Windham County VT Homes for Sale

• 

  

  

  /38

  $645,000

  • 4 Beds
  • 3 Baths
  • 2,740 Sq Ft

  1161 Little Pond Rd, Londonderry, VT 05148

  Beautifully renovated 4-bedroom home with a stylish 2-bedroom accessory dwelling, offering the perfect blend of modern comfort, flexibility, and Vermont charm. Whether you're looking for space for extended family, guests, or the potential for rental income, this thoughtfully designed property offers endless possibilities.Step inside to discover contemporary upgrades throughout, where every

  Carrie Mathews Winhall Real Estate

  1161 Little Pond Rd, Londonderry, VT 05148
• 

  

  

  /30

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  255 Fitts Rd, Wardsboro, VT 05355

  Ready for its next stewards, this cozy home has been cherished by the same family for many years and is set on 10 acres of open land and woodlands. Enjoy a peaceful rural setting conveniently located between two of southern Vermont’s premier ski destinations: Stratton Mountain Resort and Mount Snow. At the heart of the house is an inviting kitchen featuring updated cabinets, soapstone

  Heidi Bernier Berkley & Veller Greenwood Country

  255 Fitts Rd, Wardsboro, VT 05355
• 

  

  

  /23

  $475,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356

  Meticulously maintained and thoughtfully updated, this rare top-floor, two-bedroom, two-bath condominium in the coveted Seasons on Mount Snow trailside community is a standout opportunity.This spacious two-level residence features a desirable floor plan with a primary suite on the main level and a private second ensuite bedroom upstairs, offering comfort and flexibility for family and guests

  Patricia Fitzpatrick Skihome Realty

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356
• 

  

  

  /33

  $249,000

  • 1 Bed
  • 468 Sq Ft

  246 Mann Rd, Wilmington, VT 05363

  Location, location, location! This rare opportunity is surrounded by the beautiful Haystack Golf Course, offering an unbeatable setting in one of southern Vermont's premier resort destinations. The property currently features a camp and a one-car garage, allowing you to enjoy the land immediately while planning your dream home or future getaway. Just minutes from Mount Snow, The Hermitage Club,

  Jeffrey Brisson Cohn & Company

  246 Mann Rd, Wilmington, VT 05363
• 

  

  

  /24

  $269,400

  • 1 Bed
  • 1,350 Sq Ft

  2903 State Forest Rd, Townshend, VT 05353

  This is such a blank canvas for you to make your own. Taken down to the studs with a newer roof, windows, and siding, this home is ready for you to come in and make it your own. Seller has never lived here, so the Buyer will have to do their due diligence. Lot is currently 1.5 acres, but the boundary line will be adjusted prior to closing to make the lot around 5+/- acres including river frontage

  Jim Bellville Bellville Realty

  2903 State Forest Rd, Townshend, VT 05353
• 

  

  /17

  $115,000

  • Land
  • 4 Acres
  • $28,750 per Acre

  00 S Ryder Pond Rd, Whitingham, VT 05361

  Discover the perfect setting for your Vermont getaway or future home on this beautiful 4-acre lot located at the end of a quiet dead-end road with direct access to a private pond. The gently sloping, wooded landscape offers privacy, natural beauty, and an ideal mix of mature trees and usable terrain for your vision. A Vermont wastewater permit is already in place, making it even easier to start

  Patrice Schneider Southern Vermont Realty Group

  00 S Ryder Pond Rd, Whitingham, VT 05361
• 

  

  /6

  $329,000

  $9K PRICE DROP

  • Land
  • 47.58 Acres
  • $6,915 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of NH mountains & valleys. A super roadway already exists, providing access to places around the 47 private acres. Several places to build, affording long range views & glorious sunrises. Perfect location for that magical place you've been waiting to build. Ski area resort amenities are a short drive right around the corner, while Brattleboro & the CT River Valley

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
• 

  

  /33

  $139,000

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

  185 Valley View Rd, Dover, VT 05256

  Rare opportunity to own a beautiful 5-acre wooded parcel in a peaceful country setting. Set back from the paved public road, this property offers privacy while remaining easily accessible year-round. A state Wastewater Permit for a 4-bedroom home is already in place, making it easy to begin planning your dream home or Vermont getaway. The land features a gentle, slightly sloping topography that's

  Chad Lackey Deerfield Valley Real Estate

  185 Valley View Rd, Dover, VT 05256
• 

  

