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Single Family Homes for Sale

Scroll down to browse single family homes for sale in the Woodstock region of Vermont. Contact us if you have any questions or if you would like to schedule a time to visit a home. Create an account to save your favorite homes and to receive email notifications when similar listings become available. 

1959 Cox District Road, Woodstock, VT 05091

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4429915

  • Residential Single Family
  • Listing Agent Name Richard Higgerson
  • Bedrooms 9
  • Bathroom 6
  • Construction Existing

A modern architectural masterpiece and important work by award winning and internationally recognized architect Rick Joy, Woodstock Farm presents a dramatic shingle and stone house and barn set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close proximity to Dartmouth College in Hanover, New Hampshire. The high concept contemporary design is executed with the sharpest attention to craft and draws on the vernacular of the rural northeast. The main residence offers a 152-foot elongated gable house with massive end walls of Lake Champlain bedrock and cedar cladding on the roof and side walls. Set at a subtle angle to the barn, the north facade of the main house engages the purity of the setting and looks out onto a large, deep, spring fed swimming pond and the rolling pastureland, hills and mixed northern hardwood forests that comprise the property.

Listed by Richard Higgerson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2358 Long Hill Road, Woodstock, VT 05071

Price$5,500,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 foot Old Baldy Mountain with 360-degree views and a small private cabin at the summit.

Listed by T Story Jenks and Ruth Sudduth of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Woodstock, VT 05091

Price$5,450,000

Est. Mortgage: $/month

Pending

MLS Number 4720968

  • Residential Single Family
  • Listing Agent Name Christopher Lang
  • Construction Existing
  • Bathroom 8
  • Bedrooms 6

Located at the end of a private road in Woodstock, Vermont on a hilltop with long range views of the Green Mountains, is a stunning six-bedroom eight-bathroom residence that is exceptional in every detail. First is the land itself, 30.39 +/- acres that fold over the ridge on either side with fields, woodlands and miles of John Morton trails for fitness and recreation. At the height of the land is the home. Private and secluded, all you hear are the sounds of nature, and as you look out over the landscaped yard and swimming pool to the cascading ridges and mountains beyond, Feng Shui is omnipresent. It was the land - its views, privacy and serenity - that drew the owners to the property eight years ago and for good reason. Parcels like this are exceptionally hard to find let alone buy. Which explains why after using the property for several years the owners decided to completely remodel and expand the circa 2008 home. Finished in 2016, the transformation is extraordinary inside and out. Everything is top of the line with custom and trade-only finishes and fixtures throughout. The house is also fully automated and has high-speed Comcast Internet and great cell-phone reception. Using an iPad, you can control temperature, lights, speakers, shades, alarms and security cameras, onsite or remotely via the Internet. Simply put, this is one of the nicest offerings in Northern New England; a perfect house on a perfect parcel in a perfect location.

Listed by Christopher Lang of LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21 Havelok Hill Road, Strafford, VT 05072

Price$4,700,000

Est. Mortgage: $/month

MLS Number 4712391

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5

"HAVELOK HILL" is privately situated in the midst of +/- 600 acres in lovely Strafford, Vermont. The land component is the most extraordinary parcel our firm has ever offered for sale, including absolutely stunning long-range mountain views from the main residence that includes the White Mountains of New Hampshire to the east, and to the west, the Green Mountains of Vermont including direct views (from the patio area) of Mt. Ascutney, Okemo, Killington, Pico, Camels Hump and Mt. Mansfield (Stowe) among others. The property has five secluded ponds, approximately 200 acres of upland meadows, and eight miles of improved interior roads and riding trails for every conceivable type of outdoor activity - all on your own private compound. The main residence is situated at the height of land, perfectly oriented towards the views. The present owners spared no expense in designing a residence of the highest quality and taste, centered around a magnificent 1,500 square foot (30 x 50) wood-paneled great room ("the concert hall") with a 24-foot vaulted ceilings, 8-foot custom-built mahogany french doors to the patio/view, and a massive fieldstone fireplace. The property also includes a four-bedroom guest or caretaker's cottage - nearby but out of view of the main residence. Located nearly equidistant between Woodstock, Vermont and Hanover, New Hampshire, Havelok Hill offers incredible privacy and quietude, with access to the best the Woodstock-Hanover area has to offer.

