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.

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.

2358 Long Hill Road Woodstock VT 05071

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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5000 Route 106 Reading VT 05062

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4738758

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 7,982

The right dose of Vermont living: high meadows, mountain views, in the heart of horse country near Woodstock, end of the road, and complete privacy. Warner Hill Farm's beginnings as a late 1700's sheep farm have been transformed into a comfortable, but distinguished property that has been on the cover of House Beautiful and featured in Architectural Digest. Today, this well-stewarded property, with its own helipad, is sited on 120 acres and is one of the most exceptional properties in Vermont taking inspiration from Old World elements including a gracious courtyard, Dutch gables, and formal gardens. A gated one-mile drive wends up through the trees to open on to a verdant landscape of rolling meadows and ponds. To the west there are expansive views of the mountains and lavish sunsets. The home has a gourmet kitchen, five bedrooms, 6.5 bathrooms and spacious living spaces. Connected by a breezeway is a guest room ensuite. Behind the house is a stone patio next to a deep, clear pond fed by a cascading waterfall. A gym, office and home theater can be found across the courtyard. A 4-stall horse barn, is attached to a party barn with a massive stone fire place and cathedral ceilings. Down an allée of maple trees is the pool. Also, on premise is a caretaker's house/guest house with 3 bedrooms and stunning views. There is an extensive network of trails for walking, cross-country skiing or riding, and connects to GMHA trails. Close to Killington and Okemo for skiing.

Listed by T Story Jenks and Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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1001 Atwood Lane Woodstock VT 05091

Price$3,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4762434

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,701

“The Hill” is a modest name for an exceptionally private 82+/- acre hill top meadow at a 1,780' foot elevation with breathtaking 270-degree views of the Green and White Mountain ranges. Located within 4.8 miles of Woodstock village, this is a property designed to enjoy country living and the outdoors. The c2002 custom cedar shingle 3-bedroom residence (2,688 square feet) was designed by AIA award winning Truexcullins, a firm known for high craftsmanship and sustainable, enduring architecture. Created to integrate with the natural surroundings, the spacious living areas take advantage of the stunning unobstructed views with large windows and high ceilings, and is finished with cedar plank walls and trim, antique pine floors, soapstone counters, fir trusses, exposed beams, and a 2-story fieldstone fireplace. Tucked away with its own views, privacy and rustic comfort is a 2-bedroom classic cabin (1,013 square feet) with a floor-to-ceiling stone fireplace. The grounds are a balance of meadows and woodlands laced with reconstructed stonewalls. There is a 1.5-mile maintained trail for walking and skiing, a 1/3-acre swimming pond with a fishing shack, a “Hobbit House” built into the side of a hill, and a lean-to with a fire pit sited on a prominent overlook. Adjacent is 300-acre town-owned land with reservoir, extensive trail network, and a 186-acre conserved property. The Hill overlooks Mt. Tom and the protected Marsh Billings Rockefeller National Park.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

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, guest house 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 and one bedroom guest house are 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

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. Currently it is being completely re-sided with beautiful cedar shingles (photo #4). Architect designed and unquestionably one of the nicest homes in Woodstock. There is beautiful interior space, newly created guest quarters, four working stone 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 commercial refrigerator, and even space for a kitchen herb garden. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. 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 are finished to an exacting level of detail. The grounds have a duck pond, ancient stone walls, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Enjoy distant valley views from the stone patio and Happy Valley Road is on the easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, skiing, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat from the busyness of life.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

Price$2,850,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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3147 Mt. Hunger Road Barnard VT 05031

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4755552

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 4,531

"HONEY HILL FARM” - located in desirable Barnard, Vermont, has been in the same family for more than 30 years, with both land and residence meticulously and lovingly maintained throughout the family's stewardship of the property. Situated on 264.4 surveyed acres, the land component is comprised of open pastures and conserved and managed woodlands with miles of trails for walking, x-c skiing and snowshoeing, biking or other outdoor pleasures. The property has beautiful long-range mountain views, a deep swimming pond, perennial gardens, and a lovely mountain brook that courses through the property, plus a wonderful and totally private swimming pool in the center rear of the residence with access from the living room and the kitchen. A nearby barn - a portion of which was once utilized as a caretakers apartment - provides storage for motorized toys and vehicles. The residence itself is a classic Vermont farmhouse design with slate roofs, three fireplaces, covered porches and an attached guest apartment above the attached three-car garage. The living room, which has exceptional woodwork, can easily accommodate large parties for entertaining. Five bedrooms, four baths, and three half-baths in total. House boasts excellent mechanicals, backup generator, security systems, underground wires, and more. High speed internet is available via EC Fiber. 18 mins to Woodstock, 10 mins to I-89, and 30-45 minutes to a private airport and skiing at numerous major Vermont ski resorts.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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5000 Route 106 Route Reading VT 05062

