Windham County Real Estate

Welcome to Windham County, Vermont—a hidden gem nestled in the heart of New England. Known for its breathtaking landscapes and vibrant communities, Windham County offers a unique blend of rural charm and modern convenience, making it an ideal place to call home.

With its rolling hills, lush forests, and picturesque villages, Windham County is a nature lover's paradise. Outdoor enthusiasts can enjoy an array of activities, from hiking the scenic trails of the Green Mountains to skiing at renowned resorts like Stratton and Mount Snow in the winter months. The county is also home to pristine lakes and rivers, perfect for fishing, kayaking, and summer picnics.

Windham County boasts a rich cultural tapestry, with a variety of local events and festivals that celebrate its heritage. The charming towns of Brattleboro, Bellows Falls, and Wilmington are filled with quaint shops, art galleries, and farm-to-table restaurants that showcase the best of Vermont’s local produce. You’ll find a warm, welcoming community that values sustainability and the arts, making it a wonderful place to connect with neighbors and make lifelong friends.

Education is a priority here, with a number of highly regarded public and private schools, as well as access to higher education institutions. The region is also known for its strong sense of community, where residents come together to support local initiatives and businesses.

Whether you’re seeking a serene retreat or an active lifestyle, Windham County offers the perfect backdrop for your next chapter. Explore the beauty, culture, and community of this enchanting Vermont county, and discover why so many have chosen to make it their home.

Newest Listings in Windham County

$625,000

4 Beds ⋅ 3 Baths ⋅ 5103937 MLS

Built in 1962, this inviting home perfectly balances peaceful country living with convenient access to local amenities. Near to an extensive network of hiking, cross country skiing and mountain bike trails offering spectacular views. Size and layout invite single-family. Whether seeking a peaceful retreat or active lifestyle, this property in a welcoming community has it all. Home Highlights: A large, recently renovated granite and stainless steel kitchen opens to a large living and dining room with hardwood flooring and pellet stove. Through the French doors is a large screened-in porch with access to a beautifully landscaped backyard and pond. Extensive basement with laundry and lots of storage. A 12' x 18' powered outbuilding holds potential as a studio or guest cottage. Upstairs rooms provide additional space and two more bedrooms. Bathrooms have all been recently renovated; master bath upstairs with walk-in shower, and a full bathroom and half-bath are located on the first floor. A two-car garage with an attached workroom has covered access to house through a breezeway. An accessible ramp leads to a front deck and additional entry. Flowering trees, a perennial bed, a sweeping paved driveway and beautiful views. Prime Location: Putney offers well-regarded public and private schools, a thriving arts and culture scene, orchards, farmer's markets, shops and thriving businesses. 12 mins to Brattleboro, 1.5 hrs to Bradley International Airport, 2.25 hours to Boston.

279 Westminster Rd, Putney

$499,000

3 Beds ⋅ 3 Baths ⋅ 5103908 MLS

Welcome to Cloister Falls, a truly special offering in the Green Mountains! Tucked among extensive grounds with mature gardens, a pond, and thoughtfully landscaped outdoor spaces, this 3+ bed plus den and office, 3 bath log home offers a setting that feels connected to the surrounding Vermont landscape. The property's signature feature is its swimming hole and waterfall , a natural gathering place for relaxing, entertaining, or enjoying the sound of moving water right outside your door. Inside, the home has both comfortable and impressive gathering spaces and a flexible floor plan. The formal living room is centered around a stone wood-burning fireplace and framed by natural wood details and rich textures throughout. The country kitchen features cherry cabinetry, granite countertops, and a vintage-inspired Glenwood propane and wood cookstove with plenty of workspace, counter and storage. The main level also includes a library or office space, spacious den, and solarium, creating multiple options for work, hobbies, or quiet retreat spaces.The second floor offers two inviting guest bedrooms one with a view of the pond and gardens and the either with its own balcony. A generously sized guest bath is also on this level along with a primary suite featuring a private bath and dual walk-in closets. An attached two-car garage with 2nd floor adds convenience while the surrounding grounds provide room to garden, explore, and enjoy the outdoors through every season. The walk to the screen house past the pond gives a secret garden feel. From there, take the foot bridge into your 25 acres for exploration. This is a property where the landscape and home come together to create a special experience and offering that doesn’t come along often.

