Refine Search
Sort by
2745 Bonnyvale Rd, Guilford
$475,000
5049450 MLS
This property is arguably one of the most extraordinary pieces of land of its size in southeastern Vermont. With 106+- acres; The view from the top of the 6-acre field is nothing short of spectacular with sweeping extensive views & beautiful sunsets. Peace and tranquility abound. Nature abounds here, with the northern property line marked by an ancient, magnificent stone wall that separates Guilford and Brattleboro. If those walls could talk, what stories they could tell! In spring, you will know when the honey locust trees bloom on Star Dust Hill; the fragrance drifts through the air—it's truly magical. Established as part of Kindness Farm circa 1785, the property holds traces of history waiting to be discovered as you explore its ecologically diverse acreage. The land features a long road frontage, and power and internet are available at the street. Access to town is via well-maintained roads. This would be a perfect spot for equestrians to live out their dreams. The dark night sky is excellent for stargazing, and the property boasts hundreds of feet along the clear, cool waters of Broad Brook. In the neighborhood is The Bonnyvale Environmental Education Center. Easy access to downtown Brattleboro with a bucolic setting. A little over 2 hours to Boston and 3.5 hours to NYC, 35 minutes to Mount Snow.

2745 Bonnyvale Rd, Guilford

Lake Hill Rd, Whitingham
$475,000
5062093 MLS
A once-in-a-lifetime chance to own the “Gates Lot”, 36 acres on private Laurel Lake in Southern Vermont! Tucked away on this 17-acre spring-fed lake—reserved only for landowners—you’ll find peace, quiet, and endless recreation. Paddle out at sunrise, cast a line from your own shoreline, swim in the clear waters with loons calling in the distance, or relax at your own private dock. No motorboats, just pure Vermont serenity. This expansive property offers a mix of open meadow, mature woods, and generous lake and road frontage, with multiple potential building sites and possible subdivision (with proper engineering and permits). The VAST snowmobile trail crosses the property, providing direct access to miles of winter adventure right from your doorstep. Held in the same family for 100+ years, the property’s meadow even played host to a community golf course. Perfectly situated on a public road, you’re only 20 minutes to Mount Snow, minutes to Wilmington, and close to I-91 and Bradley Airport. For bigger water adventures, nearby Harriman Reservoir offers miles of boating and water skiing. Build your dream retreat, create a family compound, or simply invest in a breathtaking slice of Southern Vermont paradise.

Lake Hill Rd, Whitingham

111 Jockey Hollow Rd, Dover
$475,000
5040373 MLS
Set on 47.87 picturesque acres in East Dover, Vermont, this striking timber-framed barn offers a rare blend of craftsmanship, open land, and mountain lifestyle just minutes from Mount Snow and The Hermitage Club. With open land and sweeping mountain views, the property is ideally suited for a private estate, equestrian retreat, or recreational escape. The custom Timber Framed barn features a classic cupola, vertical wood siding, and a standing seam metal roof, all thoughtfully designed to complement the surrounding landscape. Utility infrastructure, including underground power, a waste water permit for a 4 bedroom house, and well are already in place, laying the groundwork for future development. Whether you're seeking a basecamp for outdoor adventures or envisioning a legacy property to build your dream home, this offering combines rural beauty with convenient proximity to skiing, golf, dining, and village amenities. A unique opportunity to own a significant piece of Vermont just a short drive from resort life.

111 Jockey Hollow Rd, Dover

430 Huckle Hill Rd, Vernon
$468,000
6 Beds ⋅ 3 Baths ⋅ 5060510 MLS
Welcome home! This inviting property offers the perfect blend of privacy and comfort. Nestled in a peaceful wooded setting, surrounded by classic stone walls and a year-round stream, this home provides the Vermont lifestyle you’ve been dreaming of! Inside, the main level features gleaming hardwood floors with radiant floor heat and an open-concept layout with vaulted ceilings. The bright kitchen offers granite countertops, stainless steel appliances, a breakfast bar, and space for a kitchen table. The adjoining dining area easily accommodates a large table for gatherings. The living room slider opens to a Trex deck overlooking a spacious backyard. The primary bedroom includes a private bathroom, while the two additional bedrooms share a second full bath. There is also a finished walk out lower level/basement expanding your living space. This space includes a second full kitchen with granite counter tops, a large family room, 3 bedrooms with spacious closets, a full bath, and laundry room. Double doors open to a private patio. Making this level ideal for an in-law suite, extended family, guests or, with the separate entrance, a rental space. Request a tour today and make this beautiful property the next place you call home!

