Woodstock Homes with Acreage

Home with Land in Woodstock VTWoodstock, Vermont is often cited as one of the prettiest towns in America. Owning a home on a large-acre lot is your chance to own a part of this quintessential Vermont town.

Woodstock real estate provides residents with the opportunity to stroll the pedestrian downtown, visit galleries, and partake in a variety of outdoor activities like biking, hiking, skiing, fishing, and golfing. After an active day, dine at one of the town's many renown restaurants. You can catch first-run movies at Pentangle Arts, a concert at nearby Dartmouth College’s Hopkins Center for the Arts, or a play at White River Junction’s Northern Stage.

With a home on a large-acreage parcel, you can keep horses and other livestock, build a garden to your specifications, have pasture or woods. Much of the real estate sited on 10+ acres in Woodstock also has excellent long-range views of the surrounding mountains.  

Woodstock VT Homes with Land for Sale

Find your perfect Woodstock, VT home with a lot of acreage below or contact Bassette Real Estate. One of our experienced brokers or buyer agents will be happy to help you.

View all Homes for Sale in Woodstock

1959 Cox District Road Woodstock VT 05091

Woodstock, VT1959 Cox District Road

Price$10,500,000

Est. Mortgage: $/month

MLS Number 4820913

  • 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, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4809703

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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2574 Garvin Hill Road Woodstock VT 05091

Woodstock, VT2574 Garvin Hill Road

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4804667

  • 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. Subject to current use conservation program. 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: 2.88% last updated on Aug 6, 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$2,600,000

Est. Mortgage: $/month

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This secure Vermont retreat sits high on a hill on 55 protected acres. Architect designed, a premier builder, and built on the history and character of two fully reconstructed antique post & beam frames. Unquestionably one of the nicest homes in Woodstock. Five (5) bedrooms, four (4) bathrooms, & over 6,000 sq-ft of living space finished to an exacting level of detail. There is beautiful interior space, private guest quarters, four working fireplaces, & high-end master bathroom finishes. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas range, and a large Sub-Zero refrigerator. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors are quintessential Vermont architecture. The grounds have a duck pond, old stone walls, mature maple trees, a four-car garage, & an impressive 4-stall timber frame horse barn. A newer cedar shake roof & re-sided cedar shingle in 2019 complement all the modern conveniences of the 21st century - high speed internet, whole house generator, underground power. Most of the neighbor's holdings include protected land in VT Current Use. Happy Valley Road is on the exclusive easterly side of town with quick access to, and away from, the major metro hubs of Boston & New York City. Did we mention the two snowmobiles & 6-wheeled Polaris Ranger included in the sale? Enjoy snowmobile trails, wandering the estate, biking & sledding on your secure Vermont domain! Check out the house video!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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2352 Curtis Hollow Road Woodstock VT 05091

Woodstock, VT2352 Curtis Hollow Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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

Pending

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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2525 Barnard Road Woodstock VT 05091

Woodstock, VT2525 Barnard Road

Price$850,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4807367

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,552

Classic Civil War era farmhouse thoughtfully and comprehensively renovated with modern mechanical systems, including installation of radiant heat in the main living level. The home enjoys wonderful natural light in all seasons. A flexible use floor plan consists of an eat-in Country Kitchen. spacious family room with field-stone fireplace, a study that is used periodically as a bedroom and a double living room with pellet stove. A winding stairway ascends to the second with 3 bedrooms sharing an enormous bathroom with laundry. The third floor attic has been repurposed as a master bedroom sanctuary. On summer nights the northerly windows can open to allow the sounds of water cascading in the boundary brook and lull you to sleep. Located north of Woodstock Village, the property is within walking distance of the Marsh-Billings-Rockefeller National Park, VAST corridor and a network of trails at the end of Grassy Lane that wander through hundreds of acres of unspoiled rural land. Horse barn, pond and two active brooks. Paddocks and open pasture invite agricultural activities. Barn mounted solar array is net metered to reduce or eliminate electrical expenses.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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509 Darling Road Woodstock VT 05071

Woodstock, VT509 Darling Road

Price$795,000

Est. Mortgage: $/month

Pending

MLS Number 4811921

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,008

A very rare opportunity to own 60 acres of land with total privacy and majestic long range views that include Mt. Ascutney all the way to Mt. Sunapee. The land is bordered by protected land so there will be no development that will be seen from the house sites . 40 Acres are in the Current Use Program with a 2 acre house site exemption. There is a large spring fed pond accessed by a path through the woods. Darling Road is a dead end road so one is assured of a very quiet , peaceful setting . The cabin is very cozy with a large screened porch and deck. Access to Woodstock and South Woodstock are less than 15 minutes away and Skiing at Okemo and Killington are 40 minutes away. All types of sports for every season are readily available . This is truly a SPECIAL property !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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965 Deer Brook Way Woodstock VT 05091

Woodstock, VT965 Deer Brook Way

Price$665,000

Est. Mortgage: $/month

MLS Number 4807039

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,192

House in the Sun is a perfect gem sited beautifully on 11.5 acres with spectacular long range views, a pristine pond, and forest area with trails and a stream. The cape style house is a tasteful architectural blend of classic Vermont charm and contemporary design. The open concept kitchen/living/dining area that opens to a deck is warm and inviting for gathering and entertaining while taking in the panoramic view. The main level also offers an office/den as well as a bedroom with full bath. The master bedroom suite on the second level is detailed with vaulted ceilings, exposed beams and lovely large windows that capture that view! There are two additional bedrooms and bath on the second level for family and guests. Enjoy all the seasons in Vermont swimming in the pond, exploring the stream, and hiking/snowshoeing the open field and forest paths. Private but conveniently located within minutes to dining, theatre and shopping in Woodstock Village and 15 minutes to Killington Mountain Resort.

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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6656 South Road Woodstock VT 05071

Woodstock, VT6656 South Road

Price$599,000

Est. Mortgage: $/month

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located in Historic South Woodstock adjacent to the Green Mt. Horse Association, with direct access to miles of horse riding trails. Enjoy the warmth and charm of living in a classic antique VT farmhouse with the option to work from home with fiber optic, symmetrical speed internet up to 800 Mbps. There's a one bedroom In-law apartment to provide overflow accommodation, and additional income. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen The family room/ library opens onto a broad stone terrace, lovely, established gardens and playground. Potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system. Two and a half hours from Boston and five hours from NYC makes this property convenient for a full-time residence or a second home. Short drive to the rich cultural assets of Dartmouth College and easy access to Dartmouth Hitchcock Medical Center.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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 August 7, 2020.