Woodstock VT Homes $0 to $30000000
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- Under Contract
Price Change! reduced by $86,500 down 12% on August 24th 2025
$698,500 | $451 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 1550 | Acres: 0.16 WOODSTOCK VT
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Description:Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances, maple flooring and lighting that opens into the dining room accented with a lovely bay window for additional lighting. High ceilings with moldings throughout. Living room features lots of windows and propane stove for those looking to curl up with a book on a cold winter day. Ample room for entertaining. New front door opens to a renovated wrap around covered porch for afternoon tea. Upstairs has 3 bedrooms, renovated bath, shiplapped walls along with all the charm that comes with a 1920's home. New windows, lovely perennial gardens accented with stunning apple tree in front yard when it bloom...as well as a privacy fence. Come take a look... charming cottage in one of America's prettiest towns.........Seller is a licensed real estate agent in the State of VT
- Under Contract
$795,000 | $469 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1694 | Acres: 0.42 VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT
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Description:This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A comprehensive renovation several years ago opened the main level floorplan to eliminate partitions adapting the house to modern lifestyles. The backyard rises in tiers from the lower level with picnic table and grilling area to an elevated plateau used for expansive vegetable and flowers gardens. Truly a joyful place to call home in the heart of Woodstock's historic community.
- Under Contract
$798,000 | $610 per sq.ft. | 2 Beds | 2 Baths | Total Sq. Ft. 1308 | Acres: 5.33 WOODSTOCK VT
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Description:Built in 2019, this charming Cape-style home is nestled on five sunny, private acres just minutes from Woodstock Village. Thoughtfully designed and beautifully constructed, the home offers efficient, low-maintenance living in a coveted location. With excellent solar exposure, stunning sunset views, and lovely hillside scenery, it’s bright, warm, and welcoming year-round. The interior features a gorgeous open kitchen with quality finishes, two beautiful bathrooms, and two comfortable bedrooms. With a four-bedroom septic system already in place, the home offers easy potential for future expansion. Outside, the property is equally exceptional. A custom bluestone patio invites outdoor dining and relaxation, while professionally designed raised beds and a high-end greenhouse (high tunnel) provide everything needed for productive gardening. Established perennial gardens surround the home with vibrant seasonal color, and private trails (cut in and ready to enjoy) lead to the top of the property for peaceful walks and sweeping views. Whether you’re seeking a full-time residence, a Vermont retreat, or a property to grow into over time, this home offers rare flexibility, natural beauty, and a connection to one of New England’s most picturesque villages. Showings begin 7/7/2025. No showings 7/15/2025 - 7/20/2025.
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$810,000 | $488 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1660 | Acres: 0.19 WOODSTOCK VT
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Description:Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and pickleball courts. The homeowners have meticulously updated the property, featuring a stunning new kitchen and a refreshed second-floor bath, blending modern comfort with timeless charm. Unwind on the covered porch with a favorite drink while soaking in the serene surroundings. The inviting living room has a cozy gas fireplace, perfect for cool evenings. The spacious dining area opens to the expanded kitchen, boasting elegant cabinetry, sleek quartz countertops, and top-quality appliances. Newly installed pine flooring adds sophistication throughout. With three spacious bedrooms and two updated bathrooms, each room is designed for comfort. A versatile sitting room off the primary bedroom is perfect as a playroom or quiet study. Additional features include a new boiler, new dining room windows, and upgraded wiring with 200 AMP service. The property also offers a two-stall garage with partially finished space above, presenting endless customization possibilities. Whether you're seeking a forever home or a peaceful retreat, this move-in-ready gem is a must-see! Schedule a showing today!
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$845,000 | $1,408 per sq.ft. | 2 Beds | 1 Baths | Total Sq. Ft. 600 | Acres: 6.07 WOODSTOCK VT
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Description:Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.
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$845,000 | $493 per sq.ft. | 2 Beds | 2 Baths | Total Sq. Ft. 1714 | Acres: 15.8 WOODSTOCK VT
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Description:Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials. The home was carefully, and lovingly constructed by the owner who's family has farmed the land for generations. Sited to optimize the Northeasterly views across the GMHA equestrian campus, up the Kedron Valley and beyond, the property benefits from bright morning sun, and shady afternoons. Lovely ancient stonewalls lace through the landscape with mature stands of Birch, Maple and Ash. Full walk out basement for expansion. Free standing barn with open pasture ideal for animals, studio space or equipment storage. Commercial Range in photos has been removed, and not being offered for sale. Photos of furnished rooms have been digitally enhanced. No drive-ups please.
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Price Change! reduced by $54,500 down 6% on August 28th 2025
$845,000 | $265 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3190 | Acres: 2.94 WOODSTOCK VT
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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 $50,000 down 6% on October 3rd 2025
$869,000 | $224 per sq.ft. | 5 Beds | 5 Baths | Total Sq. Ft. 3886 | Acres: 2.36 WOODSTOCK VT
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Description:This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a kitchen with granite countertops, island with seating & storage, double pantry and all new appliances; dining room with fireplace, an all season sun room w/gas fireplace and deck access, a wonderful new laundry room with half bath, lovely primary bedroom and bath with soaking tub, tiled zero step shower(roll-in), & double sinks, & living room w/fireplace. Lots of light and warm wood floors throughout. Two bedrooms with sitting areas and lots of storage and full bath upstairs. The connected 2 bedroom apartment lends flexibility-it can be used as additional living space, overflow for guests or for extra income as a rental. Full kitchen,first floor bedroom and bath,second floor bedroom & storage loft and one car garage with second driveway, private entrance, deck and laundry.The back of the property slopes down to a babbling brook and then up to meet direct trail access to Mount Peg.Expansive deck,generator,attached two car garage & partially finished walk out basement with tons of storage, a recreation room or office and powder room too. So many possibilities!Call for showings starting 9/8.
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Price Change! reduced by $108,000 down 12% on September 17th 2025
$877,000 | $318 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 2760 | Acres: 10.1 WOODSTOCK VT
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Description:This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house .The dwelling has a wrap around deck overlooking the meadows and pond with views to the south. Antique stone walls are reminiscent of days gone by .If privacy but convenience to Woodstock village is your goal you need not look further. Some of the features include hardwood floors , open floorplan that includes dining and living room , large downstairs game room. Easy access to Killington, Okemo Mountain and of course Woodstock's own Saskadena Six for Skiing . Golf, tennis . biking and fishing are just a few of the many outdoor activities in the area . Pentangle Arts provides music and theater throughout the year. Woodstock was named the prettiest small town in America . Come make it your home in this amazing property. Call today for an appointment.
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Price Change! reduced by $50,000 down 6% on September 23rd 2025
$895,000 | $438 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2044 | Acres: 4.1 WOODSTOCK VT
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Description:Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting. Inside, you’ll find a sun-drenched home featuring four bedrooms, two full baths, a cozy living room with a fireplace, and an open-concept kitchen, dining, and family area—perfect for gathering and entertaining. The grounds are equally inviting, with mature landscaping, fruit trees, and ample space for gardening, play, or simply relaxing outdoors. A classic barn-style two-car garage offers abundant storage, with a spacious second level ready to be finished into a studio, guest suite, or office. Whether you’re hitting nearby hiking trails or skiing at Saskadena Six, this serene retreat is perfectly positioned to enjoy the best of Vermont in every season.
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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