430 Huckle Hill Rd, Vernon

18 Quail Ct, Wilmington
$465,000
3 Beds ⋅ 2 Baths ⋅ 5088610 MLS
Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large windows, natural woodwork throughout, a kitchen with stainless appliances and breakfast bar, a spacious dining area open to the living room with gas fireplace and brick hearth, a main floor bedroom and full bath as well as a large mudroom for all your gear, 2 upstairs bedrooms including a large bunk room with great closet space, as well as a second full bath recently renovated, a finished walkout lower level with games, additional sleeping space, and ample room to spread out. There is also a large storage and utility room for seasonal storage or owner lock out space. There is a garage shed outside for snowmobile, a fire pit, and large entertaining deck. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management.

18 Quail Ct, Wilmington

28 Country Club Rd, Dover
$465,000
4 Beds ⋅ 3 Baths ⋅ 5045499 MLS
Often rented so book ahead. Owners open to offers. Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment. Featuring a large vaulted living room with exposed wood paneling and beams, fireplace with brick hearth, spacious dining area, breakfast bar to the updated kitchen with granite counters, a main floor bedroom and full bath, a private suite in the lower level, 2 additional guest bedrooms and a third full bath, a large family room with walkout access to the yard, nice size deck for entertaining, mudroom entry for great gear storage, covered front porch, storage shed, fire pit, ample parking, and more. This one won't last long!

28 Country Club Rd, Dover

1d Brookside Village Way Unit M22, Dover
$464,000
2 Beds ⋅ 2 Baths ⋅ 5077820 MLS
Amazing trailside, completely renovated end unit opportunity at Mount Snow. This is a beautiful and bright 2 bedroom, 2 bath unit, located adjacent to the ski-on/ski-off trail for absolutely the easiest access you can enjoy. Each unit has a ground floor ski locker to stow your gear, and then you are only a half flight up to make for easy access after a day of skiing. Enjoy the spacious living space with stone floor to ceiling wood burning fireplace, entry mudroom area with cubbies, new flooring throughout, new kitchen with breakfast bar, appliances, custom cabinets, and granite counters, southern exposure for great natural light through the many additional end unit windows, and covered deck for enjoying the Vermont scenery, overlooking the ski trail. Ample space for guests with a main floor primary suite with full updated bath and tiled shower, and a guest bedroom with second updated full bathroom. Less obvious features include a newly updated heat and hot water system, updated washer and dryer, and great closets for owner storage. The ski trail is directly adjacent to this building for ski-in/ski-out access. The newly updated amenities building has indoor and outdoor pools, a full gym, separate owner and renter hot tub areas, locker rooms, basketball court, wood and trash, and an on site management company allowing for downtime, not upkeep.

1d Brookside Village Way Unit M22, Dover

624 Boyd Hill Rd, Wilmington
$464,000
6 Beds ⋅ 4 Baths ⋅ 5040302 MLS
Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s kitchen outfitted with high-end appliances and plenty of space for preparing memorable meals. After a day on the mountain or by the water, cozy up around the wood-burning fireplace in the inviting living room, designed for après-ski lounging. With six generously sized bedrooms and four full bathrooms, there’s room for everyone to spread out in comfort. The layout is ideal for multi-generational gatherings, ski weekends, or summer getaways. Located in between Mt Snow and Lake Whitingham this home is a true four-season haven—whether you’re carving powder in winter, hiking or boating in summer, or enjoying foliage and fresh air in between. The property has a septic design for 4 bedrooms, but the house has 6 bedrooms as evidenced by the property cards from both 2019 and 2024. The septic has not failed.

