Windham County VT Homes for Sale

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  /60

  $999,000

  $89K PRICE DROP

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

  151 Townshend Rd, Grafton, VT 05146

  STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. 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 single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or

  Erin McCormick KW Vermont

  151 Townshend Rd, Grafton, VT 05146
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  /18

  $68,900

  • Land
  • 21,780 Sq Ft
  • $137,800 per Acre

  Lot 1 - 161 High Peak Way, Wilmington, VT 05363

  Introducing Lot #1 in the High Peak Development, .50-acre double lot offering the foundation for your future Vermont home. This wooded parcel provides the peaceful setting of a cabin in the woods while still being just minutes from Mount Snow, The Hermitage Club, and the year-round recreation of the Deerfield Valley.With public sewer and public water access, the building process is made

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 1 - 161 High Peak Way, Wilmington, VT 05363
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  /51

  $715,000

  • 3 Beds
  • 3.5 Baths
  • 2,895 Sq Ft

  106 Westminster Rd W, Putney, VT 05346

  Set on 25.8± scenic acres, this 3-bedroom, 3½-bath historic barn conversion offers long views across meadows to the surrounding hills within walking distance of Putney Village. It is a rare Putney combination: genuine privacy & room to explore, w/ village shops, food, arts, Putney Central School, and the town pool nearby. This property features approximately 2,300 sq ft of living space, with 595

  A.J. Bellville Bellville Realty

  106 Westminster Rd W, Putney, VT 05346
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  /26

  $494,000

  $5K PRICE DROP

  • 7 Beds
  • 2 Baths
  • 2,038 Sq Ft

  45 Blue Brook Rd, Dover, VT 05356

  Owners open to offers! A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Blue Brook Rd, Dover, VT 05356
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  /2

  $125,000

  • 4 Beds
  • 2 Baths
  • 2,644 Sq Ft

  54 Williams St Unit 56, Bellows Falls, VT 05101

  Offering over 2,500 square feet of potential. The 2.5-story layout with porches offers a project for buyers seeking sweat equity, rental income potential, or a large single-family home tailored to their needs. Located within walking distance of downtown Bellows Falls, you'll be close to shops, restaurants, the Connecticut River, and all the character this historic village has to offer. Please

  Shawna Fox BHHS Verani Upper Valley

  54 Williams St Unit 56, Bellows Falls, VT 05101
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  /29

  $19,500

  • 1 Bath
  • 332 Sq Ft

  218 Qtr.2 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Valley side unit includes: Queen murphy bed, kitchen, eating area, balcony and a full bath. Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with

  Kelly Agrillo Southern Vermont Realty Group

  218 Qtr.2 89 Grand Summit Way, Dover, VT 05356
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  /28

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  858 Sheldon Hill Rd, Wardsboro, VT 05355

  A perfect example of the ideal Vermont home. Beautiful natural woodwork abounds in this post and beam/log home hybrid built in 2005. Conveniently located on a corner lot with tremendous privacy and a spacious cul-de-sac driveway, is this perfect home with perennial gardens, a natural wood facade, stone chimney, stone walkway, large entertaining deck, patio with hot tub, and an exterior elevator

  Adam Palmiter Berkley & Veller Greenwood/Dover

  858 Sheldon Hill Rd, Wardsboro, VT 05355
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  /18

  $250,000

  $30K PRICE INCREASE

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  5362 Us Route 5, Westminster, VT 05158

  BRAND NEW SEPTIC SYSTEM!! Move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly

  Karen Hoppe Berkley & Veller Greenwood Country

  5362 Us Route 5, Westminster, VT 05158
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  /17

  $79,500

  • Land
  • 13,939 Sq Ft
  • $248,438 per Acre

  Lot 2 - 162 High Peak Way, Wilmington, VT 05363

  Discover the perfect opportunity to build your Vermont retreat on this .32 acre lot in the High Peak Development, ideally positioned adjacent to the Haystack Golf Course. This wooded parcel offers the privacy of a cabin-in-the-woods setting while still being just minutes from Mount Snow, The Hermitage Club, and all the four season recreation the Deerfield Valley offers. Charming downtown

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 - 162 High Peak Way, Wilmington, VT 05363
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  /12

  $422,000

  $43K PRICE DROP

  • 3,756 Sq Ft

  820 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 Western Ave, Brattleboro, VT 05301
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  /24

  $28,995

  • 2 Beds
  • 2 Baths
  • 745 Sq Ft

  304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units Studio unit (306) Queen murphy bed , kitchenette and full bathroom. Hotel unit (304) Two king beds and full bathroom. Units are located the valley side of the hotel . Lock out units has the benefit of using the unit as a whole or stay in one side and rent the other side out.

  Kelly Agrillo Southern Vermont Realty Group

  304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356
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  /25

  $219,000

  • Land
  • 16.9 Acres
  • $12,959 per Acre

  00 Howe Farm Rd, Jamaica, VT 05343

  Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound,

  Patrice Schneider Southern Vermont Realty Group

  00 Howe Farm Rd, Jamaica, VT 05343
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  /19

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  171 Buttonwood Dr, Brattleboro, VT 05301

  Celebrate! You have earned it! A gentle neighborhood for 55 and more, mowing, plowing and shoveling included in the HOA.. Leave the tough stuff for the young at heart! Sit snug as a bug in the sun room and watch it snow, without a care or worry, or run off to play pickle ball in the warm seasons....Want to be snow birding? Perfect set up as the home is easy care inside and out. Park a car in the

  Christine Lewis Brattleboro Area Realty

  171 Buttonwood Dr, Brattleboro, VT 05301
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  /33

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,232 Sq Ft

  717 Horsenail Hill Rd, Windham, VT 05359

  Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus

  Carrie Mathews Winhall Real Estate

  717 Horsenail Hill Rd, Windham, VT 05359
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  /47

  $1,995,000

  • 6 Beds
  • 6.5 Baths
  • 5,545 Sq Ft

  420 Ray Hill Rd, Wilmington, VT 05363

  This impressive 6-bedroom, 7-bath farm-style timber frame home, built by Davis Frame and featured on their website as “The Great White Barn,” sits on 3.51 acres just minutes from the Hermitage Club, Mount Snow, downtown Wilmington, lakes, hiking, golf, and VAST trails. Formerly known by its previous owners as “La Maison de Pommes” (House of Apples) for its old apple orchard setting, the home was

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  420 Ray Hill Rd, Wilmington, VT 05363
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  /28

  $480,000

  • 5 Beds
  • 2 Baths
  • 2,194 Sq Ft

  3327 Route 30, Jamaica, VT 05343

  Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and

  Carrie Mathews Winhall Real Estate

  3327 Route 30, Jamaica, VT 05343

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