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53 Hickory Ridge Rd S, Putney
$1,475,000
7 Beds ⋅ 6 Baths ⋅ 5091196 MLS
Hickory Ridge House is a Federal masterpiece: a definitive piece of Vermont history. Elegant and expansive, the home’s soul is rooted in the 19th century, while its heart beats with 21st-century innovation. The interiors are a masterclass in "refined rustic" design, with original features such as antique wood floors, 12-over-12 windows, crown moldings, and wood-burning fireplaces throughout the home. Five spacious bedrooms are anchored by a chef’s kitchen where rough-hewn textures meet polished, modern finishes. This meticulously restored residence features a newer roof, solar panels, and a Tesla Powerwall, offering a level of energy independence rarely found in historic homes. Outside, the lush grounds are a perennial paradise of fruit trees and colorful flowers.For those seeking the ultimate family compound, or the opportunity to create an upscale, sophisticated country inn, this 1808 Federal-style estate also hosts a charming two-bedroom cottage and has operated as a successful B&B for decades. It is proudly listed on the National Register of Historic Places, which adds to the cachet without significantly impacting your ability to make improvements. Located just moments from one of the most vibrant villages in Vermont, with world-class performances at Yellow Barn and the legendary pies of Green Mountain Orchards, this isn't just a home; it’s a front-row seat to the best of Putney. More photos of the Cottage and a full prospectus are available upon request.

53 Hickory Ridge Rd S, Putney
4 Basswood Row Unit 4A, Stratton
$1,465,000
4 Beds ⋅ 4 Baths ⋅ 5107192 MLS
Experience true resort living in this luxury 4 bedroom, 4 bathroom alpine residence in Stratton’s sought after Treetop community. Designed with sweeping mountain views and seamless ski home access, this townhouse eliminates the morning scramble so you can spend your days carving first tracks and your evenings unwinding in comfort. Imagine starting your morning in a snowy winter wonderland. Step into your dedicated ski storage room to pull on warm boots and hit the slopes directly from your doorstep no loading cars or fighting for base parking. After an exhilarating day on the mountain, ski home. Drop your gear in the ski room and head to the lower level, where your private outdoor hot tub awaits on the patio. Soak in the warm waters under falling snowflakes as the sun sets over the surrounding pines. Gather in the main living area, crafted in classic Adirondack style with rich details that capture the cozy spirit of the Green Mountains. Cook holiday meals in the open kitchen, complete with premium Café Appliances and granite countertops that flows seamlessly into the dining and living spaces. Later, step onto the covered side porch to breathe in the crisp mountain air, or retreat to the lower-level family room, the ideal second living space for kids and guests to relax. Property Highlights • Trailside Access & Mountain Views: Ski right home to your door with direct sightlines of Stratton’s peaks. • 4 Private Bedroom Suites: Thoughtful multi level layout including a lower level bunk room ideal for hosting friends and family. • Primary Suite Sanctuary: Features a private balcony, walk in closet, and ensuite bath with a soaking tub. • Gourmet Kitchen: Equipped with Café Appliances, granite counters, and a central island. • Lower Level Spa & Den: Family room opening to a patio with a private hot tub. • Ski Storage & Garage: Dedicated ski entry room plus a detached garage. • Effortless Ownership: Includes shuttle service, A/C, playground and an on-site caretaker.

4 Basswood Row Unit 4A, Stratton
4 Encore Pl, Dover
$1,400,000
6 Beds ⋅ 6 Baths ⋅ 5108251 MLS
Location is key with this turnkey home - Carinthia and the Grommet surface lift are just across the street, and you can practically ski home - it doesn't get much better. This beautiful 6-bedroom, 6-bath home offers a cozy living room with a fieldstone fireplace for that après-ski warmth and over 3600 s.f. of living space. The landscaping provides patio privacy for barbecues and hot tub time for family and friend gatherings. The oversized mudroom is convenient for your year-round sporting equipment, and the spacious garage will keep your car free of snow. This home is a must-see if you want easy access to the mountain and prefer a home to a condo. Guests always love gathering around the kitchen island, and this kitchen is large enough for your group, flowing into the dining room (currently set up for recreation) through French doors. The six bedrooms are located in wings on each side of the house, including two primary ensuite bedrooms and a family guest suite. They provide complete privacy and quiet from the living areas. A full unfinished basement provides lots of storage space or potential for a finished living space. Features include central air, covered front and back porches, public sewer, low-maintenance decking, and a tremendous location for ski and snowboard enthusiasts.

