Woodstock Homes with Acreage

Woodstock, Vermont is often cited as one of the prettiest towns in America. Owning a home on a large-acre lot is your chance to own a part of this quintessential Vermont town.

Woodstock real estate provides residents with the opportunity to stroll the pedestrian downtown, visit galleries, and partake in a variety of outdoor activities like biking, hiking, skiing, fishing, and golfing. After an active day, dine at one of the town's many renown restaurants. You can catch first-run movies at Pentangle Arts, a concert at nearby Dartmouth College’s Hopkins Center for the Arts, or a play at White River Junction’s Northern Stage.

With a home on a large-acreage parcel, you can keep horses and other livestock, build a garden to your specifications, have pasture or woods. Much of the real estate sited on 10+ acres in Woodstock also has excellent long-range views of the surrounding mountains.  

Find your perfect Woodstock, VT home with a lot of acreage below or contact Bassette Real Estate. One of our experienced brokers or buyer agents will be happy to help you.

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
  • Construction Existing
  • Bathroom 6
  • Bedrooms 9

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, Four Seasons Sotheby's Int'l Realty

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$
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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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, LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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327 Fletcher Schoolhouse Road, Woodstock, VT 05071

MLS Number 4644250

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

Bybrook Farm is a picturesque country estate , built in 1797, and completely restored with historic integrity and deluxe amenities, including custom hand planed cabinetry and finishes , reclaimed wood floors , hand hewn beams and decorative painting by renowned artist Kevin Paulsen. Sited on 26 acres, with an exquisite brook that meanders throughout the property and leads to a picturesque spring fed pond .Gorgeous and varied regional views. A rare combination of brook, pond, rolling hills, forest, mature gardens, and original stone walls, complete with charming farmhouse , classic wooden bridge and quintessential Vermont red barns. A moments stroll to historic hamlet of South Woodstock and nationally acclaimed Green Mt. Horse Association equestrian center . The best of serene country living with easy access to downtown Woodstock and nearby equestrian, golfing , tennis, skiing, restaurants, spa and fitness facilities. 5 bedrooms in the Main House, and Guest House and 2 separate kitchens provide for cozy relaxation or entertaining friends and relatives. Settle in on the stone terraces or open air porches that overlook the rushing brook ; swim , fish or relax by the serene pond; take a nature walk in the forest ; ice skate on the pond ; snow shoe or cross country ski right out your back door. Enjoy the best of spring wildflowers , summer sunshine , fall foliage and winter wonderland in this unique property. Fun for two or twenty , with separate spaces for all to enjoy !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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486 Benedict Road, Woodstock, VT 05071

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4675093

  • Residential Single Family
  • Listing Agent Name Terry Davis
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6

“Spring Hill Farm” located in the heart of Vermont's equestrian region. The renowned Green Mountain Horse Association and all the events are just up the road. This amazing property offers a 3,040 sq. ft. vintage 1820 stone cape, which has been elegantly restored while keeping the authentic charm and architectural beauty. The gourmet kitchen has stainless steal appliances, brick flooring, and pantry, along with a fireplace keeping a true country feeling. The formal dining room walls have hand painted murals, and the large gathering room, perfect for entertaining, has vaulted ceilings with hand- hewn beams and built-ins. The house is set up with 4 bedrooms, 5 bathrooms, along with 5 wood burning fireplaces. The views of the barns and pastures can be had from most every room. Included is a 3,000 sq. ft. reclaimed barn of the same era that has been beautifully restored serving as a 3-bedroom guesthouse. The guest barn has a 2 story stone fireplace, wide pine floors, full kitchen, and a generous loft with a ¾ bathroom. On the lower lever are 2 additional bedrooms, a full bathroom, and a recreational room. To complete the package is a 5-stall barn with multiple fenced pastures. With over 6,000 sq. ft. of living space there is plenty of privacy for everyone. A truly idyllic piece of Vermont! The town office has the house listed as a 3 bedroom and the guest barn as a 2 bedroom; currently the house is set up with 4 sleeping areas and 3 in the guest barn.

Listed by Terry Davis, Engel & Volkers Okemo-Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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1096 Prosper Road, Woodstock, VT 05091

Price$1,495,000

Est. Mortgage: $/month

Pending

MLS Number 4699235

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

Fabulous private timberframe residence on 34.29 acres with long-range south-facing views and direct walking access to the Marsh-Billings-Rockefeller National Park, which abuts to the east. The residence was completed in 2005 and boasts an oak timberframe and reclaimed barnboard floors. The great room has vaulted ceilings, two fireplaces, looks out at the long-range view and opens to the gourmet kitchen, beyond which is the mudroom and powder bath. With a four-bedroom septic in place, the house is currently designed as a three-bedroom residence, with each bedroom having an ensuite bath. Wonderful south-facing covered porch, side screen porch and detached 2-car garage. All expected modern mechanicals including backup generator, radiant heat throughout (except MBR), a fire sprinkler system, security system. Totally privately situation yet easy access - just 2 minutes to the Woodstock Farmers Market, 5 mins to Woodstock Green and 20 mins to the Killington Skyship.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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25 The Lane, Woodstock, VT 05091

