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Woodstock VT Homes $0 to $30000000
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Price Change! reduced by $50,000 down 8% on April 28th 2025

Description:AGGRESSIVE PRICE REDUCTION - Classic Vermont Antique Farmhouse just outside of Woodstock Village! c.1903 Dormered Cape set on approx. 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deck�perfect for relaxing or entertaining. Inside, the home exudes warmth and comfort, featuring 2,600+ sqft, four bedrooms & three bathrooms. The inviting family room boasts a wood-burning fireplace, while the cozy living room is enhanced by a gas fireplace. The kitchen, with its soapstone Hearthstone brand woodstove and charming breakfast nook, is a delightful gathering space. Updates include newer windows, septic, appliances, and mechanicals, ensuring modern efficiency while maintaining the home�s classic appeal. An oversized one-car garage provides ample storage and parking. There is additional storage above the garage with room for potential expansion into an office, game room or studio apartment. This classic Vermont farmhouse offers the perfect balance of historic charm and modern convenience, just 4 minutes from Woodstock�s vibrant village center. The Woodstock Green is only a 5 minute drive, as is skiing at Saskadena Six. Close to everything the Upper Valley has to offer while offering a peaceful retreat. A rare opportunity to own a piece of Vermont�s pastoral beauty!
- Under Contract

Description:This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont�s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons.
- New Listing!

Description:Peaceful Gully Road Retreat � Just minutes from Woodstock Village Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock�s shops, restaurants, and schools. The main level features a light-filled, open-concept layout with a dramatic vaulted foyer, spacious kitchen/living/dining area, a half bath, and a versatile den. Step out onto the expansive wraparound deck�perfect for outdoor dining, entertaining, or simply enjoying the surroundings. Upstairs, the primary suite includes a walk-in closet, private balcony access, and a newly renovated three-quarter bath. Three additional bedrooms, an updated full bath, and a large laundry area complete the second level. Additional features include: � Attached garage with workshop/storage space on the lower level � High-efficiency propane furnace and numerous recent updates including kitchen, bathrooms, and flooring � Two outbuildings: a one-bay barn and a three-bay open garage/shed for ample storage � Outdoor highlights: treehouse; level lawn; two brooks; firepit area; and walking trails A rare opportunity to own a private, move-in-ready property in a sought-after location�just minutes from the heart of Woodstock Village.
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Price Change! reduced by $95,500 down 11% on March 18th 2025

Description:This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The home has a suite of rooms on the first floor that are perfect for a home-based business or studio area (or 2 extra bedrooms plus bonus room), and a one-bedroom full bath (with office & kitchen) in-law suite upstairs with private ground-level access. The main part of the home includes three additional bedrooms, a library, a music room, living room, dining room, two full baths, dressing room, and three-season enclosed porch. The charming eat-in kitchen includes beautiful display cabinets, hand painted tiles, and built-in pantry and laundry. In the stunning custom cherry wood library with marble fireplace and private deck, bibliophiles will find more than enough shelf space for their entire book collection, and a quiet, peaceful setting in which to read. Two readers in the family? The upstairs music room is similarly equipped, also with stunning cherry wood built-ins and detailing. Two staircases provide ample access to the upstairs and contribute to the ambling nature of the home. Walk to restaurants and a river front park!
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Price Change! reduced by $96,000 down 7% on March 10th 2025

Description:Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef�s kitchen with high-end stainless steel appliances, Vermont soapstone counters, custom cabinetry, and a spacious and sunny dining room. The cozy living room boasts one of two wood stoves, creating a warm and inviting space for relaxation. The massive family room is home to the second wood stove. There are two primary en-suites, each with a fireplace and spa-like bathroom, one in a private wing of the home, while the additional bedrooms and updated baths provide comfort and style. Outside, a large, partially screened-in deck and hot tub offer perfect spots to unwind and enjoy the tranquil surroundings�there is even a sauna off the rec room! Plenty of storage is available in the two-car garage or the two-stall barn. With solar panels, propane heating, two fireplaces, and two wood stoves, this home combines eco-friendly features with modern amenities. Its peaceful setting, just minutes from downtown Woodstock, is also close to the Green Mountain Horse Association, VAST snowmobile trails, Killington Mountain, Mount Tom, and the Saskadena Six Ski Area, making it a perfect full-time residence or seasonal escape. Enjoy Vermont living or work from home with EC Fiber!
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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.
- Under Contract

Description:Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive thermal glass windows. This generous gathering space hosts a dining area and breakfast bar adjacent to an outstanding chef's kitchen. Crafted with meticulous attention to detail, this remarkable residence features four bedrooms and five bathrooms. The first-floor primary suite is a private sanctuary, boasting custom built-in 'his & hers' closets, a spacious spa-like bathroom, and a secluded sundeck. The tavern room, with its vaulted ceiling, stone fireplace and cherry wood bar makes this the go-to house for friends gathering at any time, but especially on Fourth of July. On the second floor, you'll find a luxurious Primary Bedroom with an en suite bath, an office/study with an adjacent � bath, and a whimsical Children's Suite complete with cozy sleeping alcoves, and charming nooks.Conveniently located within walking distance to Woodstock High and Middle Schools, the Union Ice Arena, and the ever-popular Woodstock Farmer's Market grocery store, this splendid home offers the perfect balance of privacy without isolation.
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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.
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Description:INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, caf�, or retail store), Post Office (with current lease), Apartment 1 (with excellent AIRBNB rental history), 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 and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge.
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Price Change! reduced by $235,000 down 10% on March 27th 2025

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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