luxury real estate for sale South Woodstock, United States

Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in the early 1800’s. The rooms are spacious, bright and inviting with exposed hand- hewn beams and pine plank floors running throughout. The updated country kitchen with soapstone counters connects to a cozy reading room with bookshelves and wood stove, and a utility/mudroom with ¾ bath, and laundry. The formal dining room offers plenty of space for gatherings. The front to back Living Room is anchored by a woodburning fireplace, and steps out to a private sunroom, and a guest room/office. Moving upstairs, there are four bedrooms and a bathroom. The 18thcentury hip roofed, post and beam English bank barn has a huge, sweeping loft space ideal for parties and entertaining. The lower level can accommodate animals, hobbies or a home occupation. The barn is surrounded by lush green pastures, and rail fencing which lead you to a network of beautiful trails for hiking. A short stroll to The Kedron Valley Inn, KV Pond, The South Woodstock Store, and Green Mountain Horse Assn. A five-minute drive to the Woodstock Village Green. Easy access to Hanover, DHMC, skiing, golf, dining, shopping and recreation.

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx. 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered with stone walls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first-floor primary suite with private bath, vaulted ceilings and new large walk-in closet. Kitchen features Thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertainment on the brick patio or the new east terrace. Enjoy a separate 3-bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off Rt. 106. This parcel is being divided off a 10.87acre lot. There is a wonderful, open site ideal for building your dream home offering privacy, trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn, dining at the Ransom Tavern and a swim in the Kedron pond! 5 miles into Woodstock Village, skiing is available at multiple resorts including Okemo and Killington as well as local Saskadena Six. Green Mt. Horse Association is around the corner. The year-round access to outdoor activities is endless. Call today for more information and a viewing. Subject to completion of the subdivision of the parcel.

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5-bedroom, 4-bathroom extended cape styled home was renovated approximately 15 years ago with handsome hard wood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the French doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom bookshelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garages and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South Woodstock, you will enjoy close proximity to the Green Mountain Horse Association, the South Woodstock Country Store, Kedron Valley Inn, and the historic Ransom Tavern. Whether you are looking to build your dream home, a private getaway, or an investment property, this land offers endless potential in a sought-after Vermont setting. Do not miss out on this rare opportunity, schedule your visit today!

Handsome condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath for those who needed a first-floor bedroom. Spacious living room anchored by a propane fireplace, nicely crafted mantle and hard wood floors. A couple of steps down takes you into a renovated kitchen with stainless appliances and traditional soapstone counters... a small eating area overlooking the back deck with privacy facing East. Tall ceilings allow this space to feel spacious with extra windows and an abundance of natural light. Second floor consisted of nice hardwood floors. A very large primary bedroom with large closet and two smaller closets in alcove for an abundance of storage and sitting area. Second bedroom is spacious with lots of sunlight. Good size full bathroom with tiled floors. Lower level has a walkout patio, large family room with lots of options for use, another 3/4 bathroom, storage and laundry. Pets are allowed! Easy access to skiing, hiking and shopping. Close to championship golf, Mtn biking trails. Minutes to historic Woodstock Green and 20 minutes to Upper Valley. Come take a look as this END UNIT -its turnkey and has the most privacy of any other unit in this complex.

Fully furnished condo nestled in a small quiet community just 5 minutes from Historic Woodstock. Super location! This unit is in very good condition- first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom are perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turnkey property

Enjoy the ease of townhouse living in this beautiful fully furnished end unit filled with natural light throughout. The setting is surrounded by woodlands and lovely landscaped grounds. The bright living room complete with wood-burned fireplace steps down to a lovely kitchen with dining area. Walk out through double sliding doors onto a private deck for one of two outdoor living spaces. There is an office/den as well as a powder room on the first floor. Upstairs there are two generous-sized bedrooms and a full bath. The lower room is finished into a very large family room with a woodstove, bathroom and laundry. Open the sliding doors to a patio for the second outdoor space perfect for entertaining friends or a quiet space to relax. The location is only a few minutes to the center of Woodstock and a short drive to Killington. Call for a private viewing.

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.

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.

Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are plenty of spots for a homesite, a family retreat, or even a simple rustic getaway to relax, recharge, and dream about the future.