4 Encore Pl, Dover
529 Coldbrook Rd, Wilmington
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 5112992 MLS
Perfectly positioned just across from the entrance to The Hermitage Club, this beautifully appointed mountain home offers the ideal balance of comfort, convenience, and Vermont charm. Whether you're heading to the slopes, enjoying a round at Haystack Golf, exploring nearby snowmobile trails, or spending the day at Lake Whitingham, this location places you in the heart of everything the Deerfield Valley has to offer. Inside, warm natural wood finishes, reclaimed barn board accents, soaring cathedral ceilings, and a dramatic wall of windows create a welcoming mountain retreat filled with natural light. The open-concept living area is anchored by a beautiful stone fireplace, offering the perfect gathering space after a day outdoors. The spacious kitchen features granite countertops, stainless steel appliances, custom cabinetry, and a generous center island that flows seamlessly into the dining and living areas, making entertaining effortless. The home offers three comfortable bedrooms plus a bonus room for additional guests or flexible living space, along with three beautifully updated bathrooms. The primary suite provides a peaceful retreat with a spa-inspired bath featuring a tiled walk-in shower, soaking tub, and quality finishes throughout. The finished lower level expands the living space with a large recreation room, perfect for movie nights, game days, or relaxing with family and friends. A two car garage offers ample room for vehicles and all of your Vermont gear. Outside, the expansive deck invites you to unwind in the private hot tub, dine outdoors, or simply enjoy the peaceful woodland setting. Whether you're looking for a full-time residence, a weekend getaway, or a four-season vacation home, 529 Coldbrook Road delivers exceptional craftsmanship, inviting living spaces, and one of the area's most desirable locations just moments from The Hermitage Club and a short drive to Mount Snow, downtown Wilmington.

529 Coldbrook Rd, Wilmington
874 Middletown Rd, Grafton
$1,350,000
5 Beds ⋅ 3 Baths ⋅ 5094211 MLS
Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions. Or perhaps it is simply the feeling of being here--a quiet sense of belonging that is difficult to explain and impossible to forget. Filled with natural light, the property has a welcoming spirit. A pond, apple orchard, perennial gardens, blueberry bushes, ancient maple trees, and historic stone walls create a landscape rich in beauty. The home sits along a quiet gravel road that forms part of one of Grafton's favorite four-mile walking loops, while trails meander through the property's 66 acres of fields and woodland. The Saxtons River traces one edge of the property. In the early nineteenth century, Major Benjamin Dwinell and his wife, Mehitable, built this home and raised eleven children here. The family prospered from the land, tending a large flock of sheep and cultivating one of the most productive apple orchards in town. By the late 1800s, Grouse Hill had begun a new chapter as a country retreat for a New York family. Over the years it has served as a boarding house, an inn, a full-time residence, and a cherished second home. Through each chapter, it has remained what it is today: a gracious and welcoming place that draws people in, encourages them to linger, and leaves a lasting impression. 22 miles from Okemo. 2 hours 44 minutes from Boston and 4 hours 19 minutes from New York.

874 Middletown Rd, Grafton
131 133, 141 Green St, Brattleboro
$1,350,000
5093440 MLS
What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very pleasant lawn space. An investment with nothing major to put on the "to-do" list. Separate 2 bedroom carriage house, with garage, would be fantastic for owner quarters

131 133, 141 Green St, Brattleboro
494-498 Goodaleville Rd, Jamaica
$1,315,000
5 Beds ⋅ 4 Baths ⋅ 5101688 MLS
4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, a high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a 1BR apartment with SMEG appliances, in-unit laundry, and a private hot tub. Below are heated storage and a screened porch. The restored barn offers parking and an EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and a welcoming front porch complement the peaceful setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Listing agent is related to seller. See neighboring property MLS #5101689.

