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$535,000
3 Beds ⋅ 3 Baths ⋅ 5086258 MLS
Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, après ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more!

14 High Top Rd Unit B124, Wilmington
$439,000
3 Beds ⋅ 2 Baths ⋅ 5085682 MLS
Tucked away in plain sight, this beautifully maintained three bedroom, two bath ranch offers the perfect blend of privacy, comfort, and convenience on a 1.1 acre lot in Westminster, Vermont. Step inside through a welcoming mudroom with ample closet space, leading into a thoughtfully updated kitchen featuring an island sink and new granite countertops perfect for both everyday living and entertaining on the weekends. The open concept kitchen, dining, and living area is the heart of the home, showcasing cathedral ceilings and a cozy wood-burning stove set within a classic brick fireplace. Hardwood floors run throughout, adding warmth and continuity. The spacious primary suite includes a private ensuite bath and walk in closet, while two additional bright bedrooms and a second full bath provide plenty of space for family or guests. A separate family room offers even more flexibility, filled with natural light and ideal for gatherings or relaxation. Enjoy peaceful mornings on the front porch watching the sunrise or unwind on the private back deck overlooking scenic local vistas, your very own apple trees and a prime gardening opportunity should you like growing your own food. The outdoor firepit and grilling area make it easy to host and enjoy the beauty of the surrounding landscape. A two-car attached garage with automatic doors ensures convenience year-round, especially during Vermont winters. Downstairs, a massive dry gorgeous basement offers endless possibilities whether for storage, a workshop, or future finished space. This hidden gem is ready to welcome you home, come see it for yourself.

3669 Us Route 5, Westminster
$253,000
2 Beds ⋅ 1 Baths ⋅ 5085393 MLS
This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Price increase reflects work done to reinforce roof structure. If you have been looking for a true Vermont getaway, this property delivers!

51 Golding Rd, Windham
$499,000
4 Beds ⋅ 2 Baths ⋅ 5084477 MLS
Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort. The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine floors and a cozy wood-burning fireplace, delivering that classic Vermont feel. The primary suite with its own bath, along with two additional bedrooms, are located on the main level for easy living. The lower level expands the living space with a workshop, a recreation room complete with an indoor hot tub, and direct walkout access to the backyard. A fourth bedroom and a versatile bonus room provide additional flexibility for guests, a home office, or hobbies. The community offers an indoor pool for year-round enjoyment and a outdoor tennis court. Whether you're seeking a full-time residence or vacation getaway, this home is ready to deliver a mountain lifestyle at its best.

1229 Sheldon Hill Rd, Wardsboro
$399,000
4 Beds ⋅ 2 Baths ⋅ 5083153 MLS
Now Offered at $399,000! Exceptional Value Near Mount Snow & Stratton. Classic Vermont Home with Stunning Hilltop Views – Minutes from Mount Snow & Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout Pond, and access to the VAST snowmobile trail network, the property is perfectly positioned for skiing, hiking, boating, snowmobiling, and year-round recreation. Filled with natural light, the home features warm wood floors, large windows that capture the surrounding scenery, and a spacious 15' x 24' patio overlooking the private backyard, an ideal setting for relaxing or entertaining after a day of adventure. Thoughtful updates provide comfort and peace of mind while preserving the home's timeless Vermont character. The renovated kitchen features granite countertops and modern cabinets, while Andersen vinyl windows improve energy efficiency throughout. Improvements include a generator hook-up and switch, roof replaced in 2014, high-efficiency furnace installed in 2015. A 12' x 30' storage shed offers space for outdoor equipment, tools, or a workshop. Whether you're searching for a full-time residence, a weekend retreat, or a four-season getaway, this property offers an exceptional opportunity to own a classic Vermont home in an outstanding location at an attractive value. Listing agent related to the seller.

