Woodstock VT Real Estate

Woodstock has a year-round population of approximately 3,500 and is the area’s largest township. It consists of both fulltime working residents and their families, as well as retired, recreational and seasonal residents. A short weekend commute of 2 to 2 1/2 hours from Boston, where the majority of the second homeowners reside, the area also draws a significant number of visitors from other New England communities and New York City. Woodstock boasts a wide range of cultural activities sponsored by the local arts council, Pentangle.

The Woodstock Union High School and Middle School provide secondary education for the children from Woodstock and the surrounding towns of Barnard, Pomfret, Reading, Killington, Plymouth, and Bridgewater.

Parents who live in Hartland and West Windsor can also choose to send their children to Woodstock’s middle and high schools. Known for providing a first class college preparatory curriculum, Woodstock was recently honored at the Kennedy Center for Performing Arts for having the most outstanding arts, music, and theater department for any school of its size in the country.

Browse Woodstock VT Real Estate for Sale

Scroll down to browse real estate for sale in Woodstock, Vermont. Create an account to save your favorite Woodstock property listings and to receive email notifications when similar listings become available. Contact us to schedule a tour of your favorite properties or if you have any questions. 

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 of 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 of 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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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 of Bassette 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 of 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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28-32 The Green Street Woodstock VT 05091

Woodstock, VT28-32 The Green Street

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4798172

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 10
  • Bedrooms 9

3 attached residences, on picturesque Woodstock Village Green! 2 elegantly proportioned brick townhouses, with an attached circa 1830 traditional clapboard home! The gracious interiors, of the brick townhouses, feature attractive antique detailing, high ceilings, multiple fireplaces. The western townhouse, 30 The Green, is fully renovated by quality craftsmen. Ground level is an open floor plan featuring stylish kitchen, dining area, living room with fireplace, and a half bath. A 2nd floor is dedicated to a large primary bedroom, with ensuite bath and walk-in closet! A 3rd floor has 2 comfortable guest bedrooms and full bath. The eastern townhouse, 28 The Green, presents antique detailing, exposed beams, wood flooring, 9 foot ceilings, 3 fireplaces and opportunity to renovate a traditional 3 level home, to suit one's taste. The traditional clapboard #32 The Green has a tastefully renovated contemporary interior with 3 bedrooms, 3 baths, and a finished lower level. Off street parking and a detached 2 car garage are useful amenities. These Woodstock Village landmark properties present a unique opportunity! The 3 bedroom residence at #30 is turn key and luxuriously appointed, for immediate residency. The antique residence at #28 is a very rare opportunity to renovate a traditional Woodstock Village Green residence to indulge new owner's preferences. The clapboard home at #32 is stylishly contemporary and comfortable! All 3 present level walking to Woodstock Village amenities!

Listed by John Wetmore of William Raveis Woodstock

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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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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 C. Bradley of Williamson Group Sothebys Intl. 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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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 of 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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SAWYER Woodstock VT 05091

Woodstock, VTSAWYER Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4467517

  • Land
  • Acreage 282.81
  • Zoning RESIDENTIAL

An incomparable 282.81 acres of conserved woodstock land! The quality acreage to compliment the construction of an unparallel residential compound. This desirable location is within one half mile of historic woodstock village. The property benefits from long range views and managed woodlands.

Listed by John Wetmore of William Raveis 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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28-30 The Green Street Woodstock VT 05091

Woodstock, VT28-30 The Green Street

Price$1,450,000

Est. Mortgage: $/month

MLS Number 4796400

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6

Prominently situated, on the picturesque Woodstock Village Green! This elegantly proportioned brick townhouse is comprised of 2 distinct residences! Complimenting the stately brick exterior are gracious interiors, with attractive antique detailing, high ceilings and multiple fireplaces. Located in the western portion of the townhouse, #30 The Green has been totally renovated by quality local craftsmen. The ground level has an open floor plan featuring a stylish kitchen, a dining area, a living room with wood burning fireplace, and a half bath. The 2nd floor is entirely dedicated to a large primary bedroom, with ensuite bath and walk-in closet! On the 3rd floor are 2 comfortable guest bedrooms and a full bath. Located in the eastern portion of the townhouse, #28 The Green presents antique detailing, exposed beams, wood flooring, 9 foot high ceilings, 3 fireplaces and the opportunity to renovate a traditional 3 level home, to suit one's taste. Off street parking, with a detached 2 car garage, is a useful amenity of the townhouse. This Woodstock Village landmark property presents a unique opportunity! The 3 bedroom residence located at #30 is turn key and luxuriously comfortable, for immediate residency. The antique residence at #28 is a very rare opportunity to renovate a traditional Woodstock Village Green residence to indulge a new owner's preferences. The location is excellent! Level surface walking to all of the numerous amenities of Woodstock Village awaits the new owner!

Listed by John Wetmore of William Raveis 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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4 The Green Woodstock VT 05091

Woodstock, VT4 The Green

Price$1,345,000

Est. Mortgage: $/month

Pending

MLS Number 4702840

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 10
  • Square Feet 6,800

This elegant 1827 stone federal-style former residence is located on a quiet corner of the Woodstock Green and is one of village's historic properties. A complete renovation of the 6,800 square feet in 2010 brought back the impressive period finishes, and provided space for 5-6 office suites (3 kitchenettes) and a 4-bedroom 3rd floor apartment. The zoning, overall floor plan, large rooms, and high ceilings open the possibility for a single or multi-family property. Ten private parking spaces are located at the back of the building accessed from Mechanics Street. The building is zoned Central Commercial and has town water & sewer. 100% occupancy.

Listed by T Story Jenks of 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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4 The Green Woodstock VT 05091
Pending

MLS Number 4700265

  • Commercial
  • Year Built 1827
  • Acreage 0.29
  • Area Business District

This elegant 1827 stone federal-style former residence is located on a quiet corner of the Woodstock Green and is one of village's historic properties. A complete renovation of the 6,800 square feet in 2010 brought back the impressive period finishes, and provided space for 5-6 office suites (3 kitchenettes) and a 4-bedroom 3rd floor apartment. The zoning, overall floor plan, large rooms, and high ceilings open the possibility for a single or multi-family property. Ten private parking spaces are located at the back of the building accessed from Mechanics Street. The building is zoned Central Commercial and has town water & sewer. 100% occupancy.

Listed by T Story Jenks of 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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458 Woodstock Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,290,000

Est. Mortgage: $/month

MLS Number 4713272

  • Land
  • Acreage 4.57

It has been said that the highest and best use of this property would be a combination of constructing residential units, in the private rear acreage, and commercial development, of the highly visible road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. A portion of the property was affected by a breached fuel storage tank. All clean-up work has been completed, with no residual evidence of petroleum distillates. The site has the Brownsfield Redevelopment Program approval. Full documentation is readily available. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! Location, Location, Location!

Listed by John Wetmore of William Raveis 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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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.