494-498 Goodaleville Rd, Jamaica
4427 W Hill Rd S, Jamaica
$1,295,000
5 Beds ⋅ 4 Baths ⋅ 5090616 MLS
A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who return to experience this special home year after year. Inside, the expansive open-concept living areas were made for gathering after a day on the mountain, while thoughtfully designed private spaces allow everyone room to relax and recharge. Curl up beside one of two fireplaces as the snow falls outside, host movie nights in the impressive 11-foot home theater, or gather in the great room around the 90-inch TV for game day. The lodge experience continues outdoors, where four-season entertaining takes center stage. Grill and dine beneath the stars, soak in the six-person hot tub, unwind in the eight-person sauna, then end the evening around the fire pit surrounded by the peaceful Vermont forest. Every detail has been considered to create a property that feels less like simply a house and more like a destination. There is room for extended family, friends, ski weekends, holidays, and generations of memories—all with the comforts and amenities of a private mountain resort. Whether you're searching for a quintessential Vermont escape to enjoy yourself, a gathering place for family and friends, or a property with an established rental history and repeat clientele, this remarkable lodge offers a combination that is increasingly difficult to find. Arrive, settle in, and experience the Vermont lifestyle exactly as it was meant to be.

4427 W Hill Rd S, Jamaica
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
224 Cobble Ridge Rd, Londonderry
$1,250,000
5 Beds ⋅ 5 Baths ⋅ 5095311 MLS
Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations. Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace anchors the living space. The kitchen with premium appliances flows into the dining and living areas, creating an inviting setting for entertaining and everyday living. The main residence features three ensuite bedrooms, including a lower-level suite and an upper-level suite that could each serve as a primary bedroom, depending on how the home is used. Additional living spaces provide flexibility for guests, recreation, remote work, or additional sleeping accommodations. A separate one-bedroom guest cottage offers added privacy and versatility. Designed for both gathering and retreat, the property includes multiple decks, a covered porch, open meadow, and expansive fenced acreage. A three-car garage and solar power system further enhance functionality and efficiency. Conveniently located near Stratton, Bromley, Magic, and Okemo Mountains, as well as Lowell Lake, Manchester, Weston, Londonderry, and South Londonderry, the property provides easy access to skiing, hiking, cycling, fishing, golf, shopping, dining, and cultural attractions throughout the region. 224 Cobble Ridge Road presents a rare opportunity to own a private Southern Vermont retreat combining quality craftsmanship, flexible living spaces, and exceptional access to the region's four-season amenities.

224 Cobble Ridge Rd, Londonderry
364 Houghtonville Rd, Grafton
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 5095837 MLS
At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle in one of Vermont's most picturesque communities. As you arrive you are welcomed by beautifully landscaped grounds, mature perennial gardens, and a private wooded setting that creates a true sense of seclusion. Despite its peaceful surroundings, the property is just minutes from Grafton Village and within 45 minutes of several premier Southern Vermont ski resorts, making it an ideal year-round residence, vacation home, or family retreat. Offering four bedrooms, four bathrooms, and numerous living and gathering spaces, the home is perfectly suited for hosting family and friends. The well-appointed chef's kitchen features an island with seating, abundant workspace, and easy access to the home's entertaining areas. A spacious family room with a stunning stone fireplace, private bath, and loft above serves as a centerpiece of the home, while three additional working fireplaces add warmth and character throughout. A second-floor den and game room provide flexible living space for relaxation, recreation, or remote work. Outdoor amenities are equally impressive. Enjoy summer days by the inground swimming pool, tend to the gardens, or explore the surrounding landscape. For horse enthusiasts, the property includes a four-stall barn and fenced pastures. Additional features include a two-car garage, clean and spacious basement, garden shed, and abundant storage throughout. Whether you're searching for a Vermont equestrian property, luxury country home, or four-season retreat near skiing and outdoor recreation, this remarkable Grafton estate offers you the very best.