  /31

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  65 E Birch Rd Unit 43, Stratton, VT 05155

  Welcome to Your Stratton Mountain GetawayDiscover the ultimate in mountain convenience with this turnkey, ground level condo in the highly sought after Vantage Point community. Featuring a spacious 2 bedroom, 2 bathroom layout, this home boasts a bright, open concept living, dining, and kitchen area designed for effortless entertaining and relaxation. Positioned in an unbeatable location,

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  65 E Birch Rd Unit 43, Stratton, VT 05155
• 

  

  /32

  $875,000

  • 4 Beds
  • 4 Baths
  • 3,374 Sq Ft

  11 Stone Ridge Loop, Dover, VT 05356

  Beautiful custom home in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This contemporary farmhouse design has been just recently updated throughout to offer country charm with modern amenities for turn key enjoyment. The interior boasts a large great room with soaring windows, great natural light, and a new gas fireplace on stone hearth, a large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  11 Stone Ridge Loop, Dover, VT 05356
• 

  

  /10

  $149,000

  • 1 Bed
  • 1 Bath
  • 514 Sq Ft

  25 Elvas Way, Dover, VT 05341

  Remote cabin on 14.4 acres with the Bemis Brook running through. Trails and Class 4 Roads surround the property. Snowmobile and 4 Wheeler in the neighborhood.

  Mark Yule BHG Masiello Brattleboro

  25 Elvas Way, Dover, VT 05341
• 

  

  /4

  $49,900

  • Land
  • 21,780 Sq Ft
  • $99,800 per Acre

  000 Hinkley Brook Rd, Grafton, VT 05146

  Welcome to your opportunity to own a picturesque half acre of land in the charming town of Grafton, VT. Nestled in the heart of nature, this serene parcel boasts a gentle slope, providing the perfect canvas for your dream home or getaway retreat. Enjoy the tranquil sounds of Hinkley Brook as you overlook its scenic beauty from your future property. Whether you're seeking a peaceful escape from

  Jamie Watson BHG Masiello Keene

  000 Hinkley Brook Rd, Grafton, VT 05146
• 

  

  /31

  $375,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,502 Sq Ft

  715 Chase Rd, West Townshend, VT 05359

  In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for

  Christine Lewis Brattleboro Area Realty

  715 Chase Rd, West Townshend, VT 05359
• 

  

  /3

  $735,000

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  771 Stratton Mountain Access Rd Unit 457, Stratton, VT 05360

  Incredible combination of location and amenities. Walk across the street to the ski slopes and Stratton Village with its shops, restaurants, and year-round activities. This top-floor condominium features soaring ceilings, abundant natural light, and a desirable two-bedroom, two-bath layout. Long Trail offers a year-round heated outdoor pool, hot tubs, and a sauna. Heated underground parking, ski

  Cheyanne Pugliese

  771 Stratton Mountain Access Rd Unit 457, Stratton, VT 05360
• 

  

  /29

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft

  12 Encore Place, Dover, VT 05356

  Mountain Modern Living with unmatched trail views of Carinthia at Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of the Mountain. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  12 Encore Place, Dover, VT 05356
• 

  

  /27

  $245,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 2,496 Sq Ft

  11 Evergreen Ln, Brattleboro, VT 05301

  This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

  Janet Lucier Barrett & Valley Assoc. Inc

  11 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /60

  $750,000

  • 6 Beds
  • 4.5 Baths
  • 3,259 Sq Ft

  492 Dover Rd, Newfane, VT 05351

  Own a piece of Vermont history with this charming 1854 home, formerly known as The ThreePenny Lodge and now known as The Cardinal Lodge, nestled in the heart of desirable Newfane near skiing, trails and year-round recreation. Cross a picturesque, covered bridge on your way home and discover a property full of character, currently operating as a successful Airbnb with a live-in caretaker. Whether

  Kerry Mulverhill

  492 Dover Rd, Newfane, VT 05351
• 

  

  /4

  $825,000

  • Land
  • 216 Acres
  • $3,819 per Acre

  6036 Jacksonville Stage Rd, Halifax, VT 05358

  Imagine 216 acres of rolling fields, peaceful woodlands, and a productive sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this remarkable Southern Vermont property offers an exceptional opportunity for those seeking a private estate, working farm, equestrian

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Halifax, VT 05358
• 

  