1905 Turkey Mountain Rd, Jamaica

$299,000

3 Beds ⋅ 2 Baths ⋅ 5103897 MLS

Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation. High speed internet keeps you connected, a reliable Buderus boiler provides heat and hot water, and most windows have been updated to double glazed vinyl for improved efficiency. Inside, the layout is practical and inviting. Enter from the attached 24x24 two car garage into a substantial mudroom/laundry room - a huge perk in Vermont. The kitchen offers ample workspace and storage, opening to the dining and living areas with a wall of west facing windows. The living room fireplace is an ideal candidate for a woodstove insert, offering efficient heat with the ambiance of a traditional hearth. Off the central living area are three bedrooms, including a primary bedroom with full bath. Two additional bedrooms - or office/studio/workout spaces - plus a second full bath complete the floor plan. Outside, there’s room to garden, play, and enjoy the land. The price reflects the opportunity for a new owner to perform work and updates to build meaningful equity while enjoying a cozy home in a rural setting close to everyday necessities. Minutes from Memorial Park, trail networks, shopping, schools, the hospital, and I 91, this property delivers outstanding value at a competitive price. Don’t let it get away.

68 E Bonnyvale Ln, Brattleboro

$250,000

3 Beds ⋅ 2 Baths ⋅ 5103863 MLS

Escape to this charming turnkey cabin nestled in the hills of Southern Vermont, just a short drive from Stratton Mountain. Being sold fully furnished and as is, what you see is what you get, simply bring your personal belongings and start enjoying your mountain retreat! Privately situated on 9.7 wooded acres, this cozy getaway offers the perfect blend of seclusion and convenience. A paved driveway leads you to your own peaceful slice of Vermont paradise. The open-concept interior features a warm post-and-beam design with locally harvested wood countertops that add rustic character to the kitchen and living space. The main level offers two bedrooms, one with its own three-quarter bathroom, providing privacy and convenience for family or guests. Upstairs, a spacious open area offers endless possibilities, use it as additional sleeping space, a game room, home office, or cozy lounge area. The cabin is comfortably heated year-round by a Rinnai direct vent propane heater, with electric baseboard heat available for backup. Annual propane usage was 365 gallons total heating the cabin year-round, and the average annual electric bill was $670 total for the current owner. Whether you're looking for a four-season getaway, or a peaceful place to unwind, this inviting cabin is ready for its next owners to enjoy.

270 Castle Hill Rd, Jamaica

$40,000

2 Beds ⋅ 3 Baths ⋅ 5103862 MLS

Trailside, best ski in/out mountain location. A really comfortable end unit sleep 8. Unit 360 includes a kitchenette, comfortable living room setting, a sleep sofa, and a bedroom ensuite on the second level with a king size bed. Unit 358 boasts 2 queen size beds, a full bathroom, and a covered deck with views of the main base and mountain trails to enjoy skiers on the slopes, summer and fall views. Just imagine entertaining family and friends! Benefits of ownership include year round usage of all amenities, outdoor heated pool, sauna, owners private lounge, valet parking, full service spa, gym, ski locker. Discounts on food and retail. And a favorite perk, Space Available, that gives you the opportunity to stay in the hotel when it's not your ownership time for the discounted rate of housekeeping. You can use it, rent it or trade with RCI and enjoy resorts world wide. This unit is a lockout. You can rent it several ways, as a full 2 bedroom 3 bath sleep 8 or an hotel suite sleep 4. Quarter 3 will give you the opportunity of being able to use this property Christmas and New Year weeks.