364 Houghtonville Rd, Grafton
1845 Hatch School Rd, Halifax
$1,195,000
5 Beds ⋅ 4 Baths ⋅ 5110876 MLS
Built in 2016 and set on just over 99 acres in the hills of Halifax, this striking mountain-modern home offers an exceptional combination of privacy, open land, thoughtful energy efficient design, and easy access to Southern Vermont recreation. With five bedrooms and four baths, the home provides generous space for family and guests while showcasing beautiful architectural details throughout. Inside, radiant floors provide warmth and comfort, while European-style windows that open inward bring in abundant natural light and fresh mountain air. The spacious open-concept kitchen, dining, and living areas create an inviting setting for gathering and entertaining, and a double sided fireplace that adds warmth and character to the main living space. Outside, the property features a beautiful pond, open acreage, raised garden beds, and space for chickens, offering a wonderful connection to the land and Vermont country living. A three-car garage provides excellent storage for vehicles and recreational gear, with the added opportunity to expand the space above the garage into a future apartment or guest quarters. Ideally located for year-round enjoyment, the property is within convenient reach of Mount Snow, The Hermitage Club, and Berkshire East, with access to skiing, mountain biking, hiking, lakes, and all that Southern Vermont has to offer. With more than 99 acres, a substantial five-bedroom home, modern construction, a pond, gardens, and room to grow, 1845 School Hatch is a rare opportunity to own a distinctive Vermont retreat designed for both everyday living and four-season recreation.

1845 Hatch School Rd, Halifax
1472 Carpenter Hill Rd, Guilford
$1,165,000
4 Beds ⋅ 3 Baths ⋅ 5104005 MLS
The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance: A gracious, charming house featuring a central chimney and a unique, squared-off Palladian window over the front door - one of only four known examples in Vermont. Historic Details: Five working fireplaces (including a large living room hearth with a beehive oven), and the original one-hole privy in the carriage house. Scenic Surroundings: Located across a dirt road from a lovely pond with remnants of an old barn foundation. Revolutionary Lore: An enclosed garden near the house is traditionally believed to have been a former campsite of Ethan Allen and the Green Mountain Boys. Modern Comfort: Features 21st-century plumbing while preserving its authentic character. New septic system installed in 2020. This is an unparalleled opportunity to own a property rich in history, charm, and character. A short drive to Brattleboro and everything it has to offer. Boston: 2.5 hrs. NYC 4 hrs. {Additional 30+/- acres available for an additional $250,000}

1472 Carpenter Hill Rd, Guilford
82 N Brookwood Rd, Stratton
$1,160,000
5 Beds ⋅ 4 Baths ⋅ 5086826 MLS
Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast, this propery has the features you look for in a Resort Residence, 5 bedrooms (which includes a spacious and private primary suite wing), 4 updated bathrooms, a spacious media room that opens to a patio with hot tub and fire pit. The galley kitchen opens to a dining room and all with ease to entertaining and apres ski. This location is prime for winter ski and snowboarding as well as an incredible mountain biking trail system during the summer and fall. Hike, bike, golf and enjoy incredible year round activities. Very few homes become available in the North Brookwood neighborhood. Don't miss an opportunity to create your own mountain lifestyle in this great resort location.

82 N Brookwood Rd, Stratton
92 Oakmont Ln, Stratton
$1,150,000
2 Beds ⋅ 2 Baths ⋅ 5112718 MLS
A rare opportunity to create a true Vermont family compound, this 12.5-acre property offers not only a beautifully finished home, but also two additional building lots ready for the next chapter with underground power already in place and septic permits secured, the additional homesites offer the flexibility to build separate homes for family, all while taking advantage of the property’s beautiful mountain views. Built in 2023, the current residence features two bedrooms and two baths with a clean, modern mountain style and an easy open layout. Large windows frame the surrounding landscape and bring the changing seasons indoors, while warm wood floors, a stone gas fireplace, spacious kitchen, and comfortable living areas create a home that feels both refined and relaxed. Outdoor living is equally inviting, with a deck overlooking the grounds and long-range mountain scenery. There is a four bedroom septic permit on the home if you want to add on. For those needing exceptional garage and storage space, this property stands apart. The home includes an attached four-car garage, complemented by a brand-new detached four-car barn/garage, providing tremendous room for vehicles, recreational equipment, a workshop, or Vermont toys. Ideally located between Stratton and Mount Snow, the property offers convenient access to skiing, golf, hiking, mountain biking, dining, and everything Southern Vermont has to offer. With a nearly new home, seven total garage bays, 12.5 acres, mountain views, and a second permitted homesite already underway, this is an unusual opportunity to create a multi-generational Vermont retreat with room to grow.

