Woodstock VT
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$1,595,000 | $437 per sq.ft.
Price Change! reduced by $55,000 down 3% on July 5th 2025
1522 Barnard Road
5 Beds | 4 Baths | Total Sq. Ft. 3648 | Acres: 6.2
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
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$1,600,000 | $266 per sq.ft.
15 Central Street
4 Beds | 3 Baths | Total Sq. Ft. 6014 | Acres: 0.05
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.
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Under Contract
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$1,695,000 | $402 per sq.ft.
Price Change! reduced by $304,000 down 18% on October 3rd 2025
10 College Hill Road
5 Beds | 5 Baths | Total Sq. Ft. 4214 | Acres: 1.07
10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE. See
MLS Property & Listing Details & 35 images.
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Under Contract
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$1,750,000 | $323 per sq.ft.
Price Change! reduced by $450,000 down 26% on August 23rd 2025
2334 South Road
3 Beds | 3 Baths | Total Sq. Ft. 5422 | Acres: 31.43
Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire home is a unique showplace of clever spaces, built-ins, with custom detail throughout; featuring mahogany, cherry, and locally sourced stone. The ten room- three bedroom, three bath main residence was carefully sited to optimize a stunning northeasterly view, and to communicate directly with exterior terraces, and established gardens overlooking a pond, rolling hills and fields. There is a detached one bedroom guest house (or caretaker's cottage), garage, horse barn, equipment shed and two garden sheds. Easy access to hiking trails. Three minutes to Fitness Ctr., 15 minutes to Saskadena Six skiing. 2.25 hours to Boston, 4.5 to NYC. Property enrolled in Current Use. See
MLS Property & Listing Details & 60 images.
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$1,800,000 | $360 per sq.ft.
Price Change! reduced by $200,000 down 11% on August 8th 2025
2706 East Woodstock Road
4 Beds | 4 Baths | Total Sq. Ft. 5000 | Acres: 0.56
INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current lease), smaller Apartment 1 (with excellent AIRBNB rental history), larger Apartment 2 (The owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. 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. See
MLS Property & Listing Details & 60 images.
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$1,900,000 | $645 per sq.ft.
2394 Fletcher Hill Road
Waterfront Owned 1000 Ft. of shoreline | 2 Beds | 3 Baths | Total Sq. Ft. 2944 | Acres: 14.9
Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE. See
MLS Property & Listing Details & 33 images.
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$1,995,000 | $358 per sq.ft.
Price Change! reduced by $455,000 down 23% on September 25th 2025
851 Riverside Park Road
Waterfront Owned 48 Ft. of shoreline | 4 Beds | 4 Baths | Total Sq. Ft. 5573 | Acres: 40
"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef's kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, "All Sessons" is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region's most picturesque towns. See
MLS Property & Listing Details & 60 images. Includes a Virtual Tour
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Under Contract
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$2,400,000 | $497 per sq.ft.
1059 Carlton Hill Road
5 Beds | 5 Baths | Total Sq. Ft. 4832 | Acres: 2.64
Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perfect balance of charm and modern comfort. Just minutes from Woodstock and South Woodstock, the property enjoys both convenience and a peaceful setting. The home features generous living and entertaining spaces (remodeled in 2016 by Sargent Design Company), multiple porches, and seamless indoor-outdoor flow. The main residence offers 5 bedrooms, including a large primary suite, while the converted barn includes a private guest apartment, ideal for hosting company. Highlights include a hot tub, indoor and outdoor fireplaces, and thoughtful updates throughout that make the home as efficient and easy to maintain as it is elegant. With open spaces designed for gatherings and cozy corners for retreat, this home is equally suited for year-round living or a Vermont getaway. Outdoor enthusiasts will appreciate the home's proximity to skiing at Killington and Saskadena Six, as well as easy access to hiking, biking, and countless four-season activities. A truly exceptional property blending timeless farmhouse character with today's modern luxuries. See
MLS Property & Listing Details & 50 images. Includes a Virtual Tour
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Under Contract
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$2,599,000 | $434 per sq.ft.
41 Pleasant Street
9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46
This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont's most beloved communities. Woodstock is often hailed as "the prettiest small town in America," and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner's quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home! See
MLS Property & Listing Details & 54 images.
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Under Contract
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$2,600,000 | $650 per sq.ft.
2 Pleasant Street
4 Beds | 4 Baths | Total Sq. Ft. 3998 | Acres: 0.37
2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state's history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern convenience with original charm. The first floor features oversized, recently updated windows and several spacious high ceiling gathering rooms including a formal living room, dining room, library, and central family room. A cozy eat-in kitchen with fireplace on the north side of the house opens to a lovely landscaped yard shaded by mature maple trees. The second floor, also punctuated by high ceilings and windows to give it a bright and spacious feel, features a primary bedroom on the front side of the house with an adjoining dressing area, walk in closets, and full bath. Adjacent the primary is another sizable bedroom with its own bath, while two additional bedrooms with shared bath round out the level. The detached barn garage has space for one car and plenty of additional storage. Idyllically sited and within walking distance of local shopping, dining, schools, hiking trails, and Marsh-Billings-Rockefeller National Historic Park, this iconic Woodstock home is a rare gem. See
MLS Property & Listing Details & 43 images. Includes a Virtual Tour
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