Woodstock VT Real Estate

Woodstock, Vermont

Woodstock has a year-round population of approximately 3,500 and is the area’s largest township. It consists of both full-time 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 Williamson Group Sotheby’s International Realty to schedule a tour of your favorite properties or if you have any questions. 

318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$2,496,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4848531

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,048

“AQUENE” - This fabulous and newly renovated modern residence (and very hip guest house) were designed by renowned architect, Michael Weinberger, and are privately situated on 54.83 surveyed and conserved acres - including a pond and lovely pastoral views to distant hills. AQUENE (which means "Peace") is in a superb location in desirable South Woodstock, just a short walk to the South Woodstock Country Store and Kedron Valley Inn Bar/Restaurant, 2 mins to the Green Mountain Horse Association (GMHA) event grounds, 5 mins to the Woodstock Country Club, the Racquet and Fitness Center and 10 mins to the Woodstock Village green. The 6,048 sf main residence and 1,584 sf guest house were substantially renovated by the present owners in 2018/2019 by well-respected builder, Ambrose Construction (and JEM Woodworking for cabinetry) in such a manner as to maintain the architectural integrity of the period while creating a contemporary and infinitely more livable set of spaces for today's modern lifestyle. The guest house - with its own garage - is nearby but completely private from the main residence, with its own driveway access on the way to the main residence. See property video. AQUENE's open meadows and lawns, extensive landscaping, wonderful 4-season heated attached screen porch, hot tub, and rock garden with summer waterfall and Koi pond - make for quiet four-season enjoyment in the very best of what Vermont has to offer, in a premier location.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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945 Riverside Park Road Woodstock VT 05091

Woodstock, VT945 Riverside Park Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4864875

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,900

“THE AERIE” is the ultimate gathering/getaway house located on the Ottauquechee River just 2.1 miles (5 minutes) from the Woodstock Village Green, via Rt 4 West and the historic Lincoln Covered Bridge. The 5900 sf residence is perched on a knoll with beautiful long-range views and features a wonderful “Vermont Barn” architectural aesthetic. The residence is sited on +/- 40 private acres with an extensive network of single-track biking/hiking/snowshoeing trails and owns frontage on the Ottauquechee River. Acreage includes potential building lot with existing roadway and mountain views. Large commercial style kitchen features Viking appliances, granite counters, 2 refrigerators, pantry and custom island. Two spacious great rooms with large-screen TVs, sofas & room to gather, wet bar on 2nd floor. 4 “official” bedrooms with one other room used as a bedroom, and 3 full baths. Sleeps up to 12 guests. Private 32' heated indoor saltwater pool & Sauna). Gracious custom granite patio with dining for 18, 2 BBQs and chiminea for gatherings and a fire in the evening. The residence is being sold with all furniture and furnishings - - turnkey. This house has been very successfully and nearly continuously rented by the present owners on AirBNB. Because it is nearly continuously rented, no drive-ups please and the availability for showings is very limited. Next showing times available are: June 16, 17, 18 (until noon), 25, and June 26 (until noon).

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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23 Cowdrey Path Woodstock VT 05071

MLS Number 4850643

  • Commercial
  • Acreage 1.57

Beautiful Douglas Fir post and beam home and fully operational auto mechanics garage with 4 lifts. Property is selling as a home and fully operational business and is commercially zoned. This is a rare opportunity to live and work all in one place, or have a fantastic space for your hobby on wheels. The house features an open floorplan on the main level. Large windows and two sliders to the deck let light poor into the kitchen and living room. The Master Suite on the main level has two large walk in closets and a full bathroom with a jacuzzi soaking tub. The upstairs loft area would make a lovely office/hobby space or could easily be transformed into a private third bedroom if desired. The lower level is fully finished with a second bedroom, full bathroom, and utility room. There are also several closets for storage! Outside you will find an on demand generator, an above ground pool and a heated shed for storage or a small workspace. The auto mechanics garage has two commercial garage doors that open up to three vehicle lifts inside. A fourth lift is located under the new addition to the right of the building. There are three office rooms in the building as well. All garage equipment/tools will be included in the sale. Email for interior garage photos and more information about the business.