Price$2,795,000

Est. Mortgage: $/month

MLS Number 4739067

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 7,982

The right dose of Vermont living: high meadows, mountain views, in the heart of horse country near Woodstock, end of the road, and complete privacy. Warner Hill Farm's beginnings as a late 1700's sheep farm have been transformed into a comfortable, but distinguished property that has been on the cover of House Beautiful and featured in Architectural Digest. Today, this well-stewarded property, with its own helipad, is sited on 50 acres and is one of the most exceptional properties in Vermont taking inspiration from Old World elements including a gracious courtyard, Dutch gables, and formal gardens. A gated one-mile drive wends up through the trees to open on to a verdant landscape of rolling meadows and ponds. To the west there are expansive views of the mountains and lavish sunsets. The home has a gourmet kitchen, five bedrooms, 6.5 bathrooms and spacious living spaces. Connected by a breezeway is a guest room ensuite. Behind the house is a stone patio next to a deep, clear pond fed by a cascading waterfall. A gym, office and home theater can be found across the courtyard. A 4-stall horse barn, is attached to a party barn with a massive stone fire place and cathedral ceilings. Close to Killington and Okemo for skiing.

Listed by T Story Jenks and Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

Price$2,750,000

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. Near Woodstock, 20 minutes from Hanover, NH, 30 minutes from Killington, & 2 hours from Boston, the property is ideal for raising kids in a country setting, weekend get-a-ways & retreats in a private setting with incredible views. Relax in the 200 year-old farmhouse with ”hand-hewn beams overhead & watch the native wildlife Deer, wild turkeys, fox, hawks, owls & an incredible variety of birds. Enjoy a view with no other houses in sight & you will understand why the prior owners felt they were always on vacation; the farm was their ideal vacation place. The land consists of 230 diverse acres of northern hardwoods, spruce, hemlock & pine, open fields, active springs & long frontage on 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. Close to everything & still a tranquil refuge in a frantic world. Walk up the hill & view the river valley & you'll know this timeless land is a perfect place to grow lives & memories.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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2574 Garvin Hill Road Woodstock VT 05091

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4765394

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 6,545

"GARVIN HILL GETAWAY"- Newer custom built residence (that easily sleeps 15+) on 50 acres of farm pasture fields and woods with a fabulous long-range mountain view - just minutes from Woodstock village. Designed for family gatherings and entertaining friends, the residence also lives beautifully on one level. Wonderful open floor plan with high ceilings and large-proportioned rooms. The 1,200 sf great room / gathering area combines kitchen, dining and living room areas with stone fireplace that opens to an expansive wrap-around deck with its own indoor-outdoor entertaining space - with indoor and outdoor spaces all sharing the long-range mountain view over the pasture fields. A spacious first level master bedroom suite provides for 1-level living. Excellent mechanicals. An oversized 3-car garage - for all your motorized toys bikes, skis, kayaks and other outdoor gear - walks into a mud-laundry room and into the house. Minimal gardens and landscaping make for a low-maintenance, super-fun gathering house on 50 acres with big views, just minutes and easy access on public roads from Woodstock village.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 4644250

  • 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 .Gorgeous and varied regional views. 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. A moments stroll to historic hamlet of South Woodstock and nationally acclaimed Green Mt. Horse Association equestrian center . 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 ; swim , fish or relax by the serene pond; take a nature walk in the forest ; ice skate on the pond ; snow shoe or cross country ski right out your back door. Enjoy the best of spring wildflowers , summer sunshine , fall foliage and winter wonderland in this unique property. Fun for two or twenty , with separate spaces for all to enjoy !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 2019 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 August 21, 2019.