  /17

  $110,000

  • Land
  • 5,227 Sq Ft
  • $916,667 per Acre

  117 * Fuller Dr, Brattleboro, VT 05301

  Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you

  Rebecca Seymour Brattleboro Area Realty

  117 * Fuller Dr, Brattleboro, VT 05301
• 

  

  /23

  $395,000

  $30K PRICE DROP

  • Land
  • 133 Acres
  • $2,970 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  Motivated Sellers! Rare opportunity to own 133 +/- acres of Vermont land near the village of Putney, Vermont. Whether you are seeking a residential retreat, recreational escape, hunting terrain or exploring subdivision/development opportunities, this property offers exceptional possibilities. The 133+/- acres is pleasantly interrupted by the East Putney Brook and offers 3 points of access,

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  40 E Putney Brook Rd, Putney, VT 05346
• 

  

  /52

  $1,997,000

  • 4 Beds
  • 4.5 Baths
  • 3,631 Sq Ft

  14 Talon Dr, Stratton, VT 05360

  Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  14 Talon Dr, Stratton, VT 05360
• 

  

  /44

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  85 Browns Rd, Newfane, VT 05345

  Steeped in Vermont history and surrounded by more than 80 acres of fields, woods, and walking trails, this beautifully preserved Newfane farmhouse offers the rare opportunity to own a property where timeless character and modern comfort come together. Whether you're looking for a full-time residence, country retreat, or recreational property, this is a place to slow down and enjoy the beauty of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  85 Browns Rd, Newfane, VT 05345
• 

  

  /31

  $680,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

  Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
• 

  

  /34

  $175,000

  • 3 Beds
  • 1.5 Baths
  • 1,130 Sq Ft

  58 Scandia Village Rd, West Wardsboro, VT 05360

  Tucked away on 1.20 acres in Wardsboro, this 3-bedroom, 1.5-bath home offers a peaceful Vermont setting with plenty of outdoor space to enjoy. The home features 1,130 finished square feet with a warm, cabin-like interior, wood accents, and an inviting open living area with a wood stove insert for added comfort. The kitchen flows nicely into the main living space, creating an easy layout for

  Grayson VanHendrick Flex Realty

  58 Scandia Village Rd, West Wardsboro, VT 05360
• 

  

  /60

  $6,898,000

  New Construction

  • 5 Beds
  • 8 Baths
  • 4,000 Sq Ft

  88 Mann Rd, Wilmington, VT 05363

  A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At

  Rich Caplan Deerfield Valley Real Estate

  88 Mann Rd, Wilmington, VT 05363
• 

  

  /33

  $850,000

  $49K PRICE DROP

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

  1-C Townhouse Square, Dover, VT 05356

  Experience true ski-in/ski-out living at Mount Snow in the highly sought-after Seasons on Mount Snow community, perfectly situated on Tin Lizzy Trail just seconds from the lift. This spacious 3-bedroom, 3.5-bath townhouse features a thoughtfully designed floor plan, including two private en suite bedrooms that provide exceptional comfort and flexibility for family and guests. Designed for both

  Stephanie Sugden Real Broker LLC

  1-C Townhouse Square, Dover, VT 05356
• 

  

  /48

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
• 

  

  /10

  $129,000

  • Land
  • 2.1 Acres
  • $61,429 per Acre

  179 Oak Hill Rd, Wardsboro, VT 05353

  TWO LOTS, H-4 & H-13, you choose where to build, septic permits in place for both lots! Two, FOUR BEDROOM WASTEWATER PERMITS on file with the state one for each lot! Cleared lot on Maple with driveway installed, the other has been cut and could be ready to go easily! Don't miss this chance to own two abutting lots! Is being offered together or separate! See also MLS#5090072.

  Chris Lowe Lowe's Real Estate, LLC

  179 Oak Hill Rd, Wardsboro, VT 05353
• 

  

  /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
• 

  

  /24

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft

  456 Route 100, Wilmington, VT 05363

  Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or

  Patrice Schneider Southern Vermont Realty Group

  456 Route 100, Wilmington, VT 05363
• 

  

  /47

  $275,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  5 Camelot Dr, Wilmington, VT 05363

  Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy

  Chad Lackey Deerfield Valley Real Estate

  5 Camelot Dr, Wilmington, VT 05363
• 

  

