luxury houses for sale Winhall, United States

Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication.A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive windows frame breathtaking mountain vistas, filling the space with natural light.The gourmet kitchen features a casual dining area and connects to a separate dining room - ideal for both relaxed and formal gatherings. With six en suite bedrooms, including a luxurious primary suite with a private office, dual walk-in closets, a cedar closet, and a separate storage room, theres plenty of space for all. A custom bunk room with built-in cubbies adds a fun, functional touch for younger guests.Year-round enjoyment continues with a golf simulator, home theatre, and a detached three-car garage with a fully equipped gym. A light-filled hallway connects all levels, creating a seamless flow throughout the home.Outdoors, unwind in the heated gunite pool and hot tub or enjoy tennis, pickleball, or basketball on your private courts. Lush perennial gardens, stonework, and bluestone walkways enhance the natural setting.Whether you're seeking a private escape or a home for generations, this mountaintop retreat is your Vermont dream - just in time for ski season.

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.

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the homes striking presence is undeniable. A porte-coch?re welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chefs kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the homes most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the homes entertainment offerings.The seamless connection between indoor and outdoor living is one of the homes greatest attributes. Heated pool, hot tub and fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

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

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle.Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary.Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time while enjoying every modern convenience.The sun-filled open-concept living and kitchen area showcases handcrafted cabinetry, soapstone countertops, updated appliances, the home's distinctive Rumford fireplaces featuring a traditional baking oven. The main level includes a bedroom with fireplace, a flexible bonus room with fireplace, bath, and mudroom. Upstairs are two additional bedrooms, a full bath, office nook, and a space with future plumbing possibilities. Adding versatility and value is a charming 700-square-foot guest cottage complete with its own kitchen and bathideal for guests, multigenerational living, a caretaker, artist studio. includes a 10-acre subdividable lot

Tucked between Mount Snow and Stratton, this charming mountain retreat offers the perfect blend of adventure, comfort, and classic Vermont living. Set in the heart of Wardsboro, this property provides easy access to both year-round recreation and peaceful natural surroundings.After a day on the slopes or exploring the nearby Green Mountain National Forest, cozy up beside the inviting wood burning fireplace or unwind on the private balcony surrounded by the beauty of the Green Mountains before rejuvenating with a soak in the hot tub. A lovely screened-in porch creates the perfect space for morning coffee, summer evenings, or taking in the crisp mountain air. With an open kitchen/dining/living space and a large family/game room, this home has plenty of space to make new memories. Outdoor enthusiasts will appreciate access to nearby snowmobile trails, endless hiking opportunities, and all the recreation Southern Vermont is known for. Whether youre seeking a full-time residence, weekend getaway, or investment property, this home captures the warmth, charm, and lifestyle that make Vermont living so special.

Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right from your backyard.Thoughtfully designed with timeless craftsmanship, the home showcases timber frame construction, expansive walls of glass, and a two-sided stone fireplace that serves as the centerpiece of the main living spaces. Warm wood tones, natural stone, and quality finishes create an inviting atmosphere.The gourmet kitchen is designed for everyday living and entertaining alike, featuring a Wolf range, custom cabinetry, generous center island, and a spacious walk-in pantry offering abundant storage and prep space. The open floor plan flows seamlessly into the dining and great room, making it ideal for gathering with family and friends after a day on the slopes or exploring the surrounding mountains.All four bedrooms are ensuite, providing exceptional privacy and comfort for owners and guests alike. The luxurious primary suite offers a spa-inspired bath with soaking tub, oversized shower, and refined finishes that complement the home's timeless design.The finished lower level expands the living space with additional room for recreation, media, fitness, or overflow guests, while the attached two-car garage provides convenient storage for vehicles and outdoor gear.Meticulously maintained inside and out, this home offers the rare combination of handcrafted quality, modern amenities, and an outstanding location between Vermont's premier ski destinations. Whether serving as a full-time residence or mountain retreat.

Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed ceilings, a striking fieldstone fireplace, and expansive windows that bathe the space in natural light. The kitchen is ideal for entertaining, complete with stainless steel appliances and a breakfast bar that opens to the dining and living areas perfect for apr?s-ski gatherings or cozy evenings by the fire.Three spacious bedrooms offer comfort for family and guests, while the finished lower level adds a recreation room with a pool table and media area for year-round enjoyment. A covered front porch invites you to take in the tranquil setting, and the two-car garage and additional outbuilding provide ample storage or workspace.Surrounded by evergreens and backing up to the national forest this property is a true Vermont retreat a peaceful escape with easy access to world-class skiing, hiking, lakes, and adventure

