Windham County Homes under $1 million

Welcome to Windham County, Vermont—a hidden gem nestled in the heart of the Green Mountains. Known for its stunning landscapes, charming small towns, and vibrant communities, Windham County offers an idyllic retreat for those seeking a blend of natural beauty and a welcoming atmosphere. With rolling hills, serene lakes, and lush forests, it’s no wonder that this area attracts outdoor enthusiasts and families alike.

Windham County is home to a variety of picturesque towns, each with its own unique character. From the historic streets of Brattleboro, with its eclectic art scene and bustling farmers’ markets, to the quaint charm of Wilmington, where you can explore local shops and delightful eateries, there’s something for everyone. The county also boasts a rich cultural heritage, offering year-round festivals, art galleries, and music events that bring the community together.

For those considering a move to this enchanting area, you’ll be pleased to find a diverse selection of homes available under $1 million. Whether you’re looking for a cozy cottage, a spacious family home, or a charming farmhouse, Windham County has options that cater to various tastes and budgets. Many of these homes come with breathtaking views and easy access to outdoor activities such as hiking, skiing, and fishing, making it the perfect place for both relaxation and adventure.

In Windham County, you can experience the best of Vermont living without breaking the bank. Embrace the tranquility, community spirit, and natural beauty that this remarkable region has to offer—your dream home awaits!

Newest Windham County Homes under $1 million

$339,000

2 Beds ⋅ 2 Baths ⋅ 5113651 MLS

There’s so much to love about this home! Enter through an enclosed mudroom, perfect for storing all your outdoor gear. The kitchen offers abundant storage, a dedicated baker’s counter, and a convenient breakfast bar with seating. Beautiful hardwood floors flow throughout the kitchen, dining, and living areas. The first floor features two bedrooms and two full bathrooms, while the basement adds three additional heated, finished rooms, offering endless possibilities for a home office, playroom, hobby space, or more! Step outside to enjoy the deck, perfect for grilling and dining al fresco, overlooking a flat, open yard. Plus, the home is conveniently located just down the road from the town pool and recreation area!

167 Silver Ln, Vernon

$199,000

3 Beds ⋅ 1 Baths ⋅ 5113644 MLS

Looking for an affordable home with a little personality? You've found it in this colorful 3-bedroom, 1-bath home in the historic village of Whitingham, Vt. Set on 0.10 acres along a quiet, paved street with town sewer, the home is surrounded by some of Southern Vermont’s best lakes, including Sadawga Lake and Harriman Reservoir. Step inside through the French doors that separate the mudroom from a flexible living space that can become a dining room, home office, sitting area, or whatever works best for you. The first floor also includes the full bathroom, laundry area, and primary bedroom with a walk-in closet. The kitchen features an eat-in island for casual dining and opens to a spacious great room, where a large picture window brings in plenty of natural light. Bold colors throughout give the home a fun, playful energy and make each room feel a little different from the next. Keep the color, tone it down, or make it completely your own. Upstairs, two additional bedrooms continue the home's bright and bold personality. A door off the living area leads to the fenced backyard, where you can relax and enjoy the sounds of nearby Sadawga Brook on the front porch of the shed, which can be used for storage, a workshop, or play space. Major systems have been recently updated including the well pump and pressure tank (new in 2016), furnace (new in 2021) and water heater (new in 2024). The home is just 13 minutes to Wilmington, 16 minutes to Hogback Mountain’s 100-mile view, 23 minutes to Marlboro, 25 minutes to Mount Snow, and roughly 40 minutes to Brattleboro to the east and Greenfield, Mass., to the west.

105 School St, Whitingham

$420,000

2 Beds ⋅ 2 Baths ⋅ 5113634 MLS

Tucked away in the beautiful Vermont countryside, this inviting two-bedroom, one-and-a-half-bath ranch sits on 22.65 acres in the charming town of Grafton. Surrounded by a combination of open lawn and wooded acreage, the property offers a wonderful sense of privacy and plenty of room to enjoy the outdoors. Inside, the home features a spacious living room, a kitchen with adjoining dining area, and a practical single-level layout. The primary bedroom features its own convenient half bath, while a separate utility room with first-floor laundry adds everyday convenience. The sunroom provides a lovely space to sit and take in the peaceful surroundings. The basement offers plenty of additional storage space, and the attached two-car garage provides convenient parking and even more room for storage. Step outside onto the deck to entertain friends or simply relax and appreciate the natural beauty of the property. The expansive grounds provide opportunities for gardening, outdoor recreation, walking through the woods, or simply enjoying the changing seasons. Whether you're looking for a full-time residence or a quiet Vermont getaway, this property offers a wonderful combination of comfortable living, generous acreage, and a peaceful country setting, with the picturesque villages of Grafton and Chester within easy reach. Showings start 10/12/2026

286 Richards Rd, Grafton

$335,000

3 Beds ⋅ 2 Baths ⋅ 5113619 MLS

Come take a look at this three bedroom and two bath chalet in the B Section of Chimney Hill with terrific amenities. Relax on the main level in an open concept living, dining and kitchen space, living room has a woodstove and sliders to the deck to enjoy the country side views, a bedroom and a full bath. Upstairs has two more bedrooms and a full bath. An exclusive members-only clubhouse with indoor/outdoor pools, hot tub, fitness room, arcade, kids playroom, media room, library/reading nook, kitchen area with bar, BBQ area and a playground. Throughout the complex there is a fishing pond, trail system, tennis courts, ice skating rink, hiking trails and snowmobile access. Minutes from skiing, fine dining, golfing, boating, downtown Wilmington and so much more!

