Woodstock VT
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Under Contract
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$730,000 | $289 per sq.ft.
Price Change! reduced by $65,000 down 9% on August 22nd 2024
1207 Church Hill
3 Beds | 4 Baths | Total Sq. Ft. 2527 | Acres: 5.48
Historic Vermont cape house with easy access, only a mile to the Woodstock village center. There is a lot of history and character with beautiful old wood floors and beams. A covered walkway from the attached two-car garage comes into a mud-entry room and right into the classic farmhouse kitchen. Off the kitchen is a generous pantry/laundry room and a bath with shower. The spacious family room/den has a propane woodstove and is perfect for hanging out, chilling/reading or watching the ball game. On the first floor is also a classic formal dining room with lots of natural light, a first level bedroom with ensuite bath and a formal living room with wood-burning fireplace. Upstairs is the primary bedroom with a walk-in closet and ensuite bath, plus another bedroom with ensuite bath that opens into a hangout space with the classic "crooked window" like so many historic Vermont farmhouses have. There is a level side yard for hanging out/playing which also has raised bed gardens. Mechanicals have been updated with a newer Buderus furance and newer heat-exchange hot water heater. High speed internet is at the house. See
MLS Property & Listing Details & 32 images.
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$795,000 | $523 per sq.ft.
Price Change! reduced by $55,000 down 7% on August 17th 2024
13 Golf Avenue
2 Beds | 2 Baths | Total Sq. Ft. 1520 | Acres: 0.28
Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants and events on Historic Woodstock Green. Championship golf, fly fishing and skiing near by. This lovely antique cottage has hardwood floors through out, open kitchen with first floor laundry. Adjacent is sitting area and dining. First floor bedroom with adjoining bathroom with soothing green accents. Second floor boasts a generous size bedroom with an abundance of natural light, small library for those reading enthusiasts who would like to curl up with a good book on a rainy day, another bathroom and charming bedroom at the end of the hallway. Enjoy the private covered porch on the back of the house overlooking the lovely perennial gardens. An antique barn awaits to be used for a garage or possible renovations into something more. Low maintenance home, well cared for with lots of character- This property has good rental history for a buyer looking for extra income. Come take a look! See
MLS Property & Listing Details & 32 images.
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$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.
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$899,000 | $687 per sq.ft.
392 Gully Road
2 Beds | 2 Baths | Total Sq. Ft. 1308 | Acres: 5.33
Just minutes from the charming and historic Woodstock Village, this exceptional 5+ acre property offers modern comfort and expansion potential. Built in 2019, the 2-bedroom, 2-bath home features sleek white subway tile, stainless steel appliances, and thoughtful details throughout. Enter through a welcoming mudroom with natural wood accents and convenient laundry, and step into the open-concept living and dining area--ideal for entertaining or cozy nights in. A spacious first-floor bedroom and full bath offer flexibility. Upstairs, the bonus area is perfect for a home office or reading nook, with large windows framing stunning valley views. The primary bedroom features an en suite bath with a sliding barn door for a touch of rustic charm. This incredible property also has the ability to grow. Enjoy established perennial gardens, raised beds, and a professional high tunnel/greenhouse that allows you to extend the growing season. Relax on the patio surrounded by nature, enjoying breathtaking sunsets, or trek up the hill for panoramic views of the surrounding landscape. Designed to support up to 4-bedrooms, the septic system allows for future expansion. Less than 10 minutes to Saskadena Six ski area and 20 minutes to Killington Resort, this location is a dream for outdoor enthusiasts. Enjoy world-class dining and shopping just minutes away in Woodstock. This unique property blends modern comfort with natural beauty in one of Vermont's most idyllic locations. Showings begin 10/22. See
MLS Property & Listing Details & 59 images.
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$985,000 | $335 per sq.ft.
