Windham County VT Houses for Sale

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  /42

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  37 Pleasant View Ln, Wilmington, VT 05363

  4 bed, 3.5 bath, true log home w/excellent layout over 3 finished floors, 2 car garage, 5 acres, private pond, Mount Snow views, snowmobile trail access and all nicely tucked away on a dead end road. Just 2.2 miles to Rt 100 for easy access to downtown Wilmington shops and dining, Mount Snow Resort, the exclusive Hermitage Club, Harriman Reservoir and marina and multiple area golf courses. Even

  Jacki Murano Southern Vermont Realty Group

  37 Pleasant View Ln, Wilmington, VT 05363
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  /44

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  24 Antler Loop, West Dover, VT 05356

  This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  24 Antler Loop, West Dover, VT 05356
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  /25

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft

  5 Alpine Loop Rd, Dover, VT 05356

  Tremendous opportunity to own an updated chalet at the base of the Mount Snow ski resort and Carinthia Freestyle Terrain Park. This charming home sits nestled on a quite loop just south of the mountain with direct walking and hiking trail access. The home features a large open floor plan with updated kitchen, stainless appliances, granite counters, and island, sunny living room with wood burning

  Adam Palmiter Berkley & Veller Greenwood/Dover

  5 Alpine Loop Rd, Dover, VT 05356
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  /22

  $275,000

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
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  /58

  $764,900

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  Step back in time without sacrificing comfort at the Woolley House, an exquisite 1818 Brick Federal style home nestled in the postcard-perfect village of Grafton, Vermont. This rare property seamlessly blends early 19th-century craftsmanship with thoughtful modern upgrades. Original details are beautifully preserved throughout, including four elegant Regency fireplaces, a central cooking hearth

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /49

  $999,800

  • 4 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  60 Forest Heights Rd, Stratton, VT 05360

  Spectacular Soaring Post and Beam located on the Dover/Stratton town line. This fabulous home boasts soaring vaulted ceilings in the living room with a wall of windows bringing the view into your home complete with a cozy brick fireplace that sets the perfect ambiance. The kitchen is a chef’s delight, featuring granite countertops with eat in dining, a center island, half bath and easy access to

  Richard Caplan Deerfield Valley Real Estate

  60 Forest Heights Rd, Stratton, VT 05360
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  /48

  $495,000

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft

  1 Pheasant Ln, Dover, VT 05356

  Whether you are unwinding from a long day at the slopes of Mount Snow or you just enjoyed 18 holes at the Country Club, relax and get away with this beautiful home located in Partridge Run. This home boasts 3 bedrooms, 3 full bathrooms plus a Loft! You are welcomed upon entry by a very spacious mudroom with ample room to store your equipment for all seasons. The living, kitchen and dining areas

  Tobin Twelves Skihome Realty

  1 Pheasant Ln, Dover, VT 05356
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  /49

  $369,000

  • 4 Beds
  • 2 Baths
  • 2,202 Sq Ft

  20 Newell Hill Rd, Wardsboro, VT 05355

  Now offering multiple buyer credits, including a $10,000 credit at closing—ask your agent for full details. Enter through the oversized mudroom, which once served as the town post office, from the attached three-bay garage with automatic doors. This home features generous rooms throughout, starting with a large kitchen and dining area, a living room, two main-level bedrooms, and a full bath.

  Erica Reynolds Southern Vermont Realty Group

  20 Newell Hill Rd, Wardsboro, VT 05355
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  /52

  $999,000

  • 4 Beds
  • 2 Baths
  • 2,741 Sq Ft

  20 Finkel Rd, Wardsboro, VT 05355

  Nestled on nearly 260 acres, this exquisite 18th-century solid post & beam 4 bedroom 2 bath cape offers a harmonious blend of historic charm and modern convenience. Boasting original features like fireplaces, wood flooring, and exposed beams, the home is filled with character. Spacious rooms create a perfect setting for gatherings. Recent updates include a new roof, windows, furnace & oil tank;

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  20 Finkel Rd, Wardsboro, VT 05355
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  /36

  $449,000

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  44 Villager Loop, Dover, VT 05356

  Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VTVery little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

  Janet Boyd Boyd Real Estate

  44 Villager Loop, Dover, VT 05356
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  /40

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
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  /50

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,358 Sq Ft

  1917 Stowe Mountain Rd, West Halifax, VT 05358

  Welcome to 1917 Stowe Mountain Rd., a sanctuary of modern elegance nestled in the breathtaking green mountains of Halifax, VT. This luxurious contemporary residence spans 3,358 square feet and seamlessly blends sophisticated design with natural beauty. As you approach this architectural masterpiece, soaring cathedral ceilings create a sense of expansive openness. The glass and Hardie plank

  Monica Sumner BHG Masiello Brattleboro

  1917 Stowe Mountain Rd, West Halifax, VT 05358
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  /37

  $1,700,000

  • 4 Beds
  • 4.5 Baths
  • 3,808 Sq Ft

  15 Stone Ridge Loop, Dover, VT 05356

  A rare opportunity to have a luxurious mountain property with views, still with great proximity to Mt Snow. This stunning barn style post and beam is nestled on a private 5.97 acre parcel at the rear of the Village at Sawmill Farms. The siting affords gorgeous pastoral views over the common field of the community, views of the peak of Mount Snow, and mountains beyond, with 180 degree winter