624 Boyd Hill Rd, Wilmington

157 Newfane Hill Rd, Newfane
$462,500
3 Beds ⋅ 3 Baths ⋅ 5096005 MLS
Welcome to a home with a story. Originally the 1787 residence of local blacksmith Marshall Newton, this property has been a cherished family retreat for the last fifty years. One of only two original settlements on Newfane Hill that are still there. It’s a place with "old world" charm—like centuries-old wall paneling —but also a new 2025 standing-seam roof and extensive insulation upgrades. This is a property with a lot of soul. The heart of the home is the bright living room, which flows into a charming office perfect for any creative spirit. The main-floor bedroom offers easy living, while two guest rooms await upstairs. Outside, you’ll find stone walls, perennial gardens, and enough land to explore or even subdivide. After years of being a deeply loved home, it’s ready for the next generation to move in, update, and make it their own. Enjoy the peace of a quiet country road while staying less than 10 minutes from wood-fired pizza at The Fat Crow and the Newfane Store with a great local deli. Whether you’re heading to the slopes of Mt. Snow or commuting from Boston or NYC, this is Vermont living at its finest. Sellers must find suitable housing.

157 Newfane Hill Rd, Newfane

136 School Marm Ln, Townshend
$460,000
3 Beds ⋅ 2 Baths ⋅ 5092871 MLS
OPEN HOUSE Sunday 6/7/26 1-3PM. Live every day like you're on vacation. Ideally set on 4± acres with sweeping views and minutes from town, this beautifully maintained contemporary cape offers comfort, convenience, and charm. Enjoy private evenings on the expansive deck taking in spectacular sunsets and views to the ski mountains. Inside, the thoughtfully designed three-bedroom, two-bath home features an open-concept living area with vaulted ceilings, wall-to-wall sliding doors, and abundant natural light. Recent updates include lovely concrete countertops, Vermont plank flooring, New Zealand wool carpeting and refreshed baths. The main level also features a bright bedroom, full bath, and spacious room currently used as a den but suitable as a large first-floor bedroom. Upstairs, a scenic landing captures the view and creates the perfect reading nook or home office, leading to another bath and a generously sized bedroom. A full, walkout basement provides exceptional potential for expansion, whether you envision a family room, fitness space, workshop, or gear storage area. Originally two separate parcels, the property offers ample road frontage and room for additional building. Outside find open meadows, established perennials, mature trees, and detached garage. Located on a fully town-maintained road just minutes from Route 30, this home provides easy access to all the area has to offer. Start your winter mornings with coffee overlooking the ski slopes and return after a day on the snow to relax by the cozy propane fireplace. Located within 30 minutes of several major ski areas, this property is ideal for year-round recreation. The vibrant community of Townshend features schools, a hospital, pharmacy, post office, library, full-service market, and beloved local events including the Pumpkin Festival and Grace Cottage Fair Day. A perfect primary residence, vacation getaway, or investment opportunity, this special property delivers Vermont living at its finest.

136 School Marm Ln, Townshend

167 Peck Ln, Westminster
$460,000
3 Beds ⋅ 3 Baths ⋅ 5087841 MLS
Privately set along a quiet gravel road in desirable Westminster, this distinctive, character filled home offers a truly unique Vermont living experience, nestled within a peaceful, nature-filled setting surrounded by mature plantings, milkweed, and established ornamental trees. Rich in character and warmth, the property provides true privacy while being just minutes to I-91, local shops, and the Putney Co-op. Inside, the home is spacious and welcoming, with a stunning central fireplace that serves as a natural gathering place. A wood stove behind adds both charm and efficiency, with a thoughtfully designed rear entry for easy wood loading—keeping the main living spaces clean and comfortable (a must see). The first floor features an open layout with a kitchen, dining, and living area, along with a half bath and convenient first floor laundry. Upstairs are three nicely sized bedrooms, a full bath, and pull-down attic access. There are two staircases—one on each side of the home for convenience, and an enclosed "catwalk" leads to the finished accessory dwelling unit above the garage. Designed for year-round comfort, the home includes multiple heat sources for colder months and mini splits for summer cooling. Enjoy the outdoors from several enclosed/screened porches offering sun or shade throughout the day. The surrounding woods with trails enhance the serene setting, ideal for those seeking nature. Additional features include a two-car garage and a finished accessory dwelling unit, two Tesla Powerwalls (leased and transferable) adds peace of mind during outages and a new leach field was installed in 2016. A unique property blending comfort, character, and convenience—clearly loved and thoughtfully maintained. Once there, you won't want to leave.

