- Woodstock VT Homes $0 to $30000000
- Change Town
-
Narrow your price range.
-
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
View Details & 58 images
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
View Details & 21 images
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
View Details & 58 images
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
View Details & 38 images
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
View Details & 30 images
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.
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
Designed by BSC DATA