$997,000 $249 per sq.ft. Weathersfield VT Home »

Price Change! Reduced by $302,000 down 30% on September 18th 2025
4 Beds | 5 Baths |   Total Sq. Ft. 4009  |  Acres: 13.78
Sunday Jun 29, 2025
Description: Spacious Country Retreat with Stunning Views! Experience the perfect blend of space, privacy, and scenic beauty in this impressive country home. Set on 13.78 acres, this property offers expansive outdoor and indoor living, with amazing panoramic views. Inside, you'll find large sunlit rooms including oversized bedrooms, a mudroom, and second floor laundry for convenience. The open concept living area flows seamlessly to a beautiful deck where you can relax and take in the peaceful setting. A 2-car garage and additional outbuildings provide plenty of storage, while the open land has been set up to receive chickens or other small livestock. Designed for comfort and self-sufficiency, the property includes a whole house generator, ensuring year-round security and peace of mind - no matter the weather. Located in a school choice area and just a short drive to town this home offers seclusion without sacrificing a great location while offering tranquility or space to grow! See MLS Property & Listing Details & 57 images.

$525,000 $205 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $225,000 down 43% on October 10th 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2557  |  Acres: 0.75
Monday May 5, 2025
Description: NEW PRICE!! Discover classic Vermont charm at The Harry Emmons House, an antique brick cape located in the village of Taftsville, ideally situated on a level, open lot. A traditional covered farm porch leads to a gathering room with a brick fireplace. The main level features bright, airy living spaces with high ceilings and exposed beams, comfortable rooms, a country kitchen, a sunny dining room, den, and a bedroom with a separate dressing area. The upper-level features two attractive bedrooms, a full bathroom, ample storage space, and room for future expansion. Additional highlights include a separate rental apartment, a two-car barn garage, and a workshop. The Harry Emmons House is conveniently close to the Village of Woodstock, Vermont, and the Upper Valley regions of Vermont and New Hampshire, making it an ideal spot for those seeking both tranquility and accessibility. See MLS Property & Listing Details & 38 images.

$549,000 $222 per sq.ft. Woodstock VT Home »

Waterfront on River Ottauquechee River
4 Beds | 3 Baths |   Total Sq. Ft. 2470  |  Acres: 1.96
Tuesday Aug 19, 2025
Description: Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you'll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather around the beautiful wood-burning fireplace after a day on the slopes, or enjoy a game in the pool table room with friends and family. Period details and thoughtful updates create a cozy balance of history and comfort, while natural light and open spaces bring the outdoors in. This home is equally suited as a vacation retreat, an investment property, or a welcoming primary residence. Wide lawns offer plenty of room for play and gardening, and river views provide a peaceful backdrop in every season. Here, relaxation and adventure are always close at hand -- whether it's skiing, hiking, or simply soaking in the Vermont lifestyle. See MLS Property & Listing Details & 35 images. Includes a Virtual Tour

$595,000 $310 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $100,000 down 17% on October 24th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 6.88
Friday Sep 12, 2025
Description: This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car garage with ample storage above is connected by a breezeway. 3 mini splits for efficiency and comfort. Backup generator, pellet stove, wood stove. Newer heat pump water heater, new windows. Huge shed barn for storage or workshop. See MLS Property & Listing Details & 43 images.

$675,000 $434 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1555  |  Acres: 0.34
Saturday Sep 6, 2025
Description: Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and large six over six windows flooding the room with natural light. The DR has original built-ins, and connects to a roomy farmhouse eat-in kitchen. Rear mudroom steps out to covered porch and detached garage. Office or overflow bedroom with 3/4 bath completes the main level. Moving upstairs there are three bedrooms, a full and a half bath. Opportunity to expand into the attic space above. See MLS Property & Listing Details & 33 images.

$725,000 $202 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1
Saturday Oct 25, 2025
Description: 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. Woodstock VT Home »

Price Change! Reduced by $25,000 down 3% on October 24th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1660  |  Acres: 0.19
Monday Sep 15, 2025
Description: 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.

$795,000 $249 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Friday Oct 24, 2025
Description: See MLS Property & Listing Details & 44 images.

$798,000 $610 per sq.ft. Woodstock VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1308  |  Acres: 5.33
Thursday Jul 3, 2025
Description: 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. Woodstock VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 600  |  Acres: 6.07
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 MLS Property & Listing Details & 14 images.

$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.

$877,000 $318 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $108,000 down 12% on September 17th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 2760  |  Acres: 10.1
Thursday Jul 3, 2025
Description: 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. 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.

$925,000 $321 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2882  |  Acres: 2.08
Thursday Oct 2, 2025
Description: 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