167 Peck Ln, Westminster

139 Buttonwood Dr, Brattleboro
$455,000
2 Beds ⋅ 2 Baths ⋅ 5075578 MLS
BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1 mile from I-91, with ease of access to cultural & recreational opportunities, shopping, dining, & medical care. Nestled on 33 acres of pristine Vermont landscape, this premier neighborhood is thoughtfully designed, offering a vibrant community center w/ library, fireplace lounge, fitness center, full kitchen, & outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, & horseshoes—perfect for staying active & social. Enjoy the ease of HOA-managed services & a lifestyle designed for freedom & fulfillment. Each home is single-story & ADA-compliant, offering ease, accessibility, & long-term comfort. Designed w/ energy efficiency in mind, these residences feature building materials & floor plans that minimize energy usage-providing a healthier, more affordable way to live. PRICED FROM $475,000 - $585,000. HOMES OFFER at least 5 rooms – kitchen, living, dining, primary BR w/ en-suite BA, & bonus room for office/study or guest BR – 2 BA’s, & a 1-car garage. UPGRADED HOMES OFFER: 2-car garage, sunroom, expanded living & guest rms, & larger yard. Some special touches that make BME homes beautiful & comfortable: finished 1 or 2-car garage; marble & porcelain tile; radiant floor heat; porch, private backyard, patio; marble sunken-floor showers & vanities; multi-zone heat & A/C; cherry cabinetry; granite countertops; walk-in closets; high-efficiency appliances & lighting. DO NOT MISS THIS OPPORTUNITY. Even if you are not quite ready to commit, reach out right away and ask to have your name put on the waiting list!

139 Buttonwood Dr, Brattleboro

38 Snow Rd, Dover
$450,450
4 Beds ⋅ 3 Baths ⋅ 5048105 MLS
Quintessential Vermont chalet with stunning southern views over rolling meadows and distant ridgelines without a neighbor in sight. Privately nestled in a serene country setting, this sweet chalet exudes warmth and character with wood flooring, a classic fieldstone wood-burning fireplace, exposed beam ceilings, and a sunlit dining area. The main level includes a thoughtfully updated kitchen with Caesarstone countertops, stainless steel appliances, and new flooring, offering both function and style, a spacious primary bedroom, beautifully tiled bath with an oversized shower, and a convenient half bath with laundry. Upstairs, you'll find three additional bedrooms and a hall bathroom with oversized tile shower, providing ample space for family and guests. The exterior features a covered front entry, storage room for winter gear, sun deck overlooking the view perfect for gatherings and grilling, 14x7 woodshed, a detached oversized garage with a large workshop and an unfinished 24x12 bonus room ideal for future studio. The open, sun-drenched yard is accented with perennial plantings, offering a perfect blend of natural beauty. This home has been well maintained over the years with numerous improvements, roof, windows, exterior paint, fully renovated kitchen and bathrooms, and a newly installed furnace to name a few. Nice country setting yet only minutes from Mount Snow, golfing and lakes. This home is perfect for year-round living or a peaceful getaway.

38 Snow Rd, Dover

340 Tyanoga Rd, Whitingham
$450,000
5098583 MLS
WATERFRONT! WATERFRONT! 756' OF WATERFRONT!! Not only will you enjoy stunning lakefront living- you'll own part of the lake itself with this exceptional 8.3-acre parcel on beautiful Lake Sadawga. Nestled at the end of a quiet cul-de-sac, this private property offers water views and the perfect setting to build your dream home, for full-time living or a second home for quiet enjoyment. Much of the groundwork has already been completed, making it easy to bring your vision to life. This property features: drilled well already in place; underground electric service installed; septic plan; expansive 8.3 acre lot with privacy and scenic surroundings. With the essential infrastructure already in place, you can focus on designing the home you've always wanted. Don't miss this rare opportunity to own a spectacular lakefront property with the added ownership of part of the lake itself!

