Windham County VT Homes for Sale

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  /29

  $450,000

  $139K PRICE DROP

  • 7 Beds
  • 5 Baths
  • 3,518 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
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  /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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  /60

  $1,200,000

  • 5 Beds
  • 5 Baths
  • 3,906 Sq Ft

  8 Twin Rocks Rd, Dover, VT 05356

  Extraordinary VT Mountain Property w/ Stunning Barn Minutes to Mt Snow & convenient access to VT's renowned VAST snowmobile Trails System. Mountain Retreat w/amazing Income & Expansion Potential. Tucked away at end of a quiet country road in desirable West Dover, this remarkable 5-bdrm, 5-bath contemporary offers the perfect blend of privacy, recreation & opportunity. This property is ideally

  Jen Baker Connecticut River Valley Realty

  8 Twin Rocks Rd, Dover, VT 05356
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  /14

  $210,000

  • Land
  • 35 Acres
  • $6,000 per Acre

  00 Vermont Route 100, Jamaica, VT 05343

  Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

  Patrice Schneider Southern Vermont Realty Group

  00 Vermont Route 100, Jamaica, VT 05343
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  /49

  $259,000

  • 5 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  6746 Vt Route 100, Whitingham, VT 05361

  Located in the charming town of Whitingham, this well-maintained historic home offers five bedrooms and open-concept living space. Upon entering, you'll find a convenient mudroom with a large coat closet. Enjoy a sun filled dining room and kitchen featuring live-edge wood slab countertops, open shelving, and a farmhouse sink. The open living room provides plenty of space to lounge and the

  Michelle O'Neil Deerfield Valley Real Estate

  6746 Vt Route 100, Whitingham, VT 05361
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  /37

  $839,000

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

  42 Blackberry Ln, Jamaica, VT 05343

  Only eight miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, and multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but

  Cheyanne Pugliese

  42 Blackberry Ln, Jamaica, VT 05343
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  /28

  $562,500

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

  29A Kingswood Rd, Dover, VT 05356

  Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned centrally in the development, offering greater separation between units, great parking, and yet easy clubhouse access. The home features an open-concept living space with vaulted ceilings, a wood-burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29A Kingswood Rd, Dover, VT 05356
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  /23

  $679,000

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

  14A Grouse Ln Unit 14A, Dover, VT 05356

  Gorgeous Post and Beam style townhome overlooking spectacular views of the Hermitage Club ski trails and sunsets over the ridgeline. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, easy nearby access to the Mount Snow ski resort, hiking and biking trails in the summer, and nearby convenience to the area's numerous lakes, dining and shopping.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14A Grouse Ln Unit 14A, Dover, VT 05356
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  /5

  $150,000

  $25K PRICE DROP

  • Land
  • 23.4 Acres
  • $6,410 per Acre

  4125 Chester Hill Rd, Grafton, VT 05146

  Escape to nature at 4125 Chester Rd, Grafton, VT—a serene 23.4-acre retreat where peaceful living meets outdoor adventure. Enjoy the soothing sounds of Hall Brook as it winds through the property, perfect for quiet reflection and leisurely strolls. Embrace the winter wonderland with nearby snowmobile trails and take advantage of the location's proximity to Okemo Mountain for a variety of

  Jamie Watson BHG Masiello Keene

  4125 Chester Hill Rd, Grafton, VT 05146
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  /55

  $1,249,000

  • 4 Beds
  • 3.5 Baths
  • 4,491 Sq Ft

  390 Pleasant Valley Rd, Brattleboro, VT 05301

  Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures

  Kristen Ziter Taylor Brattleboro Area Realty

  390 Pleasant Valley Rd, Brattleboro, VT 05301
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  /19

  $375,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,521 Sq Ft

  82 Oak Grove Ave, Brattleboro, VT 05301

  Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside

  Christine Lewis Brattleboro Area Realty

  82 Oak Grove Ave, Brattleboro, VT 05301
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  /15

  $215,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  8581 Vermont 30 Unit B, Jamaica, VT 05343

  Escape to the mountains in this charming 2-bedroom/1 bath condominium conveniently located near premier ski areas and year-round outdoor recreation. It's only 15 minutes to Stratton, 20 minutes to Bromley, and 10 to the Jamaica State Park. Enjoy easy access to skiing, hiking, biking, golf, and snowmobile trails, all just minutes from your door, and Manchester's shopping and dining are 30 minutes

  Deborah Hanst

  8581 Vermont 30 Unit B, Jamaica, VT 05343
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  /2

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  292 Deer Hill Rd, Whitingham, VT 05361

  Tucked amongst trees with a great deck. This rural location is not far from great skiing, shopping and all kinds of great dining and entertainment. Over an acre of mostly wooded lot. Property is occupied. No drive by's please..

  Susan Bellville Bellville Realty

  292 Deer Hill Rd, Whitingham, VT 05361
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  /34

  $699,000

  • 3 Beds
  • 4 Baths
  • 3,796 Sq Ft

  233 Poverty Row, Whitingham, VT 05361

  What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

  Adam Palmiter Berkley & Veller Greenwood/Dover

  233 Poverty Row, Whitingham, VT 05361
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  /37

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  239 Valley View Rd, Dover, VT 05356

  This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  239 Valley View Rd, Dover, VT 05356
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  /9

  $249,000

  $46K PRICE DROP

  • Land
  • 54.8 Acres
  • $4,544 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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  /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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  /19

  $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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  /24

  $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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  /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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  /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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  /20

  $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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  /52

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  994 W Jamaica Rd, Jamaica, VT 05343

  A Rare Riverfront Investment & Lifestyle Opportunity Nestled along the banks of a picturesque river, this magical 8.5-acre property offers a unique blend of natural beauty, privacy, and income-producing potential. Surrounded by mature trees, and the soothing sounds of the water, this is a truly special retreat in Southern Vermont. The main residence was thoughtfully updated in 2015 and features 3

  Britt Wohler

  994 W Jamaica Rd, Jamaica, VT 05343
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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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  /53

  $1,400,000

  • 4 Beds
  • 3.5 Baths
  • 3,536 Sq Ft

  1845 Hatch School Rd, Brattleboro, VT 05301

  Thoughtfully constructed in 2016 with efficiency, durability, and longevity in mind, this modern farmhouse offers 3,536 square feet of open, light-filled living space on nearly 100 private acres. Built with double-wall construction, a high-performance building envelope, and imported European triple-pane windows, the home reflects a deliberate commitment to energy efficiency and structural

  Melissa Nebelski Real Broker LLC

  1845 Hatch School Rd, Brattleboro, VT 05301
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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

  Grayson VanHendrick Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363

Showing Results 401 - 426, Page 11 of 11