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

$99,000

5101763 MLS

Discover the perfect blend of privacy, natural beauty, and convenience with this exceptional 6.4-acre parcel featuring river frontage in the heart of Southern Vermont. Tucked away in a peaceful setting, this unique property offers a rare opportunity to enjoy the serenity of nature while being just a short walk to both Jamaica State Park and the charming Village of Jamaica. Spend your days hiking, biking, kayaking, fishing, or simply relaxing by the river. Jamaica State Park is just steps away, while the village offers a restaurant, local market, and year-round community events. The property also enjoys easy access to Stratton, Bromley, Magic, and Mount Snow, making it an ideal base for four-season recreation. Surrounded by mature trees and abundant wildlife, this parcel offers the privacy and tranquility that make Vermont so special. Whether you're looking for a peaceful retreat, recreational property, or a long-term investment, opportunities like this are increasingly hard to find. Riverfront acreage within walking distance of both a quintessential Vermont village and one of the state's most beloved parks is truly a rare offering. No engineering or permitting has been completed on the property. Buyers are encouraged to perform their own due diligence regarding potential development and suitability for their intended use. If you've been dreaming of owning a piece of Vermont where privacy, recreation, and small-town charm come together, this remarkable property is ready to inspire your next adventure. The Seller's estate is in the process of obtaining the required License to Sell, which is expected to be issued within 30 days.

Worden Road, Jamaica

$35,000

5101723 MLS

Nice building lot located in the Two Brook community, conveniently situated near Haystack Golf Course and just minutes from skiing, golf, lakes, and snowmobiling. This attractive parcel offers a peaceful setting with common land bordering the rear of the property and a stream flowing through the lot, adding to its natural appeal. Power, public water, and public sewer infrastructure are available nearby making this an excellent opportunity to build your Vermont getaway or year-round home. The property is ideally located for enjoying all that the Deerfield Valley has to offer, with easy access to outdoor recreation in every season. The Davis Brook Association fee is $75 per year for a vacant lot and $595 per year once a house is built. The Cold Brook Fire District fee is $75 per year for a vacant lot. A sewer hookup fee of $7,500 applies, followed by an annual fee of $1,443 once a house is connected.

8 Two Brook Rd, Wilmington

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 5101689 MLS

10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort and less than a mile from Honeypie Restaurant and Rawsonville Market, the location offers easy access to the mountain, local favorites, and everything the area has to offer. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while quality construction and thoughtful details are evident throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for-full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property available 494-498 Goodaleville Road - MLS#5101688. Showings begin 7/24.

564 Goodaleville Rd, Jamaica

$1,450,000

5 Beds ⋅ 4 Baths ⋅ 5101688 MLS

10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three finished levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Extensive improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all three buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a self-contained one-bedroom apartment with SMEG appliances, in-unit laundry and private hot tub. Below is a large heated storage area and screened porch. The vintage barn has been stabilized and restored with parking and EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and welcoming front porch complement the setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Less than a mile from Honeypie and Rawsonville Market and only minutes from Stratton Mountain Resort. Listing agent is related to seller. See neighboring property MLS # 5101689. Showings begin 7/26.

494-498 Goodaleville Rd, Jamaica

$519,000

3 Beds ⋅ 3 Baths ⋅ 5101601 MLS

A wonderful Colonial home in Dummerston Village Vermont. Classic layout with a huge primary bedroom with double closets, 2 additional generously sized bedrooms and a full bath on the second floor. The first floor has a large family room, dining room, a full bath with laundry, and a lovely 1/2 bath. Freshly updated with a new roof, new Anderson windows, new high efficiency furnace, whole house air conditioning, remodeled kitchen with all new LG appliances, remodeled bathroom with new tile floors. Light and bright! It’s perfect!

56 Park Laughton Rd, Dummerston

$136,000

5101508 MLS

Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a true turnkey opportunity. A storage shed provides convenient space for outdoor gear and supplies, while a seasonal brook meanders through the property, adding to the peaceful setting. Enjoy the sights and sounds of nature with exceptional privacy yet remain less than two miles from Vermont Route 30 for easy access to nearby towns and recreation. Set equally between the bases of Stratton or Mount Snow - be at either lodge in 25 minutes! Currently equipped with water accessed from a new pump and generator-powered electricity. This property is ready to enjoy immediately while offering plenty of potential for future plans. Whether you're seeking a quiet camping retreat, a hunting camp, or a future homesite, this special property offers the peace, privacy, and simple pleasures that define the Vermont lifestyle.

182 Partridge Ln, Jamaica

$209,900

3 Beds ⋅ 2 Baths ⋅ 5101481 MLS

Here's a 3 bedroom, 2 bath home in Bellows Falls that's been fully renovated and is ready for someone to just move in and enjoy. No projects! All done for you! The front and side porches are a nice touch! The location can't be beat: you're right in town, close enough to walk to shops, restaurants, and everything else downtown Bellows Falls has going on. This one would suit a first time buyer, someone looking to downsize, or anyone who wants a home that's already updated and easy to live in. 7 Underhill Ave is worth a look.

