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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. 

4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$5,200,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5

4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America's most beautiful villages.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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: 2.88% last updated on Sep 9, 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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Biscuit Hill Woodstock VT 05091

Woodstock, VTBiscuit Hill

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4868865

  • Land
  • Acreage 453.82
  • Utilities None
  • Zoning residential

Biscuit and Ralph's Hills comprise a coveted 453+/- acres located adjacent to thousands of acres of conserved land on the wild western side of Woodstock, Vermont. The gently sloping topography has several outstanding building sites with views of the Woodstock hills. Years of thoughtful forest management have resulted in a healthy forest as well as a network of woods roads, including a well-constructed driveway off Fletcher Hill accessing a large, level open site with great light and elevation. The property also has access via Class 4 roads: Bourdon Rd, Arthur Morgan Rd, and Quinn Rd. Ralph's Hill adjoins Biscuit Hill with an elevation of 1,640'. Most of the property and surrounding lands were cleared for sheep in the early 1800s. While the former pastures have grown in with mature mixed woodland, vestiges remain: stonewalls and ancient roads crisscross the land and old cellar holes punctuate the landscape. Along with a carefully stewarded forest, there are multiple streams and an abundance of wildlife. As stewards of the land, the landowners' goal has been to maintain a healthy forest and to promote wildlife habitat. The northern part of the property near the top of Biscuit Hill is dominated by high quality sugar maples. There are both private trails throughout the property as well as a section of the VAST trail network. The property is bordered by the Vermont Land Trust and other large property owners.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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: 2.88% last updated on Sep 9, 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: 2.88% last updated on Sep 9, 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: 2.88% last updated on Sep 9, 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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121 Frenchs Road Woodstock VT 05091

Woodstock, VT121 Frenchs Road

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4873332

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,072

Just a short stroll from village center, located on a quiet dead end road, this tranquil oasis is sure to check all your boxes. The home features spacious, bright rooms with a seamless flow for daily living and entertaining. The open concept kitchen is well appointed with a center island, ample work space, and a generous pantry (complete with laundry), connecting to a dining room which can accommodate a crowd. Enjoy far southerly views from the spacious living room with step out balcony overlooking the gardens and grounds, and an open hearth ready for your woodstove. The main level is further completed by an en-suite guest bedroom, 2nd bedroom, and bath . The second level is comprised of a library/study with custom cherry built-ins, a Grand Master Suite, two additional bedrooms, a full bath and laundry. The lower level features a family room with fireplace, a spa room with bathroom, a mud room entry with herringbone brick floors. Entertain on the private outside deck surrounded by gardens and mature plantings. The home is sited on 12 magical acres of wooded and open land with shady trails lacing through, connecting open and fenced pasture and paddocks, and a secluded swimming pond. Equestrians will fall in love with the beautifully conceived barn (complete with heated tack room, bathroom, 5 stalls, wash stall, hydrant and storage), Indoor Riding Arena, outdoor dressage arena, and access to the National Park trail system. Showings to begin 7/24/2021

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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: 2.88% last updated on Sep 9, 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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51 Watkins Way Woodstock VT 05091
Pending

MLS Number 4869108

  • Condo
  • New Contruction New Construction
  • Village Woodstock
  • Year Built 2021
  • Square Feet 3,073

51 Watkins Barn Home Unit 1 is a 2280 square foot New Construction Vermont Vernacular Elevator Barn duplex located on a private road, Watkins Way, providing the best views of Woodstock Village rooftops, Billings Farm and Pomfret mountains. Efficiency Vermont guided design for energy efficiency, estimated STR rating of 55 to 56 which is luxury level. Great opportunity to pick your wood floors, paint colors, all with a high walkability scale rating in the village. This property is unique and cannot be replaced, high walkability, close to the restaurants, quiet private road, best views and the best access to trail system. Quite close to Mt. Peg Park access for hiking trails, and only slightly further to the amazing trail system of Mt. Tom/Marsh Billings Rockefeller Historical Park, additional recreational opportunities abound with Woodstock Country Club for golf, mountain biking, cross country skiing; Woodstock Health and Fitness Center for swimming, exercise facilities, Killington, Okemo, and historical Suicide ski and Mountain bike park, are all within an easy drive away. Seller/Owner/builder is a Licensed Sales Agent in VT. The property will be provided with a 1-year warranty. All available product warranties will be extended to new owner.

