Windham County Homes for Sale

Welcome to Windham County, Vermont, a picturesque haven nestled in the heart of New England. Known for its stunning natural landscapes, charming small towns, and rich cultural heritage, Windham County offers a unique blend of outdoor adventure and community spirit. Whether you’re seeking a weekend retreat or a permanent residence, this enchanting county is the perfect place to call home.

Windham County is renowned for its breathtaking scenery, with rolling hills, lush forests, and pristine lakes that invite exploration and relaxation alike. Outdoor enthusiasts will delight in the plethora of activities available, from hiking and biking in the warmer months to skiing and snowboarding at nearby resorts during the winter. The county is also home to the historic town of Brattleboro, where you can enjoy vibrant arts, local cuisine, and a bustling farmers’ market that showcases the best of Vermont’s bounty.

When it comes to finding your dream home, Windham County has an array of properties for sale that cater to diverse lifestyles and budgets. From charming Victorian houses and cozy cabins to modern condos with stunning views, there’s something for everyone. Each home is a gateway to the serene beauty and warm community spirit that Windham County embodies.

Imagine waking up to the sound of birds chirping and the sight of stunning mountain vistas, all while being just a stone's throw away from local shops, restaurants, and recreational activities. With homes for sale in this idyllic area, you can turn that dream into a reality. Explore the opportunities that await you in Windham County, where every day feels like a vacation!

Newest Windham County Homes for Sale

$650,000

3 Beds ⋅ 2 Baths ⋅ 5113338 MLS

Welcome to 1722 Under the Mountain Road, a private 3.02-acre retreat in a tranquil setting surrounded by horse farms, with views of Stratton Mountain. This 2-bedroom rustic cabin is nestled in a former Morgan horse farm. Full of character, the main home features wood frame, wide plank floors throughout, with an open concept layout. The floorplan includes a full kitchen, a dining room, and a living room with a wall of windows facing the private wooded landscape. A glass-walled bedroom brings a sense of openness and creativity into the space, and a versatile loft offers space for an office, a reading nook, or extra sleeping. There are additional sleeping spaces throughout the home. The full bath completes the main home. Outside, a wraparound porch invites you to relax and take in the scenery, while a hot tub and 2 outdoor fire pits make this property a true four-season escape. A separate 1-bedroom, 1-bath accessory dwelling unit provides space for guests, extended stays, or potential rental income. A 3-bay carport offers covered parking and storage. All of this is just a short drive to Magic Mountain, with Stratton, Bromley, and the shops and restaurants of Londonderry nearby. Whether you're looking for a full-time residence, a ski getaway, or a peaceful country retreat, this property is ready for you to make your own.

1722 Under The Mountain Rd, Londonderry

$539,000

3 Beds ⋅ 2 Baths ⋅ 5113279 MLS

Turnkey and ready for ski season, this beautifully renovated residence offers just under 1,600 square feet with two bedrooms, two baths, and an expansive loft providing flexible additional living and sleeping space. Set along the first hole of Haystack Golf Course, the home enjoys a convenient location just an easy walk to the clubhouse, just a few miles from The Hermitage Club and downtown Wilmington, and five miles from Mount Snow. Completely reimagined with a warm, Scandinavian-inspired mountain aesthetic, the interior combines natural materials, clean lines, and a soft, understated palette. The redesigned kitchen is a standout, featuring custom white oak shaker cabinetry, Taj Mahal stone countertops, Bedrosians Cloe White tile, white oak floating shelves, a custom range hood with natural wood detailing, and Bosch appliances. Solid white oak flooring extends throughout the main living and dining areas, complemented by updated doors and trim, new hardware, thoughtfully selected lighting, and natural wood details throughout. The living area is anchored by a wood-burning fireplace, creating an inviting gathering space after a day on the mountain. Both bathrooms have been completely renovated with Montauk Black natural slate flooring, floating vanities, new tile, fixtures and lighting. The primary bath offers a spa-like retreat with a generous walk-in shower and freestanding soaking tub. Upstairs, the spacious loft adds tremendous versatility beyond the two bedrooms, with room for additional sleeping accommodations, a home office, media space, or lounge. New carpeting in the bedrooms and loft adds warmth and comfort, while the home's cohesive mix of white oak, natural stone, warm whites, matte black accents, and muted organic tones gives the entire residence a refined and timeless feel.

