Windham County Homes for Sale

Welcome to Windham County, Vermont – a hidden gem nestled in the heart of New England, where picturesque landscapes meet a rich tapestry of history and culture. Known for its stunning natural beauty, this charming county is home to rolling hills, tranquil lakes, and vibrant forests that change with the seasons, offering a breathtaking backdrop for outdoor enthusiasts and nature lovers alike.

Windham County boasts a diverse array of towns, each with its unique character and charm. From the quaint village of Brattleboro, known for its bustling arts scene and community spirit, to the serene beauty of Putney and its welcoming atmosphere, there’s a perfect spot for everyone. The county is also home to a variety of recreational activities, including hiking, skiing, and kayaking, making it an ideal location for those who appreciate an active lifestyle.

For those looking to call Windham County home, there are numerous homes for sale that cater to a wide range of tastes and budgets. Whether you’re seeking a cozy cabin tucked away in the woods, a historic farmhouse with character, or a modern home with stunning views, the real estate options here are as diverse as the landscape itself. The local real estate market is thriving, with properties that offer not just a place to live, but a lifestyle steeped in community and natural beauty.

Explore the charm of Windham County and discover the perfect home that reflects your dreams and aspirations. Your Vermont adventure awaits!

Newest Windham County Homes for Sale

$349,000

3 Beds ⋅ 1 Baths ⋅ 5113983 MLS

This charming 3 bedroom, 1 bathroom ranch in a quiet Dummerston neighborhood offers comfort, versatility, and plenty of indoor and outdoor space. The wide-open living area includes an updated kitchen, beautiful wood flooring, and ample natural light. A wood stove adds the perfect touch for cozy fall and winter evenings. There’s plenty of flexible space for hobbies, a home office, or whatever suits your needs. The basement features a photography darkroom, a partially finished bathroom, and great potential for additional finished living space. Outside, enjoy a spacious, level yard and a large deck perfect for relaxing or entertaining, along with an attached one-car garage. Just 5 minutes from Putney Village and the I-91 exit, this home offers a wonderful blend of convenience, character, and possibilities!

50 Sugar Maple Dr, Dummerston

$3,900,000

5 Beds ⋅ 4 Baths ⋅ 5113882 MLS

Location, luxury, and the best of Stratton Mountain living! Just steps from Stratton Village and The Stratton Club, this exceptional mountain retreat offers convenience, privacy, and timeless Vermont charm, with the added benefit of being able to walk to the slopes! Extensively updated, the home showcases beautiful craftsmanship, soaring ceilings, exposed reclaimed timber beams, and a dramatic floor-to-ceiling stone fireplace anchoring the impressive great room. Expansive windows invite natural light and showcase the surrounding mountain landscape, while warm hickory floors create an atmosphere that is both elegant and comfortable. The stunning dining area, with its vaulted wood ceiling, distinctive antler chandelier, and walls of windows, provides a beautiful setting for entertaining. Major improvements include a complete exterior renovation, an expansive new deck offering generous space for outdoor dining and relaxation, and a beautiful stone patio. After a day on the slopes, unwind in the hot tub or gather around the fireplace for a cozy Vermont evening. In addition to five bedrooms, the thoughtfully designed interior features a spacious bonus room above the garage, a private office, and an expansive lower level with an additional bonus room, offering wonderful flexibility for entertaining, recreation, and quiet retreats. The home's proximity to the Village makes enjoying Stratton's restaurants, shops, and year-round activities effortless. Adding to its appeal, the property may transfer with a Stratton Sports Center bond, providing access to additional recreational amenities. Whether you're seeking an exceptional ski getaway or a four-season mountain home, this beautifully updated property offers an extraordinary opportunity to experience the Stratton lifestyle in one of the mountain's most desirable locations.