828 Deerbrook Way
4 Beds | 3 Baths | Total Sq. Ft. 2944 | Acres: 12.21
A gem of a property on 12 spectacular, mostly wooded, acres in the desirable Deerbrook Way area of Woodstock. Four+ miles to all the amenities of Woodstock Village and 8 miles to the Skyship Gondola at Killington. Built in 1994, this custom designed red oak Post and Beam Contemporary provides everything you would want in a primary residence or a get away vacation retreat. Situated on a 12+ acre parcel unlike most. The lot alone is an adventure with its view potential, adventurous topography and great options for adding a trapper cabin or a martini deck for enjoying the incredible Vermont surroundings. Room for everybody with four bedrooms, three full bathrooms. Bedroom on main floor with ensuite bath for main level living. Well appointed kitchen with cherry cabinets, granite countertops and brand new induction range Plus an office/study, and a light filled vaulted ceiling great room. In addition, the property includes a stone patio, a heated three car garage, solar roof top panels that reduce your monthly power bill to less than the cost of a breakfast for two, and a Tesla power wall back up power system that provides uninterrupted power in the event of a power failure. Also included is a dedicated Tesla EV charging unit. See
MLS Property & Listing Details & 37 images.
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$995,000 | $581 per sq.ft.
Price Change! reduced by $505,000 down 51% on November 14th 2024
403 Horseshoe Way
2 Beds | 2 Baths | Total Sq. Ft. 1714 | Acres: 15.8
Discover an unparalleled woodland retreat nestled on a picturesque hilltop in South Woodstock, Vermont. This extraordinary timber frame home, a masterpiece of craftsmanship, offers breathtaking views of the pristine Green Mountain Horses Association show arenas and cross-country course. Each stone, beam, and timber has been meticulously and artfully placed by the current owner, reflecting a labor of love and dedication. This unique property has been cherished by the same family since 1965, imbuing it with a rich history and a profound connection to the land. The 2-bedroom, open-concept hillside retreat is enveloped by a serene hardwood forest, accessed via a private driveway aptly named Horseshoe Way. This path honors the farrier who envisioned and created this sanctuary as a tribute to a family of farmers who devoted their lives to their community. The home itself is a testament to Vermont's heritage, constructed from materials carefully curated from some of the state's most iconic early barns and sawmills. Every element of this residence tells a story, blending the past's rustic charm with modern comforts. Whether you seek a peaceful haven or a base for outdoor adventures, this South Woodstock retreat offers a unique opportunity to embrace a lifestyle of tranquility and natural beauty. Don't miss your chance to live on a parcel steeped in Vermont's history and create your own cherished memories in this remarkable woodland sanctuary. See
MLS Property & Listing Details & 43 images. Includes a Virtual Tour
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$995,000 | $312 per sq.ft.
598 East Woodstock Road
4 Beds | 3 Baths | Total Sq. Ft. 3190 | Acres: 2.94
This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The home has a suite of rooms on the first floor that are perfect for a home-based business or studio area (or 2 extra bedrooms plus bonus room), and a one-bedroom full bath (with office & kitchen) in-law suite upstairs with private ground-level access. The main part of the home includes three additional bedrooms, a library, a music room, living room, dining room, two full baths, dressing room, and three-season enclosed porch. The charming eat-in kitchen includes beautiful display cabinets, hand painted tiles, and built-in pantry and laundry. In the stunning custom cherry wood library with marble fireplace and private deck, bibliophiles will find more than enough shelf space for their entire book collection, and a quiet, peaceful setting in which to read. Two readers in the family? The upstairs music room is similarly equipped, also with stunning cherry wood built-ins and detailing. Two staircases provide ample access to the upstairs and contribute to the ambling nature of the home. Walk to restaurants and a river front park! See
MLS Property & Listing Details & 32 images.
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$1,095,000 | $354 per sq.ft.
Price Change! reduced by $400,000 down 37% on September 10th 2024
16 Church Street
Waterfront Owned 4 Beds | 3 Baths | Total Sq. Ft. 3089 | Acres: 0.52
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.
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$1,245,000 | $265 per sq.ft.
Price Change! reduced by $205,000 down 16% on August 7th 2024
119 English Mills Way
5 Beds | 5 Baths | Total Sq. Ft. 4698 | Acres: 5.1
An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional upper level bedrooms with 2 full baths, a family room with an attractive soap stone wood burning stove, a bright kitchen with cherry cabinets and an attached 2 car garage. The well conceived design presents the practical opportunity for single level living utilizing the gracious ground floor bedroom suite. Alternatively, the 5 bedrooms, on 3 levels, can satisfy a whole gang! The lower level private suite could present comfortable accommodations for an in-residence caregiver. Outside, a large wrap around deck transitions to pleasant sunny lawn areas with perennial gardens. Within walking distance are Mt. Tom's hiking trails! The property benefits from owner's who have taken pride in maintaining their beloved home! An attractive home that benefits from a thoughtful interior design! Equally suited for use as a well located year round residence or to be the vacation home that can accommodate friends and family alike! Skiing at Suicide Six as well as all the well known Woodstock Village amenities of shopping, dining and cultural events are just minutes away! Truly a great Woodstock property! See
MLS Property & Listing Details & 40 images.
