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.

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477 Thistle Hill Road Pomfret VT 05053

Pomfret, VT477 Thistle Hill Road

Price$1,775,000

Est. Mortgage: $/month

MLS Number 4791217

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 2
  • Square Feet 5,691

Thistle Hill Retreat - tucked into the Pomfret Hills is the best combination Vermont views and setting along with direct access to the Appalachian Trail system. Property is a delight in all seasons - exciting visuals for the horticulturalist throughout the warmer months, follow the seasonal wildlife changes, and plenty for the outdoor enthusiast. Wonderful for entertaining with generous spaces, gorgeous sight lines, and a spiritually grounding environment. This is an experience worth sharing with friends and family. Main house constructed during WWII with onsite concrete work commissioned by John Taylor Arms. He chose concrete to avoid losing his artwork to fire a second time. The home was substantially renovated and reimagined in 1998 by owner/artist to modernize and return to John Taylor Arms' original proportions. Please see the virtual tour for an intimate view of the property. Less than 20 minutes to Woodstock and White River Junction less than 15 minutes to Quechee.

Listed by Derek Cosentino, BHG Masiello Group/Quechee

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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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249 Densmore Hill Road Hartland VT 05048

Hartland, VT249 Densmore Hill Road

Price$1,600,000

Est. Mortgage: $/month

MLS Number 4767801

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 2,959

This superbly maintained Vermont Cape residence captures stunning sunsets from a vantage point overlooking westerly river valleys to the peaks of Killington and Shrewsbury. The home is offered fully equipped and furnished for gracious country living. A large multipurpose barn, run-in and fenced pasture reflects the traditional use in 'horse country' with GMHA (Green Mountain Horse Association) trails providing access throughout the surrounding area. A mix of open fields, apple trees and northern hardwoods is defined by old stone walls. A spring fed pond is a year round source of water for a variety of wildlife thriving in the sparsely populated community. Ideal situation for those seeking the peace and quiet of rural New England.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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20 Gray Road Hartland VT 05048

Hartland, VT20 Gray Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 4805827

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,536

The best view of Woodstock and the National Park is in Hartland at a cabin called Sun Hill. Built in 2019 on 122+/- acres with 3 bedrooms and 2 baths, the “have to have it” quality of this special property is exceptional. First, the view is mesmerizing and dynamic as changing sunlight, hues and shadows travel across the hilltops and valleys below to the ridges and peaks beyond. Sunrise and sunsets are extraordinary. Second, the home is charming and comfortable, well-built, easy to maintain and takes full advantage of the view and being outside. The first floor has 9 ½ foot ceilings with 8-foot tall double-hung windows and 2 sliding glass doors, one to the timber-framed porch and 5-person hot tub, the other to the patio made of Vermont slate. All of the kitchen cabinets, bathroom vanities and post & beam frames were custom made by local artisans using cherry, oak and pine sourced from the property. Third, the home is completely private surrounded by nature yet located only 3 miles from the Woodstock village green on the east side of town saving time to get to I89 and I91. It also has high speed Internet and cell reception plus a second 4-bedroom septic permit. The last feature is a wonderful old barn and 20-acre field on the west boundary. Perfect for storing equipment, you can hike down to it using one of several trails or drive. Not in view of the cabin, what was farmed here long ago could be farmed again.

Listed by Christopher Lang, LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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97 & 99 Darling Road Woodstock VT 05071

Woodstock, VT97 & 99 Darling Road

Price$1,575,000

Est. Mortgage: $/month

Pending

MLS Number 4767586

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,749

High Riding's 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson's (NYC Mayor Fiorello LaGuardia's “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible. The “Studio” at 97 Darling Road, a 2,384 square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio. The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a swimming pond. There are over 800 sugar maples- tapped for maple syrup, apple trees, well maintained pastures, forest, private riding and hiking trails and a 3-stall stable.