16 Sawmill Rd, Stratton

$799,000

4 Beds ⋅ 4 Baths ⋅ 5113792 MLS

Set amidst 23+ acres of picturesque Vermont countryside, this exceptional country estate offers a rare combination of privacy, expansive living spaces, and endless opportunities for recreation. Perched along a gentle hillside and surrounded by beautifully landscaped grounds, rolling lawns, blueberry bushes, mature trees, trails through the woods and a pond, the property captures the beauty of Vermont in every season. Offering over 3,500 square feet of living space, this spacious Colonial has been thoughtfully updated throughout, including all new plumbing in 2018, a new roof and skylights in 2025 and the addition of a large barn with electricity and water in 2019, providing exceptional space for equipment, storage, hobbies, or recreational pursuits. Designed for both comfortable everyday living and effortless entertaining, the home features a generous eat in kitchen with granite countertops, gas range, and double ovens. The impressive 20’ x 24’ family room is a true gathering space, showcasing soaring wood ceilings, a wet bar, and multiple French doors opening to an expansive 900+ square foot deck. A formal dining room, inviting living room with a beautiful stone fireplace, and additional flexible living space complete the main level. Upstairs, the spacious primary suite offers a private retreat with its own fireplace, balcony, and ensuite bath featuring a jetted soaking tub, double vanities, and recently updated shower. Two additional bedrooms and a full bath provide comfortable accommodations for family and guests. Two heated, walk up attic spaces offer exciting possibilities for future expansion. Outdoor enthusiasts will appreciate direct access to the VAST snowmobile trail system. Whether enjoying peaceful mornings overlooking the landscape, entertaining on the expansive deck, exploring the acreage, or relaxing beside the pond, this extraordinary property offers an idyllic Vermont lifestyle with room to live, gather, and explore.

845 Hall Rd, Halifax

$2,700,000

5 Beds ⋅ 6 Baths ⋅ 5113717 MLS

Crafted by Vermont Barns / Wadsworth Design Build, this custom timber frame home in Stratton, Vermont, brings together beautiful craftsmanship, generous living spaces, and a peaceful National Forest setting just 15 minutes from both Mount Snow and Stratton Mountain. With five bedrooms, six bathrooms, and two bonus rooms for additional sleeping space, the home offers ample room for family and guests. At the heart of the home, an expansive open kitchen, dining, and living area showcases the warmth and architectural beauty of the timber frame. A dramatic wall of windows draws the surrounding mountain landscape indoors and fills the gathering space with natural light. The floor-to-ceiling stone wood-burning fireplace anchors the living room, creating an inviting setting for après-ski gatherings. With generous space to prepare meals, gather around the dining table, and relax by the fire, the open layout keeps everyone connected. An expansive mudroom provides a practical arrival point with room for ski gear, boots, and the essentials of Vermont mountain life. Two bedrooms feature ensuite baths, providing added comfort and privacy. The primary suite offers a private retreat with a balcony perfectly positioned to take in mountain sunrises. The lower level provides another welcoming space to gather, complete with a custom bar for relaxed evenings and entertaining. Outdoor living is equally inviting, with a screened porch for leisurely meals and quiet mornings, a back deck with a fire pit for evenings together, and a hot tub for unwinding after a day on the mountain. The surrounding forest creates a peaceful backdrop throughout the seasons. An attached two-car garage adds everyday convenience, while a detached barn with a second-floor gym expands the property’s versatility. Thoughtfully designed for both gathering and retreat, this distinctive timber frame home offers enduring craftsmanship and easy access to the best of Southern Vermont.

58 Red Hawk Rise, Stratton

$339,000

2 Beds ⋅ 2 Baths ⋅ 5113651 MLS

There’s so much to love about this home! Enter through an enclosed mudroom, perfect for storing all your outdoor gear. The kitchen offers abundant storage, a dedicated baker’s counter, and a convenient breakfast bar with seating. Beautiful hardwood floors flow throughout the kitchen, dining, and living areas. The first floor features two bedrooms and two full bathrooms, while the basement adds three additional heated, finished rooms, offering endless possibilities for a home office, playroom, hobby space, or more! Step outside to enjoy the deck, perfect for grilling and dining al fresco, overlooking a flat, open yard. Plus, the home is conveniently located just down the road from the town pool and recreation area!

