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Homes For Sale Woodstock VT

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.

Woodstock VT Real Estate

Contact Williamson Group Sotheby’s International Realty to schedule a showing or if you have any questions. Create an account to save your favorite real estate listings and to receive email notifications when similar listings become available. 

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2018 Church Hill Road Woodstock VT 05091

Woodstock, VT2018 Church Hill Road

Price$2,275,000

Est. Mortgage: $/month

MLS Number 4969169

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 4,610
  • Bathroom 4

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the spring-fed swimming pond. Designed for gracious country living the eat-in kitchen and generous great room are accented by a fieldstone fireplace and vaulted ceilings. The primary bedroom suite and two guest bedrooms are located on the main living level with a walk-out level offering an additional bedroom with media and exercise areas. A 'bonus room' used as a studio is available for many alternative pursuits. Fifty acres of private woodland and open meadows is laced with trails enabling access to nature year round. A small stable is a resource to take advantage of South Woodstock's network of horse trials and miles of gravel roads. A private retreat within minutes of Woodstock's Village Green or the South Woodstock and the Green Mountain Horse Association. The best of all possible worlds.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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72 Frenchs Road Woodstock VT 05091

Woodstock, VT72 Frenchs Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4968402

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4

Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the grand living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a Primary with ensuite bath and a quaint sitting room. In addition to the main house, there is a detached garage with an apartment above and a 1 bedroom cottage set back on the premises. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away.

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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$1,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4961421

  • Residential Single Family
  • Village Woodstock
  • Square Feet 3,123
  • Bathroom 5
  • Construction Existing

This is a rare coveted home on Mountain Avenue in the heart of Woodstock set on a quiet 2+ acre lot. Enjoy the convenience of Village life within a four-minute walk over the Middle Covered Bridge to vibrant downtown. This elegant 1825 Cape has been beautifully maintained over the years and boasts 4 bedrooms, 5 baths, beautiful wide pine floors, newer kitchen, attached 2-car garage and separate cottage that could be your office or studio. Spend your summer evenings on the screened back porch overlooking a lovely private landscaped acres -- for gardening, play and pets. Close proximity to the Upper Valley, Quechee, ski resorts, schools, trails, shopping, restaurants, Mt. Tom for hiking and so much more.

Listed by Melissa Robinson of Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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2876 Hartland Hill Road Woodstock VT 05091

Woodstock, VT2876 Hartland Hill Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4967464

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing
  • Square Feet 3,350

This property is the quintessential classic Vermont farmhouse featuring the "big house, little house, backhouse, barn" concept. Conveniently located only 1.4 miles from the center of Woodstock village the home is surrounded by lovely gardens the Happy Valley brook and open meadows. The magnificent post and beam barn's upper level serves as parking space for multiple cars and abundant storage. The lower level has several stalls for animals that lead out to a paddock. The house has recently been completely renovated while retaining the lovely antique features . The rooms are filled with natural light and there is access to outdoor spaces throughout . The window from the fabulous "cook's kitchen" looks out to the open meadows beyond. The stone fireplace in the large family room is perfect for cozy fires on snowy winter days with amazing views from the French doors that open to a spacious deck perfect for entertaining. Living room with cathedral beamed ceiling and fireplace leads to a covered porch surrounded by perennial gardens. The bedroom floor plan provides privacy for multiple people. Close by is the Woodstock Inn Sports Center and Golf Club. Skiing at Killington and Woodstock's own Saskadena Six are minutes away . Two and half hours to Boston and 5 hours to NYC.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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282 Fletcher Hill Road Woodstock VT 05071

Woodstock, VT282 Fletcher Hill Road

Price$1,750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4953523

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Square Feet 2,329

This classic Yankee Barn home is sited on a plateau protected from the north providing sweeping views over South Woodstock to Mt. Ascutney and beyond. The expansive glass windows and sliding doors open onto wide deck & an adjacent covered porch to enjoy the seasonal fine weather. A handsome multi-purpose horse barn and equipment shed are generously sized for recreational equestrian & farm use with open fields & pastures offering supplemental grazing areas. The open post & beam great room is spacious with gathering spaces framing the field stone fireplace with a secluded study or occasional bedroom adjacent. A private loft and bedrooms are on the upper level. Designed for comfortable country living & to take best advantage of the extraordinary world surrounding you. Flowering trees, shrubs and a luminus birch grove accent the elegant natural landscaping. Located in the heart of horse country.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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113 Prosper Road Woodstock VT 05091

Woodstock, VT113 Prosper Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4959862

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 1
  • Square Feet 3,380

A rare opportunity to advance a premier Woodstock estate to its finest possibilities. This circa 1840 four-bedroom antique Farmhouse is sited on 18+ acres of idyllic rolling meadows on the southern end of the coveted Prosper Road. Just a few minutes walk to the Woodstock Farmers Market. A gracious and private tree lined approach gently climbs to a stately home, a gorgeous antique four-story barn, and a smaller barn. Other prominent features include its large windows and how this home takes full advantage of natural light and drawing in the peaceful surrounding Vermont landscape. The exterior siting and interior layout are superb to develop your dream property with excellent options to modernize the kitchen space, customize a primary bathroom, and work with the generously proportioned rooms with 8 foot 6 inch ceilings - remarkable for this period. Many fine details from a stately fireplace, heavy granite porch footings, picture rails, romantic private porch off the primary bedroom, and so much more. You will also appreciate walking to town via Rose Hill or hitting the Mount Tom trailhead just up Prosper Road. This estate homestead has not been available for over 100 years and your thoughtful investment of time and talent will realize your historic Vermont treasure.