340 Tyanoga Rd, Whitingham

606 Old Stowell Hl, Londonderry
$450,000
4 Beds ⋅ 2 Baths ⋅ 5096078 MLS
Tucked along a country road just beyond the village, shopping center and Pingree Park, this charming cedar shake Cape combines historic New England character with remarkable energy efficiency. Thoughtfully renovated with a comprehensive deep-energy retrofit, the home offers modern comfort while preserving its vintage appeal, including exposed hand-hewn beams and original architectural details dating back more than 125 years. Extensive improvements include insulated walls and foundation, an R-90 attic, standing seam metal roof, upgraded electrical service, heat pumps for efficient heating and cooling, a rebuilt chimney with stainless liner, and a 6 kW rooftop solar array. The result is a comfortable, low-maintenance home with exceptionally low operating costs and net-zero energy potential. Inside, warm living spaces blend historic charm with modern conveniences. Updates over the years include improved electrical systems, added indows and replaced windows where needed, renovated stairs, updated fixtures, and newer appliances. A wood stove hook up adds potential for additional ambiance and supplemental heat. Outside, the property offers a spring-fed pond, mature woodland, perennial gardens, raised beds, and a stone patio with fire ring for enjoying Vermont's four seasons. Though modest in size, the setting feels expansive with neighboring open fields and woods providing a sense of connection to nature. Located in the heart of the Southern Green Mountains, the property is just minutes from Bromley, Magic, Stratton and Okemo Mountains, and countless hiking, biking, cross-country skiing, and paddling destinations nearby. Weston Village, Manchester, and Chester are all within easy reach, offering theater, dining, shopping, and year-round cultural events. An uncommon opportunity to own an adorable and highly efficient Vermont home near town where historic character, sustainability, and four-season recreation come together in one convenient location. All measurements approx

606 Old Stowell Hl, Londonderry

163 Howe Farm Rd, Jamaica
$450,000
3 Beds ⋅ 3 Baths ⋅ 5094647 MLS
***BEST AND HIGHEST DUE BY 6/23/2026 AT 5PM*** Let the sunshine in! This beautifully maintained 3-bedroom, 3-bath home features an open-concept kitchen, living, and dining area centered around a stunning floor-to-ceiling brick fireplace. Cathedral ceilings and abundant windows fill the space with natural light, creating a warm and inviting atmosphere. The spacious primary suite offers a private full bath, while two additional bedrooms and another full bath are conveniently located on the main level. A charming loft overlooks the entryway, providing flexible space for a home office, reading nook, or additional sleeping area. The finished lower level is perfect for entertaining and accommodating guests, featuring a second fireplace, movie projector with surround sound, heated radiant entryway, bonus bunk room, full bath, laundry room, and ample storage space. The kitchen is equipped with stainless steel appliances, and numerous upgrades that were completed to home in 2019. Outside, enjoy every season from the expansive deck, complete with grill, fire pit area and hot tub at ground level. Additional highlights include a durable standing-seam roof, circular driveway, and a private setting tucked back from a town-maintained road. A beautiful stone retaining wall provides excellent curb appeal and a welcoming first impression. Located in a town with no zoning restrictions and just minutes from Stratton Mountain, this property offers the perfect combination of comfort, convenience, and year-round recreation.

163 Howe Farm Rd, Jamaica

994 W Jamaica Rd, Jamaica
$450,000
3 Beds ⋅ 3 Baths ⋅ 5093205 MLS
A Rare Riverfront Investment & Lifestyle Opportunity Nestled along the banks of a picturesque river, this magical 8.5-acre property offers a unique blend of natural beauty, privacy, and income-producing potential. Surrounded by mature trees, and the soothing sounds of the water, this is a truly special retreat in Southern Vermont. The main residence was thoughtfully updated in 2015 and features 3 bedrooms, 2.5 bathrooms, and a highly efficient split heating and cooling system installed in 2023. Comfortable and well-appointed, the home serves as an ideal primary residence, vacation getaway, or investment property. Adding to the property's appeal are two exceptional off-grid guest cabins designed for the growing glamping market. The first cabin, constructed in 2019 and situated near the river, features a one-bedroom design, kitchen, loft sleeping area, and wood/pellet stove hookup, creating a memorable guest experience. A second off-grid cabin, completed in 2024, offers a one-bedroom layout with loft sleeping space, wood/pellet stove hookup, and a peaceful connection to nature. The property's income potential is substantial, with the guest cabins projected to generate approximately $60,000 annually in gross rental income, while the main home has demonstrated gross rental income of approximately $48,634 annually. Whether you're seeking a Vermont retreat, a hospitality venture, or a combination of both, this property presents a compelling opportunity with multiple revenue streams. Only 10 Min. to Stratton Mountain Resort and 20 Min. to Mount Snow Resort. Bromley and Magic Mountain within 30 min. drive. Rarely does a property combine riverfront beauty, modern improvements, off-grid luxury accommodations, and strong investment potential in such a remarkable setting.

