- Woodstock VT Homes $0 to $30000000
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$695,000 | $304 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 2288 | Acres: 0.15 Waterfront Shared WOODSTOCK VT
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Description:A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!
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$749,000 | $451 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!
- New Listing!
$750,000 | $328 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 2285 | Acres: WOODSTOCK VT
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Description:Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.
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$815,000 | $248 per sq.ft. | 5 Beds | 4 Baths | Total Sq. Ft. 3284 | Acres: 2.84 WOODSTOCK VT
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Description:This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway.
- Under Contract
Price Change! reduced by $168,000 down 21% on October 30th 2025
$817,000 | $296 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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$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.
- Under Contract
$895,000 | $566 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 1580 | Acres: 0.08 WOODSTOCK VT
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Description:Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed courtyard. First floor also features a mudroom, new 1/2 bath, family room and gracious formal living room accented with bookshelves. Second floor consists of a large primary bedroom, a guest bedroom and newly renovated full bathroom and laundry room. Third level has another 2 bedrooms or could be used as offices. This residence is the south side (left side) of the building and includes new mini split a/c units, a storage shed and perennials gardens. Walk to all of towns amenities, shops and restaurants. Mt. Tom National park and hiking behind the house for those nature enthusiasts, championship golf, skiing and fly fishing near by. 20 minutes to the Upper Valley and Dartmouth. Wonderful opportunity to own this charming home in one of Vermonts prettiest towns.
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Price Change! reduced by $200,000 down 20% on October 21st 2025
$985,000 | $354 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.
- Under Contract
$1,195,000 | $448 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32 WOODSTOCK VT
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Description:Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler’s pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces — including a fireplaced living room with gas insert and a den warmed by a wood stove — offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock’s celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington’s Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best.
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$1,495,000 | $564 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2650 | Acres: 5 WOODSTOCK VT
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Description:Known affectionately as “Green Gable Farm,” this beautifully renovated 1884 Vermont farmhouse sits on 5 picturesque acres in Woodstock, complete with a year-round babbling brook, just minutes from South Woodstock, the Woodstock Inn Fitness Center, golf course, cross-country ski trails, mountain biking, and the Woodstock Village Green. The current owners undertook a comprehensive renovation, thoughtfully preserving the home’s historic character—including original barnboard floors and exposed beams—while updating every major system and living space. New mechanicals, upgraded insulation, all new double-pane windows, central HVAC with heating and cooling, high-speed fiber internet, new baths, and a fully redesigned kitchen bring modern comfort to this classic country home. The architecturally reimagined floor plan creates an open, inviting first floor centered around a gourmet eat-in kitchen with Viking appliances, farmhouse sink and abundant workspace. A highly functional mudroom entry, marble tile floors, new laundry room, full bath, and first-floor bedroom add everyday practicality. The kitchen flows into a cozy sitting area with fireplace and additional flexible living spaces ideal for dining, reading, or entertaining. Upstairs are 2 spacious ensuite bedrooms, including a serene primary suite with dressing area, double sinks, smart toilet, glass-enclosed shower, and freestanding soaking tub overlooking stone walls, open fields, and berry patches. Sliding doors off the kitchen open to a large rear deck featuring a heated 12’ swim spa for year-round enjoyment. A charming historic shed-barn offers space for a workshop, studio, or recreation area, while unfinished space above the attached two-car garage provides expansion potential for future guest or living quarters. Much of the furniture and furnishings are available separately, making Green Gable Farm a rare turnkey opportunity blending historic Vermont charm, modern comfort, and an exceptional Woodstock location.
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Data last updated May 28th, 2026
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