Woodstock VT Homes $0 to $30000000
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- Under Contract
$2,600,000 | $650 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 3998 | Acres: 0.37 VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT
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Description:2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern convenience with original charm. The first floor features oversized, recently updated windows and several spacious high ceiling gathering rooms including a formal living room, dining room, library, and central family room. A cozy eat-in kitchen with fireplace on the north side of the house opens to a lovely landscaped yard shaded by mature maple trees. The second floor, also punctuated by high ceilings and windows to give it a bright and spacious feel, features a primary bedroom on the front side of the house with an adjoining dressing area, walk in closets, and full bath. Adjacent the primary is another sizable bedroom with its own bath, while two additional bedrooms with shared bath round out the level. The detached barn garage has space for one car and plenty of additional storage. Idyllically sited and within walking distance of local shopping, dining, schools, hiking trails, and Marsh-Billings-Rockefeller National Historic Park, this iconic Woodstock home is a rare gem.
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$3,500,000 | $644 per sq.ft. | 6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 10 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 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.
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$3,500,000 | $681 per sq.ft. | 6 Beds | 8 Baths | Total Sq. Ft. 5142 | Acres: 0.36 WOODSTOCK VT
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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.
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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: 65.45 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 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.
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$8,000,000 | $1,486 per sq.ft. | 3 Beds | 4 Baths | Total Sq. Ft. 5384 | Acres: 68.92 WOODSTOCK VT
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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.
802-295-1355
The Clerkin Agency, P.C.
565 Maple Street, White River Junction, VT. 05001
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Data last updated October 11th, 2025
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