5 First Ln Unit 4, Wilmington

$375,000

3 Beds ⋅ 1 Baths ⋅ 5113271 MLS

Come see this sweet, well-kept 3-bedroom ranch. The heart of the home is its inviting open concept living area, featuring a handsome stone fireplace with a pellet stove insert for easy fires in the winter. The fully updated kitchen has abundant Kraftmaid cabinets, an island with seating, quartz counters, and Energy Star appliances. Enjoy meals and company in the warm weather on the wrap-around deck, easily accessible from both the kitchen and living area. A hallway, a few steps up from the kitchen, leads to the three bedrooms; the primary bedroom is large enough for a king-size bed. The spacious, updated ¾ bath has a contemporary vanity and tasteful tile flooring and shower finishes. Added bonuses include a two-car garage, a shed for storage or a workspace and extra space to finish in both the attic and basement. Accented with attractive ledge outcroppings, the land - ideal for recreation and gardening- has a blend of both level and sloping areas as well as a mix of sun and shade. Caring for the home will be easier thanks to the home’s vinyl siding, newer windows, standing seam metal roof and vinyl plank flooring throughout the interior. The ideal location offers the best of both worlds: a tranquil rural retreat set on a quiet road, but only minutes to downtown Wilmington, 20-minutes to the Mt. Snow resort and close to year-round recreation on Lakes Harriman, Raponda, Sadawga, snowmobile and hiking trails and much more. All furnishings available for an additional fee. Showings start on October 11. Open House Sunday, October 11 11am-1pm, Monday October 12 10am-12pm

180 Parsons Rd, Wilmington

$150,000

2 Beds ⋅ 1 Baths ⋅ 5113182 MLS

This West Wardsboro chalet is looking for someone to bring it back to life! Full of potential and ready for renovation, this property offers the perfect opportunity to create your own Vermont mountain getaway. The town lists the property as a three-bedroom, though it currently features one bedroom plus a loft, offering flexibility for future improvements. Set on a nice lot in a convenient location, you’re just 10 minutes from Mount Snow and under 20 minutes from Stratton Mountain, with easy access to skiing, snowboarding, hiking, biking, and year-round outdoor adventure. Enjoy the best of southern Vermont with shopping and dining nearby, while still having a peaceful setting to call home. Bring your vision, your tools, and a little love this chalet could become the mountain retreat you’ve been looking for!

81 Scandia Village Rd, Wardsboro

$1,850,000

4 Beds ⋅ 5 Baths ⋅ 5113171 MLS

The view astonishes the moment you arrive, easily one of the most impressive in the valley. Set high on 35.4 private acres, it looks directly toward Mount Snow and Haystack, with a long paved driveway creating a true sense of arrival and remarkable privacy just minutes from Mount Snow. This beautiful post-and-beam home was built for gathering, with multiple spaces that let everyone spread out without losing the feeling of being together. At the heart of the home is the soaring great room, where exposed timbers, warm wood tones and walls of glass frame the mountain view. A custom masonry fireplace anchors the room and throws impressive warmth throughout the house. The open kitchen, dining and living areas flow easily together and out toward the screened porch, deck and lawn, giving the main level an easy connection to the outdoors. The primary en suite is also on this level, allowing for true one-level everyday living. Upstairs are three additional bedrooms along with two fun loft areas that create their own hangout spaces for reading, games, or simply escaping with a book. The finished walkout lower level offers space for a home gym, another media area, a full bath and additional finished bonus rooms that can flex with changing needs. Above the attached garage, more finished bonus space offers more options for an office, studio, recreation room or overflow space. Outside is where this property becomes hard to duplicate. With more than 35 wooded acres, there is room to roam, explore and escape into Vermont. Walking trails and direct access to snowmobile trails put four-season recreation right outside the door, while the paved driveway and attached garage make everyday mountain living practical. With a main-level primary suite, multiple finished bonus spaces, extensive recreation areas and an extraordinary combination of acreage, privacy and direct mountain views, it offers minutes to Mount Snow.

