Windham County Real Estate

**Discover the Charm of Windham County, Vermont**

Nestled in the heart of southern Vermont, Windham County is a picturesque region that perfectly blends natural beauty, rich history, and vibrant community life. Known for its rolling hills, lush forests, and pristine waterways, this county is a haven for outdoor enthusiasts and those seeking a serene lifestyle.

Windham County boasts a diverse range of activities year-round. In the warmer months, residents and visitors alike can explore the stunning trails of the Green Mountain National Forest, indulge in kayaking on the Connecticut River, or take in the breathtaking views from the summit of Mount Wantastiquet. As the leaves turn in autumn, the county transforms into a canvas of vibrant colors, making it a prime destination for leaf-peeping and photography.

Culturally rich, Windham County is home to charming towns like Brattleboro, put on the map by its thriving arts scene, eclectic shops, and delightful eateries. The annual Brattleboro Literary Festival and the vibrant local farmers' markets are just a few examples of the community's commitment to celebrating creativity and local culture.

Education and community are at the forefront in Windham County, with a variety of schools and programs that foster lifelong learning. The sense of belonging here is palpable, with friendly neighbors and a welcoming atmosphere that makes everyone feel at home.

Whether you’re looking to settle down, invest in a vacation property, or simply explore a new area, Windham County offers an enchanting blend of nature, culture, and community that is hard to resist. Come and discover why so many have fallen in love with this hidden gem in Vermont!

Newest Listings in Windham County

$575,000

5114115 MLS

This Historic Brick Building locally known as the Flat Iron Building due to its unique architecture offers endless possibilities. Located in the heart of the village of Bellows Falls. It has high visability and ample access to parking. Whether you are seeking a residential project, studio office space, retail or hospitality space, this property is ready to fulfill your goals. Each of the spacious light filled floors have soaring ceilings, separate electric and the 3rd floor has its own heating system. Recent improvements include updated bathrooms, new windows, roof & new hot water heaters. The ground floor space is rented to The Flat Iron Cooperative Cafe & Coffee Shop. Bellows Falls village is the quintessential marketplace with unique shops, dining, galleries, village farmers market and a historic railroad station with Amtrac service to NYC.

51 Square, Rockingham

$275,000

3 Beds ⋅ 1 Baths ⋅ 5114102 MLS

Just right! All spiffed up, shinny and ready to move right in. Sweet aging in place home on one level, level back yard, and minutes from grocery stores, hospital and Memorial Park! Just starting out? 3 bedrooms gives you room for expansion, hobbies or an aging parent. This affordable home should go most programs, has lots of light, and is a perfect beginner home. Check it out and start a new chapter; leave the rentals behind and invest in your future!

43 Winter St, Brattleboro

$368,000

4 Beds ⋅ 2 Baths ⋅ 5114079 MLS

Welcome to this lovingly maintained country property situated on 5.5 acres in Whitingham, Vermont. Offering a wonderful combination of open pasture, wooded acreage, and privacy, this property has so much to offer. The two-story home has been thoughtfully cared for by its long-time owners and features abundant natural light throughout the main living level. A delightful sunroom provides additional living space with direct access to the deck, perfect for enjoying the peaceful surroundings. A walk-out basement adds flexible space with access to the front yard. Outside, you’ll find beautiful open fields, wooded areas, and a spacious two-story barn in excellent condition, complete with electricity and versatile space for storage, vehicles, hobbies, or potential equestrian use. A two-car garage with storage above is located across the road. Additional highlights include a new septic system installed in 2024, two water sources consisting of a drilled well and an original spring-fed system with an updated metal cistern, and a whole-house generator for added peace of mind. Enjoy the privacy and peaceful surroundings of country living, just five miles from downtown Wilmington. Conveniently located near Mount Snow, Harriman Reservoir, Lake Raponda, rivers, hiking trails, and golf courses, offering endless opportunities for four-season recreation. With its inviting home, beautiful acreage, useful outbuildings, and picturesque Vermont setting, this is a property offering room to live, grow, and enjoy country living for years to come.

1287 Wilmington Cross Rd, Whitingham

$139,000

2 Beds ⋅ 1 Baths ⋅ 5114039 MLS

Finally! An affordable bit of Vermont! Claim it as your own....either enjoy this older mobile home, or replace it with another or a tiny home...log cabin? Sitting near the road and utilities, it is easy to get to on a snowy ski day. The 4.6 acres runs back to Old County road and is a rolling landscape for nature walks and camping out. Choose either Mount Snow or Okemo for your day trip skiing...or hike the Pinnicle Trail only minutes away. Southern Vt has a lot to offer and this is just the starting point.

