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.

587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • Square Feet 5,412

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4913355

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Square Feet 8,225
  • Bathroom 8

SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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298 Holiday Farm Road Bridgewater VT 05035

Bridgewater, VT298 Holiday Farm Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4929847

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,757

The legacy property of OQ Farm (formerly known as the Holiday Farm) has been adapted several times throughout its historical past, most recently as a 481-acre short-term hospitality and retreat destination with an arts and spiritual focus. Featuring 8 different dwelling structures, OQ Farm offers a diverse range of accommodation options, from 1800s historic, a luxurious lodge retreat center, to sleek and modern eco-cottages, converted maple sugar shack, a studio cabin and caretaker's cabin, all taking advantage of unique views of the river valley and mountain range beyond. Boasting 1,200+ feet of river frontage along the North Branch and Ottauquechee Rivers, which flows into the Connecticut River; OQ Farm is situated equidistant between the Appalachian Trail and ski slopes of Killington and the quaint town of Woodstock - renowned as one of America's most beautiful towns. Several fenced pastures and barns provide for agricultural use beyond the sheep, alpacas, poultry and horses present currently. An extensive network of mountain biking, hiking and snowshoeing trails, and a large bonfire pit offer endless outdoor recreation and gathering opportunities.

Listed by Rachel Arsenault and Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4925674

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

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SHOWINGS WILL START SUNDAY AUGUST 21.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$3,300,000

Est. Mortgage: $/month

MLS Number 4932341

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,456

This extraordinary 115 acre property, located in the towns of Woodstock & Hartland, offers the perfect mosaic of qualities that buyers are looking for. The acreage is unencumbered and presents the perfect opportunity for a family estate, future development or equestrian opportunities with grass covered hillsides, trail systems and the GMHA just 3 miles away. The diverse topography of the property with trails throughout has an easily accessible summit offering a unique homesite location with spectacular unobstructed panoramic long range views that can be captured from sunrise to sunset. The level of stewardship is evident from the maintenance of the extensive trail systems, existing structures and grounds to the main pond that is deep and well stocked. The structures include a very comfortable two story cottage with long vista views, a large barn/garage, two stall horse barn with run-in and a split rail fenced area. There is also a three sided oversize pole barn currently being used for equipment storage located at the end of one of the trails. The property is accessed off a municipal road via (3) gated entry points. A gazebo at the summit takes in nearly 360 degree long range views providing the idyllic setting for a substantial residence. The properties captivating views and trailed woodlands stand ready to implant your vision.

Listed by Roger Danyew, Diamond Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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592 Quinn Road Woodstock VT 05091

Woodstock, VT592 Quinn Road

Price$2,975,000

Est. Mortgage: $/month

MLS Number 4932110

  • Residential Single Family
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 4,700
  • Construction Existing

This charmingly restored turn of the century Dutch Colonial 6-bedroom farmhouse is sited on 573 acres backing up to the 22,000 acre Coolidge State Forest. Long Hill Farm has the dramatic big mountain setting. The house expands to fit many guests while still intimate for a quiet weekend away. The wraparound porches take in the breeze and views to the gardens, meadows and mountains. The property and adjoining lands are threaded by miles of wide trails, connecting to the GMHA and VAST networks, providing four season access to a remarkable landscape of big trees, old orchards, and sweeping meadows. A log cabin provides a rustic retreat in the back woods. A classic end-of-the-road setting, Long Hill Farm feels miles from anywhere, yet is five minutes to pizza, ten to the Farmer's Market and 15 to Killington Skyship tram.

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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234 Hidden Ridge Farm Road Pomfret VT 05067

Pomfret, VT234 Hidden Ridge Farm Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4876336

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • 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 6-bedroom, 5-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 Dia Jenks, LandVest,Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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1246 Banister Road West Windsor VT 05037

West Windsor, VT1246 Banister Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4926647

  • Residential Single Family
  • Bathroom 4
  • Construction Existing
  • Bedrooms 3
  • Square Feet 3,690

This bright, beautiful open concept, Ennis Construction built home is privately sited in the midst of pristine rolling fields in the heart of West Windsor with an unparalleled, panoramic view of Mount Ascutney, and down the CT River Valley. The generous Great Room is anchored by a fieldstone fireplace and sweeping cathedral ceiling, and steps out to a stone terrace with a gorgeous grape arbor complete with established perennial beds, and plantings. The kitchen is spacious with plenty of counterspace for working with views from every window. The Primary Suite on the main level features a wonderful soaking tub. The two bedrooms on the second level share a bathroom. The lower level offers the perfect opportunity for a bunk room, and TV/playroom complete with 3/4 bath, and plenty of storage space. The home is attached to a two-car garage by a mudroom with powder room, and laundry room. This is one you really have to see! Proximity to Woodstock, Hanover, Interstate, skiing, trails and recreation.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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7 Laber Road Bridgewater VT 05035