43 C Upton Rd, Dover

$599,000

4 Beds ⋅ 3 Baths ⋅ 5113132 MLS

Stunning updated and expanded chalet just a short drive out of the village of Wilmington. This home sits privately on a wooded double lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home was extensively renovated and expanded and now has tremendous unique one of a kind space featuring a gorgeous vaulted living room with exposed natural woodwork, great natural light from the large windows, a wood burning fireplace and brick hearth, upscale wood flooring throughout, a beautiful kitchen with quartz counters, stainless appliances, breakfast bar, farm sink, and tile backsplash, large dining area, wet bar and entertaining area, main floor bedroom and full bath, and large mudroom for all your gear. The bedroom level features three spacious bedrooms with two more upscale baths, including tiled showers and a gorgeous pedestal tub, as well as access to the outside. Additionally there is an overflow sleeping loft, huge upper and lower decks for outdoor enjoyment and BBQs, and ample lawn space for enjoyment no matter the season. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep.

90 Big Bend Loop, Wilmington

$599,000

3 Beds ⋅ 3 Baths ⋅ 5113061 MLS

OLD BARN. NEW LUXURY. YOUR PRIVATE SOUTHERN VERMONT ESCAPE. There’s something special about a home that feels completely different from anything else—and this beautifully transformed barn conversion is exactly that. Originally an old barn, this stunning 3-bedroom, 2.5-bath home has been thoughtfully reimagined with sophisticated modern finishes, an inviting open-concept layout, and all the comforts of contemporary living both inside and out, while still preserving the character and soul of its original structure. Set on nearly 12 private acres, this is more than a home—it’s a lifestyle. Spend summer afternoons enjoying your own private pond, enjoy peaceful mornings surrounded by nature, gather with friends and family in the spacious open living areas, or simply get away from the pace of everyday life and enjoy the privacy and tranquility that Southern Vermont has to offer. An amazing opportunity to own a truly distinctive Vermont retreat.

679 Burrington Hill Rd, Whitingham

$359,000

3 Beds ⋅ 2 Baths ⋅ 5113029 MLS

Tucked into a peaceful private setting just outside Putney Village, this charming 4-acre property captures the spirit of rural Vermont living. Surrounded by woods, open space, and abundant wildlife, the property offers a wonderful sense of privacy while remaining close to the village’s lively arts, culture, and community. The 1,700-square-foot home is thoughtfully suited to first-floor living, with a comfortable primary bedroom featuring an en-suite bath. A spacious deck invites you to slow down and enjoy the changing seasons, whether listening to the sounds of nature, watching wildlife, or gathering with friends. A fabulous pond adds to the property’s natural beauty and provides a tranquil centerpiece for this special piece of land. The large two-car garage offers plenty of room for vehicles, tools, and Vermont projects, while the full barn provides generous storage above and additional space below - ideal for a workshop, studio, hobbies, or simply embracing the possibilities of country living. The partially finished basement adds even more flexible space. With its combination of privacy, acreage, pond, barn, and proximity to Putney Village, this is a quintessential Vermont setting - a place to put down roots, enjoy the land, and live at a slower, more connected pace. This property will need a bit of love and it will be well worth it! Open House Saturday Oct. 10. 11:00-1:00