137 Stratton Arlington Rd, Wardsboro
$334,000
1 Beds ⋅ 1 Baths ⋅ 5082738 MLS
Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation from skiing and snowboarding in the winter to hiking, mountain biking, and exploring in the warmer months. The existing 1 bedroom cabin with an additional loft space offers a warm and inviting atmosphere with classic country appeal, surrounded by the natural beauty that makes Vermont so special. A standout feature of the property is the newly constructed 30x36 garage, offering ample space for vehicles, equipment, or workshop use. Electric has already been brought in and the concrete floor has tubing for 3 zone radiant heating. Above, a spacious unfinished area provides exciting potential for future living space perfect for a guest suite, studio, or rental opportunity. Whether you're seeking a full-time residence or a Vermont getaway, this property combines charm, functionality, and a great country location close to outdoor adventure and beloved mountain towns.

1511 E Dover Rd, Wardsboro
$639,000
3 Beds ⋅ 2 Baths ⋅ 5082327 MLS
Gorgeous home with so many recent upgrades! Beautiful kitchen with newer updated appliances, baths, roof, windows, flooring, well pump, mini splits, high efficiency propane combo unit for heat and hot water, new pavement, three car detached garage, woodshed, fenced in doghouse area and so much more! This is truly MOVE IN READY! These are just a few of the items this homeowner has done to improve the property. The home offers a walk out basement with patio and outdoor firepit area to gather with friends and family! This home is truly a gem to show! Large front deck to take in the local ridgeline views throughout all four seasons. The property is also surveyed with two additional lots with state approved wastewater permits already on file should you want to build additional homes in the future, sell off or keep them for privacy and future use. Access to miles of trails directly from the home. Just a short drive to Mount Snow, Stratton, Bromley and Magic Mountain Ski Resorts. You’re also within walking distance to the center of town, post office, library and general store.

198 E Hill Rd, Wardsboro
$999,000
6 Beds ⋅ 5 Baths ⋅ 5082229 MLS
STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or accessory dwelling, each with its own entrance, creating versatile possibilities for expansive residential living, multi-generational housing, a vacation retreat or investment opportunity with three rentable units. The home features six bedrooms, plus a loft, and has been thoughtfully updated with new kitchens, renovated bathrooms, new windows, roofing, wide plank wood flooring, and all new mechanical systems installed in 2022-2023. An extra-large two-car garage provides abundant storage. Located in close proximity to Grafton’s well-known village destinations—including the Grafton Cheese Company, Grafton Inn, Phelps Barn, MKT Market, Grafton Trails & Outdoor Center, and the Nature Museum—the property offers convenient access to local shops, dining, recreation and skiing. With a strong rental history and extensive updates, this turn-key property presents unique opportunities and turn-key living in the heart of historic Grafton.

151 Townshend Rd, Grafton
$250,000
2 Beds ⋅ 1 Baths ⋅ 5082153 MLS
Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can also enjoy small-town charm with Easy access to local amenities, shops, and scenic views. Subject to seller finding suitable housing.

429 Vt Route 30, Newfane
$599,000
4 Beds ⋅ 4 Baths ⋅ 5082001 MLS
Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with a dedicated office space and attached garage offers over 3,000 square feet of living space. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment from winter skiing and riding to relaxing summer evenings on the deck. Inside, the home features a bright open floor plan with 10-foot ceilings on every level and wood flooring throughout. The main living area flows effortlessly from the kitchen to the dining space and into a warm, inviting sitting area anchored by a wood stove ideal for relaxed gatherings or an energetic game night with friends. The second floor offers a spacious primary suite with an ensuite bath, two additional bedrooms, a full bathroom, and a dedicated office space. A fully finished lower level adds versatility, complete with a beautiful fireplace, generous space for entertaining, and large sliders that open directly to the backyard. Outdoor living is equally impressive. An oversized front porch with an attached gazebo creates a welcoming first impression, while the expansive back deck off the dining room is perfectly sized for outdoor dining, cookouts, and comfortable patio furniture. The private yard offers space to unwind, entertain, and enjoy the peaceful surroundings in every season. Outdoor recreation is right nearby, including hiking, swimming, paddleboarding, and fishing at Grout Pond, along with the extensive backcountry mountain biking at the Stratton town forest or Stratton Recreation Center. You can also enjoy tennis, pickleball, or a swim at the neighborhood recreation center.

