerfield Valley Real Estate

  1 Frog Hollow, Wilmington, VT 05363
• 

  

  /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
• 

  

  /24

  $20,000

  • 1 Bed
  • 2 Baths
  • 754 Sq Ft

  250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356

  Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities with this spacious valley facing quarter share unit at the beautiful Grand Summit Hotel, directly at the base of Mount Snow! This sleep 6 condo is comprised of a studio unit (unit 252) with a queen murphy bed, kitchenette, sitting area and a full bathroom. This unit adjoins a hotel unit (unit 250) with 2

  Prema Fitzpatrick Real Broker LLC

  250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356
• 

  

  /37

  $749,000

  • 3 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  43C Dover Springs Ln, Dover, VT 05356

  This Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A meticulously maintained 3 bedroom, 3.5 bath unit with lots of bonus space, some recent updates and unique features. These include an open concept great room with vaulted ceilings, sunny natural light and sunset/ski trail views, wood burning double sided fireplace,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43C Dover Springs Ln, Dover, VT 05356
• 

  

  /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

Showing Results 81 - 120, Page 3 of 9