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4448 Rte 100, Wardsboro
$475,000
4 Beds ⋅ 3 Baths ⋅ 5065488 MLS
This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always maintained well by the state. Private pond with a sprawling yard. The two-car attached garage with access to both the basement and storage space above is very convenient for the colder months! Cedar exterior siding with a Brazilian rosewood oil finish, lovely hardwood flooring throughout most of the home with a walnut finish. Only two smaller rooms have carpeting. Wonderful mudroom entryway to hang your coats and boots. A surround sound system both inside and out for your enjoyment during our warmer months here in southern Vermont. This home has been lovingly cared for and enjoyed for many years! Nice concrete patio at the front of the home with custom Coolaroo shades and an additional rear deck off the back of the home with easy access through the French doors located just off the kitchen overlooking the pond. This home is a solid, well-built home with a nice layout. Very short driving distances to both Stratton and Mount Snow. Truly a hidden gem!

4448 Rte 100, Wardsboro

00 W Hill Rd S, Jamaica
$450,000
5065110 MLS
Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers significant development potential. Multiple areas throughout the property provide potential home sites with mountain views, and there is frontage available for additional points of access. Located on West Hill Road in Jamaica, VT, this property not only provides a serene and private setting but also offers convenient access to the area's many attractions. Enjoy nearby Jamaica State Park, hike, bike, and explore the West River. Take in the natural beauty of Hamilton Falls, venture to Stratton, Bromley or Magic Mountain Resorts for year-round activities, including skiing, golfing, & hiking. The charming town of Jamaica is just a short drive away, offering local shops, art galleries, and dining options. The surrounding area is rich in history, with local farms, markets, and antique shops that showcase Vermont's agricultural heritage and artisanal craftsmanship. Whether you're looking for a peaceful retreat or a base to explore all that Southern Vermont has to offer, this property presents a rare opportunity to own a piece of paradise with highly desirable features already in place.

00 W Hill Rd S, Jamaica

774 Stratton Arlington Rd, Stratton
$599,000
3 Beds ⋅ 3 Baths ⋅ 5064604 MLS
Charming Log Cabin Compound Near Stratton and Mount Snow Escape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts. The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the great room, complemented by natural wood tones, exposed beams, and cathedral ceilings that evoke classic mountain living. The kitchen and dining area flow seamlessly together, ideal for après-ski gatherings or cozy family meals. A finished lower level provides additional living and game space, perfect for entertaining or relaxing after a day on the slopes. Step outside to enjoy the covered front porch, fenced-in backyard, and raised garden beds, offering peaceful woodland views and space for outdoor enjoyment year-round. The auxiliary building adds incredible flexibility with a spacious great room, kitchen, and wood stove, ideal as a studio, or entertaining space. Below, a one-car garage and ample storage provide room for skis, snowmobiles, and all your Vermont adventure gear. This property offers the perfect blend of privacy, comfort, and proximity to some of southern Vermont’s most sought-after recreation an ideal mountain getaway or full-time home.

774 Stratton Arlington Rd, Stratton

47 Whites Hill Rd, Dover
$475,000
5063628 MLS
Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income potential. A rolling brook meanders through the heart of the property, adding tranquility and charm, while the surrounding landscape provides panoramic views that will leave you in awe, especially during peak fall foliage season. Explore miles of hiking trails, carve new paths for mountain biking, or glide through winter wonderlands with cross-country skiing right in your backyard. Whether you're looking to build your dream retreat, start a maple syrup operation, or invest in a private outdoor haven, this land is the canvas for your vision. Secluded, serene, and full of possibilities; this is more than just land; it's a lifestyle. Dover is situated in the center of southern Vermont, along the spine of the Green Mountains. There is a major ski area, Mount Snow, on its western flank. In the middle is a scenic high country that offers lovely housing developments and accessible recreation opportunities. On the east side of town is rolling farmland and open space ringed by mountains.

47 Whites Hill Rd, Dover

341 Under The Mountain Rd, Londonderry
$600,000
5 Beds ⋅ 3 Baths ⋅ 5053705 MLS
Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly spacious rooms perfect for entertaining and family gatherings. Wide pine floors, antique fireplaces, and original glazed windows add warmth and charm throughout. The main level features a large primary bedroom suite, while four additional bedrooms and a full bath upstairs provide plenty of space for guests. A cozy recreation room with a grand fireplace or the sauna is perfect for apres-ski evenings, and a separate dining building offers a private space ideal for hosting dinners or working from home as a dedicated office or studio. Outdoors, enjoy peaceful walks through the forest along an old logging road, fish or relax by your own large private pond, and take in the serene beauty of the countryside. A detached 3-car garage adds extra convenience and storage for outdoor gear or snowmobiles. Just a short drive from top ski resorts and year-round activities including hiking, biking, and nearby lakes, this Vermont farmhouse is the perfect mountain retreat.

