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.

1959 Cox District Road Woodstock VT 05091

Woodstock, VT1959 Cox District Road

Price$9,750,000

Est. Mortgage: $/month

MLS Number 4792976

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 9,515

Woodstock Farm is a modern architectural masterpiece and landmark work by award winning and internationally recognized architect Rick Joy. Based on a conceptual framework that draws from the simplest archetypical forms, this dramatic stone and shingle house and counterposed barn is set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close to ivy league Dartmouth College in Hanover, New Hampshire. Melding effortlessly into the Green Mountains, the property is sensationally experiential in nature and the design is executed with the sharpest attention to craft and detail. Drawing directly from the architectural vernacular of the rural northeast, the tension between the historical and contemporary is conveyed, to paraphrase the architect, through the massive character of the walls, through the qualities of light and dark, through spatial movement and through atmosphere. The four-bedroom main residence offers a 152-foot elongated gable house with massive end walls of quarried Lake Champlain bedrock and cedar cladding on the roof and side walls. Extraordinary, unique and exceptional in every way, Woodstock Farm presents the opportunity for a new owner to acquire an important piece of the history of modern architecture, an incomparable lifestyle, and a work of art.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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2358 Long Hill Road Woodstock VT 05071

Woodstock, VT2358 Long Hill Road

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: 3.5% last updated on Mar 26, 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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3429 Cloudland Road Pomfret VT 05067

Pomfret, VT3429 Cloudland Road

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4779987

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5,134

"SLEEPY HOLLOW FARM" - One of the most iconic properties in Vermont - Sleepy Hollow Farm is located on desirable Cloudland Road, just 10 minutes from Woodstock village. The incredibly picturesque, pastoral land component comprises 115 acres of fields, gardens, woods, trails, and two ponds. The property is conserved both in the Vermont Current Use program and by the Vermont Land Trust. Next to the large second pond is a small cabin complete with bunk beds and a wood stove - perfect when you want to go “off-grid” and camp out on your own property. The original farmhouse c. 1790 - has been updated and expanded and now connects via a radiant-heated brick passageway to a newer, fabulous barn complete with 6 horse stalls, tack room, and a large finished wood-paneled recreation room upstairs. Two other large barns with workshops and garages and for storage- are nearby. The property comes with an array of motorized vehicles and equipment including a tractor, UTV and ATVs w wheels and tracks, two dirt bike motorcycles and a diesel-powered snowcat groomer. The property also includes a separate historic 1-room schoolhouse up on Cloudland Road, that was converted into a 1 bedroom apartment perfect for guests, kids or caretakers, with some of the best views in the area - and looks down over the Sleepy Hollow Farm itself.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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37 Brothers Road Hartland VT 05048

Hartland, VT37 Brothers Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4629754

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,800

Offering some of the most beautifully managed and meticulously maintained acreage available in Windsor County, Hartland Highlands offers over 279 acres of high, rolling meadows, mixed northern hardwoods forests, four ponds, three brooks, miles of interior roads and trails and multiple developable future house sites in addition to the mid-19th century Cape and barn complex currently in place. Views from the property extend from Smarts Mountain in Lyme, NH through dramatic near range vistas of Mount Ascutney to the south. Professionally managed by the premier Upper Valley land enhancement company for more than two decades, the quality of the acreage is unsurpassed. The main house is surrounded by copious perennial gardens, antique stonewalls, grandfather maples and sweeping lawns. Multiple barns and outbuildings provide storage space for every conceivable outdoor pursuit. A true legacy property in a location less than 25 minutes from the heart of the Upper Valley, Hanover and Dartmouth College.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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1055 Sayer Road Barnard VT 05031

Barnard, VT1055 Sayer Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4687009

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 8,264

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance to Woodstock, Vermont and Hanover New Hampshire. Circa 1995 6500 sq.ft. residence with attached three-car garage and spectacular three-story, six stall post and beam barn. An additional 2000 sq.ft. in the walk-out basement finished into a media room and large conference/office area with a wet bar and full bath. 252+/- acres of conserved and managed forest and pastures with miles of maintained riding trails. The residence was five years in the building by a local builder renowned for his quality and attention to detail. Furniture-quality woodwork throughout this four-bedroom, six-bath residence with complete butler/guest apartment wing.