556 Saw Mill Rd, Wardsboro
$715,000
4 Beds ⋅ 3 Baths ⋅ 5081734 MLS
Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details are evident throughout: antique brick walkway, a side-hall layout, blind-arch entryway, fanlight transom, wide pine floors, 12-over-12 windows, and an original central cooking hearth complete with an iron crane and concealed baking ovens. What truly distinguishes the Woolley House is its remarkable versatility for today's professional lifestyle. A converted carriage barn offers three separate private office suites with garden views and exterior access, creating an ideal environment for remote professionals, entrepreneurs, consultants, creatives, or anyone operating a home-based business. Whether you need dedicated workspace for multiple household members, private client meeting areas, or room to grow, the flexibility is exceptional. Paired with fiber-optic internet service, the property delivers the connectivity modern professionals demand while offering comfort and character impossible to find in any conventional office setting. The main residence is equally impressive. The lower level features a custom marble kitchen, formal dining room, three-quarter bath, laundry, and two gracious sitting rooms. Upstairs, four bedrooms, two updated bathrooms, a lounge, a finished loft, and a library retreat offer generous, well-appointed living space. Porches at the back of the house offer three-season enjoyment. A large attic provides significant storage space or potential additional use. Outside, mature perennial gardens, a bank of beautiful rhododendrons, and one of Windham County's most admired hosta collections create a peaceful and private setting.

587 Vt Route 121 E, Grafton
$769,900
4 Beds ⋅ 4 Baths ⋅ 5081610 MLS
New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post & beam architecture and stained glass windows. The open kitchen & dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area - pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.

5 Hillwinds N, Brattleboro
$460,000
3 Beds ⋅ 2 Baths ⋅ 5081124 MLS
This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set on 5.65 acres of bright, sunny land, the property includes a greenhouse and is bordered by a picturesque stone wall along a private road. Nestled in the country village of Jamaica, it is surrounded by wooded areas teeming with wildlife, yet conveniently located just 20 minutes from four major ski resorts and close to Jamaica State Park, which offers excellent hiking and camping options. While the home requires some updating, it provides a perfect blend of rural tranquility and accessibility to Vermont's attractions.

57 Oak Ln, Jamaica
$700,000
6 Beds ⋅ 3 Baths ⋅ 5080865 MLS
Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and year-round recreation. Inside, the chef’s kitchen is both stylish and functional, featuring a farmhouse sink, generous walk-in pantry, and a sunlit eat-in area that opens to a screened porch that's perfect for hosting and relaxing. A formal dining room includes a custom Vermont live-edge farm table (conveying with the sale), while three inviting living spaces provide flexibility and comfort, including a spacious main living room with a wood-burning fireplace and a separate TV room. The home offers versatile living options with several bonus rooms ideal for home offices or guest accommodations, along with a well-appointed mudroom designed for all-season gear and a dedicated laundry room accented with rustic barn board finishes. Bathrooms have been tastefully updated with distinctive details such as tiled showers, glass block, marble countertops, stone vessel sinks, and a soaking tub, each space thoughtfully designed with its own character. Outdoors, enjoy multiple areas for gathering and unwinding, including a patio with an above-ground plunge pool. The expansive land invites exploration, whether snowshoeing or cross-country skiing right from your backyard. Additional highlights include a large antique barn, a detached four-car garage, and a charming studio guest cottage complete with a kitchen and full bath, making it ideal for visitors or potential rental income. This is a rare opportunity to own a distinctive Vermont farmhouse offering privacy, space, and four-season enjoyment, all within minutes of premier skiing and outdoor adventure.

