Williamson Group logo

Search Homes

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. 

r=25-36
2409 South Road Woodstock VT 05091

Woodstock, VT2409 South Road

Price$1,125,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4961738

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Bathroom 3
  • Square Feet 3,218

This splendid 1920 Vermont Farmhouse with Post and Beam Great Room and detached barn with a 1-bedroom guest apartment is sited beautifully on 2.74 acres that are detailed with a pond and frontage on the Kedron Brook . The main level design of the original farmhouse has been intelligently updated with the addition of a spacious open concept kitchen with vaulted ceilings and exposed beams that is accented with a cozy breakfast nook and the original walk-in pantry that flow into the fabulous Post and Beam Great Room which opens onto a deck with a lovely view of the pond. There is a separate dining room with a gas fireplace for more intimate dining. A primary ensuite bedroom. living room/study, half bath and mudroom entry complete the main level design. The second level offers 3 additional bedrooms, a full bath and office. The delightful 1 bedroom/1 bath guest apartment with separate laundry overlooks the pond and brook. A wonderful opportunity for a fabulous family vacation compound or a primary residence with rental income producing apartment. Private but convenient location within minutes of the four-season recreation, arts, theatre, and dining that make Woodstock, Vermont living so desirable! Showings begin on Wednesday July 19.

Listed by Mary Mayhew 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

60 Pleasant Street Woodstock VT 05091

MLS Number 4968499

  • Commercial
  • Village Woodstock
  • Square Feet 3,050
  • Year Built 1893
  • Acreage 0.25

Incredible opportunity to own a piece of Woodstock History that has not been up for sale in over 50 years. The Woodstock Train Station, which first welcomed passengers in the late 1800s, is a main stay in the community and is one of the first buildings to greet people as they arrive in town. It has great visibility on Rte 4 and is just across the way from the recently developed East End Park and Riverfront. The building has seen several transformations over the years but currently sits empty. Buildout is underway to have commercial space on the main level and a 2 bedroom apartment on the 2nd floor but it is basically a clean slate for someone to come in and create their own vision and next chapter for the property. Recent upgrades include all new electric, plumbing, windows, and a new roof, and both the town sewer and water lines have been replaced. This historic building has endless potential in a premier location and comes with plenty of parking out back. Sale of the property is contingent on approved subdivision.

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

60 Pleasant Street Woodstock VT 05091

Woodstock, VT60 Pleasant Street

Price$950,000

Est. Mortgage: $/month

MLS Number 4969539

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 3
  • Square Feet 2,050

Incredible opportunity to own a piece of Woodstock History that has not been up for sale in over 50 years. The Woodstock Train Station, which first welcomed passengers in the late 1800s, is a main stay in the community and is one of the first buildings to greet people as they arrive in town. It has great visibility on Rte 4 and is just across the way from the recently developed East End Park and Riverfront. The building has seen several transformations over the years but currently sits empty. Buildout is underway to have a 2 bedroom apartment on the 2nd floor and commercial space on the main level. It is basically a clean slate for someone to come in and create their own vision and next chapter for the property. Recent upgrades include all new electric, plumbing, windows, and a new roof, and both the town sewer and water lines have been replaced. This historic building has endless potential in a premier location and comes with plenty of parking out back. Sale of the property is contingent on approved subdivision.

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

71 Central Street Woodstock VT 05091

MLS Number 4956014

  • Commercial
  • Village Woodstock
  • Year Built 1990
  • Square Feet 3,678
  • Acreage 0.1

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: 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

512 East Woodstock Road Woodstock VT 05091
Pending

MLS Number 4890993

  • Commercial
  • Square Feet 7,804
  • Year Built 1946
  • Acreage 2.31

A very well known Woodstock commercial complex, with the demonstrated facility for exceptional multi-use options. The property is fully leased, with 5 excellent tenants! The desirable attribute of high visibility is combined with the easily accessed parking areas to entice customers to shop! This 2.31 acre complex features the 3 components of 2 detached buildings and an additional potential building site. The main structure is a 2 story well maintained building benefitting from a spacious open floor plan with 2448 square feet of ground floor retail space with a complimenting 1284 square feet of directly attached easily accessible storage/warehouse area. Within this substantial structure, a thoughtfully positioned 1500 square foot second floor studio is accessed through a private rear entrance, with an attractive facade. This bright and inviting commercial space is currently home to a pilates studio. Well separated from the main structure is a 2500 square foot garage style building which currently houses 3 different income producing commercial tenants. Approached up a driveway within the property a totally private rear plateau of land provides a quiet respite with pastoral views! This potential building site has obvious untapped potential! A Commercial property with a unique diversity, in a highly visible Woodstock 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Square Feet 600
  • Bedrooms 2

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

2646 Curtis Hollow Road Woodstock VT 05071

MLS Number 4954660

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Square Feet 2,352
  • Bedrooms 4

Delano Birches Farm , built in 1834, has been lovingly cared for by the present owners for 36 years. The approach is down a country lane bordered by stone walls and mature trees. The owners added a bright open family /dining room and large primary bedroom with bath. This classic country home is filled with charm . There are two stone fireplaces as well as original wood floors. The grounds include a lovely year round pond , gardens as well as a brick patio for entertaining. Only minutes from Killington for skiing and historic Woodstock village for shops and restaurants. The area offers sports and entertainment 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4935033

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,555
  • Bedrooms 5
  • Bathroom 5

