Windham County VT Homes for Sale

• 

  

  

  /27

  $599,000

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

  10 Grouse Ln Unit 10A, Dover, VT 05356

  Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  10 Grouse Ln Unit 10A, Dover, VT 05356
• 

  

  

  /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
• 

  

  

  /59

  $845,000

  • 4 Beds
  • 2 Baths
  • 2,613 Sq Ft

  170 Townshend Rd, Grafton, VT 05146

  This handsome turn-key property is available sooner than one might expect! Due to changing life developments, the owners are offering their beloved Vermont home for sale. Not long ago, the 19th century Chapman House underwent a full renovation, including a stunning new kitchen and updated baths. The kitchen features marble countertops, glass-front backlit cabinetry, a deep farmhouse sink,

  Jessica Landers Barrett and Valley Associates Inc.

  170 Townshend Rd, Grafton, VT 05146
• 

  

  

  /26

  $1,350,000

  • 7,660 Sq Ft

  131,133,141 Green St, Brattleboro, VT 05301

  What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

  Susan Bellville Bellville Realty

  131,133,141 Green St, Brattleboro, VT 05301
• 

  

  

  /40

  $489,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  494 W River St, Londonderry, VT 05155

  Welcome to 494 West River Street, a classic Vermont retreat nestled on more than 10 picturesque acres along the scenic West River in South Londonderry. Built in 1965, this four-bedroom, two-bath ranch-style home offers a rare opportunity to enjoy the natural beauty, privacy, and year-round recreation that make Southern Vermont such a sought-after destination. Set among mature trees and open

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  494 W River St, Londonderry, VT 05155
• 

  

  /44

  $475,000

  • 6 Beds
  • 2.5 Baths
  • 3,682 Sq Ft

  4303 Hinesburg Rd, Brattleboro, VT 05301

  Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambience and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

  Christine Lewis Brattleboro Area Realty

  4303 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /41

  $289,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356

  Adjusted to $289,000 making this the best value in Dover Green. Enjoy the best of Southern Vermont from this beautiful townhome in the sought-after Dover Green community, located just minutes south of Mount Snow. Whether you're looking for a year-round residence, a low-maintenance second home, or the perfect Vermont getaway, this spacious 3-bedroom, 2-bath home offers comfort, convenience, and

  Donald Koelsch Deerfield Valley Real Estate

  8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356
• 

  

  /29

  $789,000

  • 5 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  15 Sawmill Village Way, Dover, VT 05356

  Beautiful contemporary farmhouse in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This bright and airy farmhouse design sits on a private level lot, and has been completely renovated to be turn key for immediate enjoyment. The interior boasts a vaulted living room with large windows, great natural light, and a gas fireplace, there is an updated chefs

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Sawmill Village Way, Dover, VT 05356
• 

  /2

  $45,000

  • Land
  • 10,890 Sq Ft
  • $180,000 per Acre

  45 Mowing Way, Wilmington, VT 05363

  Level building lot with public sewer and water at the street. Across from the Haystack Golf Course for easy year round enjoyment. Direct snowmobile access from the lot. A short drive to the public boat launch at Lake Whitingham or Mount Snow ski resort.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Mowing Way, Wilmington, VT 05363
• 

  

  /22

  $86,000

  • Land
  • 6.2 Acres
  • $13,871 per Acre

  1297 River Rd, Jamaica, VT 05343

  Unique! Do you love to camp? swim? fish?.....this may be it for you....Over2000 feet of West River frontage with electric on site and just offpavement and at the intersection of 2 major access road to skiing andrecreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping

  Christine Lewis Brattleboro Area Realty

  1297 River Rd, Jamaica, VT 05343
• 

  

  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  2117 Pine Banks Rd, Putney, VT 05346

  Set off a country road, this renovated home offers a contemporary interior featuring an open concept kitchen, dining, and living spaces. All of these spaces are bright and welcoming and have engineered hardwood floors. The kitchen is well thought out with multiple workstations and plenty of cabinets and countertop space. The bedrooms have new carpeting and ample closet space. You'll be warm in

  Bill Hickok Berkley & Veller Greenwood Country

  2117 Pine Banks Rd, Putney, VT 05346
• 

  

  /26

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  57 Vartland Ridge, Londonderry, VT 05148

  Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated

  Jamie Wylie Stratton Real Estate

  57 Vartland Ridge, Londonderry, VT 05148
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  /52

  $499,000

  • 5 Beds
  • 4 Baths
  • 3,665 Sq Ft

  522 Vermont Route 100, Wardsboro, VT 05355

  Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the

  Lee Brown Four Seasons Sotheby's Int'l Realty

  522 Vermont Route 100, Wardsboro, VT 05355
• 

  

