Woodstock VT
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$439,000 | $271 per sq.ft.
5798 West Woodstock Road
4 Beds | 2 Baths | Total Sq. Ft. 1617 | Acres: 0.65
Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete with a wood burning fireplace. A bedroom and full bath on the first floor adds to convenience of living . The charming front porch with views of Killington is a lovely place to enjoy relaxing and entertaining friends . Make an appointment today to view this lovely property . See
MLS Property & Listing Details & 45 images.
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$525,000 | $205 per sq.ft.
Price Change! reduced by $225,000 down 43% on October 10th 2025
144 Butternut Lane
4 Beds | 3 Baths | Total Sq. Ft. 2557 | Acres: 0.75
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.
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$549,000 | $222 per sq.ft.
3364 West Woodstock Road
4 Beds | 3 Baths | Total Sq. Ft. 2470 | Acres: 1.96
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
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$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.
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$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.
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$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.
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Under Contract
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$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
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$985,000 | $354 per sq.ft.
Price Change! reduced by $200,000 down 20% on October 21st 2025
1782 Randall Road
4 Beds | 3 Baths | Total Sq. Ft. 2785 | Acres: 5.01
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.
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$1,200,000 | $439 per sq.ft.
Price Change! reduced by $50,000 down 4% on October 14th 2025
17 Linden Hill
4 Beds | 3 Baths | Total Sq. Ft. 2736 | Acres: 0.86
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.
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