92 Oakmont Ln, Stratton
2245 Burrington Hill Rd, Whitingham
$1,150,000
4 Beds ⋅ 1 Baths ⋅ 5090460 MLS
Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to the East. The property could easily accommodate a beautiful new build, or else could be rehabbed into a working dairy or gentleman's farm, with privacy and access rare to find. The main house presently features 4 bedrooms, 1 bath, a large kitchen and dining area, den, and walk in pantry. There is an attached two story barn for storage, which leads into the recently built oversized 3 car garage with 12 foot doors, ideal for equipment or classic car storage. From this you can go to the 38x144 large dairy barn with stalls, horse paddocks, and hayloft, or the tremendous oversized dairy barn with 90 stanchions between the two barns, and main room upstairs, which could be converted into amazing space for those with vision. These are the best maintained functioning farm barns I have seen in 20 years. Add to that a full equipment shed, dairy processing area, approx 40 acres of pasture and fields, sugar house, pond, a network of trails, 60 acres of mature woodlands, and an idyllic home site at the crest of the upper field, and you have everything you could possibly want in a true Vermont farm property, with enjoyment and expansion potential for years to come. Recent updates include a new roof on the house, generator, and a full clean out. Don't sleep on this one of a kind opportunity. Property is in Current Use.

2245 Burrington Hill Rd, Whitingham
201 Chester Hill Rd, Grafton
$1,149,000
3 Beds ⋅ 3 Baths ⋅ 5097006 MLS
Meticulously maintained and thoughtfully designed, this three-bedroom, three-bath home offers the perfect balance of comfort, functionality, and classic Vermont charm. Set on a picturesque parcel with stunning long-range views, the property is surrounded by mature trees, a small pond, established gardens, and simple, easy-to-maintain landscaping that enhances the natural beauty of the setting. Inside, inviting living spaces are filled with natural light, including a four-season sun room where you can enjoy peaceful mornings with a cup of coffee while taking in the changing landscape throughout the year. The thoughtfully designed floor plan provides comfortable gathering spaces that feel warm, welcoming, and perfectly suited for everyday living or entertaining. A two-car garage is complemented by a heated bonus room above, offering flexible space for additional guest accommodations, a home office, studio, or private getaway room. The custom heated barn is a truly unique feature of the property. Currently used as a woodworking shop, it also offers exceptional flexibility as an entertainment space, hobby barn, or additional guest sleeping area, making it ideal for hosting family and friends. As the day winds down, gather on the back patio and stone surrounded firepit to enjoy the sweeping views and spectacular Vermont sunsets, with simple perennial gardens creating a peaceful backdrop for relaxing or entertaining outdoors. Beyond the property itself, Grafton is one of Vermont's most treasured villages, known for its historic charm, welcoming community, and year-round recreation. Nearby Grafton Trails & Outdoor Center offers miles of hiking, cross-country skiing, snowshoeing, and skating trails, while the village is home to beloved destinations including MKT, Grafton Cheese Company and the historic Grafton Inn, all favorites for dining and spending time with friends and family.

201 Chester Hill Rd, Grafton
564 Goodaleville Rd, Jamaica
$1,115,000
4 Beds ⋅ 3 Baths ⋅ 5101689 MLS
Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort, the location offers easy access to the mountain, local favorites, and the best of southern Vermont living. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while radiant heat on all three levels adds warmth and comfort throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large, private deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for--full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property also available: 494–498 Goodaleville Road, MLS #5101688.

564 Goodaleville Rd, Jamaica
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
17a Boulder Ridge Dr Unit A, Dover
$1,050,000
5 Beds ⋅ 5 Baths ⋅ 5065579 MLS
This magnificent 5-bedroom, 4.5-bath townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design. The living room, graced with hardwood (hickory) flooring, a gas fireplace, large windows, a slider to the deck with an amazing view of Mount Snow, and a vaulted ceiling, creates an ambiance of warmth and grandeur. Each bedroom exudes tranquility, boasting wooden flooring, large windows, and ample closet space. Three bedrooms feature en-suite bathrooms, and two additional bathrooms service both the common space and the two additional bedrooms. A Large jetted tub off the primary bedroom is wonderful after a day of outdoor activity! The upgraded kitchen is a chef's dream, featuring an 8’ kitchen island, double ovens, two dishwashers, a farmer’s sink, stainless steel appliances, and quartz countertops. Adjacent to the kitchen is the dining area with the same incredible view. The lower level features another large living and entertainment space, complete with a wet-bar, mini fridge, and a large flat screen TV. A laundry room and owner’s closets add to the home's utility. With well-maintained roads and a plethora of nearby restaurants, the neighborhood offers the best of convenience and lifestyle. Envision the life that awaits...Experience it, appreciate it, make it your own. Let this be the backdrop to your new memories.

