Windham County VT Homes for Sale

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  /6

  $17,000

  • Land
  • 1.1 Acres
  • $15,455 per Acre

  00 Alpendorf Ave, Readsboro, VT 05353

  Build your dream mountain retreat in the heart of Vermont’s Green Mountains with this serene lot in Alpenwald Village, a private alpine-style community in Readsboro. Nestled across from the Green Mountain National Forest and the former Dutch Hill ski area, this parcel offers year-round recreation, peaceful surroundings, and direct access to VAST and VASA trail systems. This lot is ideal for a

  Kristen Breeden Southern Vermont Realty Group

  00 Alpendorf Ave, Readsboro, VT 05353
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  /6

  $27,000

  • Land
  • 2.2 Acres
  • $12,273 per Acre

  00 Bergrucken Ln, Readsboro, VT 05353

  Discover the perfect blend of privacy and community in Alpenwald Village with this beautiful double wooded lot. Located on a quiet street, this parcel offers a peaceful setting for your dream home or getaway cabin. The property comes with a wastewater site plan, saving you time and money as you plan your build. Enjoy year-round outdoor activities with nearby access to VAST and VASA trails,

  Kristen Breeden Southern Vermont Realty Group

  00 Bergrucken Ln, Readsboro, VT 05353
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  /35

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 3,096 Sq Ft

  11 Fornuto Rd, Wardsboro, VT 05355

  Opportunity awaits in this unique mixed-use property featuring a street-level restaurant space and a second-floor apartment. Located right in the heart of Wardsboro Village, once home to a local cafe, the main level still features brand-new commercial kitchen equipment ready for a fresh start. Convenient in-town location with good visibility, also within 10 minutes to Mt. Snow, 20 minutes to

  Jessica Samples BHG Masiello Keene

  11 Fornuto Rd, Wardsboro, VT 05355
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  /40

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,994 Sq Ft

  260 Mansfield Ln, Londonderry, VT 05148

  Enjoy breathtaking views of Magic Mountain and the surrounding Green Mountains from the deck, living room, family room, and primary suite of this beautifully updated home. Whether you're seeking a primary residence or a vacation getaway, this property offers the perfect Vermont lifestyle. Large windows allow sunlight to flood the Great Room, highlighting a stunning floor-to-ceiling stone

  Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  260 Mansfield Ln, Londonderry, VT 05148
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  /27

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft

  4668 Vermont 112, Halifax, VT 05342

  Historic hillside farm situated along the North River valley just a few miles into VT from MA on 31 acres of land. Approx. 5 acres of open sloping pasture most recently used as a sheep farm. The house is circa 1860 and has good bones and updated systems including a new drilled well, on demand HW, propane backup generator and other modern improvements. The interior of the home is in need of

  Chris Long BHG Masiello Brattleboro

  4668 Vermont 112, Halifax, VT 05342
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  /9

  $295,000

  • Land
  • 54.8 Acres
  • $5,383 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 future homesite, or continued forest management. Test pits have been completed, and results support the feasibility of a permitted septic system, paving the way for future development. Currently

  Carrie Mathews Winhall Real Estate

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
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  /25

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,536 Sq Ft

  1091 Townshend Dam Rd, Townshend, VT 05353

  Tucked away on 3 private acres, this 3-bedroom home offers the perfect blend of charm, space, and potential. Just 3.5 miles from Townshend Dam and 5 miles to the Wardsboro General Store, it's ideally located—only 20 minutes to Mount Snow and 30 to Stratton. Inside, a dramatic wall of glass with two sets of French doors floods the living space with natural light and brings the outdoors in. The

  Carrie Mathews Winhall Real Estate

  1091 Townshend Dam Rd, Townshend, VT 05353
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  /55

  $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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  /6

  $45,000

  • Land
  • 1.1 Acres
  • $40,909 per Acre

  9 Sun and Ski Rd, Wilmington, VT 05363

  Prime Land Lot – Minutes from Wilmington, Close to Mount Snow!Discover the perfect blend of seclusion and convenience with this exceptional land opportunity, ideally located just 8 minutes from Main Street Wilmington and only 20 minutes from the slopes of Mount Snow. Whether you're dreaming of a private mountain getaway, a cozy Airbnb investment, or building your forever home, this lot

  Flex Realty Group Flex Realty

  9 Sun and Ski Rd, Wilmington, VT 05363
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  /31

  $445,000

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft

  212 S Pine Banks Rd, Putney, VT 05346

  Enchanting Putney Bungalow Retreat. Tucked away in a peaceful, sun-drenched meadow, this charming Putney bungalow offers the perfect blend of privacy, nature, and character. Surrounded by mature trees, stone walls, and abundant garden space, it’s a true hidden gem just minutes from the village center. Enjoy one-level living with a cozy first-floor bedroom and full bath and laundry—ideal for