Set on two private, wooded acres, this inviting mountain retreat balances classic Vermont warmth with a spacious 3,986-square-foot layout featuring three comfortable bedrooms, a spacious loft area, and four bathrooms. Ideally situated for outdoor enthusiasts, the property offers close proximity to Vermont's VAST trail network, making year-round adventure easily accessible.The heart of the home is an expansive open-floor plan anchored by towering cathedral ceilings and a floor-to-ceiling wood-burning fireplace, where large windows frame the surrounding forest and flood the main living area with natural light. Designed for effortless daily living, the main level features a primary en-suite bedroom that serves as a quiet, private sanctuary, complete with its own spacious walk-in closet. The homes thoughtful storage continues into the guest quarters, where another of the bedrooms also boasts a generous walk-in closet.Downstairs, a newly finished 900-square-foot walk-out baement completely redefines the homes footprint with a dedicated game room, perfect for hosting friends after a day on the slopes. Friday evenings begin as the sun goes down, lighting a fire in the great room and playing pool downstairs, while Saturdays take you on the short 15-minute ride to Stratton Mountain or directly onto the local trails. Offering a warm, character-filled take on mountain living, this property delivers the ultimate high-end weekend basecamp or full-time residence.The home also features a variety of new improvements, including a full roof replacement, oversized wood-burning fireplace and mantle/tool hangers, custom-built wood holder, refinished deck, all-new waterworks, upgraded basement insulation, plumbing upgrades, exterior siding repairs, woodshed, gutters, tree work/removal, new washer and dryer, spotlights, security cameras, and updated alarm hardware/software.Showings to begin July 3, 2026

Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions provide 13 extra bedrooms, library, game room, and a vintage bar/lounge area. The Grounds: Woods, trails, 2 ponds, and a 2 bay outbuilding workshop and equipment storage. The Potential: 875 sq. ft. of bonus space ready for your finishing touches, possibly a theater or a gym? This is the ultimate gathering place for creating memories that last a lifetime. Don't just visit Vermont, own a piece of its history. All measurements approximate. Listed commercially as well, MLS#5075319

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

Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the rushing brook across the road fills the air. Just steps away, enjoy your own frontage on Wardsboro Brook, where you can create a private swimming hole, gather around a campfire under the stars, or simply relax and listen to the water flow by. The land invites endless possibilities. Picture horses grazing in the pasture, chickens in the barn, vegetable gardens and fruit trees, or create winding paths through wildflowers in the meadow. Old stone walls trace portions of the property's boundaries, while mature apple and pear trees provide seasonal harvests. The property includes a spacious 3-bedroom main residence with both formal and informal living areas, offering flexibility for entertaining or quiet evenings at home. An attached 2-bedroom guest apartment provides space for visitors, extended occupancy, or a home office setup. Between the house and barn, a fenced outdoor area offers a convenient space for recreation, pets, gardening, or outdoor gatherings. The circa-1942 barn stands ready for animals, equipment, hobbies, storage, or agricultural pursuits, while the attached 2-car garage adds everyday convenience. Located just minutes from Mount Snow and Stratton Resort, and with convenient access to the village center of Wardsboro, this property combines the peace and beauty of country living with easy access to recreation, dining, and community amenities.Come experience the sights, sounds, and possibilities of a Vermont property where history, nature, and lifestyle come together.

Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection.Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chefs kitchen, sun-filled all-season room, and a cellar tavern and game room create spaces that feel welcoming in every season. The separate two-bedroom guesthouse offers additional flexibility for hosting family and friends after long days spent exploring the mountains and surrounding countryside.From winter mornings skiing Stratton, Bromley, Magic, or Okemo to summer afternoons at Lowell Lake, nearby trails, swimming holes, galleries, farmers markets, and outdoor concerts, life here naturally follows the rhythm of Vermonts changing seasons. Evenings return home beside the fire, gathering over dinner, sharing stories, and settling into the quiet beauty of the Green Mountains.Set along scenic Route 11 near the Catamount Trail and just a short drive to Manchester and Weston, this is more than a home. It is a place to create traditions, welcome generations, and experience Vermont at its most timeless and authentic.Floor plans and video tours available online. All measurements approximate.

This charming two-story Colonial in Manchester offers a comfortable and functional layout with plenty of living space. The first floor features a kitchen with a wood burning fireplace, along with dining and living areas perfect for everyday living and entertaining. A mudroom provides convenient access to the attached garage.Upstairs, youll find three additional rooms offering flexibility for bedrooms, a home office, or guest space, plus a finished attic area that can be used as a bonus room, studio, or recreation space.Outside, enjoy a private yard surrounded by mature natural landscaping and a deck overlooking the peaceful setting, creating the perfect place to relax and enjoy the outdoors.The property located in Manchester on 1.10 acre and Winhall (the land 0.84 acre) All measurements approximate

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

Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed bedrooms, five fireplaces, original wood and marble floors, and handsome moldings throughout. The home has been thoughtfully expanded to include a sun-filled country kitchen with custom cabinetry, formal and informal dining rooms, a library, family room, and multiple living spaces that open to marble terraces and gardens.Enhancing the estate are extraordinary amenities, including a marble in-ground swimming pool with stone terrace, a tennis court, and a one-bedroom caretakers cottage with attached garage for on-site management or guest overflow. A 2,400 square foot three-bedroom guest house, created from the original c.1796 post-and-beam barn, blends historic charm with modern comfort. A goat and chicken barn, equipment barn, and a separate 30 x 60 seven-bay toy and car barn provide abundant storage and the opportunity for a true Vermont farmstead lifestyle or a spectacular car collection. The grounds are equally captivating, featuring mature landscaping, open meadows, orchards, perennial gardens, and stone walls. Pergolas, walkways, and extensive marble terraces.

