Greater Woodstock Area Homes with Acreage (Over 25 Acres)

Homes in the Greater Woodstock, Vermont Area with over 25 acres of land are special, indeed. Imagine stepping out of your home situated on a large piece of land to million-dollar views of the Green Mountains or of one of the area's many charming towns.  

Large-acre real estate in the Greater Woodstock area features a variety of home styles, from antique farmhouses to modern construction to rambling family and vacation compounds. Some of these parcels have ponds or rivers running through them. On a property with many acres, you can keep horses and other livestock, build a garden to your specifications, have pasture or woods.

In the Greater Woodstock area, you’re never far from varied dining options, entertainment, and amenities in towns such as Barnard, Reading, Bridgewater, Pomfret, and West Windsor.

Greater Woodstock VT Houses with Land for Sale

Find your perfect Greater Woodstock, VT home with over 25 acres of land below or contact Bassette Real Estate. One of our experienced brokers or buyer agents will be happy to help you.

186 Reading Farms Road Reading VT 05062

Reading, VT186 Reading Farms Road

Price$6,375,000

Est. Mortgage: $/month

MLS Number 4866260

  • Residential Single Family
  • Bathroom 15
  • Bedrooms 17
  • Construction Existing
  • Square Feet 13,010

Upon the first glance of the massive estate you notice the generations of carefully curated and thoughtful planned landscaping, expansive meadows and lawns, stocked fish ponds which catch the reflection of the main house as you drive by. You might even get a glimpse of the Merganser Hooded Ducks who nest each year. Owned for 100 years, the property has graced the cover of House Beautiful and in Architectural digest. The estate compound includes a main house reminiscent of an country manor with 9 bedrooms, 9 bathrooms, extensive living areas, a Library which is in the original cape built 1776 with original floors. Also a theatre, gym and 2 bedrooms with one bath. A carefully situated gazebo catches the evening sunsets through mature pines. Features a entertainment barn complete with kitchenette, 3 bed, 2 bath and pavilion for large groups or events. Also a cottage offering 3 bed,1.5 bath and kitchen. After a stroll on your private trails relax in the heated pool at the end of a mature maple alley. The estate is listed at 120 acres with an additional 115 acres available for a true kingdom of 235+. Many have tried replicating the setting at great expense to capture the estates decades of devotion to the grounds which cannot duplicated. Close to skiing and heart of horse country with access to GMHA trails. Minutes to Historic Woodstock. Presently being used as a Special Events venue as well as the owner''s primary home. Possibility of Owner financing and/or joint ownership.

Listed by Derek Eisenberg, Continental Real Estate Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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: 3.09% last updated on Oct 21, 2021
* 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$3,200,000

Est. Mortgage: $/month

MLS Number 4885504

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

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: 3.09% last updated on Oct 21, 2021
* 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: 3.09% last updated on Oct 21, 2021
* 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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797 North Road Barnard VT 05031

Barnard, VT797 North Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4877325

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 5,806
  • Construction Existing
  • Bathroom 4

Designed and built by the current owners in 2008, the house is in the middle of a 27-acre parcel. The land includes open meadows, a spring-fed pond, fenced paddocks and pastures, and a riding arena. Trails wind through two wooded areas on either side the property. Combining historically inspired details with modern construction techniques and state-of-the-art systems, the owners created a sense of space and volume with a functional and organized floor plan. A dramatic center staircase is the focal point of the entry. Throughout the first floor are 12-foot ceilings. Large windows and elegant room proportions create interiors that are grand yet livable. An open concept kitchen and a formal dining room provide options for entertaining. Off the front hall is a large mudroom, a washer/dryer, sink, open shower for dogs or muddy boots and an automatic dog door. The first-floor bedroom suite includes 2 separate bathrooms. A private screened porch off the bedroom is wired for a hot tub. Thoughtful attention to detail can be found in every room from the custom woodwork, stone and tile choices down to the cabinet knobs in the kitchen. There are 10-foot ceilings throughout the second floor with 3 generously sized bedrooms with large closets (one bedroom is being used as a exercise studio) and a full bathroom. In the center of the second floor is a large room with limitless potential. A mahogany, L-shaped farmers porch runs on the north and east sides of the house.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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234 Hidden Ridge Farm Road Pomfret VT 05067

Pomfret, VT234 Hidden Ridge Farm Road

Price$2,475,000

Est. Mortgage: $/month

MLS Number 4876336

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 6
  • Construction Existing
  • Square Feet 11,200

