$845,000 $493 per sq.ft. Woodstock VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1714  |  Acres: 15.8
Monday Jun 9, 2025
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. See MLS Property & Listing Details & 37 images.

$869,000 $224 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $50,000 down 6% on October 3rd 2025
5 Beds | 5 Baths |   Total Sq. Ft. 3886  |  Acres: 2.36
Saturday Sep 6, 2025
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. See MLS Property & Listing Details & 60 images.

$895,000 $438 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $50,000 down 6% on September 23rd 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2044  |  Acres: 4.1
Sunday Jun 1, 2025
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. See MLS Property & Listing Details & 50 images.

$944,999 $440 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2150  |  Acres: 1.49
Thursday Jun 5, 2025
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 . See MLS Property & Listing Details & 55 images.

$985,000 $513 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1920  |  Acres: 6.02
Tuesday Jul 1, 2025
Description: PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you'll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot. Well-planned interior space, inside you will find a warm and inviting atmosphere, offering an eat-in kitchen enhanced by the heat from the wood stove or relax by the fireplace in the living room open to the dining room. The primary bedroom with a full bath featuring a jacuzzi tub, while the remaining rooms provide flexible options for guests. Recent updates like a new oil tank, freshly painted interior, and a new water pressure tank ensure reliable modern living. Located just minutes from the heart of Woodstock, this home gives you easy access to local favorites like the Billings Farm and year-round fun at Okemo Mountain Resort. Whether you're into skiing, hiking, or something entirely more relaxed, there's something nearby for everyone. The neighborhood boasts a strong sense of an upscale community while maintaining a rural, secluded vibe. It's that rare find that feels remote but keeps you close to all the essentials. Ideal for year-round living or a seasonal getaway, this property invites you to experience the best of Vermont in a setting that's equal parts comfort and character. See MLS Property & Listing Details & 45 images.

$985,000 $354 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $200,000 down 20% on October 21st 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2785  |  Acres: 5.01
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 MLS Property & Listing Details & 37 images.

$1,150,000 $518 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $150,000 down 13% on October 30th 2025
3 Beds | 3 Baths |   Total Sq. Ft. 2220  |  Acres: 1.53
Tuesday Sep 23, 2025
Description: Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive--every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air conditioning. A brand-new two-car garage will be completed before closing, adding convenience and value. Inside, light-filled spaces showcase new, wide-plank white oak flooring, a beautifully designed kitchen, and spa-like bathrooms. The thoughtful floor plan includes a private office, perfect for working from home or creative pursuits. Outdoors, a covered porch with handsome stone entry steps frames gorgeous northerly views, and the roomy 1.53 acre lot provides plenty of room for gardening and outdoor activities. This turnkey home is a rare find: a character-filled property where every detail has been reimagined, offering modern comfort, low-maintenance peace of mind, and proximity to all that makes Woodstock one of New England's most desirable communities. See MLS Property & Listing Details & 57 images. Includes a Virtual Tour

$1,200,000 $439 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $50,000 down 4% on October 14th 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2736  |  Acres: 0.86
Monday Sep 29, 2025
Description: Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary ensuite with step-in shower, and a glass-lined sunroom create an effortless flow. Thoughtful conveniences include a mini-split for year-round comfort, laundry on the main level, and an eight-foot slider off the dining room that opens to a private deck overlooking the backyard. Upstairs, an apartment with private entrance extends the home's versatility with its own kitchen, living area, ¾ bath, and two bedrooms--perfect for guests, extended family, or private quarters. Outdoors, the property is framed by beautifully established perennial gardens and an expansive yard, offering rare in-village green space on +-.89 acres! A paved drive, two-car garage with overhead storage, standby whole-house generator, and public water and sewer add to the ease of ownership. The location is unmatched--just a street away from the elementary school, Vail Fields, the Village Green, and miles of walking trails. Schedule a private showing and see this grand home for yourself! See MLS Property & Listing Details & 35 images.