341 Under The Mountain Rd, Londonderry

343 Haystack Rd, Wilmington
$420,000
7 Beds ⋅ 5 Baths ⋅ 5033174 MLS
An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above the garage provides extra versatility—whether for guests, family, or potential rental income. Located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Sellers is highly motivated and welcomes all reasonable offers. Property being sold AS IS.

343 Haystack Rd, Wilmington

36a Boulder Ridge Dr, Dover
$1,560,000
5 Beds ⋅ 5 Baths ⋅ 5047757 MLS
Brand new luxury townhome with breathtaking Mount Snow & Hermitage Club views. Introducing a newly built, well thought out townhome spanning over 4,300 square feet, perfectly positioned just minutes from Mount Snow and The Hermitage Club. This exquisite residence combines modern mountain living with upscale comfort, offering five spacious bedrooms and five beautifully appointed bathrooms. Step inside to an open concept living area where soaring ceilings, wide plank wood floors, and a floor to ceiling stone fireplace set a warm and inviting tone. Large windows frame panoramic mountain views, providing one of the best views of Mount Snow in the valley! The gourmet kitchen is a chef’s dream, featuring a generous island ideal for entertaining. Upstairs, the primary suite is a private sanctuary with spectacular views, a luxury spa inspired bathroom with a freestanding soaking tub, custom walk in shower, and designer finishes. Each of the additional bedrooms is spacious and bright. The walkout lower level serves as a versatile additional living space with a spacious family/media room, two additional bedrooms, and a full bath -- ideal for movie nights, games, or relaxing après-ski. Enjoy year round mountain living with a private deck with stunning, direct views, ample storage, a mudroom for ski gear, and effortless access to Vermont’s premier slopes and outdoor adventures. Buyers need to be aware that the developer is currently in a Chapter 11 Bankruptsy proceeding. Outcome and timing is unknown as of 10/9/2026.

36a Boulder Ridge Dr, Dover

56 Handle Rd, Dover
$2,395,000
6 Beds ⋅ 7 Baths ⋅ 5063234 MLS
Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler’s panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood floors and beautifully tiled baths create a warm refined atmosphere. Upstairs the primary suite offers a fireplace and luxurious bath. An additional en-suite bedroom and three more bedrooms, laundry room, and two full baths provide plenty of space for family and guests. Dual staircases, tiled entry, and both front and back foyers highlight the home’s thoughtful design. The grounds are equally impressive with a covered front porch that overlooks the sprawling south facing lawn with winter views of haystack. A serene screened veranda, back deck and stone patio with fire pit invite outdoor gatherings. An oversized-attached two car garage, whimsical children’s playhouse and an incredible post and beam barn with full lower level perfect for all your recreational vehicles complete the offering. Exquisite gardens, stone walls and meticulous land scaping surround this rare property, ideally located across from the esteemed Hermitage Inn and exclusive Hermitage Club with easy access to all area activities.

56 Handle Rd, Dover

314 Putnam Forest Rd, Grafton
$1,295,000
5 Beds ⋅ 4 Baths ⋅ 5062867 MLS
Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside. At the heart of the home is a dramatic two-story great room, offering panoramic forest views and anchored by a wood stove for cozy winter nights. Heat pumps ensure year-round climate control, while thoughtful design provides comfort across three spacious levels, including a game room, exercise area, and home office. A spiral staircase leads to a bonus loft space on the fourth floor--ideal as a studio, library, or creative escape. Step outside to your own private sanctuary: a stone patio outfitted with a sauna, hot tub, fire pit, and grill--perfect for relaxing or entertaining under the stars. The property includes a state-approved wastewater permit for a future 4-bedroom cabin, offering excellent potential for expansion or guest accommodations. Conveniently located just 3 miles from Grafton Village and within easy reach of Okemo, Magic Mountain, and Bromley for skiing, plus direct access to VAST snowmobile trails. Stay connected with fiber optic internet, and rest easy with a backup generator. The property is being offered fully furnished and enrolled in Vermont's Current Use program for tax benefits.