133 Valley Cemetery Rd, Athens

$2,625,000

5 Beds ⋅ 8 Baths ⋅ 5114037 MLS

Discover a rare opportunity to complete a spectacular custom timber-frame residence on 25 private acres in the heart of Southern Vermont's premier four-season recreation destination. Ideally situated adjacent to the Haystack Golf Course and The Stack Restaurant, just minutes from the exclusive Hermitage Club and Mount Snow Resort, this partially constructed home offers an exceptional combination of privacy, natural beauty, and incredibly close proximity to world-class skiing, golf, and year-round outdoor adventure. This impressive residence showcases beautiful timber-frame craftsmanship, soaring ceilings, dramatic architectural details, and expansive windows that bring the surrounding Vermont landscape indoors. With much of the home's construction already completed, the next owner has the exciting opportunity to select the finishes and personal touches that will make this remarkable property their own. The thoughtfully designed floor plan envisions approximately 7,000 square feet of finished living space across three levels. At the heart of the home, a magnificent two-story great room with a dramatic fireplace and walls of windows will create a stunning gathering space. The adjoining dining area and spacious kitchen are designed for effortless entertaining with convenient access to expansive outdoor decking and views. The main-level primary suite envisions a private retreat with a generously sized bedroom, luxurious bath, and dual walk-in closets. Upstairs, two additional en suite bedrooms will complement a dedicated office or open loft overlooking the great room. The walkout lower level adds exceptional possibilities for entertaining and relaxation, planning for a spacious recreation room, wet bar, sauna, movie theatre, and bunk room with a large full bath and storage closet. Above the oversized 2 car garage with room for ATVs or snowmobiles is a great space with another full bath providing additional flexibility for a home gym, family room, or sleeping space.

29 Mountain Rdg, Wilmington

$129,000

5114033 MLS

INVESTORS, LANDLORDS & OWNER-OCCUPANTS - HERE’S YOUR OPPORTUNITY! Whether you’re looking to expand your rental portfolio, create two income-producing units, or live in one unit while the other helps offset your mortgage, this two-unit, up-and-down multifamily property is ready for its next chapter. The heavy lifting has already begun! The current owner has completed the deconstruction, removing all drywall and taking the interior down to the studs, creating a true blank canvas for your vision. Building permits were issued for the deconstruction work already completed. Additional improvements have been made throughout the property, including replacement of the existing chimney with an insulated stainless steel chimney, as well as upgrades to the roof, heating, and electrical systems. The first-floor unit has its existing systems in place, while the second-floor unit will require systems to be installed as part of the renovation. Outside, enjoy a nice, flat yard and plenty of paved parking. With much of the initial demolition already completed, you can focus on designing and finishing the property to fit your investment goals. Bring your contractor, bring your vision, and bring your plans - this clean slate is ready for its next transformation! Come take a look and see what you can create.

139 Frost St, Brattleboro

$395,000

3 Beds ⋅ 2 Baths ⋅ 5114026 MLS

Privacy, space and location! This Vernon home truly offers the best of both worlds. Set back from the road with a paved driveway and tucked into a beautiful wooded setting, this 1700 + sq ft, 3-bedroom, 2-full-bath home offers the peace and privacy you desire while keeping Brattleboro and I-91 just minutes away. Step inside and you immediately appreciate the light, bright interior, abundance of windows with very pretty views, light paint colors, gorgeous hardwood flooring and charming arched doorways. There is a spacious eat-in kitchen and an inviting living room with a woodstove, creating the ideal place to unwind. Oil baseboard heat throughout, with multiple zones, adds comfort and efficiency. The floor plan is wonderfully flexible. One bedroom and a full bath are conveniently located on the first floor, ideal for one level living, guests, or a home office. Upstairs are two very large bedrooms and another full bath. The walk-out basement is great space for storage, hobbies, a workshop, or even conversion back to the original garage space. Enjoy the convenience of being so close to Brattleboro, shopping, dining, and entertainment while taking advantage of some of Vernon's attributes: lower taxes, school choice for grades 7-12, no zoning and the great recreation center and pool. Private, spacious, flexible, and convenient! Showings by appointment only.

606 Franklin Rd, Vernon

$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

$69,500

5113775 MLS

Lovely wooded building site in the Dover Hills not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. Backs up to a 250+ acre property for great privacy to the rear, with easy access to snowmobile trails, easterly view potential, and a 4 bedroom septic design in place.

11 Ledge Rd, Dover

$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

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