Windham County VT Homes for Sale

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  /50

  $2,099,000

  • 5 Beds
  • 5.5 Baths
  • 5,235 Sq Ft

  6 Trail View Ln, Dover, VT 05356

  Enjoy stunning views, privacy, and luxury, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, tennis courts, game room, on site management company, and direct shuttle service between your

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Trail View Ln, Dover, VT 05356
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  /39

  $25,000

  • Land
  • 21,780 Sq Ft
  • $50,000 per Acre

  30 Upper Howes Way, Wilmington, VT 05363

  Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

  Sigrid Pickering Chimney Hill Realty

  30 Upper Howes Way, Wilmington, VT 05363
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  /6

  $229,000

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

  2 Gold Medal Cir, Stratton, VT 05343

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

  Andrew King Stratton Real Estate

  2 Gold Medal Cir, Stratton, VT 05343
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  /5

  $270,000

  • 6 Beds
  • 2 Baths
  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
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  /16

  $259,900

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

  1270 Melendy Hill Rd, Guilford, VT 05301

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

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
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  /35

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355
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  /2

  $95,000

  • Land
  • 14.7 Acres
  • $6,463 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
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  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /13

  $54,900

  • Land
  • 3.69 Acres
  • $14,878 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

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

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
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  /54

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
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  /21

  $179,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  40 Brookside Dr Unit 8, Brattleboro, VT 05301

  Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a

  Angela Sherman Brattleboro Area Realty

  40 Brookside Dr Unit 8, Brattleboro, VT 05301
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  /30

  $399,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation—from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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  /29

  $495,000

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

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Classic Vermont Home with stunning hilltop views, minutes from Mount Snow and Stratton. Set on a peaceful New England hilltop, this traditional-style home offers beautiful local and long-range views. Its highly desirable location is just 6 miles from both Mount Snow and Stratton ski resorts, and 6 miles to Grout Pond, providing VAST snowmobile trail access and summer activities.Filled with

  Donald Koelsch Deerfield Valley Real Estate

  137 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /33

  $85,000

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

  402 Fox Mountain Rd, Wilmington, VT 05363

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

  Sigrid Pickering Chimney Hill Realty

  402 Fox Mountain Rd, Wilmington, VT 05363
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  /39

  $575,000

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

  256 Potter Rd, Wardsboro, VT 05355

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

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  256 Potter Rd, Wardsboro, VT 05355
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  /3

  $450,000

  • Land
  • 3.38 Acres
  • $133,136 per Acre

  Lot 4 Mountain Ridge Estates, Wilmington, VT 05363

  Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 3.38+ acres overlooking the 18th tee box and mountains beyond for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 4 Mountain Ridge Estates, Wilmington, VT 05363
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  /12

  $399,000 New Construction

  • 4 Beds
  • 2 Baths
  • 3,700 Sq Ft

  442 Mcmillan Rd, Whitingham, VT 05342

  New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels.

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
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  /19

  $194,000

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

  189 North St, Dover, VT 05356

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

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  189 North St, Dover, VT 05356
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  /26

  $500,000

  • Land
  • 71 Acres
  • $7,042 per Acre

  00 Turkey Mountain Rd, Jamaica, VT 05343

  Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of

  Jessica Landers Barrett and Valley Associates Inc.

  00 Turkey Mountain Rd, Jamaica, VT 05343
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  /45

  $28,500

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, Dover, VT 05356

  Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious valley-side lockout unit, comfortably sleeps 8. Unit 204 is a hotel room with 2 king-size beds, a full bath, & a deck. The adjoining

  Donna Brown Skihome Realty

  204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, Dover, VT 05356
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  /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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  /35

  $399,900

  • 4 Beds
  • 3 Baths
  • 4,488 Sq Ft

  35 School St, Bellows Falls, VT 05101

  This single-family Victorian home located in the village of Bellows Falls has lots of space for family and friends! Four bedrooms, three full baths, a second-floor laundry room, two kitchens, two living rooms, three bonus rooms, and even an area for a potential apartment above the one-car garage! The open-concept updated kitchen/living room offer plenty of storage and seating for everyone and

