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70 Atkinson St, Rockingham
$500,000
6 Beds ⋅ 3 Baths ⋅ 5114348 MLS
Exquisite! Feel the life, the romance of history and the charm of an era waiting to be recaptured...Front stairs! back stairs! third floor for the maid!...bedrooms grouped around a child's dream play room. Capture the essence....tall windows, high ceilings...room to breathe...room to dance...room to love. Perfectly decorated, precisely maintained, delightfully presented. All that AND...updated in reverence to the era, but functional for those who appreciate the modern way of life. New kitchen, baths, appliances top those polished and gleaming floors. Outside is as lovely as in...with a large lazy porch off the kitchen, topped by a Juliette balcony for star gazing and enjoying the lights of the town. The lovely patio sweeps into a special garden wrapping the barn....2 stories high...First floor bed and bath allows for aging in place while guests and family have an abundance of space for visiting. Versatile with 3 kitchens, just think of all the Holiday cooking! Join the rebirth of a town loved by its residents, enjoyed by visitors, and respectful of these lovely ladies who have come back to their prime.

70 Atkinson St, Rockingham
39 Pikes Falls Rd, Jamaica
$249,000
3 Beds ⋅ 2 Baths ⋅ 5114286 MLS
Step into a piece of Jamaica Village history. Once home to the F.E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building’s commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, exposed beams, and natural light from the original storefront windows and door. A vintage interior sash window adds another unexpected architectural detail. The kitchen features sage cabinetry, granite tile counters, a pot rack, sunny breakfast area, and walk-in pantry. A cozy living and dining room offers a comfortable gathering space, while upstairs bedrooms retain original wide pine floors and vintage details. Both bathrooms have been updated, and the oil tank, on-demand hot water heater, pressure tank, and well pump have all been recently replaced. Garden beds and a painted harlequin porch floor add personality outside, while the covered porch invite you to enjoy morning coffee and the rhythm of village life. A rare opportunity to own a property with a story to tell and the potential to make it your own. Buyers who appreciate historic homes and are comfortable with a project will find opportunities to build on its existing character.

39 Pikes Falls Rd, Jamaica
43 Winter St, Brattleboro
$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
1287 Wilmington Cross Rd, Whitingham
$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
133 Valley Cemetery Rd, Athens
$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
29 Mountain Rdg, Wilmington
$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
606 Franklin Rd, Vernon
$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
50 Sugar Maple Dr, Dummerston
$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
16 Sawmill Rd, Stratton
$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
845 Hall Rd, Halifax
$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
58 Red Hawk Rise, Stratton
$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
167 Silver Ln, Vernon
$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
105 School St, Whitingham
$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
286 Richards Rd, Grafton
$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
19 View Rd, Wilmington
$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
3531 Rte 5, Westminster
$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
23 Shincracker Way, Wilmington
$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
625 Black Mountain Rd, Brattleboro
$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
36 Ives Rd, Wilmington
$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
154 Depot St, Jamaica
$489,000
6 Beds ⋅ 5 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
230 Valley View Rd, Dover
$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
3 Lightning Ledge Way, Wilmington
$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
1722 Under The Mountain Rd, Londonderry
$650,000
3 Beds ⋅ 2 Baths ⋅ 5113338 MLS
Welcome to 1722 Under the Mountain Road, a private 3.02-acre retreat in a tranquil setting surrounded by horse farms, with views of Stratton Mountain. This 2-bedroom rustic cabin is nestled in a former Morgan horse farm. Full of character, the main home features wood frame, wide plank floors throughout, with an open concept layout. The floorplan includes a full kitchen, a dining room, and a living room with a wall of windows facing the private wooded landscape. A glass-walled bedroom brings a sense of openness and creativity into the space, and a versatile loft offers space for an office, a reading nook, or extra sleeping. There are additional sleeping spaces throughout the home. The full bath completes the main home. Outside, a wraparound porch invites you to relax and take in the scenery, while a hot tub and 2 outdoor fire pits make this property a true four-season escape. A separate 1-bedroom, 1-bath accessory dwelling unit provides space for guests, extended stays, or potential rental income. A 3-bay carport offers covered parking and storage. All of this is just a short drive to Magic Mountain, with Stratton, Bromley, and the shops and restaurants of Londonderry nearby. Whether you're looking for a full-time residence, a ski getaway, or a peaceful country retreat, this property is ready for you to make your own.

1722 Under The Mountain Rd, Londonderry
180 Parsons Rd, Wilmington
$375,000
3 Beds ⋅ 1 Baths ⋅ 5113271 MLS
Come see this sweet, well-kept 3-bedroom ranch. The heart of the home is its inviting open concept living area, featuring a handsome stone fireplace with a pellet stove insert for easy fires in the winter. The fully updated kitchen has abundant Kraftmaid cabinets, an island with seating, quartz counters, and Energy Star appliances. Enjoy meals and company in the warm weather on the wrap-around deck, easily accessible from both the kitchen and living area. A hallway, a few steps up from the kitchen, leads to the three bedrooms; the primary bedroom is large enough for a king-size bed. The spacious, updated ¾ bath has a contemporary vanity and tasteful tile flooring and shower finishes. Added bonuses include a two-car garage, a shed for storage or a workspace and extra space to finish in both the attic and basement. Accented with attractive ledge outcroppings, the land - ideal for recreation and gardening- has a blend of both level and sloping areas as well as a mix of sun and shade. Caring for the home will be easier thanks to the home’s vinyl siding, newer windows, standing seam metal roof and vinyl plank flooring throughout the interior. The ideal location offers the best of both worlds: a tranquil rural retreat set on a quiet road, but only minutes to downtown Wilmington, 20-minutes to the Mt. Snow resort and close to year-round recreation on Lakes Harriman, Raponda, Sadawga, snowmobile and hiking trails and much more. All furnishings available for an additional fee. Showings start on October 11. Open House Sunday, October 11 11am-1pm, Monday October 12 10am-12pm