Room to roam, big views, privacy, space for everyone: This exceptional Vermont recreational retreat on 75.8+/- private acres has sweeping vistas from Killington to New Hampshire. The 8-bedroom, 6-bath residence is set up to provide suites for privacy, as well as comfortable gathering spaces opening to the views of meadows on to layered hills and distant mountains. Extensive recreational amenities include an in-ground heated pool, clay tennis court, sledding hill and, of course, the beautiful countryside to explore. Horses and their people will appreciate the 85 x 150 heated and sprinklered indoor arena complex with a 5-stall stable, viewing area with kitchen and office, ample hay storage, 2-bedroom apartment, 80 x 100 outdoor arena, 6-stall field barn and post & rail fenced pastures. Located within 15 minutes of Woodstock on a quiet country road. Bring your friends and your horses, or just soak up the quiet.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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935 Dana Road Pomfret VT 05053

Pomfret, VT935 Dana Road

Price$2,350,000

Est. Mortgage: $/month

Pending

MLS Number 4879160

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 4,316
  • Construction Existing
  • Bathroom 3

Picture “Vermont Farm” and this is that farm. Clapboard farmhouse, huge old timber frame barn, assemblage of other farm buildings amid rolling fields threaded with brooks, stone walls, and giant sugar maples. The 4 bedroom farmhouse is elegant in its simplicity, with high ceilings and big windows, facing south overlooking the late 1700s barn, outbuildings, orchard, gardens, and animals grazing in the pastures. For 240 years, only two families have owned O.L. St. John Farm, a 276 acre parcel that spans a half-mile valley. In 1761, the year the town of Pomfret was chartered, Isaac Dana was granted land and journeyed north from Connecticut to clear the forest and build a farm. Isaac's farm remained in the family until 1966 when it was purchased by another family from Connecticut. They raised beefalo, horses, sheep, pigs, chickens, guinea hens, bees, dogs, barn cats and three children. They practiced organic farming before organic was a thing. The farm's edible landscape includes apples, gooseberries, currants, rhubarb, blueberries, raspberries, asparagus and blackberries. Old logging roads crisscrossing the property are great for mountain biking and hiking. The Appalachian Trail borders the southern boundary of the property. There are multiple springs and brooks throughout the farm that could support the construction of a pond. The property is conserved with an easement with the Upper Valley Land Trust. High-speed internet. No showings on September 7th.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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932 North Road Barnard VT 05031-0133

Barnard, VT932 North Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4877795

  • Residential Single Family
  • Bedrooms 7
  • Construction Existing
  • Square Feet 11,200
  • Bathroom 10

THREE CENTURY FARM- Iconic gentleman's farm with stunning southerly and westerly views in ideal location minutes from Silver Lake and just north of Woodstock, Vermont. The property has been renovated several times over the years in such a way as to maintain the authentic historic charm of the original homestead while adding modern conveniences and amenities. Many features were custom made for the house such as the mantles and bathroom vanities. Brand new windows were installed throughout, accentuating the bright and spacious interiors with beautiful natural light and providing gorgeous views of the landscaped grounds. The main house features 5 bedrooms and is teeming with renovation potential, awaiting your finishing touches and/or additions (such as a formal kitchen on the first floor of the main house). The guest barn is one of the nicer renovations done in the area, and is perfect for entertaining. It features a primary bedroom and tasteful en suite on the third level, an elegant kitchen, additional bedroom, and a great room with 26' ceilings and a cozy wood stove. The farm sits on nearly 50 mostly open acres with beautiful historic stone walls and woodlands for recreating or a sugaring operation. There are 3 stalls in the heated barn, a cute tack room, and plenty of exterior space for horses on the grounds. (Note: Furnished photos are virtually adjusted.)

