luxury real estate for sale Windsor County, United States

Lovely views overlooking the Pomfret hillside and lush meadows on a private, dead-end road in North Pomfret. Quiet and peaceful. This ranch style home has many upgrades, with a 2-bay attached garage for easy access to the dwelling. It features all one floor living with 3 bedrooms, spacious living room, dining area with new kitchen - views and an abundance of natural light throughout. The basement could be finished for an additional 800+ square feet or turned into a workshop- ample storage. Generator on site, large deck expanding the back of the house overlooking meadows and view. New systems. Easy access to Upper Valley, Dartmouth or historic Woodstock- skiing, fly fishing and shopping within 15 minutes. Come take a look!

Set along scenic Pomfret Road, 8133 Pomfret Road offers the charm and character of a classic Vermont farmhouse in the heart of Pomfret. This 3-bedroom, 2-bath home, originally built in 1875, is situated on approximately 2 acres and features exposed beams, wood floors, and a woodstove that adds warmth and character to the living space. A screened-in porch steps out to a beautiful stone patio with a propane fire table, creating an inviting place to relax, entertain, and enjoy the peaceful Vermont surroundings.Outside, thoughtful landscaping, established gardens, fruit trees, maple trees, and a chicken coop offer a touch of Vermont homesteading, with the opportunity to tap your own trees and enjoy making maple syrup for family and friends. A workshop provides valuable space for projects, hobbies, or additional storage, while the attached garage adds everyday convenience. Membership in a community solar array and efficiency upgrades brings an energy-conscious element to this historic property.Blending period character with comfortable living spaces, inviting outdoor areas, and opportunities for gardening and homesteading, the property is well suited for year-round living or a Vermont country retreat in one of the area's most picturesque communities.

Welcome home to this serene piece of Vermont paradise! The property offers an escape to a privately sited cape home featuring 3 bedrooms, 2.5bathrooms with covered and open outdoor entertaining spaces both overlooking an exclusively owned, spring-fed, swimming pond and long-range pasture views - all enveloped by mixed forest land of hard- and softwood. Inside the home gleaming hardwood floors are throughout, a central wood stove provides cozy warmth in the colder seasons to the open cathedral dining and living space. A kitchen with granite countertops, ample storage, and a center island ensure prep space for large and small gatherings. The main level is outfitted with direct entry from the attached garage, a laundry room, powder room, living/dining room, kitchen, and primary ensuite with direct access to the yard. Upstairs 2 additional bedrooms, a full bathroom, cedar closet, and plenty of storage make primary or guest living convenient. The property is further benefitted by a separate, fully outfitted and compliant commercial kitchen which could be utilized for agricultural or other value-added product processing, or repurposed as a guest cabin, studio, or home office. An owned solar array and whole-house generator supply sustainability and reliability while the neighboring 500 acres surrounding the property add insulating privacy and tranquility.

Build Your Vermont Dream in Sharon, VT. Nestled along scenic Howe Hill Road on 22.9 acres offering two building lots with convenient access to power and ultra-high speed fiber optic (EC Fiber) internet at the street. Lot 1 features a three-bedroom waste water permit on 15.4 acres with direct access off Howe Hill Road. Lot 2 has a five-bedroom waste water permit with spectacular mountain view potential. Build on one and save the other lot for future family compound or rental investment. Sharon offers the sought-after high school of choice program to top-rated schools; location is just one mile from I-89 for an easy drive to Upper Valley amenities: Dartmouth College, in Hanover, Dartmouth Hitchcock Medical Center (DHMC) in Lebanon, and Historic Woodstock Village in Vermont. The town of Sharon has approved the subdivision of the 22.9 acres parcel.

Pristine Pomfret land with views of Mount Ascutney. Build your dream home on this exceptional parcel in one of Pomfret’s most scenic and well-preserved settings. Surrounded by large landholdings and conserved farmland, yet just 10 minutes from Woodstock with easy access to Quechee and Route 4, this property offers a rare combination of privacy and convenience. Historic stone walls, mature hardwoods, and a meandering stream create a quintessential Vermont landscape, with the potential for both pastoral and mountain views. Held by one family for decades, this is an uncommon opportunity to own and steward a truly special piece of land. Offered subject to receipt of state and local subdivision permits. Preliminary survey available.