994 W Jamaica Rd, Jamaica

300 Westminster West Rd, Rockingham
$450,000
2 Beds ⋅ 2 Baths ⋅ 5088698 MLS
Located on four acres of picturesque land, this enchanting log home is surrounded by established gardens and the soothing sounds of Barnes Brook. The property features thoughtfully situated decks, offering lovely views of the brook and allowing residents to fully enjoy the natural beauty of the landscape. At the heart of the home is a beautifully crafted stone fireplace, creating a warm and inviting atmosphere. The main floor includes a sunroom adjacent to the country kitchen, providing a tranquil space to appreciate the surroundings. Stone stairs lead to the second floor, where two dormered bedrooms share a Jack & Jill full bath with a classic clawfoot tub. A cozy room on the first floor is versatile and can be used as a guest room or office. The layout also includes a laundry and a three-quarter bath, completing the first floor. An attached two-car garage connects to the mudroom, offering convenience and functionality. The basement provides space for a workshop or a pool table and includes a fireplace for added comfort. Outdoor features comprise a paved driveway, raised garden beds, fruit trees, and an ornamental pond, enhancing the charm and practicality of the property. This country property is conveniently located within a mile from the Saxtons River Village, I-91, ski areas, and NH. Showings begin Saturday 5/16/26.

300 Westminster West Rd, Rockingham

383 S Wardsboro Rd, Newfane
$450,000
3 Beds ⋅ 3 Baths ⋅ 5088263 MLS
Steeped in local history and meticulously preserved, this immaculate 1906 schoolhouse-turned-residence is a rare find in the heart of Newfane. After two decades as a cherished family retreat, this pristine three-bedroom home is ready for its next chapter. Positioned at the scenic intersection of South Wardsboro and Grout Pond Roads, the property is a true sensory sanctuary, where the gentle murmur of Smith Brook meets lush backyard vistas. The interior is a masterclass in blending historic character with modern sophistication. At its heart lies a chef-inspired kitchen adorned with exquisite granite countertops, while the fully finished lower level offers a versatile family room, private gym, and dedicated shower. Thoughtful details abound, including oversized garage doors designed for adventure-ready SUVs. Best of all? This is a true turn-key opportunity, sold completely furnished—from the linens to the glassware—allowing you to step into the Vermont lifestyle the moment you receive the keys. Delayed showings until May 16th, with an Open House from 10-1 p.m.

383 S Wardsboro Rd, Newfane

44 Cedar St, Brattleboro
$450,000
3 Beds ⋅ 2 Baths ⋅ 5086268 MLS
Welcome to 44 Cedar St! A charming and inviting 3-bedroom home located in a highly desirable neighborhood. This home offers a bright and functional open-concept kitchen with a pantry and plenty of additional storage, flowing seamlessly into the main living space, filled with abundant natural light and a warm, welcoming atmosphere. The living room features a hearth and fireplace with a woodstove insert, perfect for cold winter days and nights. A convenient mudroom provides lots of storage space and helps keep everyday living organized. A half-bath is located on the first floor, while two additional bedrooms and a full bathroom are situated on the second floor, offering ideal flexibility for guests, family, or a home office. The main level also includes a spacious primary bedroom that enjoys direct access to a beautifully landscaped, fenced-in backyard—creating a private, peaceful outdoor retreat perfect for relaxing or entertaining. This versatile space can also function as an additional living area, studio, or flex space to suit your needs. Enjoy quiet mornings or unwind in the evenings on the screened-in front porch—an inviting extension of the living space perfect for relaxation. Outside, a charming pergola creates a delightful setting for entertaining, dining al fresco, or gathering with friends and family in a serene outdoor environment. This beautifully maintained home is situated just minutes from the Retreat Trails and Harris Hill Ski Jump, and within walking distance to downtown, offering the perfect blend of outdoor recreation, convenience, and small-town charm. Don’t miss the opportunity to make this warm, inviting, and truly special home your own! Showings will begin on Friday, May 8th, with an Open House on Saturday, May 9th from 11:00 AM – 2:00 PM.