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom, 2-bath home offers the character of a traditional New England property with comfortable, move-in-living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean, inviting feel while preserving the home’s classic farmhouse charm. An attached barn/garage offers excellent storage and flexible space for outdoor gear, a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full-time residence or a Vermont getaway, this property offers an excellent opportunity to enjoy one of Vermont’s most desirable areas at an attractive price point. Call today for a private viewing.

Constructed in 2025 and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk-in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with astone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate.

THE SUGAR HOUSE — Beautifully renovated in 2007, this light-filled Vermont home is ideally located in the heart of historic Bridgewater, just 10minutes from the charm, dining, and culture of the village of Woodstock. Offering the perfect balance of four-season recreation and classic New England character, the property is equally suited as a primary residence, weekend retreat, or investment opportunity. The home features three bedrooms, two updated bathrooms, an open-concept kitchen and living area, and fully modernized systems for easy ownership. Outside, enjoy a true Vermont lifestyle with nearby swimming holes, hiking and biking trails, horseback riding, the Bridgewater Mill, and local favorite Ramunto’s Pizza all within easy reach. The VAST trail is located just behind the property, providing direct access to winter adventures and peaceful summer walks through the Green Mountains. A spacious two-car garage includes a large second-floor workshop or studio space, while the charming chicken coop offers flexibility for hobby farming, storage, or relaxed evenings outdoors. Perfectly positioned for ski enthusiasts, the home is just a short drive to Killington Resort, Pico, Okemo, and Saskadena Six, making it an exceptional base for enjoying some of Vermont’s best skiing and year-round recreation. The property also benefits from a strong and established short-term rental history, offering excellent income potential in one of the region’s most desirable tourism corridors. Move-in ready and conveniently located near outstanding schools, outdoor recreation, and the timeless appeal of Woodstock, The Sugar House is a rare Upper Valley opportunity.

Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout. An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors stepping out to a massive deck for entertaining. The kitchen is well suited with top quality appliances, granite counters and maple cabinetry. There is a primary bedroom ensuite, and a guest bedroom, and a study on the main level. Moving downstairs, the expansive spaces offer a variety of options as extended family space, or in-law accommodation. There's a family room with fireplace, a large area for home gym, or play space. Two additional rooms for guest accommodation, a cedar closet, full bathroom, potential for a second kitchen. Outdoors, the property is magical with terraced perennial beds, mature trees and shrubs all selected to attract birds and butterflies. The oversized barn has three bays, a heated workshop/studio with bathroom, and ample loft space for hay/storage. Commercial grade generator, solar array. Lovely trail network lacing through the property. Easy access to Interstate, Woodstock, Hanover NH, skiing, golf and recreation.

Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel and connects to the exterior spaces through French doors stepping out toa covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concepts eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt roads, and trail systems (ideal for equine interests, hiking, cycling) are just outside your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC.

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price.

Perched on a private hilltop and surrounded by nature, this stunning recently renovated home offers over 141 acres of open and wooded land enrolled in Vermont’s Current Use Forestry Program. Thoughtfully designed by Beilman Design, the residence features gracious living spaces filled with natural light and an exceptional floor plan ideal for entertaining. The handsome chef’s kitchen is appointed with high-end stainless-steel appliances, beautiful countertops, and an exquisite walk-in pantry dedicated to preparation and storage. A spacious guest suite includes two bedrooms and a comfortable sitting area, while the finished lower level offers an additional recreation room with a fireplace. The luxurious primary suite features oversized walk-in closets and a gas fireplace that adds warmth and ambiance. Enjoy the peaceful surroundings from the lovely, screened porch or the expansive covered porch overlooking the sweeping lawn and natural landscape. Offering three levels of refined living, the property also includes a large, oversized barn for storage, a generator, and a driveway alarm system. Conveniently located with easy access to GMHA, skiing, championship golf, and exceptional fishing, this private retreat presents outstanding potential for a family compound or countryside getaway. Landscaping plans are available.

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.