Listed by John King of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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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540 West Woodstock Road Woodstock VT 05091

MLS Number 4872658

  • Commercial
  • Year Built 1900
  • Acreage 0.8

Highly visible Woodstock commercial property! The 2 well constructed buildings located on a sunny .8 acre parcel present multiple income options! A classic New England style building is prominently sited at the front of the property, on well traveled Route 4. With excellent signage and an easily recognized profile, this 2 story, 2800 sq. ft. building houses a 7 room office complex and also 2 privately entered 1 bedroom apartments! The quality of the 2 level office complex will satisfy any professional! On the 1st floor is a 15x11 private conference room featuring wood burning fireplace and beautiful wood floors. Adjacent is a 23x12 room encompassing a reception area and space for multiple work stations. This welcoming central business area opens to a private fenced courtyard. Completing the 1st floor is a fully equipped break room and 1/2 bath. Graceful stairs lead to a 2nd floor 13x13 executive office, 2 additional offices, a work area for files and office equipment and a 1/2 bath. Additionally within this building are the 2 well appointed 1 bedroom apartments. Excellent off street parking! Well located, at the rear of the property, is a charming cape style home! Constructed for use as his own residence a local builder known for high standards and attention to detail created an interior that will please! Truly unexpected quality and well conceived room dimensions, in a manageably sized 1540 sq. ft. home! Both buildings have excellent tenants in place! A commercial compound!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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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540 West Woodstock Road Woodstock VT 05091

MLS Number 4872920

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,692

A charming cape style home in a location convenient to access the amenities enjoyed by living in Woodstock! Constructed for use as his own residence a local builder known for high standards and attention to detail created an interior that will please! Truly unexpected quality in a manageably sized 1540 sq. ft. home! Nicely separated from this residence a detached classic New England style building houses a 7 room office complex and 2 privately entered 1 bedroom apartments! Income with excellent tenants in place! Situated at the rear of the .8 acre parcel the cape residence is in an elevated sunlit location. Entering the residence from a large deck leads into an open floor plan which encompasses living room, dining area and attractively appointed kitchen. Located off the kitchen a cozy den offers privacy and the ambience of a wood burning fireplace. A full bath completes the 1st floor. The entire 2nd floor is dedicated to a primary bedroom suite with full bath and walk in closet. On the lower level is a large 2nd bedroom, laundry room and entrance to a 1 car garage. In the front of the parcel the highly visible income property features a 7 room office complex that would satisfy any professional! Components include a private conference room with fireplace, reception/work station room, private executive office, 2 additional offices, break room, filing room and several 1/2 baths! Separately entered the 2 apartments are well finished. A residence with the bonus of income property!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 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 4,824

NEW ROOF IN 2021!! Well maintained 5 bedroom, 4.5 bath, 4,824 sqft contemporary Saltbox situated on 5.1 acres just four minutes to Woodstock village. This includes a large and gracious lower level In-Law/Guest suite with a substantial kitchen and a generous bedroom that could double as a home office, rental, or private guest quarters. There is a lovely 2002 expansion and Living/Great Room with floor to ceiling windows with plenty of light and a substantial center fireplace for easy evening conversation. Additionally, the large modern kitchen has cherry cabinetry, lots of counter space, and a practical kitchen office area. The Family/TV room has an attractive Woodstock soapstone stove that comfortably heats the home, and round out the first floor with a practical mudroom, an extra den, a formal dining room, & custom wide-board 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 and two additional large bedrooms with a common hallway full bath. Outside: Large wrap around deck, 2 car attached garage, sunny grounds, perennial gardens framing brick walkways, and adjacent to Mt Tom's hiking trails & close to Suicide Six ski area. There is local view potential if you cut a few trees and it's just 2 miles to town! 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: 2.88% last updated on Sep 9, 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 September 16, 2021.