  Karen Hoppe Berkley & Veller Greenwood Country

  212 S Pine Banks Rd, Putney, VT 05346
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  /54

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,040 Sq Ft

  17 Boulder Ridge Dr Unit A, Dover, VT 05356

  This magnificent 5-bedroom, 4.5-bath townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design. The living room, graced with hardwood (hickory) flooring, a gas fireplace, large windows, a slider to the deck with an amazing view of Mount Snow, and a vaulted ceiling, creates an ambiance

  John Redd Skihome Realty

  17 Boulder Ridge Dr Unit A, Dover, VT 05356
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  /31

  $485,000

  • 5 Beds
  • 5 Baths
  • 3,812 Sq Ft

  7 Pine Tree Ln, Dover, VT 05356

  Ready for its next chapter, this versatile property is in a great location near Mount Snow Skiing and Golf. If you are looking for a place to build some 'sweat equity' this one has amazing potential! Located on a cul de sac with only 4 other homes there is a nice sense of privacy while being close to restaurants and shopping. This unique offering is a rare opportunity with three separate

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  7 Pine Tree Ln, Dover, VT 05356
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  /54

  $2,050,000

  • 4 Beds
  • 4.5 Baths
  • 2,486 Sq Ft

  97 N Brookwood Rd, Stratton, VT 05360

  OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM!Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  97 N Brookwood Rd, Stratton, VT 05360
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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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  /39

  $175,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  236 Hall Bridge Rd, Bellows Falls, VT 05101

  Location location location! If you want to own your own piece of Vermont beauty surrounded by woods in a private setting that includes a pond, two garages, a tiny cabin and a shed, this might be the property of your dreams! The home needs TLC and updating, but taking a break on the expansive deck and enjoying the sounds and sights of nature is something you'll want to do. This property is the

  Heather Gleim CENTURY 21 North East

  236 Hall Bridge Rd, Bellows Falls, VT 05101
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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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  /60

  $798,000

  • 3 Beds
  • 3 Baths
  • 2,757 Sq Ft

  1909 Pine Banks Rd, Putney, VT 05346

  Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

  Heidi Bernier Berkley & Veller Greenwood Country

  1909 Pine Banks Rd, Putney, VT 05346
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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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  /32

  $319,000

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

  4106 Vt Route 30, Jamaica, VT 05343

  Built in 1840, this charming home has long been a part of Jamaica’s rich history. Thoughtfully updated for modern living, it features a brand-new septic system, a renovated kitchen with granite countertops, and spacious rooms filled with natural light. Perfectly located just a short walk to town and Jamaica State Park, and only 10 miles from Stratton’s lifts, this property offers the ideal blend

  Carrie Mathews Winhall Real Estate

  4106 Vt Route 30, Jamaica, VT 05343
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  /53

  $1,470,000

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

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  /41

  $499,000

  • 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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  /60

  $750,000

  • 2 Beds
  • 1 Bath
  • 17,000 Sq Ft

  24 Rockingham St, Bellows Falls, VT 05101

  Entrepreneur's Dream! Step into a world of endless potential in the historic Newberry Building. Built in 1938 with robust masonry and steel construction,this one-of-a-kind property offers the ultimate "live, work, and play" lifestyle. Situated in a prime location with excellent visibility, this building is a proven success story, having housed two of the town's most beloved restaurants: The

  Heidi Bernier Berkley & Veller Greenwood Country

  24 Rockingham St, Bellows Falls, VT 05101
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  /20

  $195,000

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

  1499 Josh Rd, Halifax, VT 05358

  46 + acres (33 AC in Halifax & 13.20 AC in Guilford) with a modified camper accessed by an existing gravel woods road off Josh Road (class 4) and beautiful pond with dock in a peaceful remote valley surrounded by over 2,000 acres of private land mostly open to recreation with miles of trails and old town roads. Josh Brook is a major trout stream and has waterfalls and deep pools for cooling off.

  Chris Long BHG Masiello Brattleboro

  1499 Josh Rd, Halifax, VT 05358
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  /54

  $1,400,000

  • 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

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
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  /18

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,712 Sq Ft

  48 Legion Rd, Newfane, VT 05345

  Adorable contemporary home nestled in the quaint town of Newfane. A perfect combination of privacy and country. Enjoy the covered porch during those warm summer days or crisp fall mornings. Ample space with the open concept living room and kitchen for endless entertainment. This home still has the rustic charm to make you feel right at home. Plenty of room for gardening and animals. Schedule your

  Katelyn Heaney Greenwald Realty Group

  48 Legion Rd, Newfane, VT 05345
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  /20

  $475,000

  • Land
  • 136.9 Acres
  • $3,470 per Acre

  0 Taft Rd Unit 5064573, Townshend, VT 05353

  In the late 1790's, General Samuel Fletcher gave a large parcel of land to young Benjamin Murdock, whose father had died from smallpox while serving in the Revolutionary War. Benjamin built a cabin and then a house, cleared and plowed the land, and with his wife raised 8 children. That land is now known as Murdock Mountain. Entering the property is like stepping into the past. The deep stone