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

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$
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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1702 North Puckerbrush Road Reading VT 05062

Reading, VT1702 North Puckerbrush Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4759535

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 7,374

A magical property located in the hills of Reading surrounded by large country properties in the heart of horse country. State Forest land abuts this property for even more protection. This home is a perfect retreat for those seeking solitude. The sweeping drive carries you through the woods to the home-site which is centered in an open area totally hidden from the town gravel road. Pleasant view are here now, with dramatic views if you chose to thin the woodland below. Walking the grounds you will find a natural landscape with added fruit trees, a new barn with storage for 2 or 4 cars and a loft, a hidden back field and even an ancient "lime kiln'. Inside there are so many quality features that you may have only dreamed about...the top of the line kitchen with Sub-Zero freezer and fridge, Wolf range, refrigerator drawers, cookbook library, and a separate prep room known as the 'gadget room'. There is an office, den, living, dining room on the first floor along with screen porch to the rear. There are two wings to the second floor..giant master suite with abundant storage and a stunning bath along with two guest rooms and a laundry room that will make you want to do your laundry. The other wing would be a perfect in-law suite or nanny's quarters with two sleeping rooms, sitting room, full bath and washer/dryer. The lower level has a large family room, gallery, exercise room and 2 storage areas. This property is second to none with Okemo and Woodstock just miles away.

Listed by Betty McEnaney, TPW Real Estate

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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1862 Lakota Road Barnard VT 05031

Barnard, VT1862 Lakota Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4773880

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 6
  • Square Feet 3,572

A 1930's getaway tuned up for the 21st century with a whimsical, yet sure-footed, sense of style. Redtop has been in the family since the early 20th century, and was built at the same time as the abutting Lakota Club, the private fishing club. The property is located off a quiet dirt road, surrounded by 59.4 acres of meadows and woodlands, with lovely far views of valleys and mountains. Summer living is centered on the wide covered porch, where breezes flow up the valley and make for relaxing reading, dozing and conversation. Winter is all about the huge stone fireplace in the living room and sledding on the long hill off the side of the house. The house is manageable in scale but sleeps a crowd, with two bedrooms on the ground floor and another 5 on the second floor, with 4 total baths. The current owner's full-on renovation has drawn repeat vacation rentals, covering the annual operating costs while giving her plenty of time to enjoy the property as a second home. It is a hit with visitors because it is fun and hip while still very Vermont (furnishings are included). The acreage offers potential for a family compound or investment value.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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5798 South Road Woodstock VT 05071

Woodstock, VT5798 South Road

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4805831

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 4,510

The Kedron Farm has long been admired for its classic beauty . Beautifully sited on a knoll looking out to the meadows and hills of the valley this extended 1850 cape complete with separate guest quarters ,large 4 story barn with 6 stall stable and equipment shed offers everything one could wish for in a country property. The grounds include gracious old maples , perennial gardens, stone walls , large swimming pond and discretely sited tennis court. The property has been meticulously cared for and combines antique features with open , modern touches. The rooms are spacious with lovely light and easy access to the outdoors. Located in the heart of horse country and the historic village of South Woodstock. 10 minutes to Woodstock , 2 1/2 hours to Boston , 5 hours to NYC.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1510 Wayside Road Barnard VT 05031

Barnard, VT1510 Wayside Road

Price$1,350,000

Est. Mortgage: $/month

MLS Number 4743181

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,862

ATWOOD PLACE- This elegant, historic Vermont farm residence is privately situated on 135 acres. It is an ideal location just 7 miles north of Woodstock Village. The main residence has been beautifully updated and maintained with a gourmet kitchen, antique historic period details, 5 fireplaces, formal dining, living room, den/library, workout room, 4 bedrooms, and 2 1/2 baths. There are acres of pastures/fields, mowed lawns, manicured gardens and flower beds bordering the road lined with handsome stone walls. Apple and birch trees abound. The spectacular stone-lined swimming pond has a nearby outdoor entertaining space with stone patio, outdoor fireplace, and a gazebo for dining. The tremendous Atwood Brook courses through the property behind the house. There is a circa 1850 barn-shed across the road. Additionally available option further down the quiet Wayside Road is a newer, larger barn with 2 apartments and a workshop/studio space on separate 27 acres. Atwood Place is also only minutes to Silver Lake in Barnard, and has easy access to the best of the Upper Valley Region of Vermont & New Hampshire, including Hanover / Dartmouth College.