  /60

  $2,895,000

  • 6 Beds
  • 4 Baths
  • 3,946 Sq Ft

  2060 Townshend Rd, Grafton, VT 05146

  A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse,

  Erin McCormick KW Vermont

  2060 Townshend Rd, Grafton, VT 05146
• 

  

  /13

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  14 Sugar Lot Ln, Jamaica, VT 05343

  Nestled in the heart of Jamaica, this pristine wooded lot offers a quintessential Vermont building canvas where privacy meets accessibility. As you pull off the quiet road onto the roughed-in driveway, you are immediately enveloped by a mature hardwoods that leads directly to a cleared homesite. This dedicated building envelope allows you to drive your car right to the center of your future

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  14 Sugar Lot Ln, Jamaica, VT 05343
• 

  

  /48

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
• 

  

  /35

  $825,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  2C Townhouse Square Unit 2, Dover, VT 05356

  Ski-in/ski-out living from this beautifully updated Seasons townhome, positioned trailside at Mount Snow. Stop in and out for meals or to check on pets, without ever taking off your boots. This well-appointed unit makes an immediate impression with its open-concept living space featuring soaring vaulted ceilings, a floor-to-ceiling stone chimney with wood-burning fireplace, and generous natural

  Adam Palmiter Berkley & Veller Greenwood/Dover

  2C Townhouse Square Unit 2, Dover, VT 05356
• 

  

  /55

  $649,500

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  800 Hubbard Hill Rd, Jacksonville, VT 05342

  This stately Colonial Revival style home is situated privately on nearly 10 acres with its awesome 3 story 30' X 40' barn accessed by a long winding driveway. The main level features include large spacious rooms with wainscoting and natural woodwork, an open kitchen/dining/living floor plan, half bath/laundry and a pantry off kitchen, proper foyer, living room with a grand fireplace, wide

  Chris Long BHG Masiello Brattleboro

  800 Hubbard Hill Rd, Jacksonville, VT 05342
• 

  

  /27

  $169,900

  • 3 Beds
  • 2 Baths
  • 2,246 Sq Ft

  1102 Route 100, Wardsboro, VT 05355

  A great, affordable starter! Mostly open concept with L/D/FM and kitchen all flowing one to the other with lots of windows for light and air, bringing the outside in. There is also a bedroom and full bath on the first floor for aging in place. Attached is a huge shed for a workshop. The big surprise and great treat is the lot across the street that borders the Wardsboro Brook and could be a

  Christine Lewis Brattleboro Area Realty

  1102 Route 100, Wardsboro, VT 05355
• 

  

  /59

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  3924 Sweet Pond Rd, Guilford, VT 05301

  Surrounded by 65 acres of glorious land w/meadows, woodland, stone walls, and the meandering Keets Brook, this exceptional property offers a blend of beauty, privacy, and thoughtful design. The grounds are exquisitely landscaped with Gordon Hayward-designed gardens, specimen trees , stone walkways and mature blueberry bushes. A saltwater pool, private rear deck, oversized two-car garage, Kohler

  Robert Doyle Berkley & Veller Greenwood Country

  3924 Sweet Pond Rd, Guilford, VT 05301
• 

  

  /4

  $499,000

  $41K PRICE DROP

  • 6,000 Sq Ft

  16 School St, Brattleboro, VT 05301

  Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a

  Kate Barry EXP Realty

  16 School St, Brattleboro, VT 05301
• 

  

  /45

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  7 High Top Unit B117, Wilmington, VT 05363

  Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and

  Sigrid Pickering Chimney Hill Realty

  7 High Top Unit B117, Wilmington, VT 05363
• 

  

  /60

  $455,000

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

  2 Wood Lot Ln Unit C-215, Wilmington, VT 05363

  Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More

  Sigrid Pickering Chimney Hill Realty

  2 Wood Lot Ln Unit C-215, Wilmington, VT 05363
• 

  

  /37

  $350,000

  • 1,918 Sq Ft

  50 Oak Grove Ave, Brattleboro, VT 05301

  Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field — grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor

  Kerry Mulverhill

  50 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /23

  $799,999

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,592 Sq Ft

  62 Potter Rd, Wardsboro, VT 05355

  Brand-new construction in process in Wardsboro, set on a spacious 2-acre parcel. Introducing a brand-new 3-bedroom, 3.5-bath home is slated for completion in late fall 2026. Inside, you’ll find beautiful natural light, wide-plank pine flooring, oversized windows, and an inviting, bright living space. The main level offers an open-concept layout with a well-appointed kitchen, dining area, and

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  62 Potter Rd, Wardsboro, VT 05355
• 

  

  /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
• 

  

