$799,000 $399 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2004  |  Acres: 30.18
Monday Jun 29, 2026
Description: If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer. See MLS Property & Listing Details & 30 images. Includes a Virtual Tour

$799,999 $308 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2600  |  Acres: 2.9
Tuesday Jul 7, 2026
Description: On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The home offers 3 bedrooms and 2.5 bathrooms, with warm and inviting open living spaces anchored by both a fireplace and a wood stove, perfect for cozy Vermont evenings. A spacious porch takes full advantage of the South Easterly views, providing an ideal spot to relax and take in the natural surroundings. A detached 2-car garage with an accessory dwelling unit studio above, complete with a 3/4 bath; ideal for guests, rental potential, or a private office/studio. A potting shed and a wood shed complete the outdoor spaces, offering ample storage and outdoo hobbies. With its combination of rustic charm, modern utility, and an central location, this property is a rare opportunity to enjoy mountain living without sacrificing accessibility to nearby amenities and recreation. See MLS Property & Listing Details & 22 images.

$1,695,000 $353 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »

Waterfront on River Ottauquechee River
4 Beds | 4 Baths |   Total Sq. Ft. 4800  |  Acres: 0.56
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 MLS Property & Listing Details & 60 images.

$2,225,000 $575 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3867  |  Acres: 15.94
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 MLS Property & 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: 9
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 MLS Property & Listing Details & 58 images.

$2,999,000 $583 per sq.ft. Woodstock VT Home »

6 Beds | 8 Baths |   Total Sq. Ft. 5142  |  Acres: 0.36
Monday Jun 22, 2026
Description: Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens. See MLS Property & Listing Details & 38 images.

$5,875,000 $1,446 per sq.ft. Woodstock VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 5384  |  Acres: 68.92
Monday Jul 13, 2026
Description: Sorgenfrei German for "carefree" captures the spirit of this remarkable property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. Built by Ennis Construction in 2015 on 68 acres, the three-bedroom home embodies the enduring appeal of timber frame architecture with soaring spaces, exposed fir beams, and exceptional craftsmanship. Mahogany clapboard siding lends timeless character to the exterior. Inside, walls of glass frame sweeping mountain views, filling the home with natural light and creating a seamless connection to the landscape. Nearly every principal room is oriented toward the views to the East. The open floor plan flows from the gourmet kitchen to the dining area and dramatic great room, anchored by a floor-to-ceiling double-sided stone fireplace. A sitting room, screened porch, deck, and the primary suite complete the main level. Upstairs are a loft office, two en suite guest bedrooms, and a media room, while the walk-out lower level is dedicated to recreation and relaxation with a gym, infrared sauna, workshop, and a temperature-controlled wine room for approximately 1,000 bottles. A three-bay garage provides ample space for vehicles, and gear. Complete end-of-road privacy, panoramic views over the Woodstock Valley, perennial gardens, open pasture for a few horses or sheep, and an extensive trail network connecting directly to the GMHA trail system create a quintessential Vermont lifestyle. Thoughtfully designed for ease of ownership, the property is as practical as it is beautiful, with an 18.5 kW solar array supporting near net-zero living. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort. See MLS Property & Listing Details & 30 images. Includes a Virtual Tour

$249,000 $371 per sq.ft. Worcester VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 672  |  Acres: 1.4
Wednesday Jun 17, 2026
Description: Rare opportunity to own a highly adaptable live/work property in Worcester with extensive infrastructure already in place. Set on 1.4+/- acres with town water, a 2-bedroom wastewater permit, 200-amp electrical service, and multiple improved buildings, this unique property offers possibilities that are increasingly difficult to find. The well-maintained mobile home has been thoughtfully updated and currently serves as a licensed commercial kitchen with a certificate of occupancy and commercial-grade improvements. The space remains functional and flexible, offering potential for continued business use, live/work arrangements, or future adaptation to suit a buyer's needs. A former three-bay garage has been converted into professional workshop space with water, mini-split heat pumps, propane heat, upgraded electrical service, and large double doors suitable for equipment or pallet access. Additional features include a detached garage, storage shed, covered RV bay, camper septic hookup, generator hookup, improved drainage, and underground power connections. Whether you're an entrepreneur, artisan producer, contractor, homesteader, agricultural business owner, or someone seeking an affordable property with significant existing infrastructure, this property is worth a closer look. The level lot, paved road access, and lack of local zoning add even more flexibility. A truly unique property where business, creativity, storage, workshop space, and residential potential come together in one versatile package. See MLS Property & Listing Details & 60 images.

$307,000 $187 per sq.ft. Worcester VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1644  |  Acres: 0.25
Wednesday Jun 24, 2026
Description: Welcome to 82 Calais Road, a charming retreat in the heart of scenic Worcester, Vermont. This warm and inviting 2-bedroom, 2-bathroom Cape Cod home blends classic 1940 character with thoughtful updates throughout the approximately 1,644 square feet of living space. Set on a manageable 0.25-acre lot, the property offers a detached garage, and a peaceful setting surrounded by rolling hills, winding country roads, and abundant outdoor recreation. Inside, you'll find a flexible layout filled with natural light, and plenty of opportunities to make the home your own. Whether you're enjoying morning coffee on the porch, relaxing by the fireplace, taking in the quiet surroundings, or taking a short drive to Montpelier for dining, shopping, arts, and cultural attractions, this home offers the best of both worlds: convenient access to town and the peaceful privacy of a small community. With an approachable price point under the town assessed value of $320,200, this property presents an excellent opportunity for first-time buyers, empty-nesters, or anyone seeking a cozy year-round home or getaway in central Vermont. Come experience the simple joys of Vermont living at 82 Calais Road. Schedule your private showing today. See MLS Property & Listing Details & 37 images.

$399,000 $295 per sq.ft. Worcester VT Home »

Price Change! Reduced by $27,500 down 7% on July 14th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 2000  |  Acres: 10.1
Friday Jun 19, 2026
Description: Let's see...Million dollar views for $399,000? My math has you up $601,000. Sounds like a great deal! Beautiful long range mountain views are yours every single day in your new home in Worcester. This three bedroom home features an open layout with the kitchen, dining area, and living room all basking in the views. An additional sunroom adds to the vibe and offers flexibility. Two bedrooms are on the main floor, and a third, larger bedroom is upstairs. With a partially finished, walkout basement, you'll realize there's more to this home than meets the eye. The detached 2 story barn provides parking, plenty of storage, and would make a nice workshop. 186 MacKenzie Road is a private retreat, that can't be seen from the road. There's a nice swimming pond which you'll be sure to appreciate this summer! (Say hi to the family of turtles who are likely to be sunning themselves on sunny days!) Current owners have an established garden area that's ready for you to take over, get your hands in your own soil, and enjoy the harvest. Stand by generator is in place, and CV Fiber provides reliable high speed internet. Yes-you CAN work from home here! See MLS Property & Listing Details & 45 images.