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26 Tremont St.
Claremont NH
603-542-5188
Rt 5 Ascutney VT
802-674-6311
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  • Viewing 11 to 30 of 32 listings « Back 1 2 Next »
  • $799,000 | $399 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2004  |  Acres: 30.18 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.


  • $799,999 | $308 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2600  |  Acres: 2.9 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The home offers 3 bedrooms and 2.5 bathrooms, with warm and inviting open living spaces anchored by both a fireplace and a wood stove, perfect for cozy Vermont evenings. A spacious porch takes full advantage of the South Easterly views, providing an ideal spot to relax and take in the natural surroundings. A detached 2-car garage with an accessory dwelling unit studio above, complete with a 3/4 bath; ideal for guests, rental potential, or a private office/studio. A potting shed and a wood shed complete the outdoor spaces, offering ample storage and outdoo hobbies. With its combination of rustic charm, modern utility, and an central location, this property is a rare opportunity to enjoy mountain living without sacrificing accessibility to nearby amenities and recreation.


  • $845,000 | $1,408 per sq.ft. | 2 Beds | 1 Baths | Total Sq. Ft. 600  |  Acres: 6.07 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.


  • Price Change! reduced by $320,000 down 37% on June 10th 2026
    $865,000 | $311 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2785  |  Acres: 5.01 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples.


  • $965,000 | $606 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2638  |  Acres: 2 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock—just seven minutes to the Woodstock Green—this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies—ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!


  • Under Contract $1,199,000 | $615 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 1950  |  Acres: 0.07 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Beautifully Restored all the way down to the studs, c. 1890 Village Home in the Heart of downtown Woodstock! Extensively renovated while preserving its historic charm, this 3-bedroom, 3-bathroom residence offers the perfect blend of character and modern convenience right in the center of EVERYTHING. Major renovations and improvements include updated spray foam insulation, walls, windows, wiring, flooring, appliances, even structural supports, and dual new heating systems with Central AC. Abundant natural light highlight the home’s timeless appeal and the new deck over the garage insures you won't miss any of the action in town. The main level features a sun-filled living room with fireplace, private study with adjoining 3/4 bath, and an open-concept kitchen and dining area with quartz countertops, stainless appliances, and direct access to a welcoming covered porch overlooking the quaint New England charm of downtown Woodstock. Upstairs are three bedrooms, including a spacious primary suite with private bath and double closets. A second full bath features a tiled shower, soaking tub, and new Washer & Dryer. The finished third floor provides an exceptional bonus space ideal for a family room, office, studio, playroom, or guest accommodations, along with a separate storage room. Additional amenities include a paved driveway, lower-level garage/storage area, town water and sewer, dual Bosch propane boilers, propane 75G hot water, central air conditioning, and low-maintenance village living. Enjoy being just steps from Woodstock’s renowned restaurants, shops, galleries, recreation, and community events. A rare opportunity to own a move-in-ready historic home in one of Vermont’s most desirable village locations.


  • New Listing! $1,375,000 | $445 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3979  |  Acres: 0.52 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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.


  • Price Change! reduced by $100,000 down 7% on June 6th 2026
    $1,395,000 | $382 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 3648  |  Acres: 6.2 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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 3–4 bedrooms, 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.


  • $1,695,000 | $353 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 4800  |  Acres: 0.56 VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT
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    VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT Homes for sale


    Description:Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate!


  • $1,895,000 | $644 per sq.ft. | 2 Beds | 3 Baths | Total Sq. Ft. 2944  |  Acres: 14.9 Waterfront Owned 1000 Ft. of shoreline | WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.


  • $2,225,000 | $575 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3867  |  Acres: 15.94 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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 woodstove, 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.


  • $2,300,000 | $659 per sq.ft. | 5 Beds | 6 Baths | Total Sq. Ft. 3489  |  Acres: 9 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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 approx 15 years ago with handsome hardwood 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 book shelves, 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 garage 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!


  • Under Contract Price Change! reduced by $1,000,000 down 40% on July 9th 2026
    $2,500,000 | $460 per sq.ft. | 6 Beds | 6 Baths | Total Sq. Ft. 5433  |  Acres: 2 Waterfront Owned WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.


  • $2,500,000 | $488 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 5127  |  Acres: 17.65 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities.


  • $2,599,000 | $434 per sq.ft. | 9 Beds | 11 Baths | Total Sq. Ft. 5993  |  Acres: 0.46 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner’s quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home!


  • Price Change! reduced by $200,000 down 7% on July 14th 2026
    $2,900,000 | $599 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 4843  |  Acres: 105.1 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef’s kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.


  • Price Change! reduced by $350,000 down 12% on July 16th 2026
    $2,950,000 | $1,003 per sq.ft. | 3 Beds | 5 Baths | Total Sq. Ft. 3682  |  Acres: 2.37 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock’s iconic Mount Tom and the Marsh-Billings Museum, Vermont’s only National Park. The property sits at the end of a quiet road with only one other neighboring residence and is surrounded by over 400 acres of conserved land. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment.


  • $2,950,000 | $527 per sq.ft. | 8 Beds | 8 Baths | Total Sq. Ft. 6200  |  Acres: 32 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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 stonewalls, 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 entertaining 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.


  • Under Contract $2,999,000 | $583 per sq.ft. | 6 Beds | 8 Baths | Total Sq. Ft. 5142  |  Acres: 0.36 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description: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.


  • New Listing! $5,875,000 | $1,446 per sq.ft. | 3 Beds | 4 Baths | Total Sq. Ft. 5384  |  Acres: 68.92 WOODSTOCK VT
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    WOODSTOCK VT Homes for sale


    Description:Sorgenfrei German for "carefree" captures the spirit of this remarkable property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. Built by Ennis Construction in 2015 on 68 acres, the three-bedroom home embodies the enduring appeal of timber frame architecture with soaring spaces, exposed fir beams, and exceptional craftsmanship. Mahogany clapboard siding lends timeless character to the exterior. Inside, walls of glass frame sweeping mountain views, filling the home with natural light and creating a seamless connection to the landscape. Nearly every principal room is oriented toward the views to the East. The open floor plan flows from the gourmet kitchen to the dining area and dramatic great room, anchored by a floor-to-ceiling double-sided stone fireplace. A sitting room, screened porch, deck, and the primary suite complete the main level. Upstairs are a loft office, two en suite guest bedrooms, and a media room, while the walk-out lower level is dedicated to recreation and relaxation with a gym, infrared sauna, workshop, and a temperature-controlled wine room for approximately 1,000 bottles. A three-bay garage provides ample space for vehicles, and gear. Complete end-of-road privacy, panoramic views over the Woodstock Valley, perennial gardens, open pasture for a few horses or sheep, and an extensive trail network connecting directly to the GMHA trail system create a quintessential Vermont lifestyle. Thoughtfully designed for ease of ownership, the property is as practical as it is beautiful, with an 18.5 kW solar array supporting near net-zero living. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.



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Copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 21st, 2026
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