You are viewing Woodstock VT Homes between $0 and $30000000 dollars.
$2,650,000 $547 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $450,000 down 17% on August 13th 2026
5 Beds | 4 Baths | Total Sq. Ft. 4843 | Acres: 105.1
Listed on Wednesday May 27, 2026
Description: CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef's kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead--with its native timbers and stone fireplace--creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House--a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience. See Listing Details & 58 images. Includes a Virtual Tour
$2,599,000 $434 per sq.ft. Woodstock VT Home »
9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46Listed on Sunday Sep 21, 2025
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! See Listing Details & 54 images.
Under Contract
$2,500,000 $460 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $1,000,000 down 40% on July 9th 2026
6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 2
Listed on Friday Jun 28, 2024
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. See Listing Details & 40 images. Includes a Virtual Tour
$2,500,000 $488 per sq.ft. Woodstock VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 5127 | Acres: 17.65Listed on Wednesday May 6, 2026
Description: See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock's rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen--complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler's pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies--including a whole-house generator and rooftop solar--offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont's finest amenities. See Listing Details & 60 images. Includes a Virtual Tour
$2,300,000 $659 per sq.ft. Woodstock VT Home »
5 Beds | 6 Baths | Total Sq. Ft. 3489 | Acres: 9Listed on Tuesday Jul 7, 2026
Description: Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view! See Listing Details & 58 images.
$2,225,000 $575 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 3867 | Acres: 15.94Listed on Wednesday Jun 17, 2026
Description: Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in the early 1800's. The rooms are spacious, bright and inviting with exposed hand- hewn beams and pine plank floors running throughout. The updated country kitchen with soapstone counters connects to a cozy reading room with bookshelves and woodstove, and a utility/mudroom with ¾ bath, and laundry. The formal dining room offers plenty of space for gatherings. The front to back Living Room is anchored by a woodburning fireplace, and steps out to a private sunroom, and a guest room/office. Moving upstairs, there are four bedrooms and a bathroom. The 18thcentury hip roofed, post and beam English bank barn has a huge, sweeping loft space ideal for parties and entertaining. The lower level can accommodate animals, hobbies or a home occupation. The barn is surrounded by lush green pastures, and rail fencing which lead you to a network of beautiful trails for hiking. A short stroll to The Kedron Valley Inn, KV Pond, The South Woodstock Store, and Green Mountain Horse Assn. A five-minute drive to the Woodstock Village Green. Easy access to Hanover, DHMC, skiing, golf, dining, shopping and recreation. See Listing Details & 60 images. Includes a Virtual Tour
$1,895,000 $644 per sq.ft. Woodstock VT Home »
1000 Ft. of Waterfront on River Ottauquechee River2 Beds | 3 Baths | Total Sq. Ft. 2944 | Acres: 14.9
Listed on Tuesday Apr 21, 2026
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. See Listing Details & 33 images. Includes a Virtual Tour
$1,695,000 $353 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »
Waterfront on River Ottauquechee River4 Beds | 4 Baths | Total Sq. Ft. 4800 | Acres: 0.56
Listed on Friday Jun 26, 2026
Description: Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! See Listing Details & 60 images.
$1,695,000 $512 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 3542 | Acres: 18.4Listed on Friday Jul 31, 2026
Description: "BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online. See Listing Details & 48 images. Includes a Virtual Tour
$1,395,000 $382 per sq.ft. Woodstock VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 3648 | Acres: 6.2Listed on Monday May 18, 2026
Description: Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef's kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces--including a wood-burning and gas-ready--add warmth and character throughout the home. The flexible floor plan includes 3-4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage--ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America's first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay--offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England's most iconic villages. See Listing Details & 58 images.
$1,375,000 $445 per sq.ft. Woodstock VT Home »
Waterfront on River4 Beds | 3 Baths | Total Sq. Ft. 3979 | Acres: 0.52
Listed on Thursday Jul 16, 2026
Description: This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything. See Listing Details & 60 images. Includes a Virtual Tour
Under Contract
$1,075,000 $355 per sq.ft. Woodstock VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 3030 | Acres: 5.1Listed on Tuesday Aug 4, 2026
Description: This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with additional direct access from the spacious 2-car garage. A mudroom connects the front and garage entries, and the back entry near the garden barn is close to the kitchen. The generous living room centers on a wood-burning fireplace with floor-to-ceiling windows spanning the width of the room. A gracious dining room adjoins the living room, den/bedroom, kitchen, and private stairway to the primary bedroom suite. The second level includes the primary bedroom with study/dressing room, walk-in closet, private balcony, and en suite bath with Italian marble vanity, tile, and surfaces. The second bedroom is illuminated by natural light and well-appointed en suite bathroom. A second-floor family/media room is separate from the sleeping areas. The property is within easy walking distance to the Village Green, shopping, entertainment, elementary school, and all resort amenities. A gem waiting to be discovered. See Listing Details & 48 images.
$895,000 $562 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $70,000 down 8% on August 11th 2026
3 Beds | 3 Baths | Total Sq. Ft. 2638 | Acres: 2
Listed on Friday Jun 12, 2026
Description: This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you're seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one! See Listing Details & 46 images.
$865,000 $311 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2785 | Acres: 5.01Listed on Monday Jul 21, 2025
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. See Listing Details & 37 images.
$845,000 $1,408 per sq.ft. Woodstock VT Home »
Waterfront on Pond2 Beds | 1 Baths | Total Sq. Ft. 600 | Acres: 6.07
Listed on Monday Jun 6, 2022
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. See Listing Details & 14 images.