19 View Rd, Wilmington

$429,000

5 Beds ⋅ 2 Baths ⋅ 5113589 MLS

There is an immense amount of space in this home. With one bedroom downstairs, 4 bedrooms upstairs, plus a family/bonus room, everyone has space of their own. The space carries over to the 2 story attached barn where both floors offer workshop and creative space. Even the basement is sprawling and usable. Enjoy Fiber internet and the most pure well water from the Westminster Aquifer. There is a new septic system and a large grassy backyard. Notable features include a pantry, an enclosed wrap-around front porch, a back stairwell off the fifth bedroom, three propane heaters and beautiful hardwood floors throughout. Enjoy being part of the Village community!

3531 Rte 5, Westminster

$999,000

6 Beds ⋅ 4 Baths ⋅ 5113557 MLS

Set among the treetops with sweeping views spanning multiple states, this Rod Williams designed classic is a sprawling 5300+ sq ft, 6 bed, 4 bath with attached 2 car garage, capturing everything there is to love about a Vermont ski retreat. Situated on 3 acres bordering community land, the property enjoys an elevated setting, exceptional privacy, expansive views including the greens at Haystack Golf Course. There is room to bring everyone together while offering plenty of space to spread out over 3 levels. Main living level designed around generous gathering spaces, soaring ceilings, expansive windows, skylights, and walls of glass opening to outdoor decks. Beautiful brick fireplace centerpiece, visible from all main living areas. Open kitchen with substantial walk-in pantry, mudroom, and laundry area. .Occupying its own wing on the main level, the primary suite is a retreat within the home, complete with spacious bedroom, sitting room, private office, large walk-in closet, and an expansive bath featuring a jetted tub, and sauna. Upstairs, private guest suite enjoys some of the home's most spectacular views.Finished walkout lower level offers four additional bedrooms, spacious rec room, another full bath with a jetted soaking tub and large shower. Separate flex room opens directly to the deck, an ideal location for a future hot tub. Generous storage areas, newer roof, easy access road, manageable driveway add practical appeal. Chimney Hill ownership includes access to an extensive collection of amenities,indoor & outdoor pools, skating, basketball, fishing pond, playground, trails, on-site management team. Short drive to downtown Wilmington, Mount Snow, Haystack, lakes, golf, and year-round outdoor recreation, this is a property that combines the character of a classic Vermont ski home with a remarkable amount of space, privacy, and views that truly steal the show.

23 Shincracker Way, Wilmington

$339,000

3 Beds ⋅ 2 Baths ⋅ 5113538 MLS

Located in the desirable Black Mountain Road area, this cozy log home includes an attached two-car garage with a workshop area, a three-season porch, and a wraparound deck. The lower level is accessible from the garage and opens into a spacious tiled mudroom. An open staircase leads to the main floor, which features three bedrooms, 1¾ baths, a living room, and a country kitchen with a dining area. The basement provides abundant unfinished space for a workshop, studio, or other creative pursuits, along with laundry, sink and a workbench. Additional outbuildings include small storage sheds. The home needs some TLC but offers worthwhile potential in a country setting, so close to town. The owners are continuing the cleanout process, and additional photos will follow. Please note that the large stones are not included.

625 Black Mountain Rd, Brattleboro

$399,000

3 Beds ⋅ 2 Baths ⋅ 5113520 MLS

Welcome to 36 Ives Road, a classic Vermont A-frame set in a quiet wooded setting just minutes from Mount Snow and a short drive from downtown Wilmington. Inside, warm natural woodwork, soaring cathedral ceilings, skylights, and abundant natural light give the home the inviting character you want in a Vermont retreat. The open kitchen, dining, and living areas create an easy gathering space, while the wood stove adds warmth and atmosphere after a day on the mountain. A loft overlooks the main living area and provides flexible space for additional sleeping, a home office, reading nook, or second lounge. Step outside to enjoy the balcony, fire pit, and peaceful surroundings, with plenty of space to slow down and enjoy the seasons. The home is being offered fully furnished, making it easy to settle in and start enjoying it right away. The location is what really ties it all together. Mount Snow is just minutes away, while downtown Wilmington offers restaurants, shops, galleries, and the charm of a historic Vermont village. In the warmer months, enjoy swimming, boating, and kayaking at Harriman Reservoir, along with miles of hiking and biking throughout the Deerfield Valley. Whether you're looking for a ski getaway, a four-season escape, or a Vermont home base to enjoy year-round, 36 Ives Road offers a relaxed setting in the heart of one of Southern Vermont’s most popular recreation areas.

