Woodstock Vermont Real Estate

Super location in the heart of Woodstock Village. Nestled on the bank of the Ottaquechee River. Easy walk to all of towns amenities and Mtn Tom for a short hike. This one bedroom condo features hardwood floors, large full bathroom and eat-in kitchen. Lots of natural light especially in the afternoon. Low list price for those who would like to come in an do some upgrades to the kitchen and bathroom. There is one assigned parking space. Seller is a licensed real estate agent in VT. Easy to show.
Super location in the heart of Woodstock Village. Nestled on the bank of the Ottaquechee River. Easy walk to all of towns amenities and Mtn Tom for a short hike. This two bedroom condo features 2 large offices, 2 large bedrooms with full bathroom, Living and dining rooms with kitchen adjacent to an antique walk in pantry. Lots of natural light especially in the afternoon. Low list price for those who would like to come in an do some upgrades to the kitchen and bathroom. There is one assigned parking space. Seller is a licensed real estate agent in VT. Easy to show.
This classic Vermont Log Home has served as the company’s model and is conveniently located minutes to the Woodstock Village. The two-bedroom, two-bath home is sited on nearly 2 acres, with an enclosed porch and deck overlooking a spring-fed pond, perennial beds, and established gardens. A one-bedroom accessory dwelling with a workshop, a handcrafted post & beam two-car garage, garden shed, and equipment shed further completes the property. A solar array offsets nearly all electrical use. On the way to Killington and nearby biking & hiking.
Gambrel style Cape sited on a corner parcel of 4+- acres of open land bordered by the Kedron Brook. Updated eat-in kitchen and baths, living room with built-ins, dining room, hardwood floors, and spacious mudroom. Upstairs en-suite primary bedroom and two additional bedrooms. Complete with detached carriage barn/garage and spacious deck. Only two miles to the village green and minutes to Mt. Peg for hiking, biking, and cross-country skiing.
Gorgeous fully restored farmhouse with modern amenities and original charm! This sunny and pristine four-bedroom home is conveniently situated in west Woodstock village - just a short drive from Killington, Hanover, and DHMC and within the desirable Windsor Central School District. Comprehensively and meticulously renovated in 2017 from roof to basement, this property boasts all new electrical and plumbing, high-quality polyethylene foam insulation, a new standing seam roof and all new appliances, fixtures, and flooring throughout. Turn-key, convenient, and low maintenance, this home is ideal for primary homebuyers, vacation enthusiasts, and investment shoppers alike. From the soapstone countertops and the exposed beams to the spacious deck and easy-keeping yard, you'll find something to enjoy in every season. Offering flexible upstairs spaces and expansion opportunities, the layout gracefully accommodates both intimate gatherings and larger crowds. With luxe farmhouse design influences and an unbeatably convenient location, this property is a rarity in the Woodstock marketplace! Showings begin 6/28/2022. No showings shall be held 7/1/2022-7/4/2022.
You're sure to fall in love with this classic log style home perched on a knoll with pleasant valley views. Located on a quiet dead-end road, steps away from the Kedron Valley Inn in South Woodstock, and a five-minute drive to the Woodstock Village Green. The rooms are spacious, with plenty of natural light throughout. The home transitions seamlessly between interior to exterior spaces with two private terraces and an oversized deck for outdoor entertaining. The living room is anchored by a a woodburning fireplace. Best of all there is a beautiful-screened porch overlooking the grounds to the view. The lower level holds great potential for expansion. There is a great detached multi-purpose barn/ garage. Access to trail system for hiking, snowshoeing and snowmobiling. Close proximity to skiing, restaurants, recreation.
PERFECT LOCATION! Just a three minute drive to downtown Woodstock. This 1.42 acre property has been owned and thoroughly maintained over the past 40 years. Gorgeous Landscaping and a beautiful artists studio behind. Attached 2 car garage/barn with multiple areas for a workshop. Stained glass embellishments throughout. Original hardwood flooring and ample amounts of natural sunlight. With a screened in porch for those beautiful evenings. First floor has two bedrooms and a full bathroom. Second floor has additional 2 bedrooms with a full bath while, the 3rd floor is a fully finished attic with a Jack and Jill on-suite. Currently used as a two family home but could be easily converted back into a single family. This home is a once in a lifetime opportunity!" Only 5 minutes to Suicide Six ski area. Property Survey (2012) and Septic Inspection (2022) available. Delayed showings starting Sunday, May 1 at the open house from 11am-2pm.