44 Cedar St, Brattleboro

81 Chapin St, Brattleboro
$450,000
3 Beds ⋅ 3 Baths ⋅ 5082621 MLS
Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a from-the-studs rebuild in 2018, serving as a pilot for high-performance building science. It is now fully electric and fossil-fuel free, featuring : Air-to-water heat pump for heating/cooling and an Energy Recovery Ventilation (ERV) system for superior indoor air quality. The home also has a super-insulated, airtight building envelope ensuring year-round comfort and efficiency, with a durable standing seam roof equipped with solar panels. The interior honors its heritage while embracing sustainable, modern design, using eco- friendly materials: copper countertops, natural linoleum flooring, and Energy Star appliances. Modern mechanical systems and smart features throughout, you get turn-key Peace of Mind.: Every major system-from insulation to infrastructure-is new, offering a rare level of durability in a vintage home. 81 Chapin Street is more than a renovation; it’s a blueprint for the future. For those seeking environmental responsibility without sacrificing historic charm, this is a truly unique opportunity.

81 Chapin St, Brattleboro

214 Putney Rd, Brattleboro
$450,000
4 Beds ⋅ 3 Baths ⋅ 5076579 MLS
Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a bygone era. Inside, the home spans a spacious 2,756 square feet, featuring four bedrooms plus bonus room and three bathrooms that provide ample room for family, guests, or creative pursuits. While the interiors are ready for a thoughtful restoration, the home's historic character serves as a beautiful canvas for your vision. This is a unique opportunity to breathe new life into a property with significant provenance, preserving its architectural soul while infusing it with modern comforts and your own personal style.The true magic of this property lies in its setting. Imagine waking up to sweeping, picturesque views of the West River Meadows, a daily reminder of Vermont's natural beauty right from your back yard. Despite this serene visual escape, you are just a short, pleasant walk from the vibrant heartbeat of downtown Brattleboro, where local shops, dining, and community events await. This residence offers the best of both worlds: a private, historic retreat with the convenience of a walkable, connected lifestyle. There are extensive berry bushes, a vegetable garden, and perennials growing on the property. Don't miss this rare opportunity.

214 Putney Rd, Brattleboro

22 Lower Howes Rd, Wilmington
$450,000
3 Beds ⋅ 2 Baths ⋅ 5073680 MLS
Set at the end of the road and lower on the hill, this chalet-style home offers many of the features buyers consistently look for in Chimney Hill. The thoughtfully designed mudroom entry includes a custom live-edge wood bench by Vermont Live Edge, along with ski, coat, and storage racks—ideal for Vermont’s four-season lifestyle. The home features three levels of living space. The ground level includes an extra living space room, laundry area, bunk room, full bath, and access to the outdoor fire pit. The main level offers two bedrooms, a full bath, and an open-concept living, dining, and kitchen area with cathedral ceilings, an island, and sliders leading to the view rail deck. A loft provides additional flexible space for guests or entertaining totaling 3 different hangout spots! Ownership includes access to Chimney Hill’s 1,200-acre, all-season resort campus and clubhouse. Amenities include indoor and outdoor heated pools, a hot tub, arcade room, children’s playroom, members’ lounge, community room, reading nook, fully equipped kitchen for HOA member use, outdoor grill area, playground, basketball and tennis courts, and an extensive multi-use trail system supporting hiking, biking, snowmobiling, cross-country skiing, seasonal pickleball, and ice skating. Additional shared amenities include a fishing pond, lookout areas, and trail access toward Haystack Mountain.The surrounding Deerfield Valley and Southern Vermont region offer year-round recreational opportunities including skiing, golf, boating, hiking, paddleboarding, access to the Green Mountain National Forest, along with local music, festivals, breweries, distilleries, shopping, and a wide range of dining options.

22 Lower Howes Rd, Wilmington

212-214 S Pine Banks Rd, Putney
$450,000
2 Beds ⋅ 2 Baths ⋅ 5065894 MLS
Enchanting Putney Bungalow and separate studio Retreat. Tucked away in a peaceful, sun-drenched meadow, this charming Putney bungalow offers the perfect blend of privacy, nature, and character. Surrounded by mature trees, stone walls, and abundant garden space, it’s a true hidden gem just minutes from the village center. Enjoy one-level living with a cozy first-floor bedroom and full bath and laundry—ideal for aging in place or simple convenience. Upstairs, a second bedroom with skylight invites natural light and stargazing at night. Large windows throughout frame tranquil views of greenery and bring the outdoors in. A true bonus- the detached, year round two-story studio is perfect for guests, artists, remote work, or a peaceful escape. Whether you're looking for a weekend getaway, a creative retreat, rental potential or a full-time residence, this unique property offers charm, privacy, and endless inspiration. A must-see in one of Vermont’s most sought-after towns.

