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Woodstock VT Real Estate

Woodstock Real Estate & Homes for Sale

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Woodstock is located in Windsor County in the southeastern part of Vermont. It has a population of approximately 3,200 and a household median income of approximately $57,000.  Neighboring towns include Bridgewater and Pomfret. Woodstock has 1 elementary school, 1 middle school and 1 high school. Browse available Woodstock VT real estate below. 

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853 Rose Hill Road Woodstock VT 05091

Woodstock, VT853 Rose Hill Road

Price$549,000

Est. Mortgage: $/month

MLS Number 4932868

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 2,604
  • Bathroom 3
  • Construction Existing

The opportunity presented by this unique Woodstock property provides much to consider! The entire 1.3 acre parcel is zoned Light Commercial Light Industrial enabling commercial venture use. There is a highly visible level lawn area directly on Route 4 that is diagonally opposite the beloved Woodstock Farmer's Market. The 2 detached residences which are accessed off desirable Rose Hill each benefit from connection to