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$1,340,000 | $504 per sq.ft.
Price Change! reduced by $335,000 down 25% on October 21st 2024
6453 South Road
3 Beds | 3 Baths | Total Sq. Ft. 2660 | Acres: 20.7
Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather (or enjoy quiet time). The first floor primary suite has lovely light and a generous soaking tub. The second floor includes a sitting area, two bedrooms, and an office. In the summer, enjoy outdoor living with a fire pit for evening gatherings under the stars. Direct access to trails for all season exploration. Equestrians will appreciate the potential to build a small barn with a paddock, and the short hack over to Green Mountain Horse Association (GMHA). Close to skiing: 23 miles from Killington, 22 miles from Okemo, and 10 miles from Saskadena Six. See
MLS Property & Listing Details & 31 images. Includes a Virtual Tour
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$1,395,000 | $540 per sq.ft.
New Listing!
1075 Westerdale Road
3 Beds | 4 Baths | Total Sq. Ft. 2584 | Acres: 41.45
This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a covered breezeway is a large 2 car garage, gorgeous horse barn with hay loft and a cozy studio apartment, making this the perfect spot for a variety of uses. Equally comfortable as a part-time or full-time home, this property is conveniently located on the western side of Woodstock, just twenty minutes from Killington's Skyeship gondola and ten minutes from downtown Woodstock. With over forty acres on prestigious Westerdale road, owners enjoy privacy and expansion potential. Offered for the first time since its inception, this property is an exceedingly rare opportunity for rolling acreage in a highly coveted location. See
MLS Property & Listing Details & 50 images.
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$1,499,000 | $409 per sq.ft.
Price Change! reduced by $100,000 down 7% on October 21st 2024
72 French's Road
6 Beds | 4 Baths | Total Sq. Ft. 3668 | Acres: 3.68
In 1880, this lovely hilltop Gambrel Colonial was designed by the prominent Manhattan Architectural Firm, McKim, Mead and White. "Rose Hill" was one of Woodstock's most prominent residences featuring the exquisite workmanship of the region's finest craftsmen. The grand scale and proportion of the rooms and the elegant period detail harken back to days of gracious gatherings with a formal DR complete with custom built-ins, a Library and a Stately Living Room anchored by a central fireplace, with direct access to a brick portico that runs the length of the home- ideal for summer entertaining. The kitchen has custom built-ins, plenty of counter space, a pantry entry, and a secondary staircase to access the second floor. A combination of indigenous hardwood floors run throughout the entire home. The sweeping formal staircase brings you to the second level with a spacious landing, and a wall of built-ins. There are a total of six bedrooms including a roomy primary bedroom with a fireplace, and three bathrooms. To the rear of the home you'll find a separate 2-car garage with a two bedroom rental unit above. Follow the footpath down to a secluded, very sweet two-bedroom guest cottage. All sited on 3.68 AC offering privacy, and plenty of space for gardening, entertaining and recreation. Just a short stroll to the Village Green and the National Park. This very special property awaits your vision to return it to its former splendor. See
MLS Property & Listing Details & 45 images. Includes a Virtual Tour
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$1,499,000 | $500 per sq.ft.
Price Change! reduced by $396,000 down 26% on October 24th 2024
1133 Atwood Lane
3 Beds | 3 Baths | Total Sq. Ft. 3001 | Acres: 28.6
**Price Improvement**Beautiful country contemporary home offers the best of Vermont living.Private yet convenient,just 6 miles from Woodstock Village and within 30 min. drive to DHMC,Dartmouth College,& Upper Valley shopping, dining, arts and amenities.Set on 28.6 acres,the property feels like a private sanctuary w/ stunning views and southern exposure.Inside,warm wood floors & finishes flow through the open 1st floor.The updated kitchen and dining room feature floor-to-ceiling windows,while the expansive living room w/wood stove opens to a deck w/ firepit and mountain views.An office,mudroom w/ direct garage access,& foyer complete the main level. Upstairs, you'll find bedrooms,bonus rooms,& updated bath w/soaking tub. The 3rd fl. primary suite offers ample storage,a cedar closet,whirlpool tub, & sitting area.Outside,the property is a gardener's paradise with fruit trees, perennials, a greenhouse, garden shed, and trails.A finished,heated studio barn includes a 1-bedroom apartment,outdoor shower, & deck.This exceptional home is perfectly located for outdoor enthusiasts-just a short drive to Killington,Okemo,& Saskadena Six ski resorts,Woodstock Country Club,Silver Lake State Park & more.The Appalachian Trail,Marsh-Billings-Rockefeller National Park,Billings Farm and Museum & miles of hiking and mountain biking trails in Woodstock & nearby towns also close by.With owned solar power,a generator, & a home filled with light and views,this property is a must-see in Woodstock VT! See
MLS Property & Listing Details & 60 images.