If you are looking for a property with both mountain and water views, this exceptional five-bedroom Manchester home is a must-see.Set on a remarkable lot featuring breathtaking vistas and approximately 400 feet of frontage along Bromley Brook, this home offers a rare combination of privacy, natural beauty, and convenience. Located just minutes from the center of Manchester and near the areas premier ski mountains, it provides the ideal Vermont lifestyle. Imagine spending summer afternoons relaxing by the running brook or enjoying a peaceful day of fishing right on your own property.The spacious residence includes a heated three-bay garage with an additional two-bedroom living space above (2003 construction), perfect for guests, office or extended family. Inside, the home features a large open kitchen, generous living areas, and a cozy wood-burning fireplace. The primary suite, complete with cathedral ceilings, enjoys serene views of both the mountains and Bromley Brook. Two additional bedrooms are located upstairs in the main part of the house.Also included is an adjacent 1.7-acre building lot, offering excellent potential for a guest house or future development.This property is a truly special opportunity combining privacy, stunning vistas, and endless possibilities. All measurements approximate. OPEN HOUSE is on July 19th from 3-5pm

Imagine a time where taverns were the heart of the community, where laughter echoed off thick brick walls and stories were told by firelight. Now see yourself enjoying the ease of Single Floor Living that includes an enormous primary ensuite, with laundry! Start your day in the completely updated kitchen and move effortlessly into the dining area and living room with an easy to light cozy propane fireplace. This majestic 4 bedroom, 3 bath 1820s Brick Federal has been meticulously preserved and offers that rare, storied tactile history but now as a reimagined luxury home just minutes from downtown and three area ski resorts! You'll be embraced by refined details, high ceilings and then, stunned to find an historic tavern and additional living space including a wine cellar in the finished basement. Auto enthusiasts will love the 4 bay detached barn with office and space for an additional dwelling unit. Equestrians will love the immediate proximity to a famous Morgan Horse Farm and living just minutes to the Annual Summer Festival in Dorset. Step into a story with sweeping Vermont mountain views that's already over two centuries old, but brand new at the same time and make it your own. Contact us today to schedule your private tour. All measurements Approximate.

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.

Welcome to this beautifully updated Cape offering 4 bedrooms and 3 bathrooms in one of Manchester's most desirable neighborhoods. Thoughtfully renovated with extensive recent improvements, this turnkey home blends classic New England character with modern style, comfort, and efficiency.The heart of the home is the bright, open-concept living space, where a beautifully renovated kitchen features quartz countertops, Samsung appliances, and a large center island that flows effortlessly into the dining and living areas, perfect for both everyday living and entertaining. A sliding door leads to the back deck and level fenced yard, where you'll find a brand new hot tub included with the home-the perfect place to relax while taking in the mountain views. Two bedrooms and a full bath complete the main level.Upstairs, the spacious primary suite features a beautifully renovated en suite bath with radiant heated floors. A second bedroom with ensuite bath and convenient second floor laundry area add both comfort and functionality.Recent upgrades include an LG heat pump system, updated baseboard heating, LED lighting, laminate flooring, updated windows and doors, custom wardrobes, a newer roof, paved driveway, and a full basement providing excellent storage.Whether you're searching for a full time residence or a Vermont retreat, this move in ready home offers the ideal combination of thoughtful updates, inviting living spaces, and outdoor enjoyment. Just minutes from downtown Manchester, you'll have easy access to restaurants, shopping, schools, golf, skiing, and year round recreation, all while enjoying the peace and privacy of a quiet residential setting.

Privately nestled at the end of a secluded drive, this quintessential Vermont retreat offers extraordinary privacy and serene mountain views in every direction. Set on a beautifully landscaped parcel with mature trees and an expansive lawn, the property exudes peace and timeless New England charm. The home features 2 bedrooms, 1.5 bathrooms, generous storage, and a detached two-car garage. A classic Vermont barn, currently serving as a recording studio, provides exceptional flexibility for creative pursuits, a workshop, or additional recreational space. Ideally located just minutes from ski areas, shopping, and Grace Cottage Hospital, this is a rare opportunity to enjoy the beauty, serenity, and convenience of Southern Vermont living.