Listed by David Donegan, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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403 North Bridgewater Road Bridgewater VT 05034

MLS Number 4803801

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,256

“Three Brothers Farm, White Fences” on the desirable North Bridgewater Road is comprised of 75.82 surveyed acres of stunning farmland, green pastures with white fences, woodland trails, ancient stone walls, a brook and absolutely spectacular, sunny long-range mountain views. An abundance of fruit trees, heavy stone walkways and patios are beautifully landscaped to welcome you home. The residence c. 1890, has been lovingly updated with modern mechanicals, bathrooms & an eat-in farmhouse kitchen complete with soapstone counters and a commercial Garland stove. The master bedroom with ensuite bath and three other bedrooms and two baths have been recently updated by the present owners. The southern solar orientation and open fields make Three Brothers Farm perfect for organic farming or as a possible orchard/vineyard. Acres and acres of fenced, open pastures and access/connections to trails on neighboring properties make the home ideal as an equestrian setting. Situated on a quiet (but paved) road just a minute from Route 4, Three Brothers Farm is located 10 minutes to the Village Green in Woodstock and 12 minutes to superb skiing via the Killington Resort Skyeship. The property's eastern side abuts the Woodstock town line. Three Brothers Farm offers that desirable combination of an historic and updated Vermont farmhouse, 75.82 acres of beautiful land, long-range mountain views, easy access, convenient location on a quiet side road, and privacy.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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117 Bible Hill Road West Windsor VT 05037

West Windsor, VT117 Bible Hill Road

Price$1,190,000

Est. Mortgage: $/month

MLS Number 4802156

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,385

MILL BROOK FARM- Superbly constructed home on 83+ mostly open acres with stunning 360 degree views of Mount Ascutney and the surrounding countryside. Mill Brook winds around the perimeter of the property offering over 4,000 feet of frontage and a wonderful spot to cool off in the summer or just enjoy the sound and water. The interiors of the house are bright, spacious and immediately comfortable. The property has been meticulously maintained and is the ideal gathering place for family and friends. There are plenty of sleeping quarters and views from most rooms in the house, many looking to the impressive mountainside. The house is surrounded by flat and slopping yards and hay fields. The property is only minutes from Brownsville, and a very short ride to the interstates, Woodstock & Hanover. The best of Vermont skiing and nature is in the backyard or nearby. There are x-country ski trails available on the property. The property is professionally landscaped and has mature trees throughout. There are a total of five garage bays- 3 attached and a 2 bay/ 4 car detached structure perfect for a car collection or toys of any size. VAST access also on property.

Listed by David Donegan, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1539 Gulf Road Barnard VT 05031

Barnard, VT1539 Gulf Road

Price$950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4694326

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 5,200

This is the perfect Vermont pastoral outdoor playground property: 84.4 acres, beautiful stone walls, and wide open lawns/birch groves which surround two massive swimming/fishing/kayaking ponds, which connect to each other via a stone waterfall right at the house. Direct access to the VAST trail for snowmobiling across Vermont to Canada. Newly built 2,900 sq. ft. fully insulated cement-floor barn-garage with multiple commercial overhead doors offers storage for 10+ motorized toys plus a large vehicle servicing workshop. The residence itself offers 5 bedrooms, 3 full baths, kitchen with wood burning fireplace and a downstairs rec/game/bunk room. Attached 2 car heated garage and private deck off the kitchen overlooks both ponds. Mechanicals include a newly installed whole house automatic generator. The property is very close to a paved road just 12 minutes to Woodstock, and 2 minutes to provisions and activities at Barnard Silver Lake / The Barnard General Store.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1606 BRIDGEWATER CENTER Road Bridgewater VT 05035

MLS Number 4766474

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 4,794

Maple Lane Farm is one of the areas earliest homesteads with land used as a cornfield by a local farmer fronting on the North Branch of the Ottauquechee River. The historic 1790 Cape farmhouse and approximately 130 acres is located across the road in a cluster of historic barns and stonewalled gardens. The property rises to the height of Southgate Mountain, where a rustic cabin was built as a private retreat with sweeping views over the valley south and westerly. The warm patina of time and character remains throughout the home, which has been updated with modern mechanical systems, wiring and plumbing. The town of Bridgewater is midway between Woodstock Village, Killington and Okemo Ski areas, offering a rural experience within close proximity to popular shopping and recreational amenities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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 2020 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 May 30, 2020.