17a Boulder Ridge Dr Unit A, Dover
350 Sunset Lake Rd, Newfane
$1,000,000
4 Beds ⋅ 3 Baths ⋅ 5089719 MLS
Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural light, and generous storage. For ease of ownership there is an automatic propane generator and the septic was redesigned in 2022. In addition to all of this is a beautifully crafted timber frame barn that utilized reclaimed beams from the original structure on the property. Rich in authentic New England character, the home showcases exposed hand-hewn beams, a stunning chef’s kitchen with custom cabinetry, a massive stone hearth with a traditional beehive oven, and a unique gardener’s foyer complete with workspace and cast-iron wash sink. The spacious first-floor primary suite offers cathedral-beamed ceilings, a charming loft area, and a private retreat-like atmosphere. A sun-filled four-season sunroom overlooks the beautifully landscaped grounds and perennial gardens. Set on a large lot of private Vermont countryside, the property includes antique stone walls, approximately 5 acres of open meadowland, apple trees, maintained walking trails, and a large fenced garden area. Outdoor enthusiasts will appreciate the close proximity to Sunset Lake, located just a half mile away for kayaking, paddling, and peaceful recreation. Ideally located just minutes from downtown Brattleboro and only 1.5 miles from a paved road, this private country estate offers the perfect blend of seclusion, convenience, and the idyllic Vermont lifestyle. Whether you are seeking a homestead, equestrian property, country retreat, or full-time residence, this one-of-a-kind Vermont farmhouse is a rare opportunity to own a truly special piece of New England paradise.

350 Sunset Lake Rd, Newfane
5 Tannery Rd, Dover
$999,000
8 Beds ⋅ 4 Baths ⋅ 5112305 MLS
Discover your mountain getaway at Mount Snow in this beautifully renovated 8-bedroom estate, perfectly suited for family gatherings, reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, the property offers breathtaking mountain views and convenient access to the slopes just a short drive away. Inside, the spacious home is designed for gathering and relaxation, featuring a dedicated office/lounge, large kitchen and dining room, game room, and an expansive living room centered around an oversized fireplace. The first floor includes a bedroom and full bathroom, while the second floor offers seven additional bedrooms and three bathrooms, providing plenty of space for family and guests. Outdoor living is equally inviting, with a large deck and sunroom off the kitchen, perfect for dining and entertaining, along with a fire pit area and covered decks featuring a sauna for the ultimate après-ski relaxation. With ample parking, a prime location, and room for everyone, this exceptional property offers year-round access to skiing, hiking, biking, golfing, and all that the Deerfield Valley has to offer. Adding to its appeal, the home has a proven history as a successful short-term rental, making it an excellent opportunity for both personal enjoyment and investment. Come experience the space, setting, and possibilities of your own Mount Snow mountain retreat.

5 Tannery Rd, Dover
47 West Rd, Wilmington
$997,000
3 Beds ⋅ 4 Baths ⋅ 5105900 MLS
Be among the first to enjoy this brand-new mountain modern home in the sought-after Chimney Hill community, with an anticipated completion date of September 2026. Thoughtfully designed for both year-round living and weekend getaways, this 3-bedroom, 4-bath home offers a bright, open floor plan filled with natural light and clean, contemporary finishes. The main living area creates an inviting space for gathering, with an open kitchen, dining, and living room designed for today's lifestyle. Upstairs, you'll find a spacious primary suite along with two comfortable guest bedrooms, offering privacy and comfort for family and friends. The fully finished lower level significantly expands the home's living space with multiple bonus rooms and a generous recreation area, providing endless possibilities for a home office, fitness room, media room, bunk room, hobby space, or additional guest accommodations. Located in Chimney Hill, owners enjoy access to outstanding community amenities including indoor and outdoor swimming pools, hot tub, fitness center, tennis and pickleball courts, skating rink, community center, hiking and snowmobile trails, and year-round recreational activities. Just minutes from Mount Snow, The Hermitage Club, Lake Whitingham, and downtown Wilmington, this exceptional new construction home offers the perfect combination of modern design, low-maintenance living, and Vermont mountain lifestyle. Photos have been virtually staged.