5 William Mundell Rd, Newfane
$329,000
2 Beds ⋅ 1 Baths ⋅ 5079827 MLS
This storybook log cabin is the kind of place you picture when you think "perfect Vermont getaway." Tucked in the middle of town, everything you want is right here, and Mount Snow resort is just over a mile away. Whether you’re chasing powder days, snowmobile/summer trails, or just a cozy escape, this spot makes it easy to do it ALL. On the MOOver public transportation route to get you around town, a stroll from your doorstep to local restaurants and shops, or hit the Valley Trails and snowmobile trails just around the corner. Convenience meets charm in the best way. Step inside and you’re instantly wrapped in warmth. A wood burning stove sets the Vermont vibe, while the open living and dining space, with vaulted ceilings, natural light, and rich wood floors, keeps things airy and inviting. The cabin features two generously sized bedrooms, an updated bath, a perfect sized kitchen, featuring a new dishwasher. Additional improvements include a new deck, newer water heater and newer full size washer/dryer. This turnkey, easy to maintain home in a premier location is ready for you to start enjoying from day one. It’s the perfect mix of rustic character and modern comfort. Cozy, efficient, and effortlessly charming, this is your basecamp for four season fun, whether you’re here for weekends, the full season, or forever.

274 Vt Route 100, Dover
$399,000
4 Beds ⋅ 2 Baths ⋅ 5079328 MLS
Open House on Sunday is CANCELED! Lovingly shaped over generations of ownership, this is one of those special properties where the setting, charm, and character come together in a way that simply cannot be replicated. Set on 1.10 acres along a woodland creek, this property shines with natural beauty and Vermont charm. A stream-fed pond adds to the tranquil setting, while old stone walls, mature trees, butterfly gardens, and timeless perennial plantings create a landscape that feels both thoughtful and historic. A true old Vermont barn stands proudly on the grounds, while a heated, inground pool offers the perfect place to float and unwind in complete serenity. The home itself is cozy yet spacious. The eat-in kitchen features a granite countertop, built-in cabinetry, and a walk-in pantry with a laundry area. The large living room is anchored by a wood-burning fireplace with an intricate hearth, built-in shelving, a bay window, and rustic wooden floors. The main level also includes a bedroom, a full bath, a private rear office ideal for remote work or creative pursuits, and a den with its own wood stove and access to the back deck. Upstairs, the primary bedroom looks out toward the mountains, offering a peaceful start and end to each day. Two additional cozy bedrooms with wood floors and a ¾ bath complete the upper level. Outside, the barn provides ample storage for wood, tools, hobbies, animals, or whatever your rural vision may hold. Additional features include a large, flat yard, a one-bay garage, a pool shed, and solar panels for energy efficiency. This property is truly unique, set on a gentle hillside with the sounds of birds and the creek as your backdrop, while still offering wonderful convenience with an easy walk to the village country store, park, and library. Mount Snow and Stratton Resorts are just a short drive away. The current owner has completed an extensive list of improvements and thoughtful updates, ensuring the home is ready for its next chapter.

405 Main St, Wardsboro
$319,000
2 Beds ⋅ 2 Baths ⋅ 5078951 MLS
Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a comfortable layout designed for easy living. High-speed Fidium Fiber internet adds modern convenience, making this home ideal as a full-time residence, weekend getaway, or investment opportunity.

3185 Higley Hill Rd, Marlboro
$619,900
3 Beds ⋅ 2 Baths ⋅ 5078071 MLS
Nestled in a postcard perfect riverfront setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Property is being offered furnished and turn key! Set on over two park like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle. Inside, you’ll find a spacious eat in kitchen with abundant counter space and cabinetry perfect for gatherings and everyday living. Flexible living areas include multiple options for relaxing and entertaining, plus a second floor space ideal for TV viewing or a home office. A finished bonus room above the attached two-car garage provides excellent guest overflow or creative studio space. The partially finished basement features a comfortable family room for additional versatility. The home offers three bedrooms, including a convenient first-floor en suite primary. Step out onto the back deck and take in breathtaking views of the river as it gently flows below. A private walking trail winds along the riverbank to the far end of the property, enhancing the serene, retreat like feel. Additional highlights include a charming carriage house with many potential uses and the peace of mind of a whole house generator. Home is also being offered mostly furnished and ready for its new owners. Located just a short distance to town amenities, this remarkable property captures the very best of Vermont living. OPEN HOUSE SATURDAY AUGUST 15th 11-1pm

300 Rte 121, Grafton
$625,000
4 Beds ⋅ 2 Baths ⋅ 5078011 MLS
This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas brick fireplace adds warmth to the living room, while the mudroom includes a built-in bench for added functionality. The lower level, with direct outdoor access, includes a family room, laundry area, and open space ready for your finishing touches. Located near VAST trails, this move-in-ready home is perfect for year-round living or a weekend ski retreat, offering easy access to Vermont’s outdoor adventures in every season.

