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

$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

8h Trailside Village Way Unit I22, Dover

$454,000

2 Beds ⋅ 2 Baths ⋅ 5113004 MLS

Slopeside living at its best at Seasons on Mount Snow! This well-maintained 2-bedroom, 2-bath condominium has been lovingly enjoyed by its owners since 2003 and has never been rented. Ideally located for easy access to the slopes, this inviting residence offers the perfect blend of mountain convenience, comfort, and resort amenities. Step inside to a warm and welcoming open-concept living space highlighted by a stunning fieldstone, floor-to-ceiling wood-burning fireplace—the perfect gathering place after a day on the mountain. The dining area and kitchen with a breakfast bar create an ideal space for entertaining family and friends. Natural light fills the home, and a private deck just off the dining area provides a wonderful spot to relax and take in the fresh mountain air. The two-bedroom layout offers privacy and flexibility, including a spacious primary suite with an ensuite bath and walk-in closet, plus a second bedroom and hall bath. Both bathrooms have received a nice refresh, including new tile. An outdoor ski locker provides convenient storage for all your winter gear, while the easy-access location makes getting to and from the slopes a breeze. Owners at Seasons enjoy exceptional recreation at the Seasons Sports Center, featuring an indoor pool, a new indoor hot tub, fitness center, game room, two lounges—including an exclusive owner-only lounge—locker rooms, and saunas. Outdoors, enjoy a seasonal in-ground pool, hot tub, dining and grilling area, and fire pit. Whether you're skiing or snowboarding in the winter, enjoying the mountains in summer, or leaf-peeping in the fall, the amenities at Seasons create a true four-season resort experience. With its prime slopeside location, generous amenities, inviting mountain interior, and rare history of never being rented, this Seasons condominium is a special Mount Snow opportunity.

8h Trailside Village Way Unit I22, Dover

$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

$55,000

5112849 MLS

Build your Vermont retreat on this oversized lot in Section B of Chimney Hill! A recent perc test indicates suitability for a three-bedroom single-family home, offering a great starting point for your plans. Enjoy full access to Chimney Hill’s amenities, including indoor and outdoor pools, a hot tub, tennis and pickleball courts, basketball, an arcade, and a trail system for hiking and exploring. Nearby boating, golf, and skiing put year-round recreation within easy reach. Conveniently located close to the Hermitage Club, Mount Snow, and the shops and restaurants of downtown Wilmington, this property offers an ideal base for enjoying Southern Vermont in every season.

123 High Top Rd, Wilmington

$499,900

3 Beds ⋅ 3 Baths ⋅ 5112846 MLS

Enjoy Vermont living in every season! This spacious 3-bedroom, 3-bath home sits on an oversized lot close to the Hermitage Club and Mount Snow, offering plenty of room to gather, relax, and unwind. Outstanding community amenities include indoor and outdoor pools, a hot tub, tennis, pickleball, and basketball courts, plus a clubhouse with an arcade and lounge. With hiking, biking, boating, golf, and skiing at your fingertips, adventure is always within easy reach. Whether you’re seeking a mountain getaway or a year-round home, this property offers space, recreation, and a convenient location to enjoy it all. The seller is open to selling the neighboring lot to the purchaser of the home. The offer is at a very fair price, and the seller is open to negotiations.

14 Hightop Rd Unit B124, Wilmington

$359,000

3 Beds ⋅ 2 Baths ⋅ 5112782 MLS

This gem is tucked away in the quiet Section C part of the super popular Chimney Hill, HOA this modified ranch style home, featuring 3 bedrooms, half and full baths, a gas fired stove in the open concept living/dining area, and a pellet stove in the Bonus Room. Careful attention to detail, landscaped gardens, Firepit, fenced in area in the back, garage/Bonus Room addition, covered porch, custom woodwork inside and out. For those who like a more rustic 'Vermonty" vibe, this is it! Stop dreaming and start living the dream! Enjoy all the amenities offered by Chimney Hill ON THE 1,200 Acre Campus with an exclusive member only Clubhouse located 2,000' up on the Hill with indoor and outdoor heated pools for year-round swimming, arcade room, après ski lounge, fully-equipped kitchen for members use, fitness room, community style hot tub, community room, playgrounds, 3 areas with tennis courts, extensive trail system, lookout, fishing pond stocked with annual kids fishing derby, seasonal pickleball and ice skating, basketball court, birchwood recreation area, and so much more! See why Southern Vermont and the Deerfield Valley are so popular, offering World Class Skiing and Shredding at Vail's Mt. Snow, and the privately owned Hermitage Club at Haystack Mt., festivals, flea markets, antiques, uniques shopping and fine dining experiences, music, mountains, boating, golf, S VT Pickleball Club, mountain biking, and so much more!

60 E Brook Xing Unit C-201, Wilmington

$189,500

2 Beds ⋅ 2 Baths ⋅ 5112756 MLS

This cozy condo faces a hillside, landscaped with beautiful mature hydrangeas. Besides beauty, the hillside offers privacy and quiet. And no headlights will shine in your windows. The seller has totally renewed the unit with a new hot water heater, newer boiler, new gas range, new microwave, new closet doors and new flooring, and it was newly painted throughout. Then it was professionally cleaned. It is ready for you to move in. Association amenities include a swimming pool, tennis/pickleball courts, basketball, hiking trails, little libraries and common area gardens. The Association takes care of all outside maintenance. Downtown Brattleboro is within walking distance. Easy living awaits you at 29 Morningside Commons.

29 Morningside Commons, Brattleboro

$135,000

5112729 MLS

Build your Vermont home on 3.25 +/- relatively level acres in Londonderry. Lot 4A Stoney Brook Road offers an appealing opportunity with a State wastewater permit in place for a five bedroom residence and power available at the road. Located in the heart of Southern Vermont, the property offers convenient access to Londonderry, Stratton Mountain, Magic Mountain and Bromley Mountain, along with skiing, hiking, outdoor recreation, local shops and restaurants, and the surrounding mountain communities. Whether you envision a full time residence, ski home or Vermont vacation home, this 3.25 acre Londonderry property combines acreage, location and five bedroom wastewater capacity with easy access to everything that makes Southern Vermont such a special place to call home.

4a 4a Stoney Brook Rd, Londonderry

$1,150,000

2 Beds ⋅ 2 Baths ⋅ 5112718 MLS

A rare opportunity to create a true Vermont family compound, this 12.5-acre property offers not only a beautifully finished home, but also two additional building lots ready for the next chapter with underground power already in place and septic permits secured, the second homesite offers the flexibility to build a separate home for family, all while taking advantage of the property’s beautiful mountain views. Built in 2023, the current residence features two bedrooms and two baths with a clean, modern mountain style and an easy open layout. Large windows frame the surrounding landscape and bring the changing seasons indoors, while warm wood floors, a stone gas fireplace, spacious kitchen, and comfortable living areas create a home that feels both refined and relaxed. Outdoor living is equally inviting, with a deck overlooking the grounds and long-range mountain scenery. For those needing exceptional garage and storage space, this property stands apart. The home includes an attached four-car garage, complemented by a brand-new detached four-car barn/garage, providing tremendous room for vehicles, recreational equipment, a workshop, or Vermont toys. Ideally located between Stratton and Mount Snow, the property offers convenient access to skiing, golf, hiking, mountain biking, dining, and everything Southern Vermont has to offer. With a nearly new home, seven total garage bays, 12.5 acres, mountain views, and a second permitted homesite already underway, this is an unusual opportunity to create a multi-generational Vermont retreat with room to grow.

92 Oakmont Ln, Stratton

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