Listed by Derek Cosentino and Audrey Micca of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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
Active With Contract

MLS Number 4945749

  • 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! This property owned by Gerrish Corporation, commonly known as “Woodstock East,” located at 458 Woodstock Road, Woodstock, Vermont, contains 4.5 acres, more or less. The property is located in the Commercial/Light Industrial Zone, allowing a multitude of commercial, industrial and residential uses of the property. The property was the site of a substantial gasoline spill in 1973. However, the property was enrolled in the Vermont Brownsfield Reuse Environmental Liability Limitation Act program (10 V.S.A. 6641-6656) in 1999 and was successfully remediated. On June 5, 2012 the Vermont Commissioner of the Agency of NaturalResources signed a Certificate of Completion, thereby providing protection to third party purchasers of the property pursuant to 10 V.S.A 6653(a) from any liability arising from any contamination on the property which occurred prior to that date, making this one the safest properties in Vermont from a pollution liability perspective. Location, location, location!!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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$1,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4945772

  • 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! This property owned by Gerrish Corporation, commonly known as “Woodstock East,” located at 458 Woodstock Road, Woodstock, Vermont, contains 4.5 acres, more or less. The property is located in the Commercial/Light Industrial Zone, allowing a multitude of commercial, industrial and residential uses of the property. The property was the site of a substantial gasoline spill in 1973. However, the property was enrolled in the Vermont Brownsfield Reuse Environmental Liability Limitation Act program (10 V.S.A. 6641-6656) in 1999 and was successfully remediated. On June 5, 2012 the Vermont Commissioner of the Agency of NaturalResources signed a Certificate of Completion, thereby providing protection to third party purchasers of the property pursuant to 10 V.S.A 6653(a) from any liability arising from any contamination on the property which occurred prior to that date, making this one the safest properties in Vermont from a pollution liability perspective. Location, location, location!!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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16 Church Street Woodstock VT 05091

Woodstock, VT16 Church Street

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4958574

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,089

16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village, it has a two-car garage with a covered walkway into the mudroom entryway (plus more outside parking). The spacious kitchen/dining area opens to the vaulted-ceiling living room, which has an INCREDIBLE view up-river. A side door leads to the side-deck that has the same view and sound of the river for outdoor dining above the river. There is a propane woodstove in the living room and woodstove in the kitchen/dining. A 1st floor bedroom has an ensuite bath and small stack washer-dryer. Upstairs is a large bedroom looking out through the great room to the river, a smaller bedroom, a bath and lovely loft area above the living room. Downstairs is a large den/rec/office, a bedroom, a bathroom, the main laundry room and mechanical room, all renovated 11 years, post the Irene storm, when the river waters came up into the lower level. There are beautiful gardens in the front and rear of the house. Occupancy available Nov 1, 2023.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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268 Willow Brook Road Woodstock VT 05091

Woodstock, VT268 Willow Brook Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 4968234

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,148

This elegant residence is an Award Winning Lindal Cedar Home. Private sited on the edge of Woodstock Village it is within walking distance of the abutting King Farm and the Woodstock Recreational Center. Constructed of massive laminated beams enabling the home to offer expansive light-filled gathering rooms on three levels. A combination chef's kitchen opens into a solarium for casual entertaining adjacent to classic formal dining area with indoor grill for celebrations and holidays. The gracious foyer opens in to a Great Room with wood burning fireplace and direct access by French Doors onto the south facing patio. The south and westerly common areas are located a discrete distance from 3 main level bedrooms two full bathrooms. An open stairway and loft overlooking the Great Room leads to the primary bedroom suite and a quiet study. The lower walkout with a second wood-burning fireplace and 3/4 bathroom is presently configured as a media and gameroom. Two attached garages provide ample space for 3 vehicles and outdoor recreational equipment. Convenient with a country environment this is a home for all seasons.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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$1,275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4962162

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,949
  • Construction Existing

This timber framed home is sited to take advantage of sweeping long range southerly views of hayfields and forest land protected by a development restriction as a gift by Laurance & Mary Rockefeller to the National Park. Expansive open spaces provide a casual living environment on three levels. The main level leads out to a wrap around deck that provides lovely spaces for entertaining . The open living room has a cozy fireplace. There are amazing views from each of these rooms. The top floor has a large main bedroom complete with study and bath. The lower level has 2 bedrooms , family room with a bath complete with a cedar sauna. There is a large two car garage with lots of overhead storage. Minutes to Woodstock village for shops and dining . Skiing at S Six and Killington minutes away. Outdoor activities for every season. .

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

26 River Street Woodstock VT 05091

Woodstock, VT26 River Street

Price$1,250,000

Est. Mortgage: $/month

Pending

MLS Number 4954906

  • Residential Single Family
  • Square Feet 3,719
  • Construction Existing
  • Bathroom 4
  • Bedrooms 6

One of Woodstock's most beautiful Greek Revival homes sited on a landscaped village lot that rolls gently down to the Ottauquechee River. The riverfront lawn is sheltered from activity on the Green and enjoys views of the iconic covered Middle Bridge. This authentic antique house is configured with the gable end facing the street and a series of westerly side entry doors. The facades are a template of aesthetic tastes with original classic architectural form modified in the late 19th Century with Carpenter Gothic elements in keeping with the Victorian style. The central country-kitchen is the common gateway to the home with more formal spaces and bedrooms located in the front portion of the residence. The original barn has evolved into a family great room/library with a wood-burning fireplace and opening onto the elevated deck overlooking the river. There are two 1st floor bedrooms with shared a bathroom and upstairs there are 2 private bedrooms and a study adapted to bedroom use that opens out to an old-fashion sleeping porch. A long bunkroom accessed off a back stairway sleeps a crowd during holidays and other occasions. This is an opportunity to acquire a rare gem of a home on the river.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 23, 2023 5:54 PM EDT