Woodstock VT Homes $0 to $30000000
Change Town
Change Town
- Under Contract
Price Change! reduced by $94,000 down 11% on February 6th 2026
$825,000 | $212 per sq.ft. | 5 Beds | 5 Baths | Total Sq. Ft. 3886 | Acres: 2.36 WOODSTOCK VT
View Details & 60 images
Description:NEW PRICE! 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! Easy to show and move-in ready!
-
$845,000 | $1,408 per sq.ft. | 2 Beds | 1 Baths | Total Sq. Ft. 600 | Acres: 6.07 WOODSTOCK VT
View Details & 14 images
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.
-
$895,000 | $566 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 1580 | Acres: 0.08 WOODSTOCK VT
View Details & 38 images
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.
- Under Contract
Price Change! reduced by $185,000 down 20% on November 22nd 2025
$915,000 | $426 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2150 | Acres: 1.49 WOODSTOCK VT
View Details & 55 images
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 .
-
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
View Details & 37 images
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
View Details & 57 images
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.
- Under Contract
$1,300,000 | $407 per sq.ft. | 4 Beds | 5 Baths | Total Sq. Ft. 3195 | Acres: 1.07 WOODSTOCK VT
View Details & 60 images
Description:Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space—perfect for a playroom, media room, fitness area, or hobbies. Central air conditioning ensures year-round comfort, while an oversized, heated garage and an in-ground irrigation system make this home convenient in every season. Step outside to a private patio, surrounded by terraced gardens and stonework that add character and curb appeal. Located in a quiet setting yet within easy reach of restaurants, shops, and the village green, this property offers modern convenience in one of Woodstock’s most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermont’s most charming village.
- New Listing!
$1,895,000 | $644 per sq.ft. | 2 Beds | 3 Baths | Total Sq. Ft. 2944 | Acres: 14.9 Waterfront Owned 1000 Ft. of shoreline | WOODSTOCK VT
View Details & 33 images
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.
-
$2,599,000 | $434 per sq.ft. | 9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46 WOODSTOCK VT
View Details & 54 images
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!
-
Price Change! reduced by $550,000 down 19% on March 13th 2026
$2,950,000 | $543 per sq.ft. | 6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 2 Waterfront Owned WOODSTOCK VT
View Details & 40 images
Description:Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.
802-295-1355
The Clerkin Agency, P.C.
565 Maple Street, White River Junction, VT. 05001
Copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed.
The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’
personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Data last updated April 28th, 2026
VT: VERMONT REAL ESTATE COMMISSION MANDATORY CONSUMER DISCLOSURE FORM
NH: NEW HAMPSHIRE REAL ESTATE COMMISSION BROKERAGE RELATIONSHIP DISCLOSURE FORM
Designed by BSC DATA