Listed by John Snyder and Andrew Holson of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1095 Eastman Road, Sharon, VT 05065

Price$3,995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4666522

  • Residential Single Family
  • Listing Agent Name Zoe Hathorn Washburn
  • Construction Existing
  • Bathroom 10
  • Bedrooms 8

EASTAWAY ESTATE - The breathtaking Eastaway Estate sits on 128 acres tucked away on a mountainside at the end of a gated private drive. The elegant main residence and guest house are perched at an elevation of 1,400 feet overlooking the Green Mountains, creating the ultimate country escape. The sophisticated contemporary homes offer the highest quality materials including mahogany ceilings and marble floors. The floor-to-ceiling windows and inviting exterior decks and terraces provide full views of the majestic professionally landscaped surroundings. An extensive trail network winds throughout the rolling, wooded property for walking, snowmobiling, cross country skiing and more. The two homes offer over 9,000 square feet of luxurious living space, including 8 bedrooms, 10 bathrooms, 7 fireplaces, 2 wine cellars, a tasting room and garages for 8 cars. There are 2 outdoor spas, 3 ponds, 2 saunas, and a beautiful in-ground pool. Enjoy sunsets from the mountain top gazebo which offers 360 degree views. This is one of the finest estate properties available in Vermont and provides true privacy while still conveniently located within a 25 minute drive to both Hanover, NH and Woodstock, VT. The interior of both homes was professionally designed and the property is being offered fully furnished.

Listed by Zoe Hathorn Washburn of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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336 Stone Bridge Way, Woodstock, VT 05091

Price$3,975,000

Est. Mortgage: $/month

MLS Number 4509981

  • Residential Single Family
  • Listing Agent Name John Wetmore
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5

Magnificent South Woodstock family compound! The estate is composed of a main residence, substantial guest home and 22.5 acres with long views. The Adirondack style main residence is constructed to the highest standard, by one of Woodstock's premier builders. A well conceived floor plan presents both generously sized common gathering areas as well as quieter private spaces. Family members, of multiple generations, are comfortably accommodated. Large bedroom suites, on 2 levels, can provide adult guests with privacy. All the expected amenities! On the lower level is the truly extraordinary private bar/entertainment area, a large 40x12 exercise room, a hot tub room, with shower, and a workshop, with space for all the motorized toys! The detached 9 room, 3 bedroom guest house is private and substantial. A beloved family compound! well sited, on 20 acres of land, at the end of a private lane, with long views of distant mountains.

Listed by John Wetmore of William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1055/1044 Sayer Road, Barnard, VT 05031

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4609102

  • Residential Single Family
  • Listing Agent Name Stan Butler
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance from Woodstock and Hanover, New Hampshire. Circa 1998 6800 square foot main residence with three-car attached garage and spectacular post and beam six-stall barn. 396 acres of managed pasture and forest with 13 miles of riding trails, one of which terminates at a hilltop picnic area with a magnificent 360 degree view a short half-mile ride from the barn. A 2400 square foot caretaker residence with an attached two-car garage and a beautiful seven-stall post and beam barn occupies a hilltop across the road from the main residence. Two ponds complete this perfect setting. The main residence was five years in the building by a local builder renowned for his quality and attention to detail. Furniture-quality woodwork throughout this four-bedroom, six-bath main residence with complete butlers apartment wing. A walkout basement level finished into a large media room and corporate size office/conference room with wet bar and full bath.

Listed by Stan Butler of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4777 Rush Meadow Road, West Windsor, VT 05089

Price$3,650,000

Est. Mortgage: $/month

MLS Number 4726033

  • Residential Single Family
  • Listing Agent Name Christopher Lang
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4

Sheep Run Farm in West Windsor, is named for the stone walled lanes where Ira Taylor, a prosperous mid-19th century farmer, herded sheep from the barn to the upper meadows. Today, a newly reimagined 2017 4-bedroom plus loft (6-bedroom septic), 6.5 bath farmhouse fits seamlessly into the classic Vermont scenery, just 3 miles to the South Woodstock store, and 8 miles to Woodstock Village. Classic on the outside, hip on the inside, the farmhouse's 1st floor has an open floor plan, with large windows and high ceilings, abundant light and views from every window. Connected buildings include a 2-bay garage, carriage house party barn, wood room and yoga studio. A huge glass door of the three-season carriage barn opens to the stone terrace, while a massive stone fireplace and soaring ceilings make this a remarkable gathering spot for family and friends, and the second floor boasts a comfortable guest suite. EC fiber provides high speed access for this smart-home to control; lights, climate, video, security, and property access via apps from anywhere in the world. The property encompasses all the right elements; the exceptionally beautiful 21+ acres, including views of rolling meadows, Rush Meadow Valley and Mount Ascutney; endless stone walls; apple trees; a cascading brook and two ponds.