36 Ives Rd, Wilmington

$489,000

6 Beds ⋅ 4 Baths ⋅ 5113514 MLS

Village living with room for possibilities! Just steps from Jamaica State Park and downtown Jamaica, this versatile home offers a wonderful opportunity to enjoy Vermont living with the added benefit of separate living spaces and potential rental income. Abutting the river, the property is currently configured as three spacious two-bedroom apartments—two with one bath and a third with two baths. Make one apartment your full-time residence or Vermont getaway while renting the others, or explore options for bringing extended family together while maintaining privacy and independence. Two apartments are currently vacant and ready for immediate occupancy. The third is home to long-term tenants who hope to stay, offering potential ongoing income. Recent improvements include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another includes a three-year-old washer and dryer along with a new dishwasher. Enjoy a location that puts outdoor adventure and village charm right outside your door. Walk to Jamaica State Park for hiking, biking, swimming, and exploring, or stroll downtown to enjoy this welcoming Vermont community. Stratton Mountain and other Southern Vermont attractions are within easy reach, making this an appealing home base in every season. Whether you envision a primary home with supplemental income, a vacation retreat with space for guests, or a future reconfiguration to suit your needs, this property offers exceptional flexibility. Any conversion or changes in use would be subject to applicable approvals. A special opportunity to make yourself at home in the heart of Jamaica!

154 Depot St, Jamaica

$489,000

5113501 MLS

An exceptional investment opportunity in the heart of Jamaica! Just steps from Jamaica State Park and the charm of downtown Jamaica, this three-unit multifamily property offers an ideal combination of location, flexibility, and income potential. Whether you’re looking to live in one unit while generating income from the others, create a Vermont getaway with rental income, or add a versatile property to your investment portfolio, the possibilities are plentiful. The property abuts the river and features three spacious two-bedroom units: two with one bath and a third with two baths. Two units are currently vacant and ready for immediate occupancy, while the third is occupied by long term tenants—offering the potential for income from day one. Consider long-term rentals, seasonal leases, or short-term rentals such as Airbnb, subject to applicable local and state requirements. Recent improvements make this an especially attractive opportunity. Updates include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another offers a three-year-old washer and dryer along with a new dishwasher. And then there’s the location! Walk to Jamaica State Park for hiking, biking, swimming, and outdoor recreation, or stroll into the village to enjoy everything this quintessential Vermont community has to offer. With Stratton Mountain and other Southern Vermont attractions within easy reach, the property is well positioned to appeal to year-round, seasonal, and vacation renters alike. Three units, multiple income possibilities, recent improvements, and an outstanding village location make this a rare opportunity to invest in one of Southern Vermont’s most desirable four-season communities.

154 Depot St, Jamaica

$465,900

4 Beds ⋅ 2 Baths ⋅ 5113479 MLS

What if your Vermont getaway was minutes from skiing, golf, hiking trails, a lake to take your boat out on and Dover’s best restaurants, yet tucked away in your own private setting? This tastefully updated ranch style, TWO UNIT home is located just 4.7 miles from Mount Snow and only 3 miles to Mount Snow Golf Club!! With three bedrooms on the main level, open concept living & kitchen, main floor laundry and a mudroom in addition to a finished lower level with its own kitchen, full bathroom, laundry and separate private entrance, this home could have income potential or be utilized as a single use property! The spacious yard sits on 1.2 acres with an expansive deck around two sides of the home and a stone patio, offering plenty of room and flexibility for year-round living or a vacation home! Stunning perennials wrap the property which bloom all summer long. The lower level has 188 square feet of interior storage; in the detached shed there is plenty of room for your outdoor equipment, ATV or lawn mower or utilize the space under the deck for kayaks and winter tires! Owners have put on a new roof in 2014, a new well pump in 2025 and maintained the property very well. Whether you're looking for a year-round home, a weekend escape or an investment opportunity, this property offers the flexibility to make it your own. Come experience the privacy, convenience, and four-season lifestyle that make this Southern Vermont location so special!

230 Valley View Rd, Dover

$289,900

5 Beds ⋅ 3 Baths ⋅ 5113467 MLS

CASH OR REHAB LOAN ONLY – PROPERTY NEEDS WORK! Ski lodge within walking distance to the Chimney Hill Clubhouse, offering 5 bedrooms, 2½ baths, and plenty of space to create your ideal Vermont getaway. Three levels include a family room with wood stove, laundry, mudroom, kitchen with island, dining area with cathedral ceiling, sunken living room with fireplace, and sliders to a multi-level deck. Natural light and woodwork add to the mountain-lodge character. Enjoy Chimney Hill’s extensive four-season amenities, including indoor/outdoor swimming, tennis, pickleball, hot tub, fitness room, skating, hiking, biking, snowmobiling, playground, clubhouse, and more. Conveniently located minutes from skiing, dining, shopping, breweries, festivals, and the Green Mountain National Forest. Property is being sold AS-IS and requires renovation. Cash sale or rehab financing required. Bring your vision and make this mountain retreat your own! This property is eligible under the First Look Initiative which expires after 30 full days on market. No investor offers until first look period expires. No offers regardless of buyer type will be negotiated within the first 7 days of listing.

3 Lightning Ledge Way, Wilmington

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