  Heather Gleim CENTURY 21 North East

  35 School St, Bellows Falls, VT 05101
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  /16

  $345,000

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

  5 Vancor Dr, Town of Rockingham, VT 05154

  Excellent! Light, Bright, Tidy! This home has it all rolled up in one nice package. Located on the outskirts (strolling distance) of the very cool village of Saxton's River, with Vermont Academy, dining, village market and, of course, the Saxton's river! Besides, the very special, level lot with a sweet view, you have curb appeal you will want to come home to! The hang out, living area is

  Christine Lewis Brattleboro Area Realty

  5 Vancor Dr, Town of Rockingham, VT 05154
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  /17

  $35,000

  • Land
  • 2.5 Acres
  • $14,000 per Acre

  123 U S 5, Westminster, VT 05158

  This 2.5 acre lot offers a level parcel of land ready for your plans. The wooded lot is composed of immature growth, easing the task of clearing a dwelling/structure site while maintaining trees for privacy. The eastern, road-side section of the parcel can be opened to a lovely view over the NH horizon. Soil testing available and possible septic areas sited. See photos and listing documents.

  Laura D'Angelo Berkley & Veller Greenwood Country

  123 U S 5, Westminster, VT 05158
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  /4

  $160,000

  • Land
  • 9.3 Acres
  • $17,204 per Acre

  00 E Putney Brook Rd, Putney, VT 05346

  Located on E. Putney Brook Rd., approx. 2.5 miles from Putney Village, this beautiful, wooded 9+ ac property offers a desirable place to build. Bring your own building plans, power is nearby, and septic design is available. Clear a prime building site on level plateau and surround your home with mature woodlands. This county location offers easy access to orchards, farmstands for local produce,

  Heidi Bernier Berkley & Veller Greenwood Country

  00 E Putney Brook Rd, Putney, VT 05346
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  /20

  $330,000

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

  3730 Route 100, Wardsboro, VT 05355

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

  Ginny Read Read Realty LTD

  3730 Route 100, Wardsboro, VT 05355
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  /3

  $500,000

  • Land
  • 1.82 Acres
  • $274,725 per Acre

  Lot 3 Mountain Ridge Estates, Wilmington, VT 05363

  Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.82+ acres overlooking the 18th fairway and mountains beyond for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 3 Mountain Ridge Estates, Wilmington, VT 05363
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  /32

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
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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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  /13

  $50,000

  • Land
  • 2 Acres
  • $25,000 per Acre

  667 Hinkley Brook Rd, Grafton, VT 05146

  Nestled along the picturesque Hinkley Brook Road, this 2-acre parcel offers a rare opportunity to build your dream retreat in the charming and historic town of Grafton, Vermont. Just a short walk from the village center, you’ll enjoy the perfect blend of privacy and convenience, surrounded by the beauty of nature and classic New England charm. This peaceful lot boasts a gently wooded landscape

  Jamie Watson BHG Masiello Keene

  667 Hinkley Brook Rd, Grafton, VT 05146
• 

  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

  Christine Lewis Brattleboro Area Realty

  93 Clark 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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  /37

  $939,000

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

  25 Boulder Ridge Dr Unit B, Dover, VT 05356

  This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design, offering a living experience par excellence. This townhouse was finished in 2021 and has the “new construction” feel. The living room, graced with hardwood flooring, a gas fireplace,

  John Redd Skihome Realty

  25 Boulder Ridge Dr Unit B, Dover, VT 05356
• 

  

  /48

  $644,000

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  774 Stratton Arlington Rd, Stratton, VT 05360

  Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  774 Stratton Arlington Rd, Stratton, VT 05360
• 

  

  /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
• 

  

  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345
• 

  

  /21

  $450,000

  • 4 Beds
  • 3.5 Baths
  • 1,800 Sq Ft

  16 Tenth Unit 40, Wilmington, VT 05363

  Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in

  Adam Palmiter Berkley & Veller Greenwood/Dover

  16 Tenth Unit 40, Wilmington, VT 05363
• 

  

  /38

  $499,000

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

  829 Pennel Hill Rd, Halifax, VT 05342

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

  Megan Quinn Southern Vermont Realty Group

  829 Pennel Hill Rd, Halifax, VT 05342

Showing Results 241 - 280, Page 7 of 9