You are viewing Woodstock VT Homes between $0 and $30000000 dollars.
$18,000,000 $1,438 per sq.ft. Woodstock VT Home »
7 Beds | 10 Baths | Total Sq. Ft. 12520 | Acres: 183.7Listed on Thursday Oct 16, 2025
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. See Listing Details & 59 images. Includes a Virtual Tour
$8,000,000 $1,486 per sq.ft. Woodstock VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 5384 | Acres: 68.92Listed on Monday May 5, 2025
Description: Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the hand crafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains. See Listing Details & 47 images. Includes a Virtual Tour
$6,750,000 $1,327 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 5087 | Acres: 65.45Listed on Wednesday Jun 4, 2025
Description: Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 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, chicken coop, 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. Showings begin June 7th. See Listing Details & 48 images. Includes a Virtual Tour
$3,500,000 $644 per sq.ft. Woodstock VT Home »
6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 10Listed on Friday Jun 28, 2024
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 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. 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. See Listing Details & 40 images. Includes a Virtual Tour
$3,500,000 $681 per sq.ft. Woodstock VT Home »
6 Beds | 8 Baths | Total Sq. Ft. 5142 | Acres: 0.36Listed on Wednesday Aug 13, 2025
Description: Conveniently located on the southwest side of the picturesque 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, functionality, modern comfort and convenience. 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 a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens. See Listing Details & 42 images.
$3,300,000 $896 per sq.ft. Woodstock VT Home »
3 Beds | 5 Baths | Total Sq. Ft. 3682 | Acres: 2.37Listed on Monday Dec 15, 2025
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. See Listing Details & 26 images. Includes a Virtual Tour
$2,599,000 $434 per sq.ft. Woodstock VT Home »
9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46Listed on Sunday Sep 21, 2025
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! See Listing Details & 54 images.
$2,395,000 $657 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $205,000 down 9% on December 5th 2025
6 Beds | 5 Baths | Total Sq. Ft. 3645 | Acres: 112.88
Listed on Thursday Oct 16, 2025
Description: Gilbert's Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first "modern" ski run in the US. Located two miles from the village center of Woodstock, the "prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7 historic structures including: 1830s Greek-revival farmhouse with bright natural light (4BR, 2 bathrooms with showers, 11 rooms total, including custom-built modern farmhouse kitchen); authentic ski lodge/guest house (2BR, 1 full bath, 6 rooms total); 1700s sleigh barn/family room with floor-to-ceiling glass, full kitchen, half bath, private deck and fireplace; restored original dairy barn with bar, dance floor and loft; modern greenhouse conservatory with its own half bath, wood stove and outdoor pavilion; farmhouse extension with garage, loft, and mudroom; detached, 5-bay shed for cars and equipment; and vintage milk house (all with ample room for expansion). A natural paradise - with stunning, unspoiled views, a huge sugar maple grove, stone walls, vineyards and acres of wildflower meadows, this property offers serene trails and expansive outdoor space. Onsite opportunities include: ski-in/ski-out, snowboarding and sledding (install your own private lift); hiking; trail running; wildlife watching; horseback riding; maple syrup production (sugaring), and the finest fall foliage, star gazing and firefly shows in New England. Nearby is the Woodstock Country Club with golf, tennis, spa and pool; multiple streams, rivers and lakes for fishing/swimming; the Green Mountain Horse Association with miles of trails; the Marsh-Billings-Rockefeller National Park carriage paths; quaint general stores, and easy access to world-class downhill skiing/mountain biking at Saskadena Six and Killington. Flood Data incorrect: Minimal/Low Flood Risk. See Listing Details & 60 images. Includes a Virtual Tour
$1,600,000 $266 per sq.ft. Village of Woodstock in Town of Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 6014 | Acres: 0.05Listed on Thursday Mar 6, 2025
Description: 15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. See Listing Details & 43 images.