56 Old Stage Rd, Putney

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 5112992 MLS

Perfectly positioned just across from the entrance to The Hermitage Club, this beautifully appointed mountain home offers the ideal balance of comfort, convenience, and Vermont charm. Whether you're heading to the slopes, enjoying a round at Haystack Golf, exploring nearby snowmobile trails, or spending the day at Lake Whitingham, this location places you in the heart of everything the Deerfield Valley has to offer. Inside, warm natural wood finishes, reclaimed barn board accents, soaring cathedral ceilings, and a dramatic wall of windows create a welcoming mountain retreat filled with natural light. The open-concept living area is anchored by a beautiful stone fireplace, offering the perfect gathering space after a day outdoors. The spacious kitchen features granite countertops, stainless steel appliances, custom cabinetry, and a generous center island that flows seamlessly into the dining and living areas, making entertaining effortless. The home offers three comfortable bedrooms plus a bonus room for additional guests or flexible living space, along with three beautifully updated bathrooms. The primary suite provides a peaceful retreat with a spa-inspired bath featuring a tiled walk-in shower, soaking tub, and quality finishes throughout. The finished lower level expands the living space with a large recreation room, perfect for movie nights, game days, or relaxing with family and friends. A two car garage offers ample room for vehicles and all of your Vermont gear. Outside, the expansive deck invites you to unwind in the private hot tub, dine outdoors, or simply enjoy the peaceful woodland setting. Whether you're looking for a full-time residence, a weekend getaway, or a four-season vacation home, 529 Coldbrook Road delivers exceptional craftsmanship, inviting living spaces, and one of the area's most desirable locations just moments from The Hermitage Club and a short drive to Mount Snow, downtown Wilmington.

529 Coldbrook Rd, Wilmington

$375,000

3 Beds ⋅ 2 Baths ⋅ 5112926 MLS

Bright, sunny solid 2-story house, tons of light, with 3 bedrooms, 1 1/2 bathrooms, on 0.4 acres, in a picturesque Guilford location. Quiet, sunny yard, with fruit and shade trees. Your neighbors are the historical society, meeting house, library, an historic brick schoolhouse, and a playscape park around the corner. All new wiring and plumbing. Basement has a concrete slab, has been structurally-reinforced, drainage is in place. The kitchen was taken out, and is now ready for your choices (the room is down to the studs). List price is adjusted for no kitchen. Pellet boiler, baseboard hot water heat. Lots of storage space. Large attached barn offers interesting possibilities. This is a classic house with lots of curb appeal. Property is being sold As Is. A local lender has offered financing through a rehab loan. Come check it out! Open House, Saturday, October 10, 11am-1pm.

4054 Guilford Center Rd, Guilford

$395,000

3 Beds ⋅ 2 Baths ⋅ 5112923 MLS

Welcome to 8 Winhall Station Road in South Londonderry, a well-located three-bedroom, two-full-bath Vermont home offering convenient access to some of Southern Vermont’s best year-round recreation. Several major ski resorts are within easy driving distance, along with nearby hiking trails, campgrounds, swimming, biking, and countless opportunities to enjoy the Green Mountains. The home offers a comfortable, practical layout that works equally well as a primary residence, vacation retreat, or ski getaway. Its location combines the peaceful feel of Vermont country living with convenient access to local schools, shopping, dining, and everyday services. Whether you are drawn to the area for skiing, hiking, camping, or simply enjoying the beauty and relaxed pace of Southern Vermont, 8 Winhall Station Road provides an excellent home base for every season. With multiple resorts and outdoor destinations nearby, this property offers a wonderful opportunity to enjoy the Vermont lifestyle year-round.

8 Winhall Station Rd, Londonderry

$550,000

4 Beds ⋅ 3 Baths ⋅ 5112916 MLS

Welcome to one of Guilford’s oldest houses. Built in 1796, this is a classic south-facing center chimney Cape, situated on 16.8 acres of mowed fields and wooded hillside terrain. This is one of those houses that the owners have taken good care of with many upgrades with an emphasis on preserving original features. The house has 4 Bedrooms, 2 ½ updated baths, kitchen with breakfast nook, dining room, front parlor and family room. The chimney in the main room has a large Rumford Fireplace with an original Bee Hive oven. There is also a mud room with storage and a covered welcoming stone porch. The properties’ several stone walls provide opportunities for flowers and gardening. HVAC consists of a steam based boiler radiator system, two Mitsubishi Heat AC Pumps and two Jotul wood stoves. There is also a large barn used to care for current and previous owners’ horses. Another building serves as a two-bay garage. Both buildings have ample storage. Hale Rd and Hinesburg Rd run through the property with land on both sides (almost 1,200 ft of road frontage). A brook provides part of the southern border. The owners have been here for over 40 years. Properties like this are a rare find.

220 Hale Rd, Guilford

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