Windham County VT Homes for Sale with Acreage

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  /60

  $4,950,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
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  /33

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  1829 W Jamaica Rd, Jamaica, VT 05343

  Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms

  

  Alison Cummings

  Cummings & Co

  (802) 471-3958

  1829 W Jamaica Rd, Jamaica, VT 05343
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  /31

  $359,000

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

  410 Tallwood Cir, Londonderry, VT 05148

  This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
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  /18

  $120,000

  • Land
  • 2.84 Acres
  • $42,254 per Acre

  111 Gib Lockerby Rd, Grafton, VT 05146

  Nestled in the rolling hills of southern Vermont, just minutes above the charming center of Grafton, this professionally developed parcel of land beckons you to build your Vermont dream home. This open and sunny lot, complete with its own small apple orchard is surrounded by timeless stone walls and lovely woodlands. Choose the best building site for you; the cleared front acre, formerly a sunny

  

  Christopher Cummings

  Cummings & Co

  (802) 424-8491

  111 Gib Lockerby Rd, Grafton, VT 05146
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  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /79

  $275,000

  • Land
  • 22.32 Acres
  • $12,321 per Acre

  81 Parish Hill Rd Unit 26, Newfane, VT 05345

  Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

  Chad Bruyette Whitetail Properties Real Estate

  81 Parish Hill Rd Unit 26, Newfane, VT 05345
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  /12

  $999,000

  • Land
  • 12.2 Acres
  • $81,885 per Acre

  Higley Hill Rd, Wilmington, VT 05363

  Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

  Community Lands Community Lands

  Higley Hill Rd, Wilmington, VT 05363
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  /4

  $59,000

  • Land
  • 3.3 Acres
  • $17,879 per Acre

  0 Hunt Rd, Wardsboro, VT 05355

  Discover the perfect canvas for your Vermont dream home on this newly created 3.3-acre parcel in Wardsboro. Tucked away in a peaceful, private setting, you’ll enjoy the quiet beauty of the surrounding woods while still being within easy reach of some of Southern Vermont’s most sought-after destinations. Spend your winters skiing at Mount Snow or Stratton Mountain Resort, and take advantage of

  Mike Masters Four Seasons Sotheby's Int'l Realty

  0 Hunt Rd, Wardsboro, VT 05355
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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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  /17

  $1,450,000

  • Land
  • 201.4 Acres
  • $7,200 per Acre

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360

  Own this large tract of land, over 200 acres that abuts over 1100 acres of Green Mountain National Forest property. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Current 18 acre gravel pit is being reclaimed and closed on this property. See the Vermont Land Use Permit 2W1316 online for further information. There are multiple

  Chris Lowe Lowe's Real Estate, LLC

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360
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  /13

  $99,000

  • Land
  • 10.05 Acres
  • $9,851 per Acre

  78 Captain Copeland Rd, Dover, VT 05341

  Set on a quiet country road, this 10+ acre parcel offers an ideal blend of privacy and convenience with easy access to Mount Snow and year-round recreation. The property is currently wooded, providing a natural setting with the potential to open up attractive mountain views. Located in a desirable area close to skiing, hiking, and outdoor activities, this land presents a great opportunity for a

  Carrie Mathews Winhall Real Estate

  78 Captain Copeland Rd, Dover, VT 05341
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  /35

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  198 E Hill Rd, Wardsboro, VT 05355

  Gorgeous home with so many upgrades over the past five years! Updated kitchen with appliances, baths, new roof, windows, flooring, well pump, mini splits, high efficiency propane combo unit for heat and hot water, new pavement, three car detached garage, woodshed, fenced in doghouse area and so much more! These are just a few of the items this homeowner has done to improve the property. The home