Tucked away on a private drive just off Route 14, this thoughtfully designed three-bedroom, two-bath Ranch offers comfortable single-level living with room to grow. An open floor plan, hardwood floors, and abundant natural light create a warm and inviting atmosphere, while the southwest-facing orientation fills the home with sunshine throughout the day. The spacious primary bedroom suite provides a peaceful retreat, and the kitchen opens to the dining area, where sliding doors lead to a Trex deck overlooking the backyard; an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. An established vegetable garden offers the opportunity to grow your own seasonal produce, while the generously sized laundry and mudroom adds everyday convenience. Nearby river access provides opportunities for recreation. The full unfinished basement offers exceptional potential for future expansion, whether you envision additional living space, a home gym, workshop, or hobby area. An oversized garage provides ample room for vehicles, outdoor equipment, and storage. Designed with efficiency and convenience in mind, the home features a Lochinvar Knight Series boiler, mini-split air conditioning, central vacuum, a newer water heater (2019), a 9 kW roof-mounted solar array, and wiring for a portable generator to provide peace of mind during outages. Offering privacy, modern mechanical systems, and easy access to South Royalton and all that the Upper Valley has to offer, this well-maintained property is ready to welcome its next owners.

Great opportunity to own a small cape in The Grove with the ability to expand. This is a 2 bedroom, 2-bath cottage all on one level with the second floor open and unfinished for the next owner to create their own personal space with endless possibilities. This is a low maintenance home with mini split air conditioning, a generator and perennial gardens. Open floor concept for ideal entertaining with an abundance of light throughout. Primary bedroom has an en-suite bathroom with soaking tub. Another guest bedroom with 3/4 bath also on the first floor. Quick walk to the Barnard General Store for breakfast or to Silver Lake for swimming and canoeing. This property does not have direct access to Silver Lake. Just 12 minutes to historic Woodstock for all amenities, shopping, dining, golf and skiing. This is a turn-key affordable home the premiere village of Barnard. Building inspection available.

This spacious, well-maintained Gambrel-style home is designed for gracious country living, with a post-and-beam frame that creates large gathering spaces accented by two fireplaces, thoughtful features, and abundant natural light. The private parcel, landscaped with perennials and flowering shrubs, is positioned on a rise overlooking the Barnard Valley towards Woodstock, a few miles south. The location offers a highly desirable balance of privacy and proximity to all resort amenities, shopping, schools, and services, all within a few minutes' drive. A versatile floor plan can be configured with 3 or 4 bedrooms, each capturing views of the surrounding countryside. The superb eat-in kitchen with a breakfast bar is central to the home, surrounded by a dining area and a family room with a well-equipped entertainment center. A separate living room connects to places for celebrating the seasons: a bluestone-paved patio in summer and a greenhouse addition with ideal solar exposure, providing a welcome source of warmth and light in winter. Highlights include updates focused on energy efficiency and modern living, such as high-speed fiber-optic service, an airtight wood stove, a gas fireplace, a heat pump water system, and Tesla batteries, which add resilience. Close to miles of trails, skiing, golf, fishing, and all of Vermont's outdoor attractions.

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

This meticulous & well-cared-for home welcomes your family and friends with its stately front porch designed by Anne Wilson. The main level is a terrific place for entertaining with large open rooms, 9’ ceilings, radiant heat, crown moldings, an abundance of windows and natural light, handsome fireplace, and lovely oak flooring throughout. Open the French doors to a comfortable private deck surrounded by the peace and quiet of the forest. The renovated kitchen with separate butler pantry, new stainless-steel appliances and soapstone countertops will surely please the most seasoned chef. Enjoy casual dining around the generous kitchen island made from antique barn wood or choose the inviting formal dining room. A cozy library features custom built-in cabinetry with room for an abundant collection. On the second floor you will find 4 spacious sun-filled bedrooms including 2 primaries with en suite bathrooms. The first primary suite features a sitting room, gas fireplace & large walk in closet with a handsome renovated bathroom. The second primary suite features a soaker whirlpool jacuzzi style tub and is perfect for guests. Abright & cheery playroom is enhanced by its dynamic bank of windows and gleaming hardwood floors. Above all of this there is a large room on the third floor with ample room for exercising, yoga or large office with tree top views and plenty of attic space for more storage. Easy access to all amenities in the Upper Valley. House comes with a garden shed, chicken coop, new whole-house generator and mini splits for A/C.

A perfect opportunity to build in this dramatic and private mountaintop location with long range views to the east and south. An excellent Barnard location in an area of estate properties. Being sold as 40 +/- acres with an additional 29 acres available. Road to building site in and septic soil tests will be performed after snow melt. Subdivision pending. A short drive to Woodstock and an even shorter drive to all the amenities of Teago including Saskadena Ski Area. Easy access to I89

This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic property to others, who can return it to private use or continue serving the community as a center of hospitality, helping to cover the costs of ownership. The Inn features original fireside dining rooms, complemented by a rustic tavern serving both classic and inventive 'pub' cuisine. The professional kitchen has undergone a thorough renovation, increased efficiency and enabling flexibility of culinary styles. Marketing opportunities are limited only by imagination, including the use of expansive lawns for weddings and events in both indoor and outdoor settings among flowering shrubs, mature shade trees, and natural landscaping. The main floor of the Inn features the professional kitchen, tavern, and dining areas. The second and third floors offer private residential accommodation, including 5 bedrooms, 2 bathrooms, and a beautifully designed open-concept country kitchen that leads to a spacious deck with views of the surrounding hills and fields. The post-and-beam barn has been repurposed as an event venue and short-term rental, with a yoga studio. The main level of the former working barn is open to a height of 36’, overlooked by the expansive hay loft. The barn is large enough to host up to 60 guests for dinner and 100 for casual events. A 2-bedroom building site beside the spring-fed pond has been approved, with additional sites potentially available by reallocating the existing septic system. The location is ideal for ‘glamping’ with nearby Silver Lake, miles of trails, and outdoor recreational activities drawing tourists throughout the year.