47 West Rd, Wilmington
Forrester Road, Jamaica
$995,000
5110773 MLS
130 acre tract, this parcel backs up to over 1100 additional acres of Green Mountain National Forest lands. This private setting is less than 3 miles to Stratton Mountain Resort. Being subdivided off a larger 200+ acre parcel. Overhead power currently existing on premise, multiple drilled wells also already on premise and there will be access to this and other lots via existing road/driveway access into this parcel that is currently in use. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 130 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 67 acres at $799k and a 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion. Currently only 15 acres of the 200+ acres is gravel pit and being reclaimed on this property. See the Vermont Land Use Permit 2W1316 online for further information. Views of both Stratton and Mountain Snow can be had from the 1800 foot elevation on the westerly plateau of this lot. Roughed in driveway has been cleared to the location with potential views and future building site(s). Don't miss your opportunity to see this amazing large tract of land that is being offered so close to Stratton yet located in Jamaica, which is a no zoning town. Stratton Jamaica Town Line is a partial boundary line of this parcel. Residential and recreational opportunities on this parcel are worthy of exploring. Please, we request in advance, no drive-bys as there is heavy equipment and work being conducted on site daily.

Forrester Road, Jamaica
1189 Cole Pond Rd, Jamaica
$995,000
5 Beds ⋅ 5 Baths ⋅ 5108207 MLS
Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery. This home is designed to accommodate a life of both leisure and adventure.

1189 Cole Pond Rd, Jamaica
179 Reed Rd, Athens
$995,000
3 Beds ⋅ 3 Baths ⋅ 5102911 MLS
Custom Swedish Cope Log Home on 14 plus acres in Southern Vermont. Hidden among the hills, this custom log home combines rugged craftsmanship with warm, open living spaces. Oversized timbers transported from Idaho were assembled in the Swedish Cope style, featuring traditional saddle notched logs that give the home its distinctive character. A cathedral style entry leads into a dramatic living area with floor to ceiling windows, local views, and a wood-burning stove. The gourmet kitchen features granite countertops, maple cabinetry, spacious island and opens to the dining and gathering areas, creating an inviting space for cooking, entertaining, or relaxing. The home offers three bedrooms, three full bathrooms, and an expansive office. The main-floor primary suite includes walk-in closets, an oversized jetted soaking tub, and a walk-in rain shower. Travertine tile extends throughout the main level, complemented by radiant-floor heating. Set on more than 14 wooded acres, the property provides exceptional privacy and plenty of room to enjoy the outdoors. A full 10 foot deep porch wraps around the entire home, while an outdoor firepit offers a peaceful gathering spot. Stone walls and established perennial flower beds frame the grounds, and a long private driveway enhances the secluded setting. Additional features include a detached three-car garage with bonus space above and a garden shed. Offered for the first time, this one-of-a-kind Vermont retreat delivers craftsmanship, privacy, and four-season comfort in a remarkable natural setting. Only a short drive to several ski resorts and golf courses.

179 Reed Rd, Athens
136 Yeaw Rd, Dover
$995,000
4 Beds ⋅ 4 Baths ⋅ 5096823 MLS
A property that truly must be seen to be appreciated, this exceptional Southern Vermont home offers the perfect balance of privacy and convenience, just minutes from Mount Snow and the village of West Dover. Filled with natural light and hardwood floors, the home offers spaces designed for both comfortable everyday living and entertaining. The beautifully renovated primary suite features a private porch and hot tub, creating the perfect place to relax after a day of work or play. Multiple gathering spaces provide room for family and guests, including the expansive great room with a movie projection screen, ideal for entertaining. The open kitchen, complete with a fireplace and wet bar, serves as the heart of the home and flows seamlessly to indoor and outdoor dining areas. Outside, a spacious deck overlooks rolling meadows and mountain views, offering a backdrop for morning coffee or evening gatherings. Adding exceptional versatility to the property are a renovated barn, a studio workshop, and a large heated and insulated steel building with endless possibilities ideal for equipment storage, hobbies, recreational vehicles, a home-based business, or creative pursuits. Offering privacy, comfort, and year-round recreation in one of Southern Vermont’s most desirable locations, this is a rare opportunity to enjoy the very best of Vermont living.