$1,595,000 $437 per sq.ft. Woodstock VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 3648 | Acres: 6.2Listed on Saturday Jul 5, 2025
Description: Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef's kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces--wood-burning, brick, and gas-ready--provide cozy warmth throughout. Upstairs, find 3-4 bedrooms including one with its own fireplace, plus a private guest room or office above the garage. A covered porch, sunny patio, inground pool with heat hookup, apiary, and dedicated garden create an idyllic outdoor lifestyle. Over 5 acres of invisible fencing allow pets to roam freely. Adjacent to the site of the country's first ski tow, with easy access to Saskadena Six and fantastic winter recreation. Bonus: a heated, plumbed two-floor barn/workshop with its own car bay--ready to become a media/game room, studio, or guest space. Easy access to I-89 and the Upper Valley. A rare opportunity for acreage, privacy, and proximity to one of New England's most iconic villages. See Listing Details & 49 images. Includes a Virtual Tour
$1,495,000 $590 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2532 | Acres: 0.79Listed on Tuesday Jul 1, 2025
Description: A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors--just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully updated bathrooms throughout. Natural light floods the living spaces, which flow easily for everyday living or entertaining. A large, unfinished studio apartment is ready for your design--perfect for an in-law suite, au pair quarters, or as a short- or long-term rental. Above the detached barn, a finished space provides a quiet work-from-home setup or creative studio. With close proximity to the Mt. Peg trail system, this location offers direct access to hiking, mountain biking, and nordic skiing, while the restaurants, shops, and cultural amenities of Woodstock Village are just a short stroll away. A rare opportunity for turn-key living in one of Vermont's most picturesque towns. Showings begin 7/5 with an open house from 10:30am - 12:30pm. See Listing Details & 41 images. Includes a Virtual Tour
$1,425,000 $414 per sq.ft. Woodstock VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 3440 | Acres: 0.83Listed on Friday Dec 12, 2025
Description: Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and flow beautifully for entertaining and every day living. Recent expansion/restoration of the attached carriage barn offers additional opportunity as an in-law, a guest suite, an income producing rental unit, or as a spectacular Great Room addition to the main home with a private deck. The grounds are lovely with mature plantings and established perennial beds. Easy access to miles of dirt roads, and trails for hiking and recreation. Recently added two-car garage with storage above, and a handy garden shed. New energy efficient windows throughout. New solar installation, leased Tesla storage power wall provide seamless power in the event of an outage. This one is a must see! See Listing Details & 46 images.
$1,300,000 $407 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 3195 | Acres: 1.07Listed on Tuesday Nov 11, 2025
Description: Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space--perfect for a playroom, media room, fitness area, or hobbies. Central air conditioning ensures year-round comfort, while an oversized, heated garage and an in-ground irrigation system make this home convenient in every season. Step outside to a private patio, surrounded by terraced gardens and stonework that add character and curb appeal. Located in a quiet setting yet within easy reach of restaurants, shops, and the village green, this property offers modern convenience in one of Woodstock's most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermont's most charming village. See Listing Details & 60 images. Includes a Virtual Tour
$1,295,000 $568 per sq.ft. Woodstock VT Home »
2 Beds | 4 Baths | Total Sq. Ft. 2280 | Acres: 0.8Listed on Wednesday Oct 29, 2025
Description: Welcome to 33 Mountain Avenue - a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one car garage. An exquisite multi-terraced exterior landscape design is predominately and privately located at the back of the property. Plentiful space for gardening, a fire-pit, or even an in-ground pool - where once there was one! Take in the trails of Mt.Tom and Marsh-Billings-Rockefeller National Park just outside your door. Enjoy a lovely stroll along Mountain Ave and thru the iconic Middle Covered Bridge to tap into a multitude of dining options, shopping, and performances at Pentangle Arts. A rare, unique, and coveted Woodstock Village location! See Listing Details & 32 images. Includes a Virtual Tour
$1,250,000 $469 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $45,000 down 4% on December 22nd 2025
4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32
Listed on Sunday Oct 5, 2025
Description: This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef's kitchen and den. New Thor stainless steel 48" propane range installed October 2025. Privately set on over 8 acres, the property offers true seclusion with the convenience of being just minutes to Woodstock Village, close to Killington and Okemo skiing, and near local favorites including Ramunto's Pizza and nearby event venues. Amenities include a private in-ground pool with expansive mountain views, plus an oversized garage/barn with storage and space above for potential guest quarters. An ideal countryside retreat for year-round living or a second home escape. See Listing Details & 42 images.