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$1,575,000 | $373 per sq.ft.
608 Fletcher Hill Road
4 Beds | 4 Baths | Total Sq. Ft. 4228 | Acres: 5.4
Open House Saturday 11/23 11:00 to 1:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef's kitchen with high-end stainless steel appliances, Vermont soapstone counters, custom cabinetry, and a spacious and sunny dining room. The cozy living room boasts one of two wood stoves, creating a warm and inviting space for relaxation. The massive family room is home to the second wood stove. There are two primary en-suites, each with a fireplace and spa-like bathroom, one in a private wing of the home, while the additional bedrooms and updated baths provide comfort and style. Outside, a large, partially screened-in deck and hot tub offer perfect spots to unwind and enjoy the tranquil surroundings--there is even a sauna off the rec room! Plenty of storage is available in the two-car garage or the two-stall barn. With solar panels, propane heating, two fireplaces, and two wood stoves, this home combines eco-friendly features with modern amenities. Its peaceful setting, just minutes from downtown Woodstock, is also close to the Green Mountain Horse Association, VAST snowmobile trails, Killington Mountain, Mount Tom, and the Saskadena Six Ski Area, making it a perfect full-time residence or seasonal escape. Enjoy Vermont living or work from home with EC Fiber! See
MLS Property & Listing Details & 53 images. Includes a Virtual Tour
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Under Contract
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$1,695,000 | $387 per sq.ft.
33 River Street
4 Beds | 4 Baths | Total Sq. Ft. 4378 | Acres: 0.47
BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hiking on Mtn Tom in your backyard. Situated on a very large lot featuring an in-ground pool accented with arbor and pool house. Lovely perennial gardens and large backyard for those seeking a vegetable garden or room for entertaining friends and family. This 4000+ sq. ft residence has generous room proportions, lots of natural sunlight and plenty of nooks for those seeking a quiet place to read a book. Handsome original wide pine floors throughout. This home was fully renovated with updated wiring, plumbing and insulation but still maintains the antique charm of a true Vt farmhouse. Original doors, 2 refurbished sunrooms, 2 covered porches overlooking the river, studio, family room and formal living room accented with a wood burning stove. Large kitchen with soapstone counters with Wolfe Gas range, ample room for cooking. Large dining area for entertaining and a first floor bedroom en suite. 2nd FL offers large primary bedroom suite with cozy sunroom overlooking the pool with views to Mtn Tom. Don't miss the 3rd floor with 2 small offices and lots of storage. The attached barn has capacity for lots of storage and options for multiple use. Walk over beautiful covered bridge to access restaurants, movie theatre and shops. Snow shoeing, championship golf, fly fishing and skiing all minutes away! See
MLS Property & Listing Details & 42 images.
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$1,999,000 | $474 per sq.ft.
Price Change! reduced by $396,000 down 20% on September 11th 2024
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 & 40 images.
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$1,999,000 | $257 per sq.ft.
Price Change! reduced by $151,000 down 8% on June 28th 2024
2709 W Woodstock Road
10 Beds | 12 Baths | Total Sq. Ft. 7769 | Acres: 5.5
Vermont is calling you! Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities, perfect for creating lasting memories. Whether you're looking for a family compound or a multi-family investment opportunity, this property offers versatility like no other providing privacy while fostering a sense of togetherness. An ideal setting for gatherings and celebrations of all sizes. The Inn building includes a commercial kitchen, several dining rooms, a tavern,and six ensuite guest rooms. The residence is perfect for a more intimate gathering with an open concept main level kitchen/living/dining experience with 3 ensuite bedrooms upstairs plus a main level, king bed suite with kitchenette while the motorcoach can be used to generate income and/or offers a special glamping experience with stunning mountain and water views of its own. Snowmobile right from your backyard! All this along the Otterquechee River on 5.5 acres in Woodstock VT! Unbelievable opportunity and location See
MLS Property & Listing Details & 40 images. Includes a Virtual Tour
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$2,000,000 | $400 per sq.ft.