314 Putnam Forest Rd, Grafton

3715 Rte 11, Londonderry
$755,000
5 Beds ⋅ 3 Baths ⋅ 5061900 MLS
Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale lighting and bath fixtures. Located in the heart of ski country with views of Magic Mountain and just minutes from Magic, Bromley, and Stratton, this is a home for the outdoor enthusiast. A large pond in the backyard invites swimming, canoeing, and paddleboarding, while the expansive back deck overlooks the water--perfect for outdoor dining and entertaining. Upstairs bedrooms feature custom built-ins, and the primary suite --set in its own wing--boasts cathedral ceilings, a beautiful bath, and serene pond views. The well-planned gear room includes ample closets, cubbies, and hooks to keep outdoor essentials organized. Pet-friendly with a fully fenced backyard, custom dog cubbies, and a pet shower. Tesla EV charger included. The vintage barn offers flexible space for storage and an opportunity for another area to entertain. Live your best Vermont life in comfort, style, and natural beauty.

3715 Rte 11, Londonderry

1950 Collins Rd, Halifax
$3,800,000
4 Beds ⋅ 8 Baths ⋅ 5062504 MLS
Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on site winery, craft brewery, and champagne making facilities, this turn-key property is ideal as a private residence, retreat, or destination business. The custom log home showcases vaulted ceilings, radiant in floor heating, hardwood and stone flooring, and imported Italian tile. A chef’s kitchen and expansive 800’ wraparound deck offer the perfect space to entertain while enjoying stunning 360 degree mountain, vineyard, and valley views. The boutique vineyard supports in-house wine production, complemented by a dedicated beer brewing system and traditional méthode champenoise champagne facility perfect for tastings or exclusive label production. The event venue includes a second commercial kitchen, two custom bars, elegant restrooms, and a 7,900 sq ft stone patio with cascading fountains ideal for weddings, retreats, and celebrations. Freshly painted and impeccably maintained, this estate offers total privacy with year round recreation nearby, including Wilmington’s fine dining, Sunset Lake, and Hermitage Golf Club. Ski Reports in all directions. A rare opportunity schedule your private tour today.

1950 Collins Rd, Halifax

24 Antler Loop, Dover
$450,000
3 Beds ⋅ 2 Baths ⋅ 5025379 MLS
This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views. A sitting area upstairs connects two bedrooms, while the first-floor bedroom and living room both have sliders leading to the backyard. The beautifully landscaped yard boasts a stone walkway lined with perennials, a deck off the side door, and an oversized attached garage. The basement is 3/4 full and unfinished with a bulkhead, plus a 1/4 crawl space. Located in the desirable Dover Manor, this home is just 6 miles from Mount Snow and 7.5 miles from the Hermitage Club, with convenient access to Brattleboro and Bennington. Built and lovingly maintained by the original owner, this home combines comfort, charm, and an unbeatable setting.

24 Antler Loop, Dover

33d White Oaks Loop, Unit 38, Dover
$459,000
3 Beds ⋅ 3 Baths ⋅ 5052090 MLS
Owners will consider offers. Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and more. The recently renovated Sugar House amenities center features indoor and outdoor pools, hot tub, gym, racquetball and basketball courts, pickleball and tennis courts, locker rooms, and a network of cross-country ski trails. Inside, the townhome offers an open-concept living space with new windows, wood-burning fireplace with brick hearth, and a spacious kitchen with updated appliances, new counters, and breakfast bar. The dining area opens to an oversized private deck — ideal for entertaining and BBQs. The main level also includes a large bunk room, fully updated tiled bath, and a rustic mudroom entry with bench, cubbies, ski locker, and covered front porch. The walkout lower level sets this unit apart from typical two-story layouts, offering two bedrooms and two full baths — including an updated primary suite option — plus a bonus TV room with laundry, owner’s closet, and exterior access suitable for adding a hot tub. An updated heating system, private side yard, and adjacent babbling brook complete the setting, and with minimal effort you could have the view cleared to be a much more expansive view of the mountain and trails. A nice opportunity for privacy, amenities, and shuttle convenience just minutes from Mount Snow.