Bridgewater, VT7 Laber Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4916129

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 4,906
  • Construction Existing

Looking for a grand yet refined Vermont home? Look no further than Stonewall Manor! Situated on closed to 30 acres, you'll be pleasantly surprised by the space provided in this home. Arts & Crafts style allows the home to grow as you enter, looking quaint & not massive, from the front elevation. 2 elevator shafts & stair chair offers wheelchair accessibility & can accommodate all needs. 2-car garage comfortably fits 3 cars & features a man cave, complete with a living area, wood stove, bath & laundry room! Stonewall Manor features 5 living rooms, 7 bathrooms, 3 full kitchens (all complete w/ granite counter tops & Bosch appliances), 3 laundry centers, & secret passages between rooms. Additional option to rent out the two private 2-bedroom apartments! Stonewall Manor was designed to fully integrate w/ surrounding land & take advantage of all the property has to offer. Front of home is stunning in the morning light, while the back is beautiful in the afternoon with the way the sun hits & reflects off the house. 4th story cupola features historic 225 yr old bar end from the original Bridgewater Boarding house, & oversees glorious surrounding views of mountains, w/ peaks over 4,000 ft-including trail map view of Killington! Stunning great room features three story windows that allow for sunlight to pour in & heat the whole house during the colder VT winter months. Exceptional property w/ so much to offer-you need to see it to truly believe its feature! Showings begin 6/22/2022.

Listed by Livian Vermont, KW Vermont

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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1350 Vermont Route 12 Pomfret VT 05053

Pomfret, VT1350 Vermont Route 12

Price$1,799,000

Est. Mortgage: $/month

MLS Number 4859544

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

A kingdom sized 265 acres of highly desirable land straddles the hilltops connecting the towns of Pomfret and Barnard! Easily accessed from the pomfret side of the parcel, a privately sited, south facing, elevated building site has been created, to benefit from pastoral views down a valley! Professionally conducted soil percolation tests have identified a location for a septic system. An energy efficient post and beam residence is in place to provide a guest house or a residence to occupy in the near term while construction of a substantial home is undertaken. Truly a 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 ability to access this large parcel from either desirable town. The opportunity presented for an easily accessed elevated building site benefitting from dramatic long range views has become truly difficult to find within the Woodstock area community. The benefit of a useful guest house is a bonus! 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: 6.7% last updated on Sep 29, 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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3482 Hartland-Brownsville Road West Windsor VT 05089

MLS Number 4928183

  • Residential Single Family
  • Village Brownsville
  • Construction Existing
  • Bathroom 3
  • Square Feet 2,738

Escape to a sustainable sanctuary in the idyllic setting of West Windsor, Vermont. Tucked away for ultimate privacy and relaxation, this spacious and serene solar-powered home has been recently updated and features new interior and exterior paint, Bertazzoni kitchen appliances, LED lighting, a new heat pump with two mini-splits, a high-efficiency electric water heater, and more. As a true modern homestead, it has been designed to be off-grid capable while reducing the impact on the environment with a Tesla battery, EV charging station, solar panels, and two wells. The organic, perennial garden delivers an orchestra of colors throughout the season and also features a host of edibles including blueberries, cherries, and strawberries. The 41 acre property, perfect for practicing silvopasture, is enrolled in current use and features pure water sources, walking trails, old-growth trees, a cool swimming pond and a second large beaver habitat, seasonal springs, mushrooms for foraging, and much more. This stylish home is 5 minutes away from Mt. Ascutney, the mountain biking mecca of Vermont, and is connected to the VAST trail system. Historic Woodstock, VT is a short 15-minute drive away, Dartmouth College is 27 minutes, and if you're craving a dose of the city, Boston is 2.5 hours away and NYC can be easily accessed via train at the nearby Windsor station. Come and relax in the nature that surrounds you.

Listed by Wynne Washburn, Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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
  • Bedrooms 3
  • Square Feet 2,016
  • Bathroom 3
  • Construction Existing

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: 6.7% last updated on Sep 29, 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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Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 5, 2022 2:39 AM EDT.