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. 

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
  • Bedrooms 3
  • Bathroom 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 of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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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: 3.13% last updated on Apr 8, 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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1239 Peterkin Hill Road Woodstock VT 05071

Woodstock, VT1239 Peterkin Hill Road

Price$2,150,000

Est. Mortgage: $/month

MLS Number 4853756

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,096

Upper Treehouse Farm is located on Peterkin Hill Road midway between the Villages of Woodstock and South Woodstock offering a wonderful sense of seclusion in close proximity to the areas most desirable amenities. Presenting in a vernacular architectural style the handsome residence consists of the original TimberPeg Post & Beam residence with its spacious gathering rooms and 5 private bedrooms on three levels and a thoughtfully integrated addition providing 4 heated garage spaces and a private 1 bedroom guest quarters with full kitchen. The handsome multi-purpose barn and all-season bunkhouse is a favorite with kids (and kids at heart). Stone patios and terraces surrounding the home are graced with perennials, flowering shrubs and a cozy fire-pit. A wide entertaining deck overlooks the swimming pond with white sand beach and rolling fields and pastures. Close to the Green Mt. Horse Association and miles of riding trails. A tranquil retreat from a busy world and ideal for celebrating both special events and everyday life with friends and family.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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

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: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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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326 Hall Circle Woodstock VT 05091

Woodstock, VT326 Hall Circle

Price$929,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4837802

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,949

This super timber framed home is privately sited to take advantage of sweep southerly views over hayfields and forest land protected by a development restriction as gift by Laurence & Mary Rockefeller to the National Park. Expansive open spaces provide a casual living environment on three floors. Gathering areas on the primary living level include an eat-in kitchen with gas cook-top & grill, new double ovens & new refrigerator. The inviting, sunny kitchen opens to a dining area warmed by a Vermont Castings wood stove. The great room is configured with a media area & a living room centered on the wood-burning fireplace. The third floor offers a private master bedroom with designer bathroom ensuite & a separate study/bedroom. The walk-out lower level has views over a stone patio & lawn to distant hills and valleys. Another handsome enamel coated Vermont Castings wood-stove warms the family room area on this level with two bedrooms & a spa bathroom that with Finnish dry sauna and a steam shower. A modern synthetic deck spans the length of the primary living level with another deck off the master bedroom. A woodland trail winds uphill through the property to a point just west of the ridgeline boundary of the Suicide Six Ski Area. Priced fully furnished & equipped with quality appointments for ease of occupancy during these challenging times.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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

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: 3.13% last updated on Apr 8, 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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5 Linden Hill Woodstock VT 05091

Woodstock, VT5 Linden Hill

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4852550

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 9
  • Bathroom 7

Well located, in a favorite neighborhood of Woodstock Village, is offered an antique 1850's home that is tastefully converted into 4 high quality residential units! The central largest residence (9 rooms, 4 bedrooms, 3 1/2 baths) occupies 3 levels of the original house. This residence benefits from graceful rooms with generous proportions. Fine interior finishes and high quality detailing include hardwood flooring, custom built cabinetry, central air conditioning and luxury fixtures. On the ground level is a living room with wood burning fireplace and built in book shelving, an entry foyer, a dining room with chandelier and a kitchen with attached laundry. On the second level is a sitting room that is flanked on either side by bedrooms with ensuite baths. A third level presents 2 additional bedrooms and a full bath. Apartments on either side of the main residence (one apartment has 7 rooms, 2 bedrooms, 1 bathroom; the other apartment has 3 rooms, 1 bedroom, 1 bathroom) have interconnected passage with the main residence to allow substantial quarters of three discrete spaces for family or friends, or the passages may be closed off for independent use. A fourth apartment (4 rooms, 2 bedrooms, 1 bathroom) has a separate entry off terraced private lawns in the rear. Each of the 4 apartments has a private entry, a complete kitchen, and each has a wood burning fireplace. A flexible floor plan presenting the opportunity for several generations to comfortably coexist with privacy!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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 April 11, 2021.