33d White Oaks Loop, Unit 38, Dover

1192 Chapel Hill Rd, Whitingham
$299,000
3 Beds ⋅ 2 Baths ⋅ 5058111 MLS
Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway. The welcoming lower level features three comfortable bedrooms, a spacious full bath with a jetted soaking tub, tiled floors, and a glass-enclosed shower, along with a convenient utility room. Upstairs, abundant natural light fills the open-concept living area where the kitchen, dining, and living spaces flow seamlessly together. A cozy wood-burning fireplace creates the perfect gathering place after a day of skiing, hiking, snowmobiling, or exploring the surrounding lakes and trails. A second full bath on the main level adds convenience for both everyday living and entertaining guests. Step outside to enjoy multiple outdoor living spaces, including a sunny second-floor deck, covered patio, established perennial gardens, and a storage shed. The mostly open lot offers space to relax, entertain, and enjoy the peaceful surroundings. Ideally located just 8 minutes from Jacksonville Village, 10 minutes from Harriman Reservoir (Lake Whitingham), 8 minutes from Lake Sadawga, and 17 minutes from Wilmington, this property provides convenient access to some of Southern Vermont's most sought-after recreation destinations. Enjoy skiing at Mount Snow and Berkshire East, boating and fishing on nearby lakes, hiking the Catamount Trail, paddling the Deerfield River, and exploring the VAST snowmobile trail network. With high-speed fiber internet available and all furnishings included, this distinctive home offers the perfect combination of comfort, character, and year-round adventure. Whether you're seeking a mountain getaway, recreational base camp, investment opportunity, or full-time residence, this turnkey Vermont property is ready to enjoy from day one.

1192 Chapel Hill Rd, Whitingham

70 Hunter Ln, Jamaica
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 5060615 MLS
Discover a truly unique four season home. In the summer, kayak and swim on a private pond. In the fall, hike the many trails that are available and enjoy the foliage. When the Winter comes, it's a ten minute trip to Stratton Mountain and afterwards, ice skate on your own back yard pond. In the spring, step outside to a private hot tub inviting you to to soak while overlooking the sprawling perennial gardens or perhaps grilling on your fabulous deck. 70 Hunter Lane, set within the private Highland Forest development in the Cole Pond community with your own private beach. Minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation, hiking biking, fishing, snowshoeing, snowmobiling and nearby skiing at three resorts. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces highlighted by two fireplaces, creating a warm and inviting atmosphere. A bonus room presently used as an art studio. Adjacent to a two car expansive garage.

70 Hunter Ln, Jamaica

27 Country Ct, Wilmington
$389,000
4 Beds ⋅ 2 Baths ⋅ 5058910 MLS
Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use trail system for biking, hiking, snowmobiling, 3 areas with tennis courts, seasonal pickleball and ice skating, year-round swimming at the Exclusive Members-Only Club House , indoor and outdoor in-ground pools, hot tub, fitness room, arcade room, small child playroom, community room, table tennis, basketball, fully-equipped kitchen for HOA members use, outdoor grill by the outdoor pool, along with a playground for young children, and members lounge. Plus, world class skiing and shredding just minutes away, golf, boating, fishing, paddleboarding, unique shops, fine dining, flea markets, festivals, music, and all the Deerfield Valley and Southern Vermont have to offer! Own this winter don't rent!!!

27 Country Ct, Wilmington

628 Townshend Rd, Grafton
$549,000
3 Beds ⋅ 3 Baths ⋅ 5060321 MLS
One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful stone hearth, and a wood-burning fireplace the perfect winter centerpiece. Bright eat-in kitchen with ample space for a breakfast table move-in ready or a canvas for your personal updates. A cozy, four-season sunroom offers additional living space and opens to a charming patio ideal for morning coffee or evening relaxation. Practical main-level features include a half bath, pantry with laundry, and a versatile dining area with room to entertain. Upstairs, the character continues: Three generously sized bedrooms, office space, and two full bathrooms. Deep windowsills, exposed brick features, and abundant natural light throughout. Additional highlights include wood and tile floors, replacement windows, and a fantastic floor plan. A large, plateau-style backyard with a sweet trail leading to a spacious open field ideal for gardening, recreation, or simply enjoying nature. A one-car garage is tucked under the sunroom for added convenience. This rare stone gem blends timeless charm with modern comfort don’t miss your chance to own a piece of Grafton history.

628 Townshend Rd, Grafton

16 Washington St, Brattleboro
$225,000
5024829 MLS
Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. Property is being offered "as is".

16 Washington St, Brattleboro

16 Washington St, Brattleboro
$225,000
5 Beds ⋅ 3 Baths ⋅ 5024828 MLS
Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. This property is offered "as is".

16 Washington St, Brattleboro

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