  /36

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,427 Sq Ft

  95 Hemlock Dr, Londonderry, VT 05148

  The smell of woodsmoke on a crisp alpine afternoon, the quiet crunch of fresh powder underfoot, and the sense that the rest of the world has dropped away, this is the reality waiting at the top of Powder Mill Ridge. Tucked into three acres of private Vermont forest, this contemporary retreat is designed less like a standard house and more like a basecamp for a life well lived.Winters mean

  Robin Apps Four Seasons Sotheby's Int'l Realty

  95 Hemlock Dr, Londonderry, VT 05148
• 

  

  /35

  $749,000

  $50K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,070 Sq Ft

  24 Snow Vidda Loop, Dover, VT 05356

  Mount Snow Retreat – Walk to the Slopes!Experience the ultimate Vermont mountain getaway in this spacious, fully furnished home, ideally located within walking distance to the Mount Snow slopes. Perfect for large families, groups, or as a vacation retreat, this inviting property features 5 bedrooms and 3 bathrooms, offering plenty of space for everyone.The open concept living and dining

  Lisa Mirando Deerfield Valley Real Estate

  24 Snow Vidda Loop, Dover, VT 05356
• 

  

  /12

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
• 

  

  /21

  $152,000

  $8K PRICE DROP

  • Land
  • 11.08 Acres
  • $13,718 per Acre

  0 Rose Ln Unit 5097818, Londonderry, VT 05148

  This 11-acre parcel is situated near Cole Pond, only a few miles from the Stratton Mountain Access Road. The lot offers several potential building sites, including an elevated area that boasts stunning views, as well as a lower option. A driveway extends approximately halfway up the property, providing access to the upper site, which features a remarkable vista of Bromley Mountain. As one

  Mike England Michael England Real Estate

  0 Rose Ln Unit 5097818, Londonderry, VT 05148
• 

  

  /21

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,053 Sq Ft

  180 Debbie Higgins Ln, Wardsboro, VT 05355

  Charming, rustic mountain-theme home in excellent turnkey condition located in the peaceful, convenient Snow Mountain Farms in Wardsboro, offering the best of Vermont living. Surrounded by nature and just minutes from scenic hiking trails, outdoor recreation, and year-round adventure, this 3-bedroom, two-story chalet is the perfect mountain retreat. Features include three updated bedrooms, two

  Patrice Schneider Southern Vermont Realty Group

  180 Debbie Higgins Ln, Wardsboro, VT 05355
• 

  

  /13

  $699,000

  • 3 Beds
  • 2 Baths
  • 3,044 Sq Ft

  661 Wright Orchard Rd, Grafton, VT 05146

  Turn-key, beautifully furnished, and ready to enjoy, this exceptional Vermont property is being offered with all brand-new furnishings included, making it a rare opportunity to step right into the Vermont lifestyle. Set on 20 private acres in the heart of Grafton, this beautifully maintained 3-bedroom, 2-bath home with a custom office offers the perfect blend of comfort, versatility, and modern

  

  Gail Beardmore

  Engel & Völkers Okemo

  661 Wright Orchard Rd, Grafton, VT 05146
• 

  

  /60

  $999,000

  $101K PRICE DROP

  • 3,374 Sq Ft

  85 Route 100, West Dover, VT 05356

  Southern Vermont's fully renovated Mount Snow income compound: five separately metered rentable units across four buildings on 2.57 level acres in West Dover, main-road frontage on VT Route 100, pond on site. About 5 minutes from Mount Snow Resort in the Deerfield Valley, on the ski-bus route from the mountain into Wilmington. Same-road neighbors include Gray Ghost Inn (sold $1,100,000, 2023) and

  Nick Sicard EXP Realty

  85 Route 100, West Dover, VT 05356
• 

  

  /19

  $63,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  2022 Route 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 Route 30, Jamaica, VT 05343
• 

  

  /46

  $869,900

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  45 Sawmill Village Way, Dover, VT 05356

  Experience the perfect blend of Vermont charm and modern comfort in this beautifully crafted custom post-and-beam home with a beautiful view, ideally located in the heart of Dover. Just minutes from Mount Snow, local restaurants, shopping, area amenities, and the scenic Valley Trail, this home offers the perfect balance of convenience and privacy in a peaceful wooded setting. Inside, many windows

  Rich Caplan Deerfield Valley Real Estate

  45 Sawmill Village Way, Dover, VT 05356

Showing Results 121 - 160, Page 4 of 12