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.

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: 3.75% last updated on Jul 11, 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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1001 Atwood Lane Woodstock VT 05091

Price$3,250,000

Est. Mortgage: $/month

MLS Number 4762434

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,701

“The Hill” is a modest name for an exceptionally private 82+/- acre hill top meadow at a 1,780' foot elevation with breathtaking 270-degree views of the Green and White Mountain ranges. Located within 4.8 miles of Woodstock village, this is a property designed to enjoy country living and the outdoors. The c2002 custom cedar shingle 3-bedroom residence (2,688 square feet) was designed by AIA award winning Truexcullins, a firm known for high craftsmanship and sustainable, enduring architecture. Created to integrate with the natural surroundings, the spacious living areas take advantage of the stunning unobstructed views with large windows and high ceilings, and is finished with cedar plank walls and trim, antique pine floors, soapstone counters, fir trusses, exposed beams, and a 2-story fieldstone fireplace. Tucked away with its own views, privacy and rustic comfort is a 2-bedroom classic cabin (1,013 square feet) with a floor-to-ceiling stone fireplace. The grounds are a balance of meadows and woodlands laced with reconstructed stonewalls. There is a 1.5-mile maintained trail for walking and skiing, a 1/3-acre swimming pond with a fishing shack, a “Hobbit House” built into the side of a hill, and a lean-to with a fire pit sited on a prominent overlook. Adjacent is 300-acre town-owned land with reservoir, extensive trail network, and a 186-acre conserved property. The Hill overlooks Mt. Tom and the protected Marsh Billings Rockefeller National Park.

Listed by T Story Jenks and Dia Jenks, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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 & 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: 3.75% last updated on Jul 11, 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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1532 Happy Valley Road Woodstock VT 05091

Price$2,895,000

Est. Mortgage: $/month

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This contemporary cape with classic Vermont lines is built on the history and character of two fully reconstructed antique post & beam frames. Currently it is being completely re-sided with beautiful cedar shingles (photo #4). Architect designed and unquestionably one of the nicest homes in Woodstock. There is beautiful interior space, newly created guest quarters, four working stone fireplaces, high-end master bathroom finishes, and 55.76 acres of playground. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas stove, a large double door commercial refrigerator, and even space for a kitchen herb garden. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. The look and feel is classic Vermont charm with all the modern conveniences of the 21st century. Five (5) bedrooms, four (4) bathrooms, and over 6,000 sq-ft of living space are finished to an exacting level of detail. The grounds have a duck pond, ancient stone walls, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Enjoy distant valley views from the stone patio and Happy Valley Road is on the easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, skiing, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat from the busyness of life.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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2352 Curtis Hollow Road Woodstock VT 05091

Price$2,300,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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343 Spruce Way Woodstock VT 05091

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4710997

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,216

This is one that you absolutely have to see! Pictures simply cannot capture the warmth, functionality and tranquility of this very special property. Located on a private dead-end road in the Cox District region of Woodstock just 8 minutes from the Village Green. The pristine long-range views can be appreciated from every room. Every inch of this lovely post and beam cape has been tastefully renovated to the highest standard with new chef's kitchen, bathrooms, systems, solar and generator. Each of the four bedrooms has it's own private bathroom. Lovely screened porch and deck overlooking stone walls, perennial beds and the view beyond. Brand new barn with separate farm road entrance, open pasture and a magnificent interior trail system. Walk out lower level with family room, office and guest accommodation. Spacious, private heated room above the attached three car garage for studio, recreation room or for home occupation. Excellent equine potential.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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 4753809

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 3,960

This custom-built residence is privately situated on 10+ acres with lovely mountain views, a stream, woods and pond. The residence - constructed in 2003 - has been beautifully maintained, and is move-in-ready. Designed for one-level living, the 3-car attached heated garage walks into the main level complete with beautiful, open floorplan, cherry floors, a large gourmet kitchen, lots of light and windows, a lovely sunroom, a unique circular room that leads into the large 1st level master bedroom suite with walk-in closets, large bath area and it's own private office and balcony. There are 3 additional bedrooms and 2 baths upstairs (with expansion framed & ready both above the garage and in the lower level). Extensive landscaping and stone walls. A lovely stream and pond on the property can be viewed and heard from the master bedroom balcony. Superb mechanicals with top-of-the-line Viesmann radiant heating system, whole-house automatic backup generator, security/fire system, central AC in the upstairs bedrooms. If you are seeking a beautifully built and maintained residence, privately situated in an area of substantial homes just minutes to the Village Green, this is a must see.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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661 Deer Brook Way Woodstock VT 05091

Price$730,000

Est. Mortgage: $/month

MLS Number 4764089

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,912

The whole package - private, extremely well-maintained and thoughtfully designed house, mountain view, and an incredible swimming pond - with convenient access to the village of Woodstock and Killington Mountain Resort. The multiple spring-fed swimming pond is truly exceptional with several docks for lounging, a diving board, and a screened-in cabana for dinner parties as well as a small room for changing into swim attire. The remaining ~13-acre land component is nicely landscaped with open space for recreation and a walking trail that leads to a brook. Entering the house, a spacious and bright mudroom connects the 2-car attached garage to the main living space. The chef's kitchen with walk-in pantry is well oriented to take in the view and connects seamlessly to the adjacent living space - with a sliding glass door that opens to an expansive deck. A formal entry, dining room, living room and half bath complete the first level. The master bedroom with bathroom is very private and features ample closet space, its own deck overlooking the pond and view, and a skylight that is positioned to gaze up at the stars at night. Three other bedrooms are also located on the second level. The finished walkout basement receives plenty of light and is currently setup as a den/bar and game room, with a ¾ bathroom, workshop, and hot tub room. Solid mechanicals include central AC, a separate air conditioning wall unit in the master bedroom, and a generator hook up.

Listed by Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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271 Gabert Road Woodstock VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4753233

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,480

Enjoy stunning views from this gracious, private country home. The open floor plan affords easy flow for entertaining. The large windows take in the distant views as well as the beautifully landscaped grounds, gardens and pond. The main level includes large living room with fireplace, dining room with balcony, gourmet kitchen with custom cherry cabinets , bedroom and bath large, laundry and 2 car attached garage. The master suite includes bedroom with balcony, private sitting room that could be used as a nursery, office, and spacious his and her master bath. Lower level has 30x15 family room with fireplace as well as bedroom with bath. There is a generator and for year round comfort, air conditioning. Large closets, lots of storage and generous proportioned rooms filled with lots of sunlight as the house is oriented to the South. The property has the possibility of another homesite. Minutes to historic Woodstock and all of its amenities . Close to Killington and world class skiing. This is truly a very special property !

Listed by Carol Wood and Gretchjen Smith, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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6656 South Road Woodstock VT 05071

Price$650,000

Est. Mortgage: $/month

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located on the southerly side of South Woodstock across from the Green Mt. Horse Association, with direct access to miles of horse riding trails. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, lovely gardens and playground.The homestead includes a guest apartment periodically rented, and additional potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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$647,000

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: 3.75% last updated on Jul 11, 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 July 17, 2019.