Expansive long-range southerly views to Mount Ascutney create a breathtaking backdrop from the living room, dining room, and the custom full-length deck complete with a screened gazebo. Framed by mature trees that provide both shade and privacy, the setting offers a perfect balance of seclusion and spectacular scenery.Ideally located on sought-after Fairbanks Turn, this beautifully crafted three-bedroom, two and one-half-bath Post-and-Beam home enjoys exceptional privacy while remaining just minutes from the Club and the Village of Woodstock. Thoughtfully designed for comfortable year-round living, the home features a first-floor primary suite, allowing for convenient single-level living.The warm and inviting interior showcases exposed beams, soaring spaces, and hardwood and bamboo flooring throughout the kitchen, living room, and dining area. The primary suite, loft, and upper-level bedrooms are comfortably carpeted, creating welcoming retreats for family and guests.A drive-under two-car garage and additional parking at the front entrance provide easy access in all seasons. The lower level offers excellent utility and flexibility, featuring cedar closets, a workshop, a ski-tuning area, and a bonus room ideal for hobbies, fitness, or additional living space.Surrounded by natural beauty and designed with timeless craftsmanship, this exceptional Post-and-Beam home is a wonderful opportunity to enjoy mountain views, privacy, and all that Quechee and the Upper Valley have to offer.

Perched on 2.7 private acres with a stunning westerly exposure, this exceptional contemporary Cape captures sweeping views of Vermont's rolling hills, including the slopes of the Quechee Ski Hill. Framed by mature birch trees and towering pines, the setting is both peaceful and picturesque, offering spectacular sunsets and year-round beauty. Designed for comfort and gathering, the home features an expansive mudroom with a custom live-edge bench that opens directly to a grilling deck overlooking the view. A covered porch stretches the full length of the rear of the home, providing an inviting outdoor living space from which to enjoy the surrounding landscape and remarkable sunsets. Inside, the warm and welcoming five-bedroom, three-and-a-half-bath floor plan is ideal for both everyday living and entertaining. Hardwood floors flow from the mudroom through the kitchen, dining area, and living room, where a soaring cathedral ceiling and handsome brick fireplace create a dramatic yet comfortable centerpiece. The home offers the convenience of a first-floor primary bedroom suite along with a first-floor laundry room, making single-level living an attractive option. All five bedrooms are comfortably carpeted, providing warmth and comfort throughout the private living spaces. The finished lower level provides additional living space with a spacious family room, game area, wet bar, and wood stove perfect for gathering with family and friends after a day of skiing, hiking, or exploring the Upper Valley. Additional features include central air conditioning on the first floor, easy access to Jake's Market, and a location just minutes from Woodstock, Quechee, and the area's many recreational and cultural amenities. As an added benefit, the property has demonstrated exceptional short-term rental performance. Combining breathtaking views, privacy, generous living spaces, and a truly magical Vermont setting, this is a rare opportunity to enjoy the very best of Upper Valley living.

Set against sweeping views of Mount Ascutney, this distinctive property offers the kind of Vermont escape buyers rarely findprivate, spacious, and designed for gathering. Thoughtfully expanded over time, the home seamlessly blends two living spaces, creating an ideal setting for hosting extended family and friends while still offering comfort and privacy for all.The newer portion of the home is centered around light and connection, with an open-concept living, dining, and kitchen area anchored by a custom stone fireplace and framed by floor-to-ceiling windows that capture the mountain views. Step out onto the sun-drenched deckperfect for morning coffee, apr?s-ski evenings, or summer entertaining. The primary suite offers a peaceful retreat with its own private deck, ensuite bath, walk-in closet, and dedicated office space.The original wing of the home provides additional room for guests, featuring four bedrooms, kitchen and its own living area, as well as direct access to a second deck overlooking the surrounding landscapecreating a natural separation that makes hosting effortless.Whether used as a single expansive home or configured to offer private guest accommodations, the layout supports a range of lifestylesfrom weekend retreats to extended stays.Located in the heart of Brownsville, just moments from the trails and outdoor recreation of Mount Ascutney, this property offers four-season appeal. Enjoy easy access to the charm of nearby Woodstock, as well as skiing at Okemo and Killington, and the cultural and dining destinations of the Upper Valley.A rare opportunity to create a true Vermont getawaydesigned for connection, relaxation, and year-round enjoyment.

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.

Well-maintained Nordic Haus 1BR/BA condo with loft and separate study, ready for new owners. This corner unit has a covered porch, an updated kitchen, and upgraded flooring. Enjoy comfortable, low maintenance living just steps from Ascutney Outdoors for hiking, biking, skiing, and winter tubing. Minutes from the acclaimed Brownsville Butcher Pantry, with easy access to I-91. This property is ideal for first-time buyers, investors, or those seeking a weekend getaway. Right of First Refusal (ROFR)