Listed by Stan Butler, Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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1532 Happy Valley Road Woodstock VT 05091

Woodstock, VT1532 Happy Valley Road

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. Architect designed, premier builder, and unquestionably one of the nicest homes in Woodstock. It has a newer cedar shake roof and has been completely re-sided with beautiful cedar shingles in 2019. There is beautiful interior space, newly created guest quarters, four working 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 Sub-Zero refrigerator, and even space for a kitchen herb garden. 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 finished to an exacting level of detail. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. The grounds have a duck pond, ancient stone walls, mature maple trees, a four car garage, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Happy Valley Road is on the exclusive easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat.

Listed by John Bassette, Bassette Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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6310 Bryant Road Hartland VT 05091

Hartland, VT6310 Bryant Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 4693928

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,900

"HUBBARD FARM” - Fully renovated, classic, historic hilltop farm property on +/- 130 acres with long-range mountain views of Killington, a swimming pond, tennis court, open meadows and a 3-mile private trail network - much of which is enrolled in the Vermont Current Use Program. The recently and beautifully fully renovated residence has hip, contemporary styling, a large gourmet kitchen, two den/family rooms, a private dining room, expansive wrap around porch oriented to take in the view, downstairs recreation room, 5 fireplaces, radiant heat throughout, MBR with bath and steam shower, and other fully renovated bedrooms and baths. Russound speaker sound system throughout the 1st floor & porch. Large breezeway leads to the huge historic post-and-beam barn that presently serves as a garage. Located approximately 7 minutes from the village green in Woodstock, Vermont - with end of road privacy - this property has access only from Woodstock, a South Woodstock mailing address and emergency services, but is legally located in the town of Hartland. Truly a special property and residence with all the features most desirable in a Vermont getaway, relocation or retirement home.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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327 Fletcher Schoolhouse Road Woodstock VT 05071

MLS Number 4796716

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,308

Bybrook Farm is a picturesque country estate, built in 1797, and completely restored with historic integrity and deluxe amenities, including custom hand-planed cabinetry and finishes, reclaimed wood floors, hand hewn beams and decorative painting by renowned artist Kevin Paulsen. Sited on 26 acres, with an exquisite brook that meanders throughout the property and leads to a picturesque spring fed pond. A rare combination of brook, pond, rolling hills, forest, mature gardens, and original stone walls, complete with charming farmhouse, classic wooden bridge and quintessential Vermont red barns. The best of serene country living with easy access to downtown Woodstock and nearby equestrian, golfing, tennis, skiing, restaurants, spa and fitness facilities. 5 bedrooms in the main house, and guest house and 2 separate kitchens provide for cozy relaxation or entertaining friends and relatives. Settle in on the stone terraces or open air porches that overlook the rushing brook and pond. Take a nature walk in the forest; ice skate on the pond; snow shoe or cross country ski right out your back door. The corporation which is the legal owner of this property is subject to a federal bankruptcy filing, and any agreements with respect to the purchase and sale of this property will require approval from a Federal bankruptcy court. Excellent location just a short walk to the Kedron Valley Restaurant, South Woodstock Country Store, 2 mins to GMHA and 10 mins to Woodstock Village Green.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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604 Delano Road West Windsor VT 05089

West Windsor, VT604 Delano Road

Price$2,070,000

Est. Mortgage: $/month

Pending

MLS Number 4669762

  • Residential Single Family
  • Construction Existing
  • Bathroom 11
  • Bedrooms 6
  • Square Feet 7,352