180 Parsons Rd, Wilmington
81 Scandia Village Rd, Wardsboro
$150,000
2 Beds ⋅ 1 Baths ⋅ 5113182 MLS
This West Wardsboro chalet is looking for someone to bring it back to life! Full of potential and ready for renovation, this property offers the perfect opportunity to create your own Vermont mountain getaway. The town lists the property as a three-bedroom, though it currently features one bedroom plus a loft, offering flexibility for future improvements. Set on a nice lot in a convenient location, you’re just 10 minutes from Mount Snow and under 20 minutes from Stratton Mountain, with easy access to skiing, snowboarding, hiking, biking, and year-round outdoor adventure. Enjoy the best of southern Vermont with shopping and dining nearby, while still having a peaceful setting to call home. Bring your vision, your tools, and a little love this chalet could become the mountain retreat you’ve been looking for!

81 Scandia Village Rd, Wardsboro
43 C Upton Rd, Dover
$1,850,000
4 Beds ⋅ 5 Baths ⋅ 5113171 MLS
The view astonishes the moment you arrive, easily one of the most impressive in the valley. Set high on 35.4 private acres, it looks directly toward Mount Snow and Haystack, with a long paved driveway creating a true sense of arrival and remarkable privacy just minutes from Mount Snow. This beautiful post-and-beam home was built for gathering, with multiple spaces that let everyone spread out without losing the feeling of being together. At the heart of the home is the soaring great room, where exposed timbers, warm wood tones and walls of glass frame the mountain view. A custom masonry fireplace anchors the room and throws impressive warmth throughout the house. The open kitchen, dining and living areas flow easily together and out toward the screened porch, deck and lawn, giving the main level an easy connection to the outdoors. The primary en suite is also on this level, allowing for true one-level everyday living. Upstairs are three additional bedrooms along with two fun loft areas that create their own hangout spaces for reading, games, or simply escaping with a book. The finished walkout lower level offers space for a home gym, another media area, a full bath and additional finished bonus rooms that can flex with changing needs. Above the attached garage, more finished bonus space offers more options for an office, studio, recreation room or overflow space. Outside is where this property becomes hard to duplicate. With more than 35 wooded acres, there is room to roam, explore and escape into Vermont. Walking trails and direct access to snowmobile trails put four-season recreation right outside the door, while the paved driveway and attached garage make everyday mountain living practical. With a main-level primary suite, multiple finished bonus spaces, extensive recreation areas and an extraordinary combination of acreage, privacy and direct mountain views, it offers minutes to Mount Snow.

43 C Upton Rd, Dover
90 Big Bend Loop, Wilmington
$599,000
4 Beds ⋅ 3 Baths ⋅ 5113132 MLS
Stunning updated and expanded chalet just a short drive out of the village of Wilmington. This home sits privately on a wooded double lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home was extensively renovated and expanded and now has tremendous unique one of a kind space featuring a gorgeous vaulted living room with exposed natural woodwork, great natural light from the large windows, a wood burning fireplace and brick hearth, upscale wood flooring throughout, a beautiful kitchen with quartz counters, stainless appliances, breakfast bar, farm sink, and tile backsplash, large dining area, wet bar and entertaining area, main floor bedroom and full bath, and large mudroom for all your gear. The bedroom level features three spacious bedrooms with two more upscale baths, including tiled showers and a gorgeous pedestal tub, as well as access to the outside. Additionally there is an overflow sleeping loft, huge upper and lower decks for outdoor enjoyment and BBQs, and ample lawn space for enjoyment no matter the season. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep.

90 Big Bend Loop, Wilmington
679 Burrington Hill Rd, Whitingham
$599,000
3 Beds ⋅ 3 Baths ⋅ 5113061 MLS
OLD BARN. NEW LUXURY. YOUR PRIVATE SOUTHERN VERMONT ESCAPE. There’s something special about a home that feels completely different from anything else—and this beautifully transformed barn conversion is exactly that. Originally an old barn, this stunning 3-bedroom, 2.5-bath home has been thoughtfully reimagined with sophisticated modern finishes, an inviting open-concept layout, and all the comforts of contemporary living both inside and out, while still preserving the character and soul of its original structure. Set on nearly 12 private acres, this is more than a home—it’s a lifestyle. Spend summer afternoons enjoying your own private pond, enjoy peaceful mornings surrounded by nature, gather with friends and family in the spacious open living areas, or simply get away from the pace of everyday life and enjoy the privacy and tranquility that Southern Vermont has to offer. An amazing opportunity to own a truly distinctive Vermont retreat.

679 Burrington Hill Rd, Whitingham
529 Coldbrook Rd, Wilmington
$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
4054 Guilford Center Rd, Guilford
$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

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