Listed by David Donegan, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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63 Hartwood Way Hartland VT 05048

Hartland, VT63 Hartwood Way

Price$1,995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4856960

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,078
  • Construction Existing

This truly special property starts at the end of a private road with a driveway that winds up through split rail lined paddocks to a cape style farmhouse situated perfectly to take in the stunning long range mountain views. Comprised of 45+ acres, the property includes a 5 stall horse barn with tack room and wash stall as well as 2 additional outbuildings. There are open fields, a riding arena and a nice swimming pond. Inside there is an open eat-in country kitchen that connects to the dining room and an office/bedroom. Through the front hall is the living room with wood burning fireplace which opens into the beautiful great room with cathedral ceilings, wood beams and a stone fireplace. A set of french doors open to the mountain views out front and another set leads to the deck and pond out back. Through the great room lies the Primary bedroom suite with jacuzzi tub, walk-in closet and private laundry. Upstairs are 2 good sized bedrooms, a full bath, and a 2nd laundry room. Located above Taftsville and less than a mile from Rte 4, this prime location is just minutes from Woodstock Village and 20 minutes to the Hanover/Lebanon area. Showings begin on 4/30/21.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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1350 Vermont Route 12 Pomfret VT 05053

Pomfret, VT1350 Vermont Route 12

Price$1,900,000

Est. Mortgage: $/month

MLS Number 4859544

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,729

Unlimited potential! 265 acres of highly desirable land straddling the hilltops connecting the towns of Pomfret and Barnard! On one edge of the property, there is a privately sited south facing and energy efficient post and beam residence. Truly a kingdom size parcel of a size and scope that would typically only be found in the most rural of locations! However, the numerous well known amenities of Woodstock Village are just 5 miles and a few minutes away! The owners who wisely assembled the land parcel components necessary to create this volume of acreage, are dedicated to conserving significant parcels of land within our community. They have indeed succeeded! With Town of Pomfret frontage on Route 12 and Town of Barnard frontage on the Stage Road, there is the opportunity to access the large parcel from either desirable town. The opportunity is presented for elevated building sites benefitting from dramatic long range views. The quality acreage and the prime location to compliment the construction of an unparalleled residential compound!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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174 Advent Hill Road Hartland VT 05048

Hartland, VT174 Advent Hill Road

Price$1,850,000

Est. Mortgage: $/month

MLS Number 4846107

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,628
  • Bedrooms 4
  • Bathroom 2

A spectacular landscape of mountain views, meadows bounded by stone walls and ancient maples, a pond, trails, apple trees, full equestrian amenities, and an abundance of choice for places to build a spectacular home and compound. Hamilton Farm is on a quiet country road 15 minutes outside the village of Woodstock. The land parcel of 157 acres is on some of the prettiest land in Vermont with big views that face East toward the White Mountains. A vast network of carriage trails offers miles of opportunity for extensive walking, cross-country skiing or mountain biking. Fulling Brook runs through the property and the pond attracts blue heron and other wildfowl. An additional 127 acres is available. For many years it has been the home of the Hamilton Rare Breeds Foundation, whose goal was to preserve rare breeds including the Poitou donkey, Dale ponies and Chocktaw mustangs. It was also a state-of-the-art training center for combined driving with its “hazards” and two large rings. Pat Hastings, the farm manager, trained here to qualify for the FEI Driving World Championships. The equestrian facilities include a ten stall indoor arena complex, a foaling barn and a 4 bedroom apartment and office, an outdoor sand dressage arena, a larger driving arena and numerous fenced paddocks with run-in sheds. 15 miles from Lebanon Airport; 15 miles from Suicide Six; 19 miles from Dartmouth College and 27 miles from Killington.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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974 Cemetery Hill Road West Windsor VT 05089

West Windsor, VT974 Cemetery Hill Road

Price$1,800,000

Est. Mortgage: $/month

Pending

MLS Number 4764706

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,884

White Fox Farm's c. 1790 yellow clapboard farmhouse and attached red barn is set just outside the village of Brownsville on a quiet country road where it seems like more horses go by than cars. The 39 acres scale of the farm is manageable with the key Vermont features: a pond, pastures and big views of Mt. Ascutney. The five-bedroom house underwent a major renovation in 2012. The kitchen with its hand hewn beams was enlarged to include a sitting area with views over the field, and outfitted with top-flight appliances for a cook that likes to prepare meals while surrounded by family and friends. Pssst…there is a secret room, believed to be part of the Underground Railway. There are fireplaces in the living room, the two master bedrooms, the birthing room (now used as an office), dining room and paneled family room. The third level is a great place for innovative thoughts (the owner launched a business here) with a two-room study with built in book shelves and a ¾ bath. Throughout the house there is a sense of fine craftsmanship that has stood the test of time in form and function. White Fox Farm is integral to the Green Mountain Horse Association community as the 83-mile marker for the hundred-mile ride.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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 2021 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 October 27, 2021.