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$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

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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

$
$
%
$/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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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: 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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: 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

97 & 99 Darling Road Woodstock VT 05071

Woodstock, VT97 & 99 Darling Road

Price$1,575,000

Est. Mortgage: $/month

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: 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

343 Spruce Way Woodstock VT 05091

Woodstock, VT343 Spruce Way

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4710997

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,216

This is one that you absolutely have to see! Pictures simply cannot capture the warmth, functionality and tranquility of this very special property. Located on a private dead-end road in the Cox District region of Woodstock just 8 minutes from the Village Green. The pristine long-range views can be appreciated from every room. Every inch of this lovely post and beam cape has been tastefully renovated to the highest standard with new chef's kitchen, bathrooms, systems, solar and generator. Each of the four bedrooms has it's own private bathroom. Lovely screened porch and deck overlooking stone walls, perennial beds and the view beyond. Brand new barn with separate farm road entrance, open pasture and a magnificent interior trail system. Walk out lower level with family room, office and guest accommodation. Spacious, private heated room above the attached three car garage for studio, recreation room or for home occupation. Excellent equine potential.

Listed by Danny Kogut, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

457 Peterkin Hill Road Woodstock VT 05071

Woodstock, VT457 Peterkin Hill Road

Price$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4774508

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,360

Stunning long range mountain views on nearly 40 acres of mostly open level field/pasture and woods with a stream on a very desirable road with substantial neighboring properties in Woodstock just 11 mins to the Woodstock Green. An authentic three bedroom log cabin with open kitchen-dining-living area and covered porch all look out at the really amazing long-range mountain view. A sun porch, three bedrooms and two baths with a full concrete basement complete the log cabin itself. Nearby is a post-and-beam barn-office space, insulated and heated with overhead door, plus a separate large garden shed for storage of all kinds of outdoor toys, equipment, gardening supplies. The mostly level / gently sloping fields create a big playground, an area for gardens or animals, and/or a second building site with easy access further back on the property, which would also share the stunning long-range mountain view. Very rare opportunity to buy this kind of land and view with a charming and very livable log cabin, with lots of potential for renovations or new construction in a great location in Woodstock at an attractive entry price point.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

6656 South Road Woodstock VT 05071

Woodstock, VT6656 South Road

Price$650,000

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 on the southerly side of South Woodstock across from the Green Mt. Horse Association, with direct access to miles of horse riding trails. 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 is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, lovely gardens and playground.The homestead includes a guest apartment periodically rented, and additional 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.

Listed by Danny Kogut, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1522 Curtis Hollow Road Woodstock VT 05091

MLS Number 4743887

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,816

Well maintained custom Colonial being sold for the first time. Situated on a peaceful country road with access to abundant land and forest. Spacious and pleasing floor plan, open kitchen appointed with granite tops, custom cabinetry and slate flooring. The living room has 18-foot ceilings creating a view from the upper loft. The ground floor master bedroom suite is accented with a large full bath with both step in shower and a jetted tub and plenty of closet space. Three bedrooms and two more bathrooms are upstairs and a bonus room for guests, crafts or recreation. The large basement could also be partitioned if needed. For extra storage or recreation/farming there is a 28x38 pole barn. The land has a gradual slope which could be cleared for agricultural use. This property is currently subject to and benefits from a current use plan. Come enjoy the covered porch, hear the stream while relaxing and absorbing the local views.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1880 Curtis Hollow Road Woodstock VT 05091

MLS Number 4783272

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,604

Rustic Vermont hunting lodge with spectacular mountain views on 66.5 acres. This corner lot (Mecawee & Curtis Hollow) boasts a 4 bedroom home that has been a 2nd home getaway and recreational playground for the same family since the 1950's. Inside, the large kitchen with counter seating opens into the dining area which flows directly into the long living room that is accented with a huge stone fireplace at the end of the room. Off the kitchen is the master bedroom with ensuite bath and through the living room are 3 bed and bunk rooms and another full bath. There is an enclosed porch which leads out to a wooden deck that overlooks the rolling fields and takes in the amazing views to the Northeast. Roughly two thirds of the property is wooded with the VAST snowmobile trail cutting through it. There are multiple streams that run through and along the property as well as old stone walls. Across from the driveway is the entrance to the Coolidge State Forest and a few miles up Mecawee Rd. is the Mecawee Fishing Club. It is only 10 minutes to Woodstock Village and just 25 minutes to the Killington Mtn. base lodge. This is a unique property with endless possibilities that can be subdivided. A must see!

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

700 John Darling Road Woodstock VT 05071

Woodstock, VT700 John Darling Road

Price$450,000

Est. Mortgage: $/month

MLS Number 4764458

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,196

Tucked away at the end of a one mile Class IV road on 10 very private acres bordered by the Woodstock Town Forest in very desirable South Woodstock. No traffic noise, only the sounds of the birds and the stream that meanders through the woods behind the house. The house is powered by state-of-the-art solar so power failures are never an issue and you never get an electric bill. The open format layout of the first floor creates bright unobstructed living space perfect for everyday living and warm friendly space for entertaining. All the details on most buyers' check lists are here: attached garage, large mudroom, huge pantry, three baths, three bedrooms, master bedroom with updated en suite bath and the world's largest walk-in closet and full walkout basement. Recent upgrades include: updated kitchen and pantry, new high efficiency propane boiler, totally updated solar system, new Kohler generator, new deck and new Jotul woodstove. The location of the property is perfect with the South Woodstock General Store, the Kedron Valley Inn & Pub and GMHA all just minutes away plus convenient to skiing, golf, snowmobiling, health club, and all the amenities of Woodstock Village.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Broker Reciprocity

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.