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
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 9,515

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4,165

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. Landscape design by Shep Butler includes an orchard of 110 productive apple trees with varieties such as Macoun, Empire, Cortland, Spartan and Macintosh.

Listed by T Story Jenks, LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 6,796

"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 three 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 and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,308

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: 4.17% last updated on Apr 18, 2019
* 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

Active With Contract

MLS Number 4734913

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 6,040

Circa 1820 stone cape with 10' ceilings has been elegantly restored while keeping the authentic charm and architectural beauty. Chefs can enjoy the gourmet kitchen, which has quality stainless steel appliances, brick flooring, a walk-in pantry, along with a fireplace keeping a true country feeling. Beautiful windows and hand painted murals adorn the formal dining room. A small cozy family room located off of the kitchen features a fireplace, built-in cabinets, and French Doors leading to the stone patio. The rustic living room has vaulted ceilings, hand-hewn beams, with a large fireplace; perfect for entertaining. Presently the house is used as a 4-bedroom, featuring 5 bathrooms, and 5 wood burning fireplaces. The reclaimed barn of the same era has been beautifully restored serving as a 3-bedroom guesthouse. Open floor concept with a two-story stone fireplace, full kitchen, den, and large sleeping loft. The walk-out basement has two bedrooms, full bathroom, utility room, and a recreation room with French Doors. Completing the package is a rustic 5-stall barn with multiple fenced pastures. Green Mountain Horse Association and riding trails are just up the road. With over 6,000 square feet of living space there is plenty of privacy for everyone. Square footage includes both buildings. A truly idyllic Vermont property!

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Active With Contract

MLS Number 4663484

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 4,866

EXCEPTIONAL 14 ACRE PROPERTY, MINUTES FROM WOODSTOCK VILLAGE. Beautifully constructed with custom details like gorgeous millwork, Brazilian cherry floors, nine-foot 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 long-range 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. With flexible spaces and the potential for additional square footage, this home checks all the boxes!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,960

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,793

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: 4.17% last updated on Apr 18, 2019
* 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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353 Cabot Road Woodstock VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4737344

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,542

A very comfortable Woodstock home, beautifully sited, on 18 acres, to enjoy long views and substantial sun light! The practical floor plan features a primary bedroom suite, with ensuite bath and walk in closet, on the first floor. For convenience, in Winter weather, direct access from an oversize garage leads into a long mud room. The living room is designed for entertaining! This central gathering area is anchored on one end, by a dramatic stone fireplace, features wood beams overhead, and ever changing pastoral views over a large open field, toward distant hills. The first floor is completed with a view oriented dining room, a well designed kitchen and a formal entry foyer. On the second floor are 3 bedrooms, full bath and a den. A full basement provides multiple areas for workshop space and has a fully finished office space, with a private walk out entrance. An inground swimming pool provides Summer entertainment. The diverse land is comprised of both acres of open land and a sugarbush with a sugarhouse structure. A beloved family homestead that is waiting for its next generation of occupants.

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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326 Hall Circle Woodstock VT 05091

Price$689,000

Est. Mortgage: $/month

MLS Number 4691364

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,949

Privately sited and superbly maintained, this timber-framed New England style home offers incredible southerly views over the Ottauquechee River Valley. You can enjoy watching the lights of Woodstock Village a mile distant from every room. The home was constructed by one the areas finest post and beam builders using traditional mortise and tenon joinery on display throughout. Spacious common areas all open onto patios and decks on each level of the residence. Generously sized bedrooms and well-appointed baths provide private space for family and guests. This wonderful and quiet country setting is just minutes from restaurants, recreation offerings at Suicide Six Ski area, Woodstock's Golf Course, Athletic Club and all resort amenities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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925 Fletcher Hill Road Woodstock VT 05091

Price$625,000

Est. Mortgage: $/month

MLS Number 4734771

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,248

Four Lite Designs impeccably and intelligently renovated Gambrel is beautifully nestled on an open and sunny ten acre hillside dotted with stonewalls, maple trees, and a babbling brook all within minutes of downtown Woodstock! The updated floorplan consists of an open concept kitchen/dining area, living room, office/study and slate tiled entryway on the main level and a spacious second level comprised of a master bedroom with ensuite bath, two additional bedrooms, full bath, and laundry room. New oak hardwood floors throughout compliment the light filled rooms. Enjoy the pristine view of the quintessential Vermont hillside detailed with stone walls from the handsome mahogany deck! The extensive 2018 renovation included all new Marvin windows, new electric panel and wiring, updated plumbing, and new roof and wall insulation that meets or exceeds efficiency standards and EC Fiber ready for 2019! Superb location for either a primary home or secondary home and excellent potential as an income producing vacation rental as this property is currently exempt from town zoning short term rental restrictions. Easy access to dining, theatre, shopping, Killlington, Suicide Six, Marsh Rockefeller National Park, Green Mountain Horse Association, and Woodstock Health and Fitness Center. Simply a must see! Virtually staged photos of the dining room, living room, and master bedroom were used as noted.

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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1522 Curtis Hollow Road Woodstock VT 05091

MLS Number 4743887

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,816

Well maintained custom Colonial being sold for the first time. Situated on a peaceful country road with access to abundant land and forest. Spacious and pleasing floor plan, open kitchen appointed with granite tops, custom cabinetry and slate flooring. The living room has 18' ceilings creating a view from the upper loft. The ground floor master bedroom suite is accented with a large full bath with both step in shower and a jetted tub and plenty of closet space. Three bedrooms and two more bathrooms are upstairs and a bonus room for guests, crafts or recreation. The large basement could also be partitioned if needed. For extra storage or recreation/farming there is a 28x38 pole barn. The land has a gradual slope which could be cleared for agricultural use. This property is currently subject to and benefits from a current use plan. Come enjoy the covered porch, hear the stream while relaxing and absorbing the local views.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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Copyright 2019 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated April 25, 2019.