Windham County VT Homes for Sale with Acreage

• 

  

  

  /3

  $60,000

  • Land
  • 1.1 Acres
  • $54,545 per Acre

  63 Villager Loop, Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  63 Villager Loop, Dover, VT 05356
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  /38

  $475,000

  • Land
  • 133.1 Acres
  • $3,569 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

  Geralyn Donohue Engel & Völkers Okemo

  40 E Putney Brook Rd, Putney, VT 05346
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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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  /42

  $499,990

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

  555 Vermont 9, Wilmington, VT 05363

  MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
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  /8

  $48,000

  • Land
  • 6.1 Acres
  • $7,869 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
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  /12

  $224,000

  • Land
  • 19.6 Acres
  • $11,429 per Acre

  227 Gault Rd, Wardsboro, VT 05355

  This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

  Victoria Woods Brattleboro Area Realty

  227 Gault Rd, Wardsboro, VT 05355
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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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  /12

  $36,999

  • Land
  • 2 Acres
  • $18,500 per Acre

  14 Brickyard Rd, Dover, VT 05341

  Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

  David White OwnerEntry.com

  14 Brickyard Rd, Dover, VT 05341
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  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /3

  $500,000

  • Land
  • 5.05 Acres
  • $99,010 per Acre

  Lot 1 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 5+ acres overlooking the 18th hole and mountains beyond for year

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
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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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  /3

  $500,000

  • Land
  • 1.1 Acres
  • $454,545 per Acre

  Lot 2 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 1.1 acres overlooking the fairway of the 18th hole and mountains

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
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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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  /9

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vermont 30, Jamaica, VT 05343

  Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

  Helen Nault

  4441 Vermont 30, Jamaica, VT 05343
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  /52

  $1,150,000

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

  5 Tannery Rd, West Dover, VT 05356

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

  Michelle O'Neil Deerfield Valley Real Estate

  5 Tannery Rd, West Dover, VT 05356
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  /38

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /9

  $269,000

  • Land
  • 54.8 Acres
  • $4,909 per Acre

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

  Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a possible future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax savings and can remain in the program under new

  Carrie Mathews Winhall Real Estate

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
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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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  /33

  $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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  /12

  $325,000

  • Land
  • 3.42 Acres
  • $95,029 per Acre

  2366 Middletown Rd, Landgrove, VT 05148

  This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  2366 Middletown Rd, Landgrove, VT 05148
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  /39

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The Hermitage Club Experience the perfect fusion of luxury, privacy, and adventure in this beautifully renovated 4,950 sq ft home set on 1.62 acres of tranquil Vermont countryside. Ideally positioned between Mount Snow and the private Hermitage Club, this home offers a rare opportunity for refined mountain living

  Derek Greene Derek Greene

  3 Shannon Ridge Rd, Dover, VT 05356
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  /41

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,153 Sq Ft

  487 Vermont Route 100, Londonderry, VT 05148

  Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

  Jamie Wylie Stratton Real Estate

  487 Vermont Route 100, Londonderry, VT 05148
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  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 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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  /41

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
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  /54

  $999,000

  • 5 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
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  /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
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  /39

  $499,000

  • Land
  • 80.11 Acres
  • $6,229 per Acre

  47 Whites Hill Rd, Dover, VT 05341

  Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

  Joe Castaluccio Winhall Real Estate

  47 Whites Hill Rd, Dover, VT 05341
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  /12

  $125,000

  • Land
  • 15.6 Acres
  • $8,013 per Acre

  0 Thayer Rd, Westminster, VT 05158

  Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

  Steve Schoppmeyer BHG Masiello Brattleboro

  0 Thayer Rd, Westminster, VT 05158
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  /18

  $299,000

  • Land
  • 1.06 Acres
  • $282,075 per Acre

  12 Someday Rd, Dover, VT 05356

  Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  12 Someday Rd, Dover, VT 05356
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  /60

  $2,749,000

  • 6 Beds
  • 7 Baths
  • 6,400 Sq Ft

  56 Handle Rd, Dover, VT 05356

  Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler’s panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood

  Rich Caplan Deerfield Valley Real Estate

  56 Handle Rd, Dover, VT 05356
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  /50

  $397,000

  • 4 Beds
  • 2 Baths
  • 3,300 Sq Ft

  715 Chase Rd, West Townshend, VT 05359

  Welcome to 715 Chase Road where you will find peace, tranquility and even convenience. This home offers so much bang for its' buck, you must come see it to believe it. Three bedrooms one full bath and laundry on the main level along with den, breakfast room and inviting living area with wood burning fireplace. The kitchen boasts plenty of counter and cupboard space with newer appliances and a

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  715 Chase Rd, West Townshend, VT 05359
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  /20

  $99,500

  • Land
  • 10.27 Acres
  • $9,688 per Acre

  0 Theresa Ln, Wilmington, VT 05363

  This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

  Lisa Mirando Deerfield Valley Real Estate

  0 Theresa Ln, Wilmington, VT 05363
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  /39

  $895,000

  • 5 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3715 Route 11, Londonderry, VT 05148

  Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

  Cheyanne Pugliese

  3715 Route 11, Londonderry, VT 05148
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  /3

  $275,000

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

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  /59

  $275,000

  • 2 Beds
  • 1 Bath
  • 715 Sq Ft

  81 Parish Hill Rd, Newfane, VT 05345

  Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

  Chad Bruyette Whitetail Properties Real Estate, LLC

  81 Parish Hill Rd, Newfane, VT 05345
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  /60

  $549,000

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
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  /44

  $1,140,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen! Featuring four spacious bedrooms, this home provides plenty of room for

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  

  /59

  $589,000

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  628 Townshend Rd, Grafton, VT 05146

  One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

  Jessica Landers Barrett and Valley Associates Inc.

  628 Townshend Rd, Grafton, VT 05146
• 

  

  /17

  $2,495,000

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

  4 Gold Medal Cir, Stratton, VT 05343

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

  Andrew King Stratton Real Estate

  4 Gold Medal Cir, Stratton, VT 05343
• 

  /2

  $70,000

  • Land
  • 2.01 Acres
  • $34,826 per Acre

  0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

  Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails. Enjoy the peace of a quiet country setting where you can listen to

  Kerry Mulverhill

  0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

Showing Results 81 - 120, Page 3 of 5