Listed by Christopher Lang and Dia Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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37 Brothers Road, Hartland, VT 05048

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4629754

  • Residential Single Family
  • Listing Agent Name Richard Higgerson
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing

Offering some of the most beautifully managed and meticulously maintained acreage available in Windsor County, Hartland Highlands offers over 279 acres of high, rolling meadows, mixed northern hardwoods forests, four ponds, three brooks, miles of interior roads and trails and multiple developable future house sites in addition to the mid-19th century Cape, guest house and barn complex currently in place. Views from the property extend from Smarts Mountain in Lyme, NH through dramatic near range vistas of Mount Ascutney to the south. Professionally managed by the premier Upper Valley land enhancement company for more than two decades, the quality of the acreage is unsurpassed. The main house and one bedroom guest house are surrounded by copious perennial gardens, antique stonewalls, grandfather maples and sweeping lawns. Multiple barns and outbuildings provide storage space for every conceivable outdoor pursuit. A true legacy property in a location less than 25 minutes from the heart of the Upper Valley, Hanover and Dartmouth College.

Listed by Richard Higgerson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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535 Peace Mountain Way, Woodstock, VT 05091

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4659067

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5

"PEACE MOUNTAIN" is a private estate with breathtaking views of the Ottauquechee River Valley. Custom built in 2008, Peace Mountain is a spectacular Arts & Crafts shingle style home situated on 183 acres with a vaulted ceiling yoga/recreation room and scenic trails for hiking, snowmobiling, mountain biking and cross country skiing for year round recreation. It is designed for gracious living and offers total peace and tranquility. Spacious gathering rooms open out to a wide veranda surrounding 3 sides of the home with a beautiful stone fireplace and grilling area for 3 season use. The property includes five river stone fireplaces as well as a wood-fired pizza oven in the kitchen to enjoy in winter evenings. Peace Mountain was designed for an active family and extended family and includes a climate controlled hardwood yoga studio/basketball court, rock climbing wall with spectacular views and an expansive storage area for outdoor recreation equipment. Convenient to the Killington Ski area, Dartmouth College and is located four miles from the Woodstock Village. Off private road leading to the house is direct access to VAST snowmobile trails to east and west. Multiple building sites served by underground utilities. Located at the end of a paved private road engineered for New England's rugged weather. The Peace Mountain Ranch is an exceptional property and is ideal for a residence, yoga retreat, corporate retreat, or family gathering compound.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1055 Sayer Road, Barnard, VT 05031

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4687009

  • Residential Single Family
  • Listing Agent Name Stan Butler
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance to Woodstock, Vermont and Hanover New Hampshire. Circa 1995 6500 sq.ft. residence with attached three-car garage and spectacular three-story, six stall post and beam barn. An additional 2000 sq.ft. in the walk-out basement finished into a media room and large conference/office area with a wet bar and full bath. 252+/- acres of conserved and managed forest and pastures with miles of maintained riding trails. The residence was five years in the building by a local builder renowned for his quality and attention to detail. Furniture-quality woodwork throughout this four-bedroom, six-bath residence with complete butler/guest apartment wing. Property also available with 396 acres and a 2500 sq.ft. post and beam caretaker residence. See MLS#4609102.

Listed by Stan Butler of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2912 Route 12 Road, Barnard, VT 05091

Price$2,900,000

Est. Mortgage: $/month

MLS Number 4672496

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6

"TWIN PONDS" - The land component of Twin Ponds is a private and pastoral setting on 52.2 acres with two ponds, open high meadows with lovely views of distant hills, two streams with waterfalls that course through the property (and by the main house and guest house) and a new post-and-beam barn with horse stalls, chicken coop and room for tractors and other motorized toys. The main residence has a post & beam great room with 25-foot stone fireplace and views, beautiful eat-in gourmet kitchen, large master bedroom suite, large downstairs game/rec/office space and bedrooms to sleep 15+. The “Gristmill” guest house is nearby complete with open living/dining/kitchen, full bath and bedroom - and has a separate water source from a gushing Vermont spring. The land is in Vermont Current Use conservation program, comprised of woodlands, open meadows, stone walls, apple trees, wildlife pond and separate swimming pond. Appalachian trail is nearby. First rate mechanicals include full back-up generator, six bedroom septic, full security system and more. This property has a Woodstock postal address and phone number and is 9 minutes to the town green in Woodstock Village, but is a legal parcel of the town of Barnard. Easy access to ski resorts and Hanover/Dartmouth.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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