Exposed beams and wide board wood floors accentuate the classic interior of this 5 bedroom Woodstock home! Pastoral views, large terraced lawns and massive stonewalls define the striking exterior landscape! When you enter through the classic front entrance a memorable first impression is created with the wood floors and exposed beams that are found throughout the main level. To the left is a living room with wood stove and attractive book case. To the right is a ground floor primary bedroom with ensuite bath. The rear of the main level is dedicated to a bright kitchen with classic wood cabinetry and a well complementing dining room area. Up a traditional front stairway are 2 bedrooms on the left side and a bath. On the right is a large bedroom with ensuite bath. When exiting the home from the kitchen a large covered porch leads to an attached oversized 2 car garage with plenty of space for a workbench and sports equipment storage! Separately entered from this covered porch, in a wing connecting the main house to the garage, is a bedroom with bath. The location of this detached 5th bedroom could easily become an office area conveniently nearby to but yet separated from the home. Additionally, a detached barn, with a full cement foundation, provides practical storage underneath and large 30x19 workshop/studio space above. For many years, this archetypical Vermont property was a bed and breakfast. By updating the baths and adding appliances it will become truly a memorable home!

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

7 Golf Avenue Woodstock VT 05091

Woodstock, VT7 Golf Avenue

Price$735,000

Est. Mortgage: $/month

MLS Number 4966983

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Square Feet 3,579
  • Bedrooms 5

Super location! Nestled in the historic village of Woodstock- Built in 1832- this 3500+ squ foot home boast tall ceilings with handsome hardwood floors, kitchen with an island, mudroom and cathedral ceilings in the family room. There is a first floor master suite with office, updated bathroom with tile and soapstone counters. Large bookshelves accent the dining room that expands into a sunlit living room...ample room for entertaining. Lots of antique character still found in this property. Second floor has an apt with separate entrance or the entire floor can be converted into bedrooms. Third floor features two more rooms for offices, play room or the option of another master suite... Second/Third floor need some work/updating- for those with creativity- a perfect space to enhance and create a desired floor plan for your needs. Very large detached barn/garage with storage/office above. Pleasant backyard for gardening and entertaining along the Kedron Brook. Easy access to Vail field and all the shops and restaurants in the village. Mt Peg entrance is across the street for those hiking enthusiasts. Championship golf and fly-fishing a short distance away as well as Dartmouth, Killington and Okemo Mtns. Great opportunity to own a large home in the village-

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

512 East Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4880820

  • Commercial
  • Village Woodstock
  • Square Feet 5,244
  • Year Built 1946
  • Acreage 1.31

A well known Woodstock commercial property, with exceptional multi-use potential! The property is fully leased, with excellent tenants. The desirable attribute of high visibility is combined with the easily accessed parking areas to entice customers to shop! The well maintained building benefits from a spacious open floor plan and presents 2200 square feet of ground floor retail space with a complimenting 1500 square feet of easily accessible storage/warehouse area directly attached to the retail area. Thoughtfully separated from the highly visible retail store a 1500 square foot second floor studio is accessed through a private rear entrance with an attractive facade. This bright and inviting additional commercial space is currently home to a pilates studio. Approached up a driveway within the property a totally private rear plateau of land provides a quiet respite with pastoral views! This potential building site has obvious untapped potential! A Commercial property with a unique diversity, in a highly visible Woodstock 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

418 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT418 Fletcher Hill Road

Price$699,000

Est. Mortgage: $/month

MLS Number 4966735

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 3,135
  • Bathroom 3
  • Construction Existing

Located on a lovely country road in South Woodstock this very charming custom built log home enjoys long range mountain views. Enjoy entertaining on the wrap around porch and dining in the year round enclosed sunroom. The well appointed kitchen with sitting area makes cooking a dream . The main level has vaulted ceilings , stone hearth , wood floors and beautiful log beams. There are two bedrooms and a full bath. The upstairs has the principal bedroom , bath and loft study/den. The lower walk out level can be used for a game room/exercise space. There is tons of storage on that level . The oversize garage leads into a spacious mudroom with laundry and pantry .The location makes access to skiing at Killington , Six and Okemo only a short drive away . Green Mt. Horse Association is less than 10 minutes away as well as the historic town of Woodstock with all of its many amenities . Call for an appointment today.

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

708 E Woodstock Road Woodstock VT 05091

Woodstock, VT708 E Woodstock Road

Price$599,000

Est. Mortgage: $/month

MLS Number 4969496

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Bathroom 1
  • Square Feet 1,034

This charming home is the perfect place to relax and unwind and is less than a mile from the heart of Woodstock with shops and restaurants. Wake up to stunning views of the mountains, then spend your days exploring the nearby hiking trails. In the evenings, enjoy a glass of wine on the deck in the secluded garden. 25 minutes to Dartmouth College 30 minutes to Dartmouth Hitchcock Medical Center 20 minutes to VA hospital 23 minutes to Killington Skyship Base Lodge 6 minutes to the Athletic Club for golf, mountain bike trails, indoor/outdoor tennis and an expansive Nordic ski trail system. Recent upgrades include new electrical and plumbing, a new bathroom, new kitchen with quartz countertops, new appliances including an electric heat pump water heater, spray foam insulation and new windows throughout. The septic will need to be replaced, but all plans and permits are in place and a credit will be issued for the installation cost. Showings by appointment. Seller is a licensed agent.

Listed by Karen DeMas 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.

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 3:53 PM EDT