  /36

  $325,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,216 Sq Ft

  6 Sycamore St, Brattleboro, VT 05301

  Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  6 Sycamore St, Brattleboro, VT 05301
• 

  

  /40

  $515,000

  $10K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,320 Sq Ft

  5735 Vt Route 11, Londonderry, VT 05148

  What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Historical authenticity has not been sacrificed in their successful

  Zachary Zupan EXP Realty

  5735 Vt Route 11, Londonderry, VT 05148
• 

  

  /34

  $355,000

  • 4 Beds
  • 1.5 Baths
  • 2,532 Sq Ft

  9 Burt St, Bellows Falls, VT 05101

  Welcome to 9 Burt Street located on one of the prettiest streets in Bellows Falls. This opportunity offers an attractive two story 2532 sqft. family home located within the center of Bellows Falls with easy walking access to all stores, dining and schools. It is located on a beautiful street bordered by well kept family homes. The first floor includes a fireplace in the family room, a formal

  David White OwnerEntry.com

  9 Burt St, Bellows Falls, VT 05101
• 

  

  /24

  $295,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  461 South Rd, Brattleboro, VT 05301

  This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

  Susan Bellville Bellville Realty

  461 South Rd, Brattleboro, VT 05301
• 

  

  /60

  $344,900

  $4K PRICE DROP

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

  90 Wilsons Woods Rd, Brattleboro, VT 05301

  Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient

  Sally Fegley BHG Masiello Brattleboro

  90 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /28

  $369,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  39 Locust St, Brattleboro, VT 05301

  Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog,

  Christine Lewis Brattleboro Area Realty

  39 Locust St, Brattleboro, VT 05301
• 

  

  /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
• 

  

  /41

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft

  200 Riverdale Rd, Townshend, VT 05353

  This classic Federal-style brick home blends historic character with thoughtful modern updates, offering a lifestyle that feels both grounded and effortlessly comfortable. Set on a dead-end road, the property enjoys the rare balance of peaceful country living and everyday convenience, all within moments of the local store, hospital, pharmacy, bank, and neighboring homes. Inside, you will be

  Lee Brown Four Seasons Sotheby's Int'l Realty

  200 Riverdale Rd, Townshend, VT 05353
• 

  

  /59

  $675,000

  $25K PRICE DROP

  • 6,144 Sq Ft

  2170 N Main St, Londonderry, VT 05148

  For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner—an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that

  Jessica Ackley

  2170 N Main St, Londonderry, VT 05148
• 

  

  /54

  $385,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,852 Sq Ft

  410 School St, Westminster, VT 05158

  This historic creamery beautifully preserves the charm and craftsmanship of its 1860s origins, featuring soaring vaulted ceilings, exposed hand-hewn beams, and rich wood floors that radiate warmth and character throughout. A welcoming wraparound porch, adorned with hanging baskets and alive with birdsong, invites you to slow down and stay awhile. Inside, the open-concept living, dining, and

  Victoria Woods Brattleboro Area Realty

  410 School St, Westminster, VT 05158
• 

  

  /45

  $1,475,000

  • 7 Beds
  • 6 Baths
  • 6,292 Sq Ft

  53 Hickory Ridge Rd, Putney, VT 05346

  The Hickory Ridge House is a Federal Masterpiece. Own a definitive piece of Vermont history with this 1808 Federal-style estate, proudly listed on the National Register of Historic Places. For decades, it was a B&B. It could still be used as a very upscale, sophisticated country Inn. While its soul remains rooted in the 19th century, its heart beats with 21st-century innovation. This meticulously

  Thomas Dahlin Berkley & Veller Greenwood Country

  53 Hickory Ridge Rd, Putney, VT 05346
• 

  

  /17

  $299,000

  $14K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  2448 Burrington Hill Rd, Whitingham, VT 05361

  Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary

  Michael Purcell Berkley & Veller Greenwood/Dover

  2448 Burrington Hill Rd, Whitingham, VT 05361
• 

  

  /7

  $279,000

  • Land
  • 45 Acres
  • $6,200 per Acre

  Lot 0 Saddada Rd, Whitingham, VT 05361

  Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 0 Saddada Rd, Whitingham, VT 05361
• 

  

  /28

  $325,000

  $60K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft

  1644 Upper Dummerston Rd, Dummerston, VT 05301

  Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern with lots of counter top for the bakers and cookie makers, The laundry lives next to the kitchen and there is a second bath for visitors and guests. The sweet spot is the huge living room with a wood stove insert in the lovely fireplace. Mini-splits are already up and running for help with both heating and

  Christine Lewis Brattleboro Area Realty

  1644 Upper Dummerston Rd, Dummerston, VT 05301

Showing Results 121 - 160, Page 4 of 12