Price$999,999

Est. Mortgage: $/month

MLS Number 4663484

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4

EXCEPTIONAL 14 ACRE PROPERTY, MINUTES FROM WOODSTOCK VILLAGE. Beautifully constructed with custom details like gorgeous millwork, Brazilian cherry floors, high ceilings, gracious family rooms, and a massive granite fireplace, this spacious home is perfectly equipped to accommodate your family and friends in comfort and luxury. Two ponds, a contemporary barn, an antique barn on a fieldstone foundation, an open-air cottage, an automatic generator, an oversized two-car garage, and a finished lower-level family room make this home the perfectly equipped Vermont retreat. A screened breakfast room opens off the gourmet kitchen, and a generously proportioned mahogany-floored porch runs the length of the house - the ideal spot for breezy summer days spent admiring the views to Killington. The first-floor master suite offers his and hers walk-in closets, a steam shower, and a claw-foot tub, and each of the three ample guest bedrooms enjoys an en suite bath. This home checks all the boxes!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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2 Carlton Hill Road, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4717944

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

Own the fabulous Carlton Reservoir as your own swimming, fishing, and boating pond. Fantastic location with additional building lot for boat house, guest house, artist studio, or caretakers house. Beautiful stone walls, flat level building lot, and awesome zipline on approximately 10 acres of land and pond. Just around the corner is the fully renovated 3 bedroom/2.5 bath 3,165 sq. ft. contemporary cape with an additional finished 864 sq. ft. private media room for "wide screen TV movie nights". The house sits on an additional 13.75 acres. There is over 4,800 sq. ft. of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to escape from the hustle and bustle of life. An excellent opportunity to develop a family compound, vacation retreat, or handsome estate. Own you own little corner of heaven! Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat. For full details on the home or to purchase the home with a smaller piece of land (without the pond), see MLS #4717399 at 76 Grove Hill Road, Woodstock.

Listed by John Bassette, Bassette Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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739 Westerdale Road, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4728514

  • Residential Single Family
  • Listing Agent Name Richard Higgerson
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Constructed in 2003, this custom home on just under 11 acres of beautifully manicured land was designed with the vernacular architectural style of Vermont barns in mind and enjoys a location that is convenient to Woodstock Village and nearby Killington and Okemo ski resorts. The center of the open interior floor plan house is a magnificent Great Room with oversized windows, high ceilings, cherry floors and a granite hearth with gas stove. The Great Room opens onto a mahogany deck that overlooks established perennial gardens, stonewalls, a brook fed pond stocked with trout and mountain views to the south. A chef's kitchen with granite counters, cherry cabinetry, a generous center island work space and stainless appliances opens onto an inviting south facing sunroom with a vaulted ceiling and oversized windows. Three bedrooms and two baths on the second floor long with 1600 sqft of additional space ready for finish in the lower level & heated, attached, direct entry 3 car garage.

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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125 Hoadley Road, Woodstock, VT 05091

Price$885,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4631074

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

A handsome timber frame house situated on 78 acres of open and wooded land protected by conservation easement., designed to take advantage of privacy,quiet, an overflowing spring-fed pond and year round brook. Splendid solar exposure for great natural light .Living Room/Dining Room and Kitchen all open to each other and provide wonderful access to 4 decks opening to the pond, brook, and lovely perennial gardens. Kitchen features high quality appliances , custom cherry cabinets, with island/bar to provide a great gathering space while cooking and entertaining. Main level bedroom with bath , spectacular 2nd level master suite with cathedral ceiling, sitting room, balcony, walk-in closets and luxurious bath. Lower level consists of bedroom suite with sitting room and kitchenette. Exceptional grounds include trails for hiking, horseback riding, 24x28 barn could easily accommodate horses for this property which is in the center of the spectacular Green Mt. Horse Assoc. trail system. Just a short stroll to the village of South Woodstock and a 5 minute drive to the Woodstock Green. Convenient to skiing, spa, fitness center and recreation.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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76 Grove Hill Road, Woodstock, VT 05091

Price$755,000

Est. Mortgage: $/month

MLS Number 4717399

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

DESIRABLE NEIGHBORHOOD! Fully renovated 3 bedroom/2.5 bath 3,165 sq ft contemporary cape with an additional finished 864 sq ft private media room for "wide screen TV movie nights". There is over 4,800 sqft of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. There are numerous home living spaces (Craft Room, (2) Family Rooms, Living Room, Media Room, Office, & Dining Room). The modern 2004 kitchen renovation has plenty of cupboards for storage and there are newer 2013 Kitchen Aid appliances. There is a private master bedroom suite with built-in double closets, air conditioning, and a newly redone tiled master bath. Two additional bedrooms with hardwood floors share a common bath. The large family room has a gracious fireplace (and woodstove) to stay warm and cozy during those cold winter months. Lovely private porch and patio can accommodate large gatherings to enjoy the views as you eat a relaxing meal. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to retreat from the hustle and bustle of life. Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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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