167 Silver Ln, Vernon

$199,000

3 Beds ⋅ 1 Baths ⋅ 5113644 MLS

Looking for an affordable home with a little personality? You've found it in this colorful 3-bedroom, 1-bath home in the historic village of Whitingham, Vt. Set on 0.10 acres along a quiet, paved street with town sewer, the home is surrounded by some of Southern Vermont’s best lakes, including Sadawga Lake and Harriman Reservoir. Step inside through the French doors that separate the mudroom from a flexible living space that can become a dining room, home office, sitting area, or whatever works best for you. The first floor also includes the full bathroom, laundry area, and primary bedroom with a walk-in closet. The kitchen features an eat-in island for casual dining and opens to a spacious great room, where a large picture window brings in plenty of natural light. Bold colors throughout give the home a fun, playful energy and make each room feel a little different from the next. Keep the color, tone it down, or make it completely your own. Upstairs, two additional bedrooms continue the home's bright and bold personality. A door off the living area leads to the fenced backyard, where you can relax and enjoy the sounds of nearby Sadawga Brook on the front porch of the shed, which can be used for storage, a workshop, or play space. Major systems have been recently updated including the well pump and pressure tank (new in 2016), furnace (new in 2021) and water heater (new in 2024). The home is just 13 minutes to Wilmington, 16 minutes to Hogback Mountain’s 100-mile view, 23 minutes to Marlboro, 25 minutes to Mount Snow, and roughly 40 minutes to Brattleboro to the east and Greenfield, Mass., to the west.

105 School St, Whitingham

$420,000

2 Beds ⋅ 2 Baths ⋅ 5113634 MLS

Tucked away in the beautiful Vermont countryside, this inviting two-bedroom, one-and-a-half-bath ranch sits on 22.65 acres in the charming town of Grafton. Surrounded by a combination of open lawn and wooded acreage, the property offers a wonderful sense of privacy and plenty of room to enjoy the outdoors. Inside, the home features a spacious living room, a kitchen with adjoining dining area, and a practical single-level layout. The primary bedroom features its own convenient half bath, while a separate utility room with first-floor laundry adds everyday convenience. The sunroom provides a lovely space to sit and take in the peaceful surroundings. The basement offers plenty of additional storage space, and the attached two-car garage provides convenient parking and even more room for storage. Step outside onto the deck to entertain friends or simply relax and appreciate the natural beauty of the property. The expansive grounds provide opportunities for gardening, outdoor recreation, walking through the woods, or simply enjoying the changing seasons. Whether you're looking for a full-time residence or a quiet Vermont getaway, this property offers a wonderful combination of comfortable living, generous acreage, and a peaceful country setting, with the picturesque villages of Grafton and Chester within easy reach. Showings start 10/12/2026

286 Richards Rd, Grafton

$335,000

3 Beds ⋅ 2 Baths ⋅ 5113619 MLS

Come take a look at this three bedroom and two bath chalet in the B Section of Chimney Hill with terrific amenities. Relax on the main level in an open concept living, dining and kitchen space, living room has a woodstove and sliders to the deck to enjoy the country side views, a bedroom and a full bath. Upstairs has two more bedrooms and a full bath. An exclusive members-only clubhouse with indoor/outdoor pools, hot tub, fitness room, arcade, kids playroom, media room, library/reading nook, kitchen area with bar, BBQ area and a playground. Throughout the complex there is a fishing pond, trail system, tennis courts, ice skating rink, hiking trails and snowmobile access. Minutes from skiing, fine dining, golfing, boating, downtown Wilmington and so much more!

19 View Rd, Wilmington

$429,000

5 Beds ⋅ 2 Baths ⋅ 5113589 MLS

There is an immense amount of space in this home. With one bedroom downstairs, 4 bedrooms upstairs, plus a family/bonus room, everyone has space of their own. The space carries over to the 2 story attached barn where both floors offer workshop and creative space. Even the basement is sprawling and usable. Enjoy Fiber internet and the most pure well water from the Westminster Aquifer. There is a new septic system and a large grassy backyard. Notable features include a pantry, an enclosed wrap-around front porch, a back stairwell off the fifth bedroom, three propane heaters and beautiful hardwood floors throughout. Enjoy being part of the Village community!

