Woodstock VT Homes $0 to $30000000
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Price Change! reduced by $55,000 down 3% on July 5th 2025
$1,595,000 | $437 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 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.
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Price Change! reduced by $304,000 down 18% on October 3rd 2025
$1,695,000 | $402 per sq.ft. | 5 Beds | 5 Baths | Total Sq. Ft. 4214 | Acres: 1.07 WOODSTOCK VT
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Description:10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE.
- Under Contract
Price Change! reduced by $105,000 down 6% on July 13th 2025
$1,745,000 | $829 per sq.ft. | 2 Beds | 3 Baths | Total Sq. Ft. 2106 | Acres: 1.13 WOODSTOCK VT
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Description:Stunning Renovated Antique Cape in the Heart of Woodstock Village! Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village green, shops, restaurants, schools, and trailheads—leave the car behind and enjoy the best of village living. Every system in the home has been thoughtfully updated: all new wiring, plumbing, windows, roof, and high-performance heating and cooling. Geothermal and solar systems power the home efficiently and sustainably, while central air conditioning and radiant floor heating ensure year-round comfort. The floor plan is both flexible and inviting, with two spacious bedrooms—including a primary suite—located on the first floor and easily adaptable to accommodate a third bedroom. Upstairs, a bright, open-concept kitchen and living/dining area lead directly to a glass-covered deck that offers a birds-eye view of the surrounding gardens, village homes, and the conserved forest of Mt. Tom. Outside, extensive perennial beds, raised gardens, and mature plantings create a lush, private oasis. This is a home that lives lightly on the land while offering the walkable, in-town lifestyle so many seek—an exceptional opportunity in one of Vermont’s most desirable villages.
- Under Contract
Price Change! reduced by $450,000 down 26% on August 23rd 2025
$1,750,000 | $323 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 5422 | Acres: 31.43 WOODSTOCK VT
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Description:Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire home is a unique showplace of clever spaces, built-ins, with custom detail throughout; featuring mahogany, cherry, and locally sourced stone. The ten room- three bedroom, three bath main residence was carefully sited to optimize a stunning northeasterly view, and to communicate directly with exterior terraces, and established gardens overlooking a pond, rolling hills and fields. There is a detached one bedroom guest house (or caretaker's cottage), garage, horse barn, equipment shed and two garden sheds. Easy access to hiking trails. Three minutes to Fitness Ctr., 15 minutes to Saskadena Six skiing. 2.25 hours to Boston, 4.5 to NYC. Property enrolled in Current Use.
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Price Change! reduced by $200,000 down 11% on August 8th 2025
$1,800,000 | $360 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 5000 | Acres: 0.56 VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT
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Description:INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current lease), smaller Apartment 1 (with excellent AIRBNB rental history), larger Apartment 2 (The owner’s unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. 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.
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$1,900,000 | $645 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.
- Under Contract
Price Change! reduced by $535,000 down 27% on August 9th 2025
$1,950,000 | $557 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 3502 | Acres: 2.57 Waterfront Owned 450 Ft. of shoreline | WOODSTOCK VT
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Description:The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barn—currently used for storage—could easily be converted to accommodate a couple of horses or sheep. The 3-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a 2nd-floor ballroom with a coved ceiling and fiddler’s stage—a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers 2 bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering and creating. A timber bridge spans the waterway, connecting the property’s field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District.
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Price Change! reduced by $455,000 down 23% on September 25th 2025
$1,995,000 | $358 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 5573 | Acres: 40 Waterfront Owned 48 Ft. of shoreline | WOODSTOCK VT
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Description:"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef’s kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, “All Sessons” is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region’s most picturesque towns.
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$2,400,000 | $497 per sq.ft. | 5 Beds | 5 Baths | Total Sq. Ft. 4832 | Acres: 2.64 WOODSTOCK VT
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Description:Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perfect balance of charm and modern comfort. Just minutes from Woodstock and South Woodstock, the property enjoys both convenience and a peaceful setting. The home features generous living and entertaining spaces (remodeled in 2016 by Sargent Design Company), multiple porches, and seamless indoor-outdoor flow. The main residence offers 5 bedrooms, including a large primary suite, while the converted barn includes a private guest apartment, ideal for hosting company. Highlights include a hot tub, indoor and outdoor fireplaces, and thoughtful updates throughout that make the home as efficient and easy to maintain as it is elegant. With open spaces designed for gatherings and cozy corners for retreat, this home is equally suited for year-round living or a Vermont getaway. Outdoor enthusiasts will appreciate the home’s proximity to skiing at Killington and Saskadena Six, as well as easy access to hiking, biking, and countless four-season activities. A truly exceptional property blending timeless farmhouse character with today’s modern luxuries.
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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!
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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