  Julie Lowe Lowe's Real Estate, LLC

  198 E Hill Rd, Wardsboro, VT 05355
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  /37

  $639,000

  • 4 Beds
  • 2.5 Baths
  • 2,573 Sq Ft

  11 Strawberry Hill, Brattleboro, VT 05301

  Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

  Dan Normandeau Berkley & Veller Greenwood Country

  11 Strawberry Hill, Brattleboro, VT 05301
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  /60

  $1,088,000

  • 6 Beds
  • 4.5 Baths
  • 5,828 Sq Ft

  151 Townshend Rd, Grafton, VT 05146

  Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The property is configured to allow division into two condominium-style living spaces plus a separate artist loft or accessory dwelling, each with its own entrance, creating versatile possibilities for expansive

  Erin McCormick KW Vermont

  151 Townshend Rd, Grafton, VT 05146
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  /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
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  /31

  $619,000

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with an attached garage offers over 3,000 square feet of living space and the perfect blend of comfort, style, and refined Vermont living. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /8

  $74,900

  • Land
  • 1.1 Acres
  • $68,091 per Acre

  2 Johnson Hill, Dover, VT 05356

  Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

  Janet Boyd Boyd Real Estate

  2 Johnson Hill, Dover, VT 05356
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  /20

  $195,000

  • Land
  • 46.2 Acres
  • $4,221 per Acre

  1499 Josh Rd, Halifax, VT 05358

  Looking for true peace and tranquility? This 46.2-acre parcel faces South/SW and is located in a gorgeous remote valley with no road noise or any sound other than the sound of the crystal-clear brook crashing down the valley and the wind in the trees! The parcel does have some improvements including a modified camper with a 1000 gallon holding tank, existing gravel driveway off Josh Road (class

  Chris Long BHG Masiello Brattleboro

  1499 Josh Rd, Halifax, VT 05358
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  /5

  $72,000

  • Land
  • 6.21 Acres
  • $11,594 per Acre

  0 Crane Mountain Rd, Townshend, VT 05353

  Nestled on top of Townshend Acres this 6.21 acre surveyed lot offers a amazing opportunity to build your dream home . This mostly level wooded parcel has easy access to a town-maintained road near a neighborhood community . Outdoor activities abound ; hiking , hunting , snowmobiling all available ...outside your door. Minutes from four seasons resorts for skiing, music and biking. Convenient to

  Janet Lucier Barrett & Valley Assoc. Inc

  0 Crane Mountain Rd, Townshend, VT 05353
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  /37

  $795,000

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

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /22

  $110,000

  • Land
  • 2.5 Acres
  • $44,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Nestled in an idyllic setting at 69 Old Haven Lane, this exceptional building lot offers a rare opportunity to bypass the typical hurdles of new construction and start bringing your vision to life immediately. Located in a sought-after and peaceful pocket of Putney, this property perfectly balances the privacy of a country retreat with the convenience of an excellent location. Much of the

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /30

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  313 S Pine Banks Rd, Putney, VT 05346

  Experience the Magic of Putney, Vermont. Discover a private sanctuary in the heart of Vermont’s "Craft Capital." This meticulously maintained ranch offers the perfect blend of secluded country living and proximity to Putney’s vibrant cultural hub. Known for its world-class arts scene, organic farms, Yellow Barn Music, Next Stage Arts, Putney COOP, and iconic institutions like Sandglass Theater

  Thomas Dahlin Berkley & Veller Greenwood Country

  313 S Pine Banks Rd, Putney, VT 05346
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  /41

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,948 Sq Ft

  196 Powder Mill Rd, Londonderry, VT 05148

  Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for

  Katie Ladue Gilbert BHHS Verani Upper Valley

  196 Powder Mill Rd, Londonderry, VT 05148
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  /8

  $195,000

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  0 Stoney Brook Rd, Londonderry, VT 05148

  4.86 acre building lot in Londonderry, Vermont with mountain views of Stratton and Bromley, offering privacy, elevation, and a compelling Southern Vermont setting. Access and building site are roughed in, and the property includes a State of Vermont wastewater permit for a 5 bedroom single family residence. Private setting, just minutes to Magic Mountain Ski Area and Londonderry Marketplace, with