358/360 Qtr. 3 89 Grand Summit Way, Dover

$95,000

3 Beds ⋅ 1 Baths ⋅ 5103828 MLS

This affordable Bellows Falls home is a great value! Tucked away on a quiet dead-end street with no thru traffic, you'll enjoy peaceful living while being just a short walk to the heart of the village. Stroll to local shops, restaurants, cozy coffee shop, library, the historic opera house/movie theater, and a thriving arts community. The scenic Connecticut River is also just steps away, adding even more to this desirable location. It's within walking distance of Central Elementary School and Bellows Falls Middle School and provides an easy commute via Interstate 91 exit 6. Relax on the welcoming front porch or enjoy the spacious extra deep yard backing to acres of green space for privacy. There is plenty of room for a garden and abundant trees for shade. The extra long driveway and garage provide parking for five cars. The home has beautiful natural woodwork and old time features such as window seats and a claw foot bathtub. There is a first floor bedroom and a surprising amount of closet and storage space for a home of this age. Four ceiling fans will help cool the home. If you've been looking for an affordable home in one of Vermont's most walkable and vibrant small-town communities, this is an opportunity you won't want to miss!

6 Hyde St, Rockingham

$189,000

5103738 MLS

Discover this exceptional and private 12+ acre parcel, nestled along a quiet dead-end road and filled with natural beauty. Sun-drenched and serene, the property features a picturesque open meadow framed by timeless stone walls, creating an idyllic setting for your dream home. Thoughtfully prepared for construction, the property already includes many valuable improvements: a State of Vermont wastewater permit with an approved septic design for a three-bedroom residence, a drilled well producing an impressive 15 gallons per minute, 200-amp electrical service installed on-site, and fiber-optic internet available at the road. With generous road frontage and two access points, the gently sloping landscape offers multiple possibilities for siting a home, garage, and outdoor living spaces. Mostly wooded with mature trees, the land provides an ideal balance of open and private spaces. A charming spillway in the southwest corner adds a unique natural feature and enhances the property's peaceful character. Whether you're ready to build now or looking for the perfect location to create your future Vermont retreat, this remarkable parcel offers the rare combination of privacy, infrastructure, and scenic beauty in a truly tranquil setting.

712 Stimpson Hill Rd, Whitingham

$249,900

2 Beds ⋅ 2 Baths ⋅ 5103642 MLS

Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home office, studio, or additional living area. Fidium high-speed fiber internet is already available on site, making it ideal for remote work or streaming. Connected to town water and sewer, the property offers added convenience and potential for future improvements, subject to local permitting and applicable town approvals. A new furnace was installed in May 2026, providing peace of mind for the next owner. Lovingly owned by the same family for the past 30 years, this home is ready for its next chapter. Being sold as is, it presents a wonderful opportunity for buyers with vision to update, personalize, and build equity in a highly desirable village location.

6 Church St, Wilmington

$499,000

3 Beds ⋅ 3 Baths ⋅ 5103610 MLS

This is your chance to be part of the historic and lively community in the center of Newfane. This home underwent a complete overhaul in the early 2000s, including a new slate roof, a relocated fireplace for a more practical layout, a reinforced stone foundation with a poured concrete floor, new windows, boiler, cement clapboard, and new kitchen countertops. The main level features radiant heating, an open-concept living and dining area, a modern kitchen, and the primary bedroom with an ensuite full bath. It also includes a large bonus room with its own egress, perfect for a mudroom, office, studio, or playroom. The second floor offers two additional bedrooms, a unique bathroom, and a large attic space with great potential to be finished. Outside, the yard boasts beautiful stonework and plenty of flat, green space for gardening or activities. The property is also within walking distance to the country store, bank, restaurants, and yoga studios. You can rest easy knowing all the heavy lifting has already been done!