239 Valley View Rd, Dover
$339,000
4 Beds ⋅ 3 Baths ⋅ 5077737 MLS
Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to return it to a spacious home with 4-bedrooms, or start your own thriving business venture. The building's furnace keeps the winters warm and the summers with central air conditioning ensure year-round comfort. This property features plenty of parking, making it ideal for commercial use or family gatherings. A true highlight is the large, historic waterwheel barn, providing a space with endless potential for creative projects or storage. If you’re a handy person, the barn is a perfect opportunity for a workshop. Whether you're looking to settle into a quiet country home or embark on your next business adventure, this property is a rare find in picturesque Southern Vermont. Don’t miss your chance to own a slice of Vermont. Schedule a showing today and explore the possibilities! There are 4 pictures that are virtual renovations of rooms in the house.

6795 Vt Route 100, Londonderry
$1,498,500
7 Beds ⋅ 5 Baths ⋅ 5077331 MLS
Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town’s blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ventures. A separate barn includes a woodworking shop. In recent years, pastureland surrounding the home and pond was reclaimed for grazing goats, restoring the agrarian rhythm of the property. Wildflowers and apple trees scatter the fields. A three-quarter-mile hike through the wood reveals a cool swimming hole. Additional woodland trails invite walking, snowshoeing, and foraging for berries, mushrooms and fiddleheads. Timberland Farm is a legacy holding, and very private, yet within easy reach of Stratton, Bromley, Magic Mtn. and Okemo. 17 miles from Manchester and 26 miles from Rutland Airport. 3 h from Boston and 4 h from New York. No showings through May 16th, 2026. Showings are by APPOINTMENT ONLY. Do not drive up the driveway to view the property. Home is owner-occupied and surveillance is in effect.

4669 Vermont Rte 100, Londonderry
$728,000
3 Beds ⋅ 3 Baths ⋅ 5077225 MLS
A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both comfort and accessibility in mind, this contemporary chalet features direct shuttle service from your driveway, ample parking for guests, and a private backyard bordering forest. Enjoy easy access to nearby hiking and biking trails, along with strong curb appeal in a peaceful setting. Inside, the main level offers a spacious open floor plan with natural woodwork and abundant light throughout. The upscale kitchen includes custom hickory cabinetry, stainless appliances, natural wood island, walk-in pantry, and laundry. A wood-burning fireplace with stone hearth anchors the living space, while the dining area opens to a rear deck with hot tub. A large screened-in porch provides ideal year-round entertaining space, complemented by an updated half bath and a newly designed mudroom entry with cubbies and hidden storage for gear. Upstairs, the primary suite features a second fireplace and full bath, along with two additional guest bedrooms and a third bath. Additional improvements include energy-efficient direct-vent heating. Enjoy all the benefits of Bears Crossing amenities — including outdoor pool, clubhouse with fitness area, ping pong, pool table, tennis courts, and shuttle service — at a fraction of typical ownership costs. A rare blend of privacy, convenience, and true ski-home access.

15 Bears Den Rd, Dover
$325,000
3 Beds ⋅ 3 Baths ⋅ 5076783 MLS
Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home showcases exposed original beams, wide pine floors, and extensive natural woodwork — the timeless charm you would expect from a property of this vintage. The layout features a vaulted great room with wood-burning fireplace, vaulted dining area off the updated kitchen with stainless appliances, main-floor bunk room, second-floor primary suite, an additional guest bedroom with overflow sleeping loft, and three full bathrooms. A spacious mudroom with cubbies and closets provides excellent storage for winter gear. Additional improvements include an insulated crawlspace with vapor barrier, durable metal roof, efficient direct-vent propane Rinnai heaters, and tasteful upscale country furnishings — offered for turnkey enjoyment. An attractive price point for those seeking Vermont character, year-round recreation access, and small-town convenience without breaking the bank.