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  0 Stoney Brook Rd, Londonderry, VT 05148
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  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /60

  $725,000

  • 6 Beds
  • 3 Baths
  • 3,630 Sq Ft

  5 William Mundell Rd, South Newfane, VT 05351

  Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

  The Malley Group KW Vermont

  5 William Mundell Rd, South Newfane, VT 05351
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  /39

  $725,000

  • 5 Beds
  • 4 Baths
  • 2,962 Sq Ft

  250 Valley View Rd, Dover, VT 05356

  Unique, spacious, and just minutes to Mount Snow, this 5-bedroom, 4-bath home with a private pond is the kind of property buyers wait for. Whether for personal use, a vacation getaway, or short-term rental potential, it offers a setting to enjoy every season. Set on a beautiful 2-acre lot, the home features a large open-concept main living area with a cathedral ceiling and oversized windows that

  Melissa Nebelski Real Broker LLC

  250 Valley View Rd, Dover, VT 05356
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  /23

  $189,000

  • Land
  • 3.6 Acres
  • $52,500 per Acre

  00 Lake Hill Rd, Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd, Whitingham, VT 05361
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  /9

  $480,000

  • Land
  • 7.8 Acres
  • $61,538 per Acre

  16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

  Patricia Fitzpatrick Skihome Realty

  16 Overlook Dr, Dover, VT 05356
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  /8

  $480,000

  • Land
  • 5.08 Acres
  • $94,488 per Acre

  10 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

  Patricia Fitzpatrick Skihome Realty

  10 Overlook Dr, Dover, VT 05356
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  /43

  $625,000

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

  15 Bills Rd, West Wardsboro, VT 05360

  This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  15 Bills Rd, West Wardsboro, VT 05360
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  /40

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  1355 Whitneyville Rd, Halifax, VT 05301

  Welcome to this charming country log home set on 30.6 private acres at the peaceful end of the road. Thoughtfully positioned to capture its surroundings, the home sits just high enough to enjoy pleasant views and beautiful mountain sunsets, best experienced from the inviting covered porches and open deck. Inside, the open-concept main level features abundant windows and cathedral ceiling creating

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  1355 Whitneyville Rd, Halifax, VT 05301
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  /60

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,723 Sq Ft

  405 Main St, Wardsboro, VT 05355

  Lovingly shaped over generations of ownership, this is one of those special properties where the setting, charm, and character come together in a way that simply cannot be replicated. Set on 1.10 acres along a woodland creek, this property shines with natural beauty and Vermont charm. A stream-fed pond adds to the tranquil setting, while old stone walls, mature trees, butterfly gardens, and

  Rachel Febbie EXP Realty

  405 Main St, Wardsboro, VT 05355
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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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  /60

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3185 Higley Hill Rd, West Marlboro, VT 05363

  Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

  Flex Realty Group Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363
• 

  

  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
• 

  

  /38

  $329,000

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

  527 Route 121, Bellows Falls, VT 05101

  Move-in ready gutted and renovated home on 1.5 acres. New roof and new propane baseboard furnace and hot water system. New appliances. Insulated two-car garage. Beautiful mountain views.

  David White OwnerEntry.com

  527 Route 121, Bellows Falls, VT 05101
• 

  

  /21

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  28 Summit Meadows Cir, Dover, VT 05356

  Lovely updated contemporary chalet nestled at the base of the Dover Hills in the village of Dover, just a short drive from the Mount Snow ski resort. This convenient location affords the privacy of a home, but much easier access, and proximity to amenities, dining, shopping, and more. At the end of a loop, this home sits on a private and quiet parcel with a nice buffer of trees, level lawn, stone

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Summit Meadows Cir, Dover, VT 05356
• 

  

  /49

  $699,900

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  300 Route 121 E, Grafton, VT 05146

  Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park-like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll find a spacious eat-in kitchen with abundant counter space and

  Gary Coger Four Seasons Sotheby's Int'l Realty

  300 Route 121 E, Grafton, VT 05146

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