136 Yeaw Rd, Dover
15 Boulder Ridge Dr Unit 15A, Dover
$990,000
4 Beds ⋅ 4 Baths ⋅ 5110617 MLS
Make this your own winter ski escape, spring valley getaway, summer mountain retreat, or fall foliage getaway. 15A Boulder Ridge Dr. seamlessly blends the ease of condominium living with the scale, craftsmanship, and ambiance of a refined ski retreat. Ideally positioned directly across from Mount Snow Resort, this exceptional four-bedroom, four-bath townhome offers approximately 3,100 square feet of thoughtfully designed living space across three expansive levels. The main level welcomes you with a striking slate foyer that opens into a dramatic living area featuring vaulted two-story ceilings and abundant natural light. Expansive windows and glass doors frame picturesque views of Mount Snow, leading to a private deck where you can unwind and take in stunning sunset vistas. This level also includes a well-appointed bedroom with an ensuite bath, a comfortable living room with a floor to ceiling stone fireplace, and a beautifully designed kitchen complete with quartz countertops and premium Viking appliances. Upstairs, a lofted sitting area overlooks the main living space, creating a sense of openness while offering a cozy retreat. The primary suite features a luxurious ensuite bath with marble finishes, while an additional bedroom also with its own ensuite and marble countertops provides comfort for guests or family. The walkout lower level is designed for relaxation and entertainment, featuring a spacious recreation room, a cedar wine vault, wet bar, and beverage refrigerator. With ample room for games or movie nights, this level creates the perfect gathering space. It also includes an additional bedroom with an ensuite bath, laundry facilities, and advanced home features such as a whole-home Sonos sound system and a Vacuflo central vacuum. Recent updates include a full interior repaint, new lighting fixtures, and updated carpeting throughout. Central heating and air conditioning ensure year-round comfort, with convenient climate control on every level.

15 Boulder Ridge Dr Unit 15A, Dover
82c Greenspring Rd Unit 82C, Dover
$975,000
4 Beds ⋅ 4 Baths ⋅ 5108389 MLS
Stunning updated Greenspring townhome with direct views of Mount Snow and Greenspring only shuttle service to and from the unit and base area. This Aspen Adirondack 4+ bedroom, 4 bath unit has been gut renovated and professionally designed and furnished for a high end finish befitting discerning tastes. Featuring a vaulted great room with tremendous ski mountain and sunset views, a wood burning fireplace with stone hearth, wood floors throughout, an expanded custom kitchen with granite counters and stainless high end appliances, range hood, breakfast bar, and spacious dining area, which lead out to the large entertaining deck overlooking the view, or main floor oversized mudroom with cubbies for gear and built in boot warmers. Upstairs there are two primary suites with high ceilings and private upscale baths, there is a main floor suite with chic contemporary bath, and laundry area, and there are two large double bunk rooms in the lower level as well as another full bath for ample room for guests. There is also a large family room wired for surround, which leads to the outdoor hot tub and lower deck, as well as second lower level laundry. Less obvious features are home theater wiring, custom window treatments throughout, central a/c, custom aesthetic beams, a whole home uv water treatment system, and a recently cleared year round mountain view. Enjoy BBQs from the large rear deck, watch for the shuttle from your comfortable covered front porch, stow your gear in the large mudroom, or take in the Vermont splendor throughout the landscaped development. This unit features all the convenient Greenspring amenities including quick direct shuttle service to and from the Mount Snow base area, building maintenance, landscaping, snow removal, wood delivery, trash, on site management staff, and the recently renovated amenities center including indoor pool, full gym, game room, and tennis court.

82c Greenspring Rd Unit 82C, Dover
00 Pratt Bridge Rd, Jamaica
$975,000
5107954 MLS
Enjoy Vermont in all the seasons!! This land has a number of options! With 235 acres to call your own! Build somewhere on the property. A stream runs through for your enjoyment! Part of the West River Trail passes through as well. Harvest timber from this lot and make some $$. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy spring, summer and fall exploring your land. Road access and power is close by on the road. Start you Vermont adventure today!!

00 Pratt Bridge Rd, Jamaica

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