A highly desirable Woodstock location! Conveniently situated only a few minutes from the Woodstock Village Green, in a lush pastoral setting, is a bright 3 bedroom home. The land component of the property is truly high quality, with ample lawn area for entertaining or recreation, pleasant meadow views and a sunny exposure. All the convenience of single level living is provided in this home of a manageable size! A well conceived floor plan features a large living room/dining area with a fireplace and a dramatic bow window, a kitchen with an area for breakfast dining, a well designed sunroom, 3 bedrooms with wood flooring and 1.5 baths. The sunny back patio presents a private sitting area with tranquil views of a large meadow. The interior of the home feels comfortable and well built. The land is idyllic! Neighboring homes are substantial. All of these attributes combine to offer a property that is equally appealing as a manageable vacation home or a comfortable year round residence!
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.
Pristine, peaceful, with 5 private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock’s famous amenities – less than 10 minutes to The Woodstock Inn & Resort’s Athletic Center, 18 hole championship golf course, x- c skiing – hiking – biking trail system, fantastic dining, shopping, galleries and more! The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont! Additional land available - total of 50 acres.
This sprawling Country Cape is privately sited at the end of a tree-lined road yet only five miles to Woodstock Village. Conservation land surrounds this home with GMHA horse-riding and hiking trails right outside your door. The two stall horse barn and one mile distance to Green Mountain Horse Association make this a convenient horse property. Thoughtfully renovated spaces create a modern farmhouse design. Enter the home and step into a redesigned mudroom that leads to a generous and comfortable den. Next, enter the chef’s kitchen that boasts top-of-the-line appliances, quartz countertops and shaker cabinets. Experience three seasons of indoor/outdoor living with light-filled dining and family room spaces that open to a spacious screened porch and deck where you can entertain, relax or simply enjoy nature. The primary bedroom en-suite features vaulted ceilings and a balcony plus a surprise! Two additional bedrooms, laundry room and full bath complete the upper level. Bathrooms are newly renovated with beautiful tile work, flooring and finishes including 3/4 bath downstairs. The barn-styled guest house offers a guest suite with full kitchen and 3/4 bathroom on the second level and finished horse stalls and parking on the lower level. A new standing seam roof and Buderus heating system complete this lovely home. Simply move in and enjoy. 30 minutes to Killington, 2.5 hours to Boston and 4 hours to NYC.
Lilac Cottage: A charming Gothic Revival home in South Woodstock Village. Recently restored with a new addition that can be used as an in-law apartment or used completely by one family- stunning hand hewn beams that accent lofted ceiling capturing lovely light, there are french doors out to back gardens and handsome kitchen that opens to living/dining room. The lawn is beautifully landscaped with stone walls and perennial gardens. Enjoy two outdoor gathering spaces with a new back deck or under the charming covered front porch. A new 2 car garage with ample overhead storage is a very recent addition. This home boasts large spaces for entertaining family and guests. Gracious formal living room off a very large dining room. Hardwood floors and lots of antique character throughout this home. Enjoy the Kedron Valley Inn for a swim in the the pond or for dinner on the front porch, or gather at the country store for coffee and visits with neighbors. The Kedron Brook is across the road and Green Mountain Horse Association is a short walk away. There are endless miles of country roads and trails for hiking, biking , horseback riding and cross country skiing. This is the best of a country village lifestyle.
Highbank Cottage- A truly lovely estate nestled on the banks of the Ottaquechee River overlooking a clear view of Mtn Tom. Stunning, private backyard with beautiful landscaping and perennial gardens. Stroll down to the river or enjoy an evening under the stars at the cozy fire pit. This antique gambrel features handsome hardwood floors, first floor master bedroom suite, propane fireplace in the Living Rm with lofted ceilings for a spacious feel. The intimate dining room has ample space for a long harvest table for many guests looking out to Mtn Tom. The 2nd floor incorporates 3 more guest bedrooms and full bath. The lower level features a large office with propane stove for chilly fall days, summer kitchen and screened in porch to cozy up in the afternoon reading a book. The 'Barn' includes a 2 bay heated garage, stunning apt with bedroom/sitting area and 1.5 baths. High vaulted ceilings with beadboard walls to capture the true 'cottage' feel. Lower level has a large workshop and more storage or could be converted to a workout room. Enjoy fishing on the Ottaquechee or take a trip floating on tubes down the River on a hot summer day. All of town amenities, shops and theatre right out your back door. Suicide Six, Okemo and Killington near-by as well as championship golf, tennis and mountain biking. Very few properties in the village offer a view and river access with large apt for either friends/family or rental income. Come take a look- Its adorable!