7 Underhill Ave, Rockingham

$235,000

3 Beds ⋅ 2 Baths ⋅ 5101448 MLS

Set on 2.2 wooded acres in Marlboro, this 3-bedroom, 2-bath Cape offers 1,410 square feet of living space and plenty of classic Vermont character. The main level features a spacious kitchen and dining area, a comfortable living room with a brick fireplace and hearth, a first-floor bedroom, full bath, and convenient laundry hookups. Two additional bedrooms and a second full bath are located upstairs. Outside, the level and gently sloping grounds provide room to garden, relax, or enjoy the surrounding woods, a lovely haven for nature and wildlife viewing. A detached two-car garage offers extra-large covered parking with valuable storage space above, ideal for vehicles, toys, or business equipment. Additional highlights include fiber-optic internet availability, a private spring water source, and multiple heating options, including wood and pellet stoves. Conveniently located along Route 9 with easy access to Brattleboro and Wilmington, this residential/commercial property is ready for its second owner to make it their own.

2022 Rte 9, Marlboro

$200,000

5101445 MLS

Start your winter project now! This amazing 3 story Victorian right in the middle of one of our sweetest villages, is begging for a return to glory. You can't beat the construction, the multilayered woodwork, amazing windows, original fireplace mantels and fronts! There is a lot to do here, but the end product will be breathtaking. Currently set up as 4 apartments, with a 3rd floor bonus, but is perfect for multigenerational living. Listed as 1 bedroom apartments, because there are walk thru bedrooms, this 25 room home has doors and hallways that connect and encourage the flow originally intended, but instead of servants maybe a nanny. Cash or construction loan. Please be qualified for a construction project before requesting a viewing.

23 Main St, Rockingham

$690,000

5 Beds ⋅ 4 Baths ⋅ 5101430 MLS

Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while the covered front porch invites you to enjoy your morning coffee, curl up for a lazy afternoon, or take in the Fourth of July fireworks. Additionally, two decks provide ample space for lounging, dining, and more. Inside, the home offers a variety of spaces designed to foster togetherness and relaxation. Gather around the fire in the cozy family room for game nights, or retreat to the den for some quiet time with a good book. The great room is perfect for accommodating the entire gang, while the downstairs recreation space, complete with a pool table/ping pong and foosball, promises endless entertainment. With five bedrooms and several bonus rooms, everyone can enjoy their own private retreat. A Vermont room upon entry to the lower level provides storage for coats, boots, gear, and more. The original structure is complemented by an 840 square-foot permitted addition, which includes a two-car garage, deck, great room, and one of the bedrooms and bathrooms. This home is ideally situated close to town, allowing for easy access to shops, restaurants, village events, and public transportation. It's also just a stone's throw from Harriman’s Reservoir, where you can indulge in boating and swimming. Whether you envision this as your primary residence or vacation getaway, "Pipe Dream" has everything you need. Its prime location offers easy access to Mount Snow Resort and the Hermitage Club for skiing and snowboarding, as well as Mount Snow and Haystack public golf courses. Consider making this extraordinary house your next dream home.

57 Castle Hill Rd, Wilmington

$399,000

2 Beds ⋅ 2 Baths ⋅ 5101312 MLS

Privately nestled at the end of a secluded drive, this quintessential Vermont retreat offers extraordinary privacy and serene mountain views in every direction. Set on a beautifully landscaped parcel with mature trees and an expansive lawn, the property exudes peace and timeless New England charm. The home features 2 bedrooms, 1.5 bathrooms, generous storage, and a detached two-car garage. A classic Vermont barn, currently serving as a recording studio, provides exceptional flexibility for creative pursuits, a workshop, or additional recreational space. Ideally located just minutes from ski areas, shopping, and Grace Cottage Hospital, this is a rare opportunity to enjoy the beauty, serenity, and convenience of Southern Vermont living.

254 Lawrence Dr, Townshend

$299,000

13 Beds ⋅ 8 Baths ⋅ 5101276 MLS

Bring your vision to this unique property filled with opportunity! Offering approximately 13-15 bedrooms, this expansive home was formerly operated as a care facility and has most recently served as a residential property. With the appropriate approvals, it may also offer potential for conversion to a multi-family residence. Many of the bedrooms feature their own attached bathrooms, ranging from private half and full baths to rooms with individual sinks. The home is heated by two oil furnaces, with a propane boiler serving the third floor and two pellet stoves providing supplemental heat on the first floor. Outside, you'll find two spacious decks that are perfect for entertaining, relaxing, or enjoying Bellows Falls' local parades. While the property is in need of TLC and updating, its generous size, flexible layout, and abundance of living space create an exceptional opportunity for investors, developers, or buyers looking to restore a truly distinctive property. Bring your imagination and discover the possibilities!

99 Atkinson St, Rockingham

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