A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can be deeded as two parcels or a single 69+/- acre parcel. The location is a short drive to Woodstock and an even shorter drive to all the amenities of Teago including Saskadena Ski Area. Easy access to I89.

A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to all the amenities of Teago including Saskadena Ski Area and easy access to I 89. Subdivision pending.

Some homes just feel like magic! Set amid Vermont's picturesque rolling pastures and scenic walking trails; this exceptional property exists in perfect harmony with its natural surroundings. A private woodland trail invites peaceful strolls through the forest, while the soothing sound of the babbling brook winding through a historic 1817 stone sluiceway creates a truly enchanting setting. Mature trees and beautifully landscaped gardens provide a private outdoor sanctuary and a seamless connection to nature. Adding to the property's quintessential Vermont charm is a beautifully restored 1830's barn. Rich in history and character, the barn offers abundant space for storing vehicles ATVs recreational equipment, and more, while enhancing the estate's timeless country appeal. Large windows fill the home with natural light and framed tranquil views in every season. The inviting living room, anchored by a striking fireplace, is the perfect place to gather on crisp Vermont evenings. The thoughtfully designed kitchen features high-end appliances and seamlessly connects to a bright dining area and spacious deck, making entertaining effortless whether indoors or out. A dedicated office/studio provides ideal space for remote work creative pursuits or quiet reading. High speed internet, central AC, whole house generator, single level living, ensure comfort and peace of mind year-round. Ideally located between historic Woodstock and charming Barnard Village, home to beautiful Silver Lake, this property offers access to an abundance of outdoor recreation. World class skiing at Killington resort, and local favorite Saskadena Six are just a short drive away, with endless opportunities for every interest and season. Meticulously maintained and thoughtfully cared for, this remarkable home offers a rare combination of beauty, comfort, and convenience. A private viewing is essential to fully appreciate all it has to offer. Schedule your appointment today.

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three luxurious residences in the heart of the Village.Unit B occupies the top two floors and offers over 3,200 square feet of beautifully appointed living space with the feel of a private home. The main level features gracious living and dining rooms with a wood-burning fireplace, a spacious family room, and an en-suite study or guest bedroom with its own fireplace. The kitchen opens to the family room and is filled with southern light. A built-in bar near the dining area leads to a private balcony overlooking the Village and landscaped grounds, perfect for morning coffee or evening entertaining.The upper level opens to a charming landing with built-in bookcases, a serene primary suite, and an ensuite guest bedroom. A rear Carriage House provides covered garage and storage. With timeless character, refined interiors, and walk-to-everything convenience, this is a rare opportunity to own one of Woodstocks most photographed and cherished historic homes.

Set just up West Road in Barnard, this inviting Cape-style home offers a classic Vermont setting: a peaceful wooded backdrop, warm interior character, and easy access to village life, Silver Lake, and the outdoors. The Barnard General Store and Silver Lake, with the town hall, town library, and newly constructed fire station, are nearby. West Road also serves as a way to head toward the Chateaguay wilderness for hiking, exploring and time in nature. Inside, the home has a comfortable open flow with wood floors, natural wood trim and windows that bring in the surrounding greenery. The updated kitchen features gray shaker-style cabinetry, stone countertops, subway tile backsplash, farmhouse-style sink, tile flooring, and practical prep space. It opens to the dining area, where hardwood floors, a classic staircase, large windows, and access to the rear deck create a nice connection for daily living and entertaining. The living room offers polished wood floors, warm trim, and a relaxed place to gather. A wood-paneled entry mudroom provides true Vermont function, with slate-style flooring, hooks, seating, and room for boots, coats, and gear. The home includes three bedrooms and two full baths, with a convenient main-level bedroom and bright upper-level bedrooms featuring wide pine floors, skylights, angled Cape-style ceilings, natural trim, and storage. A small office nook adds useful space for remote work or household organization. Outdoor living is a highlight. The expansive rear deck runs along the back of the home with room for grilling, seating, and enjoying the lawn, stone walls, and mature trees. The attached garage, metal roof, gravel drive, cupola detail, and wooded setting add function and Vermont appeal. The extra-large walkout basement offers utility and storage, including additional storage beneath the garage. Whether you are seeking a full-time home or a Vermont retreat, this West Road property is an opportunity to start living in Barnard.