7 Cross St, Newfane

$715,000

3 Beds ⋅ 4 Baths ⋅ 5103555 MLS

Set on 25.8± scenic acres, this 3-bedroom, 3½-bath historic barn conversion offers long views across meadows to the surrounding hills within walking distance of Putney Village. It is a rare Putney combination: genuine privacy & room to explore, w/ village shops, food, arts, Putney Central School, and the town pool nearby. This property features approximately 2,300 sq ft of living space, with 595 addit'l finished sq ft in the walkout lower level. Exposed timber framing, hardwood and tile floors, and abundant natural light give the open living spaces warmth and character. A brick fireplace with a stove insert anchors the great room. The kitchen features a vaulted ceiling, granite center island, custom mahogany & ash cabinetry, and a generous walk-in pantry. A brick-floored mudroom adds practicality, with a convenient powder room and second workspace. A bright office/den has broad views, an ideal setting for work or creative pursuits. The 1st floor en suite opens to a private deck and includes a spacious tiled bath w/ soaking tub, separate shower and walk-in closet. Upstairs, two charming bedrooms share a full bath with tub. The walkout lower level includes a finished room for more living space. Double doors open to the backyard for an easy connection to the outdoors. An exercise room, sauna, and full bath with shower complete the finished area. A workshop provides room for tools and projects. An expansive deck extends the living space for entertaining. A firepit set among the stone walls of an old barn foundation creates a memorable place for evenings. The open fields offer ample room for a cross-country ski loop, snowshoeing, gardening, and play. Within the wooded portion of the property are a small old apple orchard and a secluded access point to a pond connected with the surrounding wetlands. Much of the acreage is protected by a conservation easement by the Vermont Land Trust, helping preserve the open fields, woodlands and rural character. Showings begin 8/8/26.

106 Westminster Rd, Putney

$769,900

4 Beds ⋅ 3 Baths ⋅ 5103550 MLS

Discover one of Putney Village's most distinctive properties. A beautifully converted 1909 brick schoolhouse that was transformed into a remarkable residence. Rich in architectural character, this 4-Bedroom, 2.5-Bath home showcases soaring 12-foot ceilings, oversized historic windows, exposed brick, hardwood floors, and expansive open spaces filled with natural light. The upper two floors offer a spacious and flexible 4-Bedroom, 2-Bath residence featuring a farmhouse-inspired contemporary kitchen with stainless steel appliances, two generous living areas, abundant storage, and individual mini-splits in every bedroom. An operational wood-burning fireplace with a brick alcove adds warmth and charm. The 1,800-square-foot first floor includes four oversized rooms, a half bath, and separate access, providing exceptional flexibility for a home office, art studio, gallery, workshop, wellness practice, or other uses permitted through the Village District approval process. A history of creative and professional uses highlights the property's versatility. Set on 1.09 acres, the grounds include raised garden beds, unique naturally intertwined trees, a spacious deck, two-car open carport, and parking for approximately six vehicles with room to expand. Additional features include a standing-seam metal roof, steam radiator heat, 200-amp electrical, updated plumbing, broadband internet, public sewer, and private water. Enjoy the convenience of sidewalks to the library, general store, restaurants, and Putney's vibrant arts community. Putney Town Forest is just 5 minutes away, Brattleboro is 10 minutes, Amtrak's Brattleboro Station is approx. 15 minutes, Interstate 91 is just minutes away, Mount Snow is about 50 minutes, and Bradley International Airport is approx. 90 minutes away. A truly rare opportunity to own a landmark Vermont property offering architectural beauty, modern comfort, and exceptional flexibility in one of southern VT most charming village settings.

4 Signal Pine Rd, Putney

$699,000

7 Beds ⋅ 5 Baths ⋅ 5103523 MLS

A rare opportunity for a family retreat or investment property! This unique offering includes two beautifully updated homes with direct snowmobile trail access and just minutes from Mount Snow. Both homes were extensively remodeled in 2014, including new roofs, windows, and doors, and each includes a private hot tub. With an excellent rental history, this property is ideal as a family compound, vacation getaway, or income-producing investment. The expanded A-Frame features 4 bedrooms, a loft, 3 bathrooms, and 2,142 square feet of living space. The charming Chalet offers 3 bedrooms, a loft, 2 bathrooms, and 1,267 square feet of living space. Whether you choose to enjoy both homes yourself or live in one and rent the other, this is an exceptional opportunity in one of Vermont's premier four-season destinations.

633 635 Rte 100th Hwy, Dover

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