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Stone Ridge Loop, Dover, VT 05356
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  /40

  $3,350,000

  • 6 Beds
  • 3 Baths
  • 3,309 Sq Ft

  36 Woffenden Rd, Wilmington, VT 05363

  Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds.Boasting a coveted southeast exposure, the home and land are cheerful

  Melissa Ellis Southern Vermont Realty Group

  36 Woffenden Rd, Wilmington, VT 05363
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  /40

  $1,995,000

  • 9 Beds
  • 9 Baths
  • 8,054 Sq Ft

  207 Brooks Ln, Londonderry, VT 05148

  This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  207 Brooks Ln, Londonderry, VT 05148
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  /35

  $295,000 New Construction

  • 2 Beds
  • 1 Bath

  2137 Brockway Mills Rd, Town of Rockingham, VT 05143

  A beautiful property needing someone to either do a barn to house conversion or build new on a scenic spot toward the back of the field which overlooks the barns, field, and hills beyond. This was a dairy farm years ago, and the barn still has some stanchions in place. Not a property for anyone to move right into since it needs finishing. This is more suited to a cash sale or special financing.

  Glenn Olney Barrett and Valley Associates Inc.

  2137 Brockway Mills Rd, Town of Rockingham, VT 05143
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  /37

  $849,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  101 North Rd, Wilmington, VT 05363

  Stunning new construction in the Chimney Hill community just outside the village of Wilmington, and a short drive to both the Mount Snow ski resort, Hermitage Club, and Lake Whitingham. Located on an easily accessible corner lot in the desirable B section at the bottom of the hill with unique double lot size allowing for tremendous expansion potential . This home was built sparing no expense and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  101 North Rd, Wilmington, VT 05363
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  /30

  $324,900 New Construction

  • 1 Bed
  • 1 Bath
  • 897 Sq Ft

  141 Mercier Rd, Brattleboro, VT 05301

  A cute cabin/camp on 8.3 acres of land. Easy access to Brattleboro, Wilmington and Dover. Off grid with a propane generator. Beautiful finishes, full kitchen and a full bath. Brand new septic system, and a dug well. Near VAST trails. Make this yours just in time for hunting season.

  Darlene Conca Keller Williams Realty Metro-Keene

  141 Mercier Rd, Brattleboro, VT 05301
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  /38

  $789,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  717 Horsenail Hill Rd, Chester, VT 05143

  Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

  Robin Apps Four Seasons Sotheby's Int'l Realty

  717 Horsenail Hill Rd, Chester, VT 05143
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  /19

  $625,000 New Construction

  • 2,716 Sq Ft

  380 Smith Rd, Jacksonville, VT 05342

  At the end of a quiet gravel road, bordered by the VAST trail and surrounded by stone walls, this rare 49.3-acre parcel offers incredible southeastern views, breathtaking sunrises and moonrises, and extreme privacy. Enjoyed as a personal getaway for over 20 years, the land is perfect for hiking, snowshoeing, hunting, or simply relaxing in nature as wildlife roam freely. The property features

  Monica Sumner BHG Masiello Brattleboro

  380 Smith Rd, Jacksonville, VT 05342
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  /12

  $425,000 New Construction

  • 4 Beds
  • 2 Baths
  • 3,700 Sq Ft

  442 Mcmillan Rd, Whitingham, VT 05342

  New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
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  /60

  $1,989,000 New Construction

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

  136 Woodsman Rd, Dover, VT 05356

  Commanding panoramic views of both Mount Snow and Haystack, this 2024-built mountain modern home blends elevated design with the comforts of Vermont living on 11.12 private acres. Featuring 4 bedrooms and 4 baths, the open-concept layout is anchored by a dramatic wall of glass that floods the interior with natural light and frames the ridgeline’s breathtaking sunsets. Designed for both function

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  136 Woodsman Rd, Dover, VT 05356
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  /18

  $1,145,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  80 Banning Rd, Putney, VT 05346

  Rare offering on Putney Mountain! Spectacular house site with new foundation and great Southern exposure awaits your vision! Includes four bedroom septic system, and drilled well. Create your new home with the included framing lumber and your team of craftsmen. House is sited in a private location, yet is accessible to the town road via an easily maintained level driveway. Additional

  David White OwnerEntry.com

  80 Banning Rd, Putney, VT 05346
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  /20

  $148,500

  • 3 Beds
  • 2 Baths
  • 2,098 Sq Ft

  843 Kentfield Rd, Whitingham, VT 05361

  Step back in time with this 1865 home, currently used as a two-family residence, which could easily be restored to its original layout. The ceiling beams have been exposed, allowing you to keep their rustic charm or cover them for a more traditional look. The attached barn would be ideal for a studio, workshop, or bonus room, offering numerous options to suit your needs. Many projects are

  Linda Benoit Highland Realty

  843 Kentfield Rd, Whitingham, VT 05361

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