$1,295,000 $419 per sq.ft. Woodstock VT Home »

Waterfront on River Ottauquechee River
4 Beds | 3 Baths |   Total Sq. Ft. 3089  |  Acres: 0.52
Saturday Aug 23, 2025
Description: 16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village, it has a two-car garage with a covered walkway into the mudroom entryway (plus more outside parking). The spacious kitchen/dining area opens to the vaulted-ceiling living room, which has an INCREDIBLE view up-river. A side door leads to the side-deck that has the same view and sound of the river for outdoor dining above the river. There is a propane woodstove in the living room and woodstove in the kitchen/dining. A 1st floor bedroom has an ensuite bath and small stack washer-dryer. Upstairs is a large bedroom looking out through the great room to the river, a smaller bedroom, a bath and lovely loft area above the living room. Downstairs is a large den/rec/office, a bedroom, a bathroom, the main laundry room and mechanical room, all renovated 11 years, post the Irene storm, when the river waters came up into the lower level. There are beautiful gardens in the front and rear of the house. SEE PROPERTY WEBSITE FOR 16 CHURCH ST WOODSTOCK FOR MORE DETAILS, FLOORPLANS HI REZ PHOTOS AND MORE. See MLS Property & Listing Details & 40 images.

$1,295,000 $568 per sq.ft. Woodstock VT Home »

2 Beds | 4 Baths |   Total Sq. Ft. 2280  |  Acres: 0.8
Wednesday Oct 29, 2025
Description: Welcome to 33 Mountain Avenue - a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one car garage. An exquisite multi-terraced exterior landscape design is predominately and privately located at the back of the property. Plentiful space for gardening, a fire-pit, or even an in-ground pool - where once there was one!  Take in the trails of Mt.Tom and Marsh-Billings-Rockefeller National Park just outside your door. Enjoy a lovely stroll along Mountain Ave and thru the iconic Middle Covered Bridge to tap into a multitude of dining options, shopping, and performances at Pentangle Arts. A rare, unique, and coveted Woodstock Village location! See MLS Property & Listing Details & 32 images. Includes a Virtual Tour

$1,295,000 $485 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32
Sunday Oct 5, 2025
Description: This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef's kitchen and den. New Thor stainless steel 48" propane range installed October 2025. Privately set on over 8 acres, the property offers true seclusion with the convenience of being just minutes to Woodstock Village, close to Killington and Okemo skiing, and near local favorites including Ramunto's Pizza and nearby event venues. Amenities include a private in-ground pool with expansive mountain views, plus an oversized garage/barn with storage and space above for potential guest quarters. An ideal countryside retreat for year-round living or a second home escape. See MLS Property & Listing Details & 40 images.

$1,300,000 $407 per sq.ft. Woodstock VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3195  |  Acres: 1.07
Tuesday Nov 11, 2025
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. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$1,495,000 $590 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2532  |  Acres: 0.79
Tuesday Jul 1, 2025
Description: A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors--just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully updated bathrooms throughout. Natural light floods the living spaces, which flow easily for everyday living or entertaining. A large, unfinished studio apartment is ready for your design--perfect for an in-law suite, au pair quarters, or as a short- or long-term rental. Above the detached barn, a finished space provides a quiet work-from-home setup or creative studio. With close proximity to the Mt. Peg trail system, this location offers direct access to hiking, mountain biking, and nordic skiing, while the restaurants, shops, and cultural amenities of Woodstock Village are just a short stroll away. A rare opportunity for turn-key living in one of Vermont's most picturesque towns. Showings begin 7/5 with an open house from 10:30am - 12:30pm. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$1,595,000 $437 per sq.ft. Woodstock VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 3648  |  Acres: 6.2
Saturday Jul 5, 2025
Description: Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef's kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces--wood-burning, brick, and gas-ready--provide cozy warmth throughout. Upstairs, find 3-4 bedrooms including one with its own fireplace, plus a private guest room or office above the garage. A covered porch, sunny patio, inground pool with heat hookup, apiary, and dedicated garden create an idyllic outdoor lifestyle. Over 5 acres of invisible fencing allow pets to roam freely. Adjacent to the site of the country's first ski tow, with easy access to Saskadena Six and fantastic winter recreation. Bonus: a heated, plumbed two-floor barn/workshop with its own car bay--ready to become a media/game room, studio, or guest space. Easy access to I-89 and the Upper Valley. A rare opportunity for acreage, privacy, and proximity to one of New England's most iconic villages. See MLS Property & Listing Details & 49 images. Includes a Virtual Tour

$1,600,000 $266 per sq.ft. Village of Woodstock in Town of Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 6014  |  Acres: 0.05
Thursday Mar 6, 2025
Description: 15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. See MLS Property & Listing Details & 43 images.