3531 Rte 5, Westminster

$999,000

6 Beds ⋅ 4 Baths ⋅ 5113557 MLS

Set among the treetops with sweeping views spanning multiple states, this Rod Williams designed classic is a sprawling 5300+ sq ft, 6 bed, 4 bath with attached 2 car garage, capturing everything there is to love about a Vermont ski retreat. Situated on 3 acres bordering community land, the property enjoys an elevated setting, exceptional privacy, expansive views including the greens at Haystack Golf Course. There is room to bring everyone together while offering plenty of space to spread out over 3 levels. Main living level designed around generous gathering spaces, soaring ceilings, expansive windows, skylights, and walls of glass opening to outdoor decks. Beautiful brick fireplace centerpiece, visible from all main living areas. Open kitchen with substantial walk-in pantry, mudroom, and laundry area. .Occupying its own wing on the main level, the primary suite is a retreat within the home, complete with spacious bedroom, sitting room, private office, large walk-in closet, and an expansive bath featuring a jetted tub, and sauna. Upstairs, private guest suite enjoys some of the home's most spectacular views.Finished walkout lower level offers four additional bedrooms, spacious rec room, another full bath with a jetted soaking tub and large shower. Separate flex room opens directly to the deck, an ideal location for a future hot tub. Generous storage areas, newer roof, easy access road, manageable driveway add practical appeal. Chimney Hill ownership includes access to an extensive collection of amenities,indoor & outdoor pools, skating, basketball, fishing pond, playground, trails, on-site management team. Short drive to downtown Wilmington, Mount Snow, Haystack, lakes, golf, and year-round outdoor recreation, this is a property that combines the character of a classic Vermont ski home with a remarkable amount of space, privacy, and views that truly steal the show.

23 Shincracker Way, Wilmington

$339,000

3 Beds ⋅ 2 Baths ⋅ 5113538 MLS

Located in the desirable Black Mountain Road area, this cozy log home includes an attached two-car garage with a workshop area, a three-season porch, and a wraparound deck. The lower level is accessible from the garage and opens into a spacious tiled mudroom. An open staircase leads to the main floor, which features three bedrooms, 1¾ baths, a living room, and a country kitchen with a dining area. The basement provides abundant unfinished space for a workshop, studio, or other creative pursuits, along with laundry, sink and a workbench. Additional outbuildings include small storage sheds. The home needs some TLC but offers worthwhile potential in a country setting, so close to town. The owners are continuing the cleanout process, and additional photos will follow. Please note that the large stones are not included.

625 Black Mountain Rd, Brattleboro

$399,000

3 Beds ⋅ 2 Baths ⋅ 5113520 MLS

Welcome to 36 Ives Road, a classic Vermont A-frame set in a quiet wooded setting just minutes from Mount Snow and a short drive from downtown Wilmington. Inside, warm natural woodwork, soaring cathedral ceilings, skylights, and abundant natural light give the home the inviting character you want in a Vermont retreat. The open kitchen, dining, and living areas create an easy gathering space, while the wood stove adds warmth and atmosphere after a day on the mountain. A loft overlooks the main living area and provides flexible space for additional sleeping, a home office, reading nook, or second lounge. Step outside to enjoy the balcony, fire pit, and peaceful surroundings, with plenty of space to slow down and enjoy the seasons. The home is being offered fully furnished, making it easy to settle in and start enjoying it right away. The location is what really ties it all together. Mount Snow is just minutes away, while downtown Wilmington offers restaurants, shops, galleries, and the charm of a historic Vermont village. In the warmer months, enjoy swimming, boating, and kayaking at Harriman Reservoir, along with miles of hiking and biking throughout the Deerfield Valley. Whether you're looking for a ski getaway, a four-season escape, or a Vermont home base to enjoy year-round, 36 Ives Road offers a relaxed setting in the heart of one of Southern Vermont’s most popular recreation areas.

36 Ives Rd, Wilmington

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