  Bill Hickok Berkley & Veller Greenwood Country

  0 Taft Rd Unit 5064573, Townshend, VT 05353
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  /22

  $357,000

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  203 Westminster Rd, Putney, VT 05346

  What a find! This nicely updated farmhouse combines the perfect blend of historic charm and modern comfort. The first floor offers a spacious, sunlit living/dining area with a classic brick fireplace, a cozy office or den, a primary bedroom suite, both with brand new hardwood floors, and additional bath with laundry. The kitchen is a true heart of the home, complete with a center island and ample

  Karen Hoppe Berkley & Veller Greenwood Country

  203 Westminster Rd, Putney, VT 05346
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  /37

  $479,000

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

  529 Finkel Rd, Wardsboro, VT 05355

  Sage Hill offers the perfect blend of privacy and convenience, set along a scenic country road yet just minutes to groceries, gas, and skiing. This contemporary home is thoughtfully tucked back into the landscape, framed by classic stonewalls and majestic oak trees. Enter directly from the carport into a tiled mudroom with closet space, ideal for storing all your outdoor gear. The main living

  Monique White Deerfield Valley Real Estate

  529 Finkel Rd, Wardsboro, VT 05355
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  /24

  $849,000

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

  Unmatched Comfort and Convenience at Stratton's Ober Tal – Walk to LiftDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village.Close enough to swing back for a quick lunch, this condo lets you make

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
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  /26

  $149,000

  • Land
  • 19.4 Acres
  • $7,680 per Acre

  2610 Lower Dover Rd, Marlboro, VT 05344

  Marlboro Sanctuary – Private Meadow Retreat. Discover this beautiful and private parcel in the heart of Marlboro, featuring an open meadow with sunny southern exposure. With generous road frontage and easy access between two charming stonewalls, a well-maintained old logging road leads you into the property. Along the way, pass by a small pond site before arriving at the expansive meadow, framed

  Monique White Deerfield Valley Real Estate

  2610 Lower Dover Rd, Marlboro, VT 05344
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  /49

  $525,000

  • 4 Beds
  • 3.5 Baths
  • 1,913 Sq Ft

  35 Birch Rd, Londonderry, VT 05148

  Nestled in the heart of Vermont’s ski country, this architect-designed home is a striking blend of whimsical artistry and alpine living. A stones throw from Magic Mountains base lodge, skiing and four-season adventure await right outside your door. Designed by a visionary architect with a love for natural light, the residence offers both artistic flair and multiple finished spaces the whole

  Mendi Michael Engel & Völkers Okemo

  35 Birch Rd, Londonderry, VT 05148
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  /24

  $365,000

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
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  /60

  $474,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  8 Little Bend Unit M-175, Wilmington, VT 05363

  Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

  Sigrid Pickering Chimney Hill Realty

  8 Little Bend Unit M-175, Wilmington, VT 05363
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  /37

  $325,000

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft

  787 Vermont 30, Newfane, VT 05345

  This Ain’t Your Average Cape Cod Cottage!Sure, this 2-bedroom, 1-bath Cape has the sweet front porch you’ve been dreaming about, perfect for sipping that morning coffee, plus a side patio that’s just begging for summer barbecues (bonus: pop on the panels and you’ve got yourself a three-season hangout!). But the real showstopper here isn’t the house—it’s the 30x40 heated workshop out

  TG Glazer Winhall Real Estate

  787 Vermont 30, Newfane, VT 05345
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  /39

  $519,000

  • Land
  • 80.11 Acres
  • $6,479 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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  /17

  $459,000

  • 5 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  46 Town Farm Rd, Wilmington, VT 05363

  3 Story home with 1 car attached garage....new vinyl siding, windows and roofing installed in 2021 along with exterior foamboard insulation.FIRST FLOOR- Open concept entirely remodeled in 2022; mudroom, kitchen, 1/2 bath, and family/dining room. Vinyl plank flooring throughout, white shiplap walls and natural tongue & groove ceilings. Vermont castings wood burning stove.SECOND

  David White OwnerEntry.com

  46 Town Farm Rd, Wilmington, VT 05363
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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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  /56

  $975,000

  • 9 Beds
  • 9 Baths
  • 5,480 Sq Ft

  3732 Vermont 30, Jamaica, VT 05343

  Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take over.This historic property boasts two dwellings and a guest cottage. Looking for a family compound to get away from it all?This is your haven! Plenty of room to have friends and family come and stay! So many options.The Main House features 4 ensuite bedrooms! The living room is a late 1700"s delight, with an

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  3732 Vermont 30, Jamaica, VT 05343
• 

  

  /19

  $65,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  2022 Vermont 30, Jamaica, VT 05343

  Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both!Stratton is just 20

  Carrie Mathews Winhall Real Estate

  2022 Vermont 30, Jamaica, VT 05343

Showing Results 81 - 120, Page 3 of 11