34 Main St, Wardsboro
$579,000
3 Beds ⋅ 2 Baths ⋅ 5076580 MLS
Owners willing to consider offers. Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the exterior setting. Inside, the updated interior showcases warm woodsy design with a vaulted living room and natural woodwork throughout. Large updated windows provide abundant natural light, complemented by a cozy wood-burning stove. The upscale kitchen features stainless appliances and flows into a spacious dining area and large deck — ideal for entertaining. The main level includes a bedroom and full bath. Upstairs offers a generous guest bedroom and loft sleeping area sharing a full bath with tiled shower and soaking tub. The fully finished lower level provides a family room perfect for overflow sleeping, games, or media space. Functional mudroom entries on both the main and lower levels make four-season living easy, with the lower level leading to a covered porch and outdoor hot tub — the perfect place to relax and take in the scenery. Beautiful furnishings are included for true turnkey enjoyment. Nearby snowmobile trails, hiking, biking, lakes, shopping, dining, and multiple ski options make this an ideal four-season retreat with tremendous rental potential.

68 Ellis Brook Rd, Dover
$235,000
2 Beds ⋅ 1 Baths ⋅ 5076241 MLS
Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard perfect for easy outdoor access. Recent updates include a new furnace, toilet, updated ceilings and lighting, fresh laminate flooring in the living room and bedrooms, a rebuilt chimney and fireplace, new windows and slider door, exterior paint, and a metal roof. A 8x12 gardening shed provides extra storage for tools and outdoor gear. Unwind in the fenced backyard by the firepit and enjoy the soothing sound of a distant brook. Just 2 miles from downtown Wardsboro, offering a country store with gas station, library, skate park, church, and post office - everything you need within easy reach. House is located 10 minutes from Mount Snow and 20 minutes to Stratton ski areas.

3153 Vt Route 100, Wardsboro
$8,200,000
6 Beds ⋅ 10 Baths ⋅ 5076041 MLS
Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape—ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home’s elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities,

557 Trager Rd, Jamaica
$335,000
5 Beds ⋅ 3 Baths ⋅ 5075630 MLS
Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat, ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property’s timeless rural appeal.

1033 Burrington Hill Rd, Whitingham
$798,000
4 Beds ⋅ 4 Baths ⋅ 5075626 MLS
Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all. Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops and restaurants of Wilmington and Lake Whitingham, this property offers year round adventure. Inside, the home is warm and inviting with natural wood trim, stone accents, and thoughtfully designed spaces for gathering. The main living area centers around a handsome stone fireplace, while the kitchen features generous workspace, custom cabinetry, and a layout ideal for entertaining après-ski. Bedrooms are well-proportioned and private, including a spa inspired bath with soaking tub and glass shower that feels like a boutique retreat. Bathroom floors have been updated with radiant heat. The lower-level playroom is a standout feature, perfect for hosting guest with a cozy gas fireplace, ample lounge space, and a wet bar that makes movie nights, game days, and ski weekends effortless. Outdoors, enjoy the sounds of the brook from the yard, relax in the hot tub after a day on the slopes, and take advantage of the additional storage shed for gear and toys. Town Rental Permit in Place with a history of rental income.

41 Two Brook Dr, Wilmington
$799,000
5 Beds ⋅ 3 Baths ⋅ 5075625 MLS
Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and ample parking. The farmhouse style home is fully updated and features an open concept floor plan with large dining/mudroom area, renovated kitchen with granite counters and stainless appliances, a formal dining room which could also serve as a play room or overflow sleeping, large bright living room with gas fireplace and brick hearth, main floor full bath, 4 spacious bedrooms upstairs as well as a second full updated bath, a large walk up attic that could be finished for even more space, a finished lower level with family room and tv area, a private second apartment space with lower rear entry including kitchenette with dining, and large 5th bedroom, and great income potential rented separate or as part of the whole. Home generator for peace of mind. Ideal for almost any buyer looking for their Vermont retreat.

32 Old Town Rd, Dover
$320,000
3 Beds ⋅ 2 Baths ⋅ 5075506 MLS
First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for!

39 Atwood St, Brattleboro

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