Woodstock Homes with Acreage

Home with Land in Woodstock VTWoodstock, 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.  

Woodstock VT Homes with Land for Sale

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.

View all Homes for Sale in Woodstock

336 Stone Bridge Way Woodstock VT 05091

Woodstock, VT336 Stone Bridge Way

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4887084

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,824

Room for all, close to town, very private: Stone Bridge is a capacious and thoughtfully-built 2002 5824sf Craftsman Style home set at the end of a private way, with a guest house on a separate lot. The two parcels total 22.65+/- acres. Stone Bridge Way is off of Densmore Hill Road, well-located between Woodstock and South Woodstock Villages in the heart of horse and gravel cycling country. Lovely views to Killington: the western exposure makes for dramatic sunsets from the wide stone patio. Comfortable in all seasons, the spaces flow from open kitchen to living and dining areas warmed by a fireplace (with a conveniently located bar off the living area). Main level primary suite, second-floor primary, plus two bedrooms with shared bath and guest suite. The lower level offers a sports pub, gym and indoor spa. Plenty of space for toys alongside the garage. The guesthouse is privately sited away from the main house, with two bedrooms, two baths, fireplaced living room, dining room, kitchen and study. The site is elevated and largely open around the houses, with woodlands on the other side of the private drive. Site quality, location, and amenities make for a great compound offering.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4884374

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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

Woodstock, VT336 Stone Bridge Way

Price$2,999,500

Est. Mortgage: $/month

MLS Number 4888494

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,824

Room for all, close to town, very private: Stone Bridge is a capacious and thoughtfully-built 2002 5824sf Craftsman Style home set at the end of a private driveway on 10.15+/- acres. Stone Bridge Way is off of Densmore Hill Road, well-located between Woodstock and South Woodstock Villages in the heart of horse and gravel cycling country. Lovely views to Killington: the western exposure makes for dramatic sunsets from the wide stone patio. Comfortable in all seasons, the spaces flow from open kitchen to living and dining areas warmed by a fireplace (with a conveniently located bar off the living area). Main level primary suite, second-floor primary, plus two bedrooms with shared bath and guest suite. The lower level offers a sports pub, gym and indoor spa. Plenty of space for toys alongside the garage. The site is elevated and largely open around the houses, with woodlands on the other side of the private drive. Site quality, location, and amenities make for a great offering. This listing is also offered with a guest house. See MLS# for more details.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4884402

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 37.8 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award-winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-level bank barn has a wide center aisle, 3 box stalls and heat throughout on the first level; hayloft and office with high-speed internet on the second level; and storage on the third level. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Daily pleasures range from a plum fresh picked eaten at the outdoor table overlooking the perennial garden Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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66 Hollow Road Woodstock VT 05091

Woodstock, VT66 Hollow Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4885504

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,350

John Curtis, a veteran of the American Revolution, received a land grant to establish a homestead in the new State of Vermont circa 1780. The fields & pastures carved out of a wilderness sustained his family for 5 generations. Stonewalls & tumbled dams remain as evidence of the industry & effort of early pioneers. The Hollow Farm consists of the striking 6 bedroom/4 bath Homestead House & the 3 Bedroom/2 bath Brook House sited in the middle of the 91-acre property. The new Homestead created in 1988 around the stone fireplace & native timber framed original home. The southwesterly exposure illuminates the spacious gathering rooms & private spaces through the enormous round windows. The interior layout reflects casual country lifestyle with an open floor plan spiraling around the central kitchen complex, which opens out on to a wide, elevated terrace, decks & balcony's on each level. Common rooms & quiet corners are visually connected & access by open stairways. The architectural form expresses the Vermont farmhouse on a grand scale with a cupola & splendid views of the surrounding fields & mountains. The property adjoins Coolidge State Forest at a place where a magical waterfall & sweet swimming hole are formed over exposed bedrock. The maintained road ends a mile or so beyond the old farmstead & continues on with miles of trails leading to South Woodstock, Plymouth & Reading townships. Nearby are Woodstock Village, the ski resorts of Killington & Okemo & public waters.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4889125

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,016

Fifty pristine, peaceful, and private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock's famous amenities - less than 10 minutes to The Woodstock Inn & Resort's Athletic Center, 18 hole championship golf course, x- c skiing - hiking - biking trail system, fantastic dining, shopping, galleries and more! Or explore your own land which features numerous hiking trails, stone walls, and a stream. Parcels of this size & quality are scarce; this one's location also has a perfect balance of privacy & convenience. The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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81 Roberts Road Woodstock VT 05091

Woodstock, VT81 Roberts Road

Price$649,000

Est. Mortgage: $/month

Pending

MLS Number 4893490

  • Residential Single Family
  • Bathroom 3
  • Square Feet 1,955
  • Construction Existing
  • Bedrooms 3

Lovely Cape home on 12 level acres with a beautiful view of Gilberts Hill across the way and the Barnard Brook snaking along the front of the property. The yard is nicely landscaped with a covered patio coming off the back of the house. Inside, there are nice maple floors and lots of natural light. There is a first floor bedroom with a 3/4 bath across the hall and an open living and dining room with a wood burning fireplace. This room connects to the kitchen and has sliding glass doors out to the patio. Upstairs, are two good sized bedrooms each with an ensuite bath, and the laundry is located in a hallway closet between these two rooms. The basement houses the utilities, has a sink, and plenty of storage. The two car garage, attached by partially open breezeway, has a large finished room above with lots of potential. This property is located just 2 miles to Woodstock Village and is close to skiing, hiking, shopping and fabulous dining. Ideal as a primary residence or second home getaway. Showings begin on 12/18/21.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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148 Iver Johnson Way Woodstock VT 05091

Woodstock, VT148 Iver Johnson Way

Price$469,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4889831

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,449

DIRECT ACCESS TO VAST SNOWMOBILING TRAILS! Wonderful Woodstock location minutes to Woodstock Village! This property is set on over 13 acres with pretty views and a pond to enjoy. The adorable brick ranch has 4 bedrooms and 2 1/4 baths. Spacious open concept living and dining area with handsome stone hearth and woodstove insert. Nicely updated kitchen. Lower level is partially finished ready for the next owner to complete to their liking. The property has a 2 car detached garage with electricity and large storage space above it. Great space for one to turn it into a recreation room or an office. Come check out this prime Woodstock spot today! Close to Killington Mountain Resort and Suicide Six Ski Area!

Listed by Marni Rieger and Will Spanos, KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2022 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 January 19, 2022.