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) available for owner occupancy with multiple additional income units in the village of Taftsville just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, café, or retail store), Post Office (with current lease), Apartment 1 (with excellent AIRBNB rental history), Apartment 2 (The owners 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 and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge. See
MLS Property & Listing Details & 60 images.
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$2,750,000 | $427 per sq.ft.
Price Change! reduced by $700,000 down 25% on September 3rd 2024
318 Ebbin Lockwood Way
3 Beds | 4 Baths | Total Sq. Ft. 6443 | Acres: 54.83
Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding Vermont countryside. The two bedroom guest cottage has its own garage and entrance off of Ebbin Lockwood Way. The 6,048 s/f main house and 1,584 s/f guest cottage were designed by architect, Michael Weinberger. The property was recently renovated: main house was upgraded and many new system improvements. From the stone terrace, there are views of a cascading waterfall flowing into a small Koi pond and perennial gardens. On the Northeast side, an outside sitting area takes in views of a long, rolling meadow with a pond and a glimpse of the local hills. The main house includes a detached garage with additional storage space. Less than 1/2 mile from South Woodstock Country Store and Kedron Valley Inn/Ransom Tavern and one mile from Green Mountain Horse Association. 25 min. from Mt. Ascutney mountain biking trails, 38 min. from Killington and 2:23 hrs. from Boston. See
MLS Property & Listing Details & 40 images. Includes a Virtual Tour
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$2,800,000 | $951 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 & 36 images.
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$2,865,000 | $818 per sq.ft.
4945 South Road
Waterfront Owned 450 Ft. of shoreline | 5 Beds | 4 Baths | Total Sq. Ft. 3502 | Acres: 2.7
The melding of the convenience of a premiere Village residence with the privacy and peace of a country estate is a rare balance. The John Arnold Cottle House achieves just such a balance. The three bedroom two story brick Federal home, built in 1811, has a prominent position on the main street in South Woodstock hamlet. It's setting belies the unique qualities the 2.7 acres offers. A drive to the lower level two car garage separates the main house and the renovated Kingley Barn, a two bedroom with loft guest house with a deck overlooking the Kedron Brook. There is a timber bridge crossing the Kedron Brook which accesses the open field and meadow and the two bay barn. The 450 feet of frontage on the Kedron Brook is an ideal tranquil retreat to enjoy the water element, firepit and surrounding environment with complete privacy. The John Arnold Cottle House has been fully renovated/restored with all of the best systems and finishes. The newer addition on the rear of the house has a gourmet kitchen, large brick fireplace, and relaxed living space. See
MLS Property & Listing Details & 43 images.
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Under Contract
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$2,950,000 | $461 per sq.ft.
Price Change! reduced by $475,000 down 16% on October 20th 2024
2055 Church Hill Road
5 Beds | 5 Baths | Total Sq. Ft. 6403 | Acres: 74.65
Nestled among verdant rolling hills, High Birch is located in one of the area's most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding natural landscape. Private and tranquil with pristine views in every direction through walls of tall windows and sweeping ceilings, the rooms are spacious, bright and inspiring- ideal for entertaining and daily living, and communicate directly with exterior spaces, terraces and decks. The kitchen and bathrooms have all been entirely renovated by Studio Nexus honoring and accentuating the original Davis design. The multi-level Great Room is anchored by a raised, polished gray marble fireplace. The Primary Suite is located on the 2nd level featuring a curved wall of windows offering a panoramic view of the neighboring valley farms, complete with a spectacular spa like wet-room, dressing room and laundry. The 2nd level is further completed by three additional bedrooms and 2 bathrooms. The lower level has direct access to the 2-car garage, an office, and spacious bunkroom. The surrounding terraces and grounds are lovely with established perennial beds. There is a swimming/skating pond and a barn for animals, storage, or to house your own sugaring operation. Offered fully furnished. See
MLS Property & Listing Details & 40 images. Includes a Virtual Tour
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Under Contract
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$3,500,000 | $579 per sq.ft.
