Woodstock VT Homes $0 to $30000000
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- Under Contract New Listing!
$925,000 | $321 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2882 | Acres: 2.08 WOODSTOCK VT
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Description:Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock location for those wanting a peaceful Vermont countryside vibe to unwind but the vibrant Woodstock Village life at the foot of your hill! The interior design presents a more refined open concept design that offers both openness but a more defined layout for functional separation and intimacy. A captivating light filled living room that opens onto a mahogany deck is centered upon a handsome fireplaced wall that is open on both sides to allow flow into a lovely eat-in kitchen detailed with quartz counters. A primary ensuite bedroom, study/office, and full bath complete the main level. The lower level presents a second living room that opens onto a patio and centers upon a second fireplace. Three bedrooms and a terrific laundry room/mudroom complete the lower level. Enjoy relaxing, entertaining, and taking in the sunsets from the westerly facing patio and deck. Perfect as a primary or secondary home with all season recreation, theatre and the arts, dining, and shopping just minutes away and easy access to all the amenities and major employment the Upper Valley has to offer. Showings begin with Public Open House Saturday Oct 4 from 1-3pm.
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Price Change! reduced by $155,001 down 16% on September 8th 2025
$944,999 | $440 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2150 | Acres: 1.49 WOODSTOCK VT
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Description:Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens. The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes , stone patio and 2 decks offering plenty of spaces for outdoor living and entertaining. The open floor plan provides easy flow and the large windows and glass doors bring the out of doors in. A big bonus is central air conditioning ! The detached 2 car garage provides lots of storage and work space area . Enjoy the charm and various amenities of Woodstock Village that consistently is named one of the prettiest small towns in America . Easy access to sports for every season.. Twenty minutes to the Upper Valley , two and a half hours to Boston and 5 hours to NYC. Call today for an appointment .
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$985,000 | $513 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 1920 | Acres: 6.02 WOODSTOCK VT
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Description:PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot. Well-planned interior space, inside you will find a warm and inviting atmosphere, offering an eat-in kitchen enhanced by the heat from the wood stove or relax by the fireplace in the living room open to the dining room. The primary bedroom with a full bath featuring a jacuzzi tub, while the remaining rooms provide flexible options for guests. Recent updates like a new oil tank and a new water pressure tank ensure reliable modern living. Located just minutes from the heart of Woodstock, this home gives you easy access to local favorites like the Billings Farm and year-round fun at Okemo Mountain Resort. Whether you're into skiing, hiking, or something entirely more relaxed, there's something nearby for everyone. The neighborhood boasts a strong sense of an upscale community while maintaining a rural, secluded vibe. It’s that rare find that feels remote but keeps you close to all the essentials. Ideal for year-round living or a seasonal getaway, this property invites you to experience the best of Vermont in a setting that’s equal parts comfort and character.
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$1,185,000 | $425 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.
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$1,250,000 | $457 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2736 | Acres: 0.86 WOODSTOCK VT
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Description:Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary ensuite with step-in shower, and a glass-lined sunroom create an effortless flow. Thoughtful conveniences include a mini-split for year-round comfort, laundry on the main level, and an eight-foot slider off the dining room that opens to a private deck overlooking the backyard. Upstairs, an apartment with private entrance extends the home’s versatility with its own kitchen, living area, ¾ bath, and two bedrooms—perfect for guests, extended family, or private quarters. Outdoors, the property is framed by beautifully established perennial gardens and an expansive yard, offering rare in-village green space. A paved drive, two-car garage with overhead storage, standby whole-house generator, and public water and sewer add to the ease of ownership. The location is unmatched—just a street away from the elementary school, Vail Fields, the Village Green, and miles of walking trails. Schedule a private showing and see this grand home for yourself! A must-see. Open house Saturday October 4th from 10 AM - 12 PM.
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$1,295,000 | $419 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3089 | Acres: 0.52 Waterfront Owned WOODSTOCK VT
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Description:16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village, it has a two-car garage with a covered walkway into the mudroom entryway (plus more outside parking). The spacious kitchen/dining area opens to the vaulted-ceiling living room, which has an INCREDIBLE view up-river. A side door leads to the side-deck that has the same view and sound of the river for outdoor dining above the river. There is a propane woodstove in the living room and woodstove in the kitchen/dining. A 1st floor bedroom has an ensuite bath and small stack washer-dryer. Upstairs is a large bedroom looking out through the great room to the river, a smaller bedroom, a bath and lovely loft area above the living room. Downstairs is a large den/rec/office, a bedroom, a bathroom, the main laundry room and mechanical room, all renovated 11 years, post the Irene storm, when the river waters came up into the lower level. There are beautiful gardens in the front and rear of the house. SEE PROPERTY WEBSITE FOR 16 CHURCH ST WOODSTOCK FOR MORE DETAILS, FLOORPLANS HI REZ PHOTOS AND MORE.
- New Listing!
$1,295,000 | $485 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32 WOODSTOCK VT
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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. 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.
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$1,300,000 | $586 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2220 | Acres: 1.53 WOODSTOCK VT
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Description:Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air conditioning. A brand-new two-car garage will be completed before closing, adding convenience and value. Inside, light-filled spaces showcase new, wide-plank white oak flooring, a beautifully designed kitchen, and spa-like bathrooms. The thoughtful floor plan includes a private office, perfect for working from home or creative pursuits. Outdoors, a covered porch with handsome stone entry steps frames gorgeous northerly views, while a charming petite outbuilding—once the farm’s milking barn—offers endless possibilities as a studio, garden shed, or retreat. This turnkey home is a rare find: a character-filled property where every detail has been reimagined, offering modern comfort, low-maintenance peace of mind, and proximity to all that makes Woodstock one of New England’s most desirable communities.
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Price Change! reduced by $155,000 down 11% on July 24th 2025
$1,395,000 | $232 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 6014 | Acres: 0.05 VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT
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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.
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$1,495,000 | $590 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2532 | Acres: 0.79 WOODSTOCK VT
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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.
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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