Country retreat outside of Woodstock perfectly designed for gathering family and friends, with exceptional craftsmanship, open floor plan, stunning panoramic views of Mt. Ascutney and complete privacy. Designed by AIA award winning architect Michael Ertel, the custom 2-story connected stone Cape Farmhouse, c. 1990, offers 7,352 ± sq. ft. of living space with 6 bedrooms. Throughout the house are mural paintings, trompe d'oeil and faux finishes - tortoise shell mantels in the living room, tiger maple paneling in the library, and intricate wood inlay floors using southern pine, maple, walnut and cherry as well as an impressive great hall with fireplaces at each end, big windows facing the view and high ceilings. The AGA stove and fireplace add a coziness to the well-appointed kitchen detailed with painted wood floors with access to a brick porch. The spa has a shower/steam room, exercise room with hand painted murals on the walls, and hot tub with grand views of the mountains. There are 4 bedrooms in the main house, and 2 bedrooms with an additional sleeping alcove in the guest wing. Approached by a private drive through the extensively landscaped 53.21 acres, the property offers the best in private, country living in the heart of the beautiful equestrian countryside.

Listed by T Story Jenks, LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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974 Cemetery Hill Road West Windsor VT 05089

West Windsor, VT974 Cemetery Hill Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4764706

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 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: 3.5% last updated on Mar 26, 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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591 High Pastures Road Pomfret VT 05091

Pomfret, VT591 High Pastures Road

Price$1,990,000

Est. Mortgage: $/month

MLS Number 4665909

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,880

Otis Hill Farm is iconic Vermont! Woods, fields & streams, working barns & fire pond with 3 stall horse barn, pool & pool-house & tennis court. Miles of trails lace woods & fields for walking, riding, cross-country skiing & snowmobiling. Only 2 miles from Woodstock Village, 20 minutes drive from Dartmouth College & 30 minutes from Killington Ski Area. The 200 year-old farmhouse displays the hand-hewed post & beam frame and is sited with expansive windows to view abundant wildlife and an incredible variety of birds The 230+ acres of land has exceptional character with natural meadows, pastures and fields interspersed in forests of northern hardwoods, spruce, hemlock & pine. Active springs supply year round water to brooks running through the property winding down to the Ottauquechee River. Enrolled in Vermont Current Land Use the farm adheres to a Forestry Management Plan to maintain vital, productive & beautiful forests. A two acre apple orchard is sited on plateau above the farmhouse. Abundant gardens with crab apple & cherry trees, raspberries, red & black currents & flowers to enhance your home all summer long. A tranquil close to all area amenities. OFFERED with different land options and prices.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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296A Town Farm Road Hartland VT 05048

Hartland, VT296A Town Farm Road

Price$1,975,000

Est. Mortgage: $/month

Pending

MLS Number 4764705

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,000

Sky Farm Estate estate consists of 236 acres of well-maintained hay fields, hardwood forests, walking trails, ponds, and a delightful cottage. The property features panoramic mountain views and a wide variety of different vistas that make you feel that you are on top of the world. There is easy passage from Town Farm Hill Road to several private building envelopes with expansive views for your dream home. Convenient access to utilities, high-speed internet, and good water are all close at hand. The estate is enrolled in the State of VT "Current Use" Forestry Plan and supports a wide variety of wildlife. There is a sugar house and over 4,000 tappable sugar maple trees for maple sugar enthusiasts. The .35 acre swimming pond with bathhouse, large open seating deck, rafts, and diving board, awaits your summer recreation activities. The Sky Farm Cottage contains 4 bedrooms and 1.5 baths with open floor concept includes a country kitchen, living room with a wood burning stove and wooden floors throughout. Other features include a stone terrace for outdoor entertaining and a covered front porch that awaits your favorite rocking chair. Sky Farm is just minutes from Woodstock Village for restaurants and shopping. It is near Killington, Suicide Six, and Okemo Mountains for Skiing, GMHA, snowmobiling, hiking, fishing and golf. This breathtakingly beautiful property is an equestrian and sportspersons paradise! Sky Farm is stunning and a rare property with lovely expansive views!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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 March 29, 2020.