212-214 S Pine Banks Rd, Putney

529 Finkel Rd, Wardsboro
$450,000
2 Beds ⋅ 2 Baths ⋅ 5064326 MLS
Sage Hill offers the perfect blend of privacy and convenience, set along a scenic country road yet just minutes to groceries, gas, and skiing. This contemporary home is thoughtfully tucked back into the landscape, framed by classic stonewalls and majestic oak trees. Enter directly from the carport into a tiled mudroom with closet space, ideal for storing all your outdoor gear. The main living area features a soaring vaulted ceiling anchored by a striking fieldstone wood-burning fireplace, a cozy galley kitchen, and a spacious sunroom with its own woodstove to keep you warm on cool evenings. The home offers two en-suite bedrooms, each with a ¾ bath, plus an open loft overlooking the living room that includes built-in storage. The full walk-out basement provides excellent potential for future expansion, imagine, a family room or media space with the option to add another bathroom. Additional highlights include a woodstove connection in the basement, backyard space and a huge deck for outdoor entertaining. Sage Hill is an inviting Vermont escape with room to make it your own, all while staying close to the region’s best skiing.

529 Finkel Rd, Wardsboro

230 Western Ave, Brattleboro
$450,000
4 Beds ⋅ 3 Baths ⋅ 5062387 MLS
This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect gathering spot in winter. Hardwood floors, custom built-ins, and fresh finishes throughout give the home both charm and polish. Upstairs, the fully re-imagined attic is the showpiece. Once just storage, it now shines as the best room in the house: a spacious bedroom suite with a radiant-heated bathroom, raised soaking tub, ductless mini-split, and dormer windows framing a Japanese red maple. Three additional bedrooms on the second floor feature updated closets, built-ins, a working fireplace and new mini-splits for year-round comfort. There's also a lovely sleeping porch off the second floor and a front foyer and back mudroom. Energy-conscious upgrades include spray-foam insulation, a heat pump hot water heater, replacement windows, and a Nest thermostat, making the home as efficient as it is inviting. Close to downtown, convenient to everywhere, including the Retreat trails. Delayed showings start with an Open House, Saturday, September 27, 10am-noon.

230 Western Ave, Brattleboro

47 Ives Rd, Wilmington
$450,000
5 Beds ⋅ 4 Baths ⋅ 5033124 MLS
Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear shed. Inside is a vaulted great room with natural wood throughout, large windows for natural light, a wood burning stove with brick hearth, kitchen with breakfast bar and stainless appliances, main floor primary bedroom with en suite full bath, two guest rooms and another full bath, a first story family room recently renovated with gas fireplace, large bunk room with attached bath, fifth bedroom with half bath, and large entry mudroom for all your snowy equipment. The home offers ample space for groups, but is intimate and cozy enough for less. A true Vermont style getaway.

47 Ives Rd, Wilmington

16 W Main St, Wilmington
$450,000
5027509 MLS
Exceptional Downtown Wilmington Business, Inventory & Real Estate Opportunity A rare chance to own a thriving business along with two distinctive structures in the heart of downtown Wilmington, Vermont. This unique offering spans .65-acre lot featuring a well-established retail building, a versatile 60x30 barn, ample parking, and existing inventory all part of the enduring legacy of The Incurable Romantic, one of the town’s most beloved businesses with over 40 years of proven success. The retail building boasts five spacious rooms on the main level dedicated to retail space, along with three upper rooms and two bathrooms. With zoning approval, the upper level could be transformed into a comfortable living space or used for as the current office or storage needs. The expansive barn, currently utilized for back stock and display items, includes a garage, and the upper open “hayloft”, offering limitless potential for creative redevelopment, event space, or expanded use. Adding to its appeal are additional parking spaces, currently leased by the nearby Crafts Inn, providing convenient access and income potential. This is an extraordinary opportunity to continue the rich history of a landmark business or to bring your own vision to life in a vibrant downtown setting that attracts both locals and tourists year-round in Wilmington, Vermont.

16 W Main St, Wilmington

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

How much is your home worth?

Get instant property value now!