Woodstock VT
Popular Searches |
|
| Woodstock Vermont Homes Special Searches |
| | Woodstock VT Homes For Sale By Subdivision
|
|
| Woodstock VT Other Property Listings For Sale |
|
|
|
|
$725,000 | $202 per sq.ft.
New Listing!
3914 South Road
Waterfront Owned 4 Beds | 3 Baths | Total Sq. Ft. 3584 | Acres: 5.1
This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont's changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons. See
MLS Property & Listing Details & 40 images.
|
|
|
|
$785,000 | $473 per sq.ft.
Price Change! reduced by $25,000 down 3% on October 24th 2025
37 South Street
3 Beds | 2 Baths | Total Sq. Ft. 1660 | Acres: 0.19
New price! 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! See
MLS Property & Listing Details & 49 images.
|
|
Under Contract
|
|
$798,000 | $610 per sq.ft.
392 Gully Road
2 Beds | 2 Baths | Total Sq. Ft. 1308 | Acres: 5.33
Built in 2019, this charming Cape-style home is nestled on five sunny, private acres just minutes from Woodstock Village. Thoughtfully designed and beautifully constructed, the home offers efficient, low-maintenance living in a coveted location. With excellent solar exposure, stunning sunset views, and lovely hillside scenery, it's bright, warm, and welcoming year-round. The interior features a gorgeous open kitchen with quality finishes, two beautiful bathrooms, and two comfortable bedrooms. With a four-bedroom septic system already in place, the home offers easy potential for future expansion. Outside, the property is equally exceptional. A custom bluestone patio invites outdoor dining and relaxation, while professionally designed raised beds and a high-end greenhouse (high tunnel) provide everything needed for productive gardening. Established perennial gardens surround the home with vibrant seasonal color, and private trails (cut in and ready to enjoy) lead to the top of the property for peaceful walks and sweeping views. Whether you're seeking a full-time residence, a Vermont retreat, or a property to grow into over time, this home offers rare flexibility, natural beauty, and a connection to one of New England's most picturesque villages. Showings begin 7/7/2025. No showings 7/15/2025 - 7/20/2025. See
MLS Property & Listing Details & 53 images. Includes a Virtual Tour
|
|
|
|
$845,000 | $1,408 per sq.ft.
234 Randall Road
2 Beds | 1 Baths | Total Sq. Ft. 600 | Acres: 6.07
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
MLS Property & Listing Details & 14 images.
|
|
|
|
$845,000 | $493 per sq.ft.
403 Horseshoe Way
2 Beds | 2 Baths | Total Sq. Ft. 1714 | Acres: 15.8
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.
Price Change! reduced by $50,000 down 6% on October 3rd 2025
3961 Hartland Hill Road
5 Beds | 5 Baths | Total Sq. Ft. 3886 | Acres: 2.36
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.
|
|
|
|
$877,000 | $318 per sq.ft.
Price Change! reduced by $108,000 down 12% on September 17th 2025
616 Rose Hill Road
3 Beds | 2 Baths | Total Sq. Ft. 2760 | Acres: 10.1
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. See
MLS Property & Listing Details & 57 images.
|
|
|
|
$895,000 | $438 per sq.ft.
Price Change! reduced by $50,000 down 6% on September 23rd 2025
100 Pomfret Road
4 Beds | 3 Baths | Total Sq. Ft. 2044 | Acres: 4.1
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.
|
|
Under Contract
|
|
$925,000 | $321 per sq.ft.
348 Laughlin Road
4 Beds | 3 Baths | Total Sq. Ft. 2882 | Acres: 2.08
Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock location for those wanting a peaceful Vermont countryside vibe to unwind but the vibrant Woodstock Village life at the foot of your hill! The interior design presents a more refined open concept design that offers both openness but a more defined layout for functional separation and intimacy. A captivating light filled living room that opens onto a mahogany deck is centered upon a handsome fireplaced wall that is open on both sides to allow flow into a lovely eat-in kitchen detailed with quartz counters. A primary ensuite bedroom, study/office, and full bath complete the main level. The lower level presents a second living room that opens onto a patio and centers upon a second fireplace. Three bedrooms and a terrific laundry room/mudroom complete the lower level. Enjoy relaxing, entertaining, and taking in the sunsets from the westerly facing patio and deck. Perfect as a primary or secondary home with all season recreation, theatre and the arts, dining, and shopping just minutes away and easy access to all the amenities and major employment the Upper Valley has to offer. Showings begin with Public Open House Saturday Oct 4 from 1-3pm. See
MLS Property & Listing Details & 31 images. Includes a Virtual Tour
|
|
|
|