Woodstock Village Home~A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, caf?s, and everything that makes Woodstock one of Vermont's most beloved destinations.Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality.Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood.Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980’s, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef’s kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything.

Honey Hill Farm is a rare and distinguished Vermont estate encompassing 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open meadows, cascading brooks, waterfalls, and around a spring-fed pond. Whether for hiking, cross-country skiing, horseback riding, mountain biking, or quiet exploration, the land offers a seldom-found level of privacy and recreation. The main residence has been masterfully reimagined through a full-scale renovation, blending timeless craftsmanship with modern luxury. At its heart lies an expansive gourmet kitchen with custom marble finishes and bespoke detailing. A four-season room with floor-to-ceiling glass doors dissolves the boundary between indoors and the breathtaking landscape beyond. Formal living spaces flow seamlessly into a richly appointed bar and billiards room and onward to a spectacular library, where exquisite millwork and tailored lighting create an atmosphere of quiet grandeur. Each bedroom suite is generously scaled and paired with indulgent ensuite baths. An extraordinary spa offers infrared and salt therapies and opens directly to a heated pool surrounded by nature. Modern systems ensure comfort and security, including radiant heat, central air, water purification, and a whole-house generator. The iconic red barn has been fully restored, with upper-level entertaining and fitness space and a beautifully appointed guest apartment below. Offered as a fully curated turnkey estate, Honey Hill includes exquisite custom furnishings thoughtfully selected to complement the home and setting, allowing for immediate enjoyment. Privately sited behind gates and shown by appointment only, Honey Hill Farm is a world unto itself and legacy in the making.

Hart’s Crossing is a home and a haven featuring a custom 21st-century residence and a comprehensively restored Civil War-era guest house, set on418 acres of private land. The property provides a refuge in nature, with a kingdom-sized backyard to explore and adventures that change with the seasons. Located at the end of a town-maintained road, the property is a 10-minute drive from either Woodstock Village or the Upper Connecticut River Valley to access the conveniences and necessities of life, yet a century away from the inconveniences, in a peaceful sanctuary. The airy and light-filled 5-bedroom main residence sits on a plateau overlooking the Ottauquechee and White River Valleys to the east and north, with sweeping views to the south along the Connecticut River through walls of windows. The historic farmhouse has been reimagined as a comfortable 2-bedroom guest cottage, featuring exposed timber framing accented by a modern kitchen and bath, with a screened porch and wide deck alongside a refreshing, spring-fed swimming pond. Nearby is a multipurpose barn with a caretaker’s apartment for farm and recreational purposes. The property is enrolled in Vermont’s Current Use program, intended to help large landowners preserve the working landscape with a professional land management plan and a reduction in property taxes as consideration. There are miles of trails enabling access to the entire property for hiking, biking, snowmobiling, and simply wandering without a watch. At the end of Sugar House Road, you’ll discover the best of today, thoughtfully combined with the timeless values of yesterday.

This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with additional direct access from the spacious 2-car garage. A mudroom connects the front and garage entries, and the back entry near the garden barn is close to the kitchen. The generous living room centers on a wood-burning fireplace with floor-to-ceiling windows spanning the width of the room. A gracious dining room adjoins the living room, den/bedroom, kitchen, and private stairway to the primary bedroom suite. The second level includes the primary bedroom with study/dressing room, walk-in closet, private balcony, and en suite bath with Italian marble vanity, tile, and surfaces. The second bedroom is illuminated by natural light and well-appointed en suite bathroom. A second-floor family/media room is separate from the sleeping areas. The property is within easy walking distance to the Village Green, shopping, entertainment, elementary school, and all resort amenities. A gem waiting to be discovered.

You immediately become aware of the very special nature of this property the moment you turn onto the tree-lined driveway winding to the top of a mild grade where the home is perfectly sited. The barn garage section was built in 2010 and the main residence was added in 2019. The many features of this house make it a perfect primary residence or a welcoming vacation retreat. Open format kitchen-dining-living area with an artfully crafted stone wood-burning fireplace as the centerpiece of this main living area. An adjoining three season room off the dining area enhances the overall livability. Features almost too numerous to mention include: a main level primary bedroom suite with walk in closet and bath with a large fully tiled walk in shower; well-designed mudroom with crafted built-ins; there is a separate adjoining wing with two bedrooms, a large bright sleeping loft, a second full sized kitchen, a sitting area and a three-quarter bath; at ground level there is an expansive bright full walk out basement; a heated oversized two car garage; a stone patio and firepit overlooking a mountain view; an outside shower and an automatic propane generator. The location is perfect, being close to Barnard General Store and Silver Lake, a short drive to Woodstock and an even shorter drive to Saskadena Ski area and all the amenities of Teago.