Set back off a quiet country road with stone walls sits this Cape Cod home on thirteen acres. A peaceful setting for those seeking privacy in South Woodstock. The fenced-in backyard is perfect for summer barbecues and long swims in the pool. Enjoy a cocktail on the covered porch while the sun sets. A mix of rolling pasture allows for gardening and equine friends. The main level of the home features hardwood oak flooring, a large living room with fireplace, an eat-in kitchen overlooking the backyard, dining room, laundry room, half bath and a bedroom suite. The upper level provides pine flooring, an additional bedroom, bonus room and bath. There is a separate guest apartment with its own entrance over the garage. The attached and detached garages offer a workshop and plenty of space for toys, vehicles and storage. Solar panels cover most of the electric overhead. Lovely landscape surrounds the yard with lilacs, roses and shrubs. Less than five minutes to Green Mountain Horse Association with easy proximity to golf, skiing and Woodstock center. Showings begin Saturday, July 9th.
Fifty pristine, peaceful, and private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock’s famous amenities – less than 10 minutes to The Woodstock Inn & Resort’s Athletic Center, 18 hole championship golf course, x- c skiing – hiking – biking trail system, fantastic dining, shopping, galleries and more! Or explore your own land which features numerous hiking trails, stone walls, and a stream. Parcels of this size & quality are scarce; this one’s location also has a perfect balance of privacy & convenience. The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont!
#3 BOND STREET is a classical example of the Greek and Colonial Revival architectural movement in the United States. Built in 1836 by Henry Lawrence, a piano manufacturer, the property transferred a year later to Oel and Sophia Billings who resided in the home they called 'The Maples' with their nine children. Their daughter Elizabeth lived in the home after her parents moved to #16 the Green and she later shared it with her brother Frederick, until he could acquire and renovate the George Perkins Marsh Mansion. The home was later the long time residence of Frank and Lucy MacKenzie. Her kindness and support of animals in service to people is remembered by naming the regional animal shelter in her honor. The residence is currently configured as three apartments, but retains the original floor plan. Evident throughout the home are elegant moldings, trim and architectural elements of the bygone era, including a greenhouse used on the north side for orchids and spacious interior porch leading to the private back yard on the northeasterly side where it provided cool shelter on summer days. A remarkable property with a special heritage as home to many who made Woodstock what it is today.
The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes’ drive of the Killington and Okemo ski resorts, respectively. Known locally as the Robinson Farm, after the family that build the handsome home and legendary barn shortly after the turn of the 20th Century. The property has been converted by the present owners into a gracious and authentic rural farm environment for vacations, weddings, and other events large and small. The historic 1905 Farmhouse Inn offers accommodation in the 7 Guest Rooms, all with private baths and gracious gathering rooms on the first floor. A 2-bedroom Innkeeper’s quarters provides private living space. The Red Barn was constructed in the style of a ‘bank barn’ with grade level entry points to the different levels of the barn where they served a variety of agricultural purposes. The massive timber frame is exposed on all levels with the upper two having been adapted for the event venue hosting up to 150 guests. The White Barn accommodates 50 guests for smaller ceremonies and other events with a wide deck providing a place of seasonal outdoor dining. 13 acres of open land and convenient location offer the potential to create a farm-to-table restaurant, direct-to-consumer shop selling local and regional goods or an immersive Agri-tourism guest experience. Less hospitality-oriented uses as a gentleman’s farm or niche farm producing or marketing local goods are great options as well.
This five-bedroom Neo-Colonial overlooks western Woodstock Village and Mount Tom from an iconic columnated verandah. Thoroughly updated and expanded by meticulous owners - including a family room addition in 2014, a remodeled kitchen and basement in 2015, a 6500 square foot veranda in 2016, and a circular driveway in 2021. Careful preservation and restoration of the antique elements lends an old-world elegance; new electrical, insulation, roofs, and heating systems provide worry-free convenience. On an uncommonly spacious village lot, just over an acre, the land offers plenty of room for your needs - a pool, a play structure, or a barn. The wide wraparound porch, landscaped patios, and abundant perennials make spring, summer, and fall a joy to experience. In the winter, relax by the wood-burning and propane fireplaces and enjoy the seasonal view of the Mount Tom star. With a flexible bedroom spaces and a discreet in-law or guest suite, this home accommodates friends and family with ease. Within close walking distance of downtown Woodstock, this extraordinary property is as rare as it is delightful.
4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America’s most beautiful villages.
A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer’s market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice
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.
SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.
Old Fitch Farm is one of New England’s most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler’s pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

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