486 Benedict Road
6 Beds | 7 Baths | Total Sq. Ft. 6040 | Acres: 38.93
"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. Excellent equestrian / horse potential with historic 5-stall barn and fencing for pastures/paddocks already in place. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main "Stone House" c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SEE FULL PROPERTY WEBSITE. See
MLS Property & Listing Details & 40 images.
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$3,500,000 | $644 per sq.ft.
61 Academy Circle
Waterfront Owned 6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 10
Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing. See
MLS Property & Listing Details & 40 images. Includes a Virtual Tour
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$3,995,000 | $777 per sq.ft.
18 The Green
6 Beds | 8 Baths | Total Sq. Ft. 5142 | Acres: 0.36
Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens. See
MLS Property & Listing Details & 40 images.
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$4,150,000 | $1,074 per sq.ft.
249 Sawyer Road
3 Beds | 5 Baths | Total Sq. Ft. 3865 | Acres: 2.37
This extraordinary residence offers breathtaking views of Billings Farm Preserve and the Green Mountains from nearly every corner, with Vermont's only national park directly in sight. The charming town of Woodstock, known for its boutiques and dining, is just a short walk away. Nestled at the end of a quiet road, the property offers unobstructed west-facing views for spectacular sunsets, surrounded by acres of undeveloped land. Woodstock's restrictive covenants ensure these views remain undisturbed, creating a peaceful, private escape. The expansive deck around the stunning pool is controlled via smartphone, with an automatic cover to ease maintenance. The adjacent pool house features a custom kitchen, a luxurious bathroom, and a cozy living area framed by floor-to-ceiling glass, offering year-round comfort with air conditioning and heated floors. The inground, heated, 30,000 gallon pool, can reach over 102° year-round, a rare feature in Vermont. An NBA hoops basketball net is installed in the shallow end for many days of fun, or if the deep end is more your style this pool offers a 9 foot deep end. This unique property offers proximity to skiing, golf, hiking, and more. The view encompasses the only National Park in Vermont. Marsh-Billings-Rockefeller in Vermont is the only national park to focus on conservation history and the evolving nature of land stewardship in America located right here in beautiful Woodstock VT! Contact us today to arrange a private tour! See
MLS Property & Listing Details & 54 images. Includes a Virtual Tour
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$6,750,000 | $1,621 per sq.ft.
2358 Long Hill Road
5 Beds | 4 Baths | Total Sq. Ft. 4165 | Acres: 465
Sited on 465 +/- private acres in South Woodstock, Birch Tree Farm was created as a retreat to bring family and friends together and to enjoy the great outdoors. The farm offers a variety of experiences, including pressing apples for cider, collecting eggs for breakfast, hiking to the cabin with 360 degree views, fishing or skating on the pond, enjoying miles of trails for walking, riding, or snowshoeing, and tapping trees for maple syrup. The relaxed vibe of the Lodge-style home, made of wood and stone, evokes a sense of mountain living, with design elements like exposed beams, a cathedral ceiling in the great room, a large stone wood burning fireplace, and floor-to-ceiling windows that frame expansive views of the mountains and the Ottauquechee Valley. Step out onto the wrap-around deck to take in an infinity pool, hot tub, stocked pond, and apple orchard. Landscape design by Shep Butler includes 10' hydrangea bushes, perennials gardens, stone walls, wild lupine in the meadow and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with seven stalls, an office/tack room, and a versatile upper level for entertaining & recreation, as well as accommodating an overflow of guests. Nine fenced pastures, two run-in sheds, a two-level storage barn, and a chicken coop enhance the farm with miles of trails connecting to GMHA. Showings begin 8-30-24 See
MLS Property & Listing Details & 39 images. Includes a Virtual Tour
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$8,000,000 | $1,486 per sq.ft.
115 Eastman Road
3 Beds | 4 Baths | Total Sq. Ft. 5384 | Acres: 68.92
Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the handcrafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains. See
MLS Property & Listing Details & 49 images. Includes a Virtual Tour
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$8,950,000 | $1,003 per sq.ft.
Price Change! reduced by $300,000 down 3% on April 8th 2024
2034 Long Hill Road
4 Beds | 7 Baths | Total Sq. Ft. 8921 | Acres: 295.59
High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23 See
MLS Property & Listing Details & 40 images. Includes a Virtual Tour
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