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$695,000 | $304 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 2288 | Acres: 0.15 Waterfront Shared WOODSTOCK VT
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Description:A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!
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$749,000 | $451 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1660 | Acres: 0.19 WOODSTOCK VT
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Description:Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and pickleball courts. The homeowners have meticulously updated the property, featuring a stunning new kitchen and a refreshed second-floor bath, blending modern comfort with timeless charm. Unwind on the covered porch with a favorite drink while soaking in the serene surroundings. The inviting living room has a cozy gas fireplace, perfect for cool evenings. The spacious dining area opens to the expanded kitchen, boasting elegant cabinetry, sleek quartz countertops, and top-quality appliances. Newly installed pine flooring adds sophistication throughout. With three spacious bedrooms and two updated bathrooms, each room is designed for comfort. A versatile sitting room off the primary bedroom is perfect as a playroom or quiet study. Additional features include a new boiler, new dining room windows, and upgraded wiring with 200 AMP service. The property also offers a two-stall garage with partially finished space above, presenting endless customization possibilities. Whether you're seeking a forever home or a peaceful retreat, this move-in-ready gem is a must-see!
- New Listing!
$750,000 | $328 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 2285 | Acres: WOODSTOCK VT
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Description:Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.
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$815,000 | $248 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 3284 | Acres: 2.84 WOODSTOCK VT
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Description:This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway.
- Under Contract
Price Change! reduced by $168,000 down 21% on October 30th 2025
$817,000 | $296 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 2760 | Acres: 10.1 WOODSTOCK VT
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Description:This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house .The dwelling has a wrap around deck overlooking the meadows and pond with views to the south. Antique stone walls are reminiscent of days gone by .If privacy but convenience to Woodstock village is your goal you need not look further. Some of the features include hardwood floors , open floorplan that includes dining and living room , large downstairs game room. Easy access to Killington, Okemo Mountain and of course Woodstock's own Saskadena Six for Skiing . Golf, tennis . biking and fishing are just a few of the many outdoor activities in the area . Pentangle Arts provides music and theater throughout the year. Woodstock was named the prettiest small town in America . Come make it your home in this amazing property. Call today for an appointment.
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$845,000 | $1,408 per sq.ft. | 2 Beds | 1 Baths | Total Sq. Ft. 600 | Acres: 6.07 WOODSTOCK VT
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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.
- Under Contract
$895,000 | $566 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 1580 | Acres: 0.08 WOODSTOCK VT
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Description:Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed courtyard. First floor also features a mudroom, new 1/2 bath, family room and gracious formal living room accented with bookshelves. Second floor consists of a large primary bedroom, a guest bedroom and newly renovated full bathroom and laundry room. Third level has another 2 bedrooms or could be used as offices. This residence is the south side (left side) of the building and includes new mini split a/c units, a storage shed and perennials gardens. Walk to all of towns amenities, shops and restaurants. Mt. Tom National park and hiking behind the house for those nature enthusiasts, championship golf, skiing and fly fishing near by. 20 minutes to the Upper Valley and Dartmouth. Wonderful opportunity to own this charming home in one of Vermonts prettiest towns.
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Price Change! reduced by $200,000 down 20% on October 21st 2025
$985,000 | $354 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2785 | Acres: 5.01 WOODSTOCK VT
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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.
- Under Contract
$1,195,000 | $448 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32 WOODSTOCK VT
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Description:Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler’s pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces — including a fireplaced living room with gas insert and a den warmed by a wood stove — offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock’s celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington’s Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best.
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$1,495,000 | $564 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2650 | Acres: 5 WOODSTOCK VT
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Description:Known affectionately as “Green Gable Farm,” this beautifully renovated 1884 Vermont farmhouse sits on 5 picturesque acres in Woodstock, complete with a year-round babbling brook, just minutes from South Woodstock, the Woodstock Inn Fitness Center, golf course, cross-country ski trails, mountain biking, and the Woodstock Village Green. The current owners undertook a comprehensive renovation, thoughtfully preserving the home’s historic character—including original barnboard floors and exposed beams—while updating every major system and living space. New mechanicals, upgraded insulation, all new double-pane windows, central HVAC with heating and cooling, high-speed fiber internet, new baths, and a fully redesigned kitchen bring modern comfort to this classic country home. The architecturally reimagined floor plan creates an open, inviting first floor centered around a gourmet eat-in kitchen with Viking appliances, farmhouse sink and abundant workspace. A highly functional mudroom entry, marble tile floors, new laundry room, full bath, and first-floor bedroom add everyday practicality. The kitchen flows into a cozy sitting area with fireplace and additional flexible living spaces ideal for dining, reading, or entertaining. Upstairs are 2 spacious ensuite bedrooms, including a serene primary suite with dressing area, double sinks, smart toilet, glass-enclosed shower, and freestanding soaking tub overlooking stone walls, open fields, and berry patches. Sliding doors off the kitchen open to a large rear deck featuring a heated 12’ swim spa for year-round enjoyment. A charming historic shed-barn offers space for a workshop, studio, or recreation area, while unfinished space above the attached two-car garage provides expansion potential for future guest or living quarters. Much of the furniture and furnishings are available separately, making Green Gable Farm a rare turnkey opportunity blending historic Vermont charm, modern comfort, and an exceptional Woodstock location.
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$1,495,000 | $410 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 3648 | Acres: 6.2 WOODSTOCK VT
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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.
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$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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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.
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$2,500,000 | $488 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 5127 | Acres: 17.65 WOODSTOCK VT
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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.
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$2,599,000 | $434 per sq.ft. | 9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46 WOODSTOCK VT
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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!
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Price Change! reduced by $550,000 down 19% on March 13th 2026
$2,950,000 | $543 per sq.ft. | 6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 2 Waterfront Owned WOODSTOCK VT
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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.
- New Listing!
$3,100,000 | $640 per sq.ft. | 5 Beds | 6 Baths | Total Sq. Ft. 4843 | Acres: 105.1 WOODSTOCK VT
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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.
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$3,300,000 | $896 per sq.ft. | 3 Beds | 5 Baths | Total Sq. Ft. 3682 | Acres: 2.37 WOODSTOCK VT
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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.
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$6,673,000 | $1,602 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 4165 | Acres: 465 WOODSTOCK VT
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Description:Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10’ hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager’s office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA’s trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.
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Price Change! reduced by $500,000 down 7% on August 29th 2025
$6,750,000 | $1,327 per sq.ft. | 4 Beds | 5 Baths | Total Sq. Ft. 5087 | Acres: 63.88 WOODSTOCK VT
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Description:Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby.
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Price Change! reduced by $3,100,000 down 21% on April 10th 2026
$14,900,000 | $1,190 per sq.ft. | 7 Beds | 10 Baths | Total Sq. Ft. 12520 | Acres: 183.7 WOODSTOCK VT
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Description:Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner’s quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.
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Data last updated May 28th, 2026
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