Windham County VT Houses for Sale

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  /59

  $549,000

  $76K PRICE DROP

  • 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
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  /35

  $2,399,000

  $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  /49

  $799,000

  $51K PRICE DROP

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

  1 Lower Highlands Rd, West Dover, VT 05356

  Custom-built 4-bedroom, 2.5-bath home ideally located less than a mile from Mount Snow. The main level welcomes you with an inviting foyer off the covered front porch and offers a well-designed layout featuring a spacious living room, formal dining room, comfortable family room, versatile den, and a well-appointed kitchen. Additional conveniences include a half bath, dedicated laundry area, and a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1 Lower Highlands Rd, West Dover, VT 05356
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  /16

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  10 Riverfront Dr, Bellows Falls, VT 05101

  This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

  Robert Alger Alger Real Estate Agency

  10 Riverfront Dr, Bellows Falls, VT 05101
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  /47

  $545,000

  • 2 Beds
  • 1 Bath
  • 1,576 Sq Ft

  211 Pleasant Valley Rd, Brattleboro, VT 05301

  Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural

  Chris Long BHG Masiello Brattleboro

  211 Pleasant Valley Rd, Brattleboro, VT 05301
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  /23

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Mill Rd, West Dover, VT 05356

  When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 3 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large vaulted living room and wood burning fireplace on brick hearth,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  7 Mill Rd, West Dover, VT 05356
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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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  /53

  $499,000

  $46K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1488 Hartley Hill Rd, Putney, VT 05346

  Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship including a brand new roof installed April 2026, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant

  Chelsea Richardson Barrett and Valley Associates Inc.

  1488 Hartley Hill Rd, Putney, VT 05346
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  /37

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  157 Newfane Hill Rd, Newfane, VT 05345

  Welcome to a home with a story. Originally the 1787 residence of local blacksmith Marshall Newton, this property has been a cherished family retreat for the last fifty years. One of only two original settlements on Newfane Hill that are still there. It’s a place with "old world" charm—like centuries-old wall paneling —but also a new 2025 standing-seam roof and extensive insulation upgrades. This

  Thomas Dahlin Berkley & Veller Greenwood Country

  157 Newfane Hill Rd, Newfane, VT 05345
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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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  /36

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  33 Forrest Ln, Newfane, VT 05345

  Tucked away off of Wardsboro Road on peaceful Forrest Lane, this 3-bedroom Gambrel home sits on a private and expansive 5.5-acre lot surrounded by nature. The ground-level entry opens to a versatile bonus room with a woodstove, previously used as a cozy family room. The front door opens to an entrance filled with natural light from oversized windows that bring the outdoors in. The main living

  Desiree Stango Berkley & Veller Greenwood Country

  33 Forrest Ln, Newfane, VT 05345
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  /60

  $995,000

  Open House 7/18 $205K PRICE DROP

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

  8 Twin Rocks Rd, Dover, VT 05356

  OPEN HOUSE- 7/18 & 7/19-from 11 to 2. Mountain Property w/ Stunning Barn. Convenient access to Mt Snow & VT's renowned VAST 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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  /39

  $639,000

  $11K PRICE DROP

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

  198 E Hill Rd, Wardsboro, VT 05355

  Gorgeous home with so many recent upgrades! Beautiful kitchen with newer updated appliances, baths, 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! This is truly MOVE IN READY! These are just a few of the items this homeowner has done to improve

  Julie Lowe Lowe's Real Estate, LLC

  198 E Hill Rd, Wardsboro, VT 05355
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  /37

  $839,000

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

  42 Blackberry Ln, Jamaica, VT 05343

  OPEN HOUSE SUN 7/5 11AM-1PM Only 8 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, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from

  Cheyanne Pugliese

  42 Blackberry Ln, Jamaica, VT 05343
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  /55

  $1,100,000

  $149K PRICE DROP

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

  390 Pleasant Valley Rd, Brattleboro, VT 05301

  Price Improvement! 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

  Kristen Ziter Taylor Brattleboro Area Realty

  390 Pleasant Valley Rd, Brattleboro, VT 05301
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  /60

  $795,000

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  947 Miller Rd, Brattleboro, VT 05301

  Stunning Southern Vermont home with views, gardens and private pond on 10 acres incoveted Dummerston, Windham County. Entering the circular drive, lush perennial gardens welcome you and the magic begins. This meticulously designed 1600-square-foot home features soaring ceilings and superior craftsmanship throughout. Thespacious kitchen includes custom cabinetry, Sub-Zero and Wolf

  Kristen Ziter Taylor Brattleboro Area Realty

  947 Miller Rd, Brattleboro, VT 05301
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  /19

  $369,900

  $15K 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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  /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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  /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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  /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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  /24

  $200,000

  • 2 Beds
  • 2.5 Baths
  • 1,530 Sq Ft

  2 Tallwood Cir, Londonderry, VT 05148

  What an opportunity to explore your creative ideas in bringing this rustic contemporary back to its glory... Sited on a beautiful lot, you can enjoy the sounds of nature while listening to a blissful babbling brook that borders the property...or entertain on the spacious deck with hookup for a gas grill. The interior has a nice, open floor plan...Enjoy the crackle of a wood fireplace... while

  Donna Murray Varick Associates Ltd

  2 Tallwood Cir, Londonderry, VT 05148
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  /60

  $1,998,000

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  32 Steep Hill Rd, Wilmington, VT 05363

  Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont’s Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern

  Rich Caplan Deerfield Valley Real Estate

  32 Steep Hill Rd, Wilmington, VT 05363
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  /52

  $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, just 0.8 miles from the Wilmington town line. Built with double-wall construction, a high-performance building envelope, and imported European triple-pane windows, the home reflects a deliberate

  Melissa Nebelski Real Broker LLC

  1845 Hatch School Rd, Brattleboro, VT 05301
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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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  /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 201 - 227, Page 6 of 6