Listed by Shenia Covey of C.G. Shepherd Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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23 Cowdrey Path Woodstock VT 05071

Woodstock, VT23 Cowdrey Path

Price$1,900,000

Est. Mortgage: $/month

MLS Number 4850633

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,584

Douglas Fir post and beam home and fully operational auto mechanics garage with 4 lifts. Property is selling as a home and fully operational business and is commercially zoned. This is a rare opportunity to live and work all in one place, or have space for your hobby on wheels. The house features an open floor plan on the main level. Large windows and two sliders to the deck let light poor into the kitchen and living room. The Master Suite on the main level has two large walk in closets and a full bathroom with a jacuzzi soaking tub. The upstairs loft area would make a lovely office/hobby space or could easily be transformed into a private third bedroom if desired. The lower level is fully finished with a second bedroom, full bathroom, and utility room. There are also several closets for storage! Outside you will find an on demand generator, an above ground pool and a heated shed for storage or a small workspace. The auto mechanics garage has two commercial garage doors that open up to three vehicle lifts inside. A fourth lift is located under the new addition to the right of the building. There are three office rooms in the building as well. All garage equipment/tools will be included in the sale. Email for interior garage photos and more information about the business.

Listed by Shenia Covey of C.G. Shepherd Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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17 Mountain Avenue Woodstock VT 05091

Woodstock, VT17 Mountain Avenue

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4856827

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,123

This circa 1825 story and a half Cape is sited on one of the most lovely and largest parcels of land in Woodstock Village landscaped with shrubs and perennials providing a succession of colorful flowers throughout the summer. The floor plan provides a gracious combination of gathering rooms with privacy afforded for quiet pursuits. A short stroll from the Village Green and Faulkner Park this superbly located home offers views of Mt. Tom and abuts the Marsh-Billings-Rockefeller National Park. A historic gem.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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 Road Woodstock VT 05091

MLS Number 4713229

  • Commercial
  • Village Woodstock
  • Acreage 4.57

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! The parcel is zoned to present multiple opportunities for successful commercial or residential development! Location, Location, Location!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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 Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,490,000

Est. Mortgage: $/month

MLS Number 4713272

  • Land
  • Acreage 4.57
  • Utilities Telephone Available

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! The parcel is zoned to present multiple opportunities for successful commercial or residential development! Location, Location, Location!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4754916

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

One of a kind! Woodstock Village! A professional designer's well conceived compound. The stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. The length of the tranquil landscaped rear grounds, lush with spectacular gardens and leading to accessible Ottauquechee River frontage, is an unexpected surprise! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the main level, a spacious kitchen, with full size informal dining area, opens in 3 directions, to either a fire-placed living room, a dramatic formal dining room or a large 16'x10.5' screened porch. On the second floor are 2 guest bedrooms, full bath, and a primary bedroom, with ensuite bath. On the 3rd level, a large unfinished attic presents endless potential! The detached guest house is perfect! On the ground level is a living room, with vaulted ceiling, a kitchen with a panty, a mud room and a bedroom with 3/4 bath. A second floor loft bedroom is 21' long! Separately, the free standing 36'x24' studio/workshop has potential only limited by your imagination! Truly an ideal property for combining residential use with a home occupation! The front view of the property has the expected classic New England appeal that typifies the residences of Woodstock Village. While the long private rear lawn, with professionally designed gardens, and accessible river frontage is an unexpected surprise!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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39 RIVER Street Woodstock VT 05091

Woodstock, VT39 RIVER Street

Price$1,175,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4814947

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,188

This striking 1903 Colonial Revival home was commissioned by Edward and Marianne Faulkner to house their farm & mill manager and his family. Massively built with timber framing, lathe and plaster on the stone foundation of an 1805 residence it replaced. The winter light flows through the south facing home overlooking the Ottauquechee River. A 1990 addition included a main level family room and master suite on the second with views north and westerly of Mt. Tom and the National Park lands. Spacious fenced back and side yards are landscaped with flowering shrubs and perennial gardens with an outdoor entertainment area featuring charcoal barbecue and Italian wood fired oven. All mechanical systems, plumbing and wiring have been replaced and upgraded, including the installation of two Tesla Power Walls to provide electrical service during extreme weather events. A short walk over the Covered Middle Bridge to all Village amenities and around the corner from Faulkner Park.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$949,000

Est. Mortgage: $/month

MLS Number 4859269

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,488

Exquisitely maintained 4-bedroom, 4.5 bath, 4,500 sqft contemporary Saltbox situated on 5.1 acres of lawn and woods just four minutes to Woodstock village. This includes a large and gracious lower level In-Law/Guest suite with a substantial kitchen and a large bedroom that could double as a home office, rental, or private guest quarters. There is a lovely Great Room with floor to ceiling windows with plenty of light and a substantial center fireplace for easy evening conversation. Additionally, there is a large modern kitchen with cherry cabinetry, lots of counter space, and a useful kitchen office area. The Family/TV room has an attractive Woodstock soapstone stove that comfortably heats the house. Round out the first floor with a practical mudroom, a game room, a formal dining room, and milled cherry flooring throughout. Privately located, the first-floor master bedroom en-suite boasts a Jacuzzi tub, large walk-in closet, and high ceilings with lots of windows that make the room sunny & bright. The second floor offers a second Master Bedroom en-suite, two additional bedrooms with a common bath, and a large storage attic. Outside is a large wrap around deck, a 2 car attached garage, sunny grounds, perennial gardens framing the brick walkways & deck, and a home adjacent to Mt Tom's hiking trails & close to Suicide Six ski area. It is just 2-3 miles to town, and the spacious living area makes this property an ideal family home. Be sure to view the 360 Matterport Virtual Tour!!

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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71 Central Street Woodstock VT 05091

MLS Number 4865687

  • Commercial
  • Village Woodstock
  • Year Built 1990

A highly visible commercial building located in Historic Woodstock Village! Architecturally designed to afford multi-use potential! 3 distinct interior spaces can function and flow together as components of a single commercial enterprise or these spaces can stand apart, as 3 separate units. Unit A comprises 1,435 square feet and is located on the east side of the lower and upper levels of the brick portion of the building. Unit B comprises 712 square feet and is located on the west side of the lower level in the wooden frame portion of the building. Unit C comprises 1,531 square feet and is located on the west side of the upper level of the wooden frame portion of the building. A prime site for a retail store, a restaurant with the added benefit of outside seating options, an office space conveniently within walking distance of all the amenities of Woodstock Village, or a combination of several of these different commercial options. This attractive brick building benefits from street level access directly on the village sidewalk as well as separate second floor access. Currently, an active restaurant is a tenant.

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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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898 Barnard Road Woodstock VT 05091

Woodstock, VT898 Barnard Road

Price$849,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4843539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,608

Prime location in Woodstock. Located a minute to Woodstock Village and Marsh-Billings-Rockefeller National Park. First time offered since 1975. Circa 1771 "Hillside" is a special property on over 31+ acres with beautiful views everywhere you look. The sprawling 5 bedroom/ 4 bath Farmhouse is the perfect place to entertain family and friends. The home has a mudroom/pantry that leads you into a large eat in kitchen. Walk out to the screened porch to sit back and enjoy your morning coffee and soak in the sweet views. The main level of the home has the original hand hewn wood beams and consists of a formal dining room, living room with wood burning fireplace, cozy library with hearth and fireplace, first floor guest room, and full bath with clawfoot tub. Take the main staircase to the second level where you will find a spacious primary bedroom suite, and two more bedrooms one which is being used as an office currently. The third level has a guest bedroom, hangout room and bathroom. The home has a spacious floor plan with the option to turn one area back to an in law suite. As you head outside you will enjoy the very private backyard with stone patio and gazebo. Stroll down to the 3 level barn and let your imagination fly. The barn is 3 barns that were merged together. This could be a great place to have a home business, artist studio or renovate it as extra recreation or sleeping space. Close to Suicide Six. Schedule a tour of this Woodstock property today. It will not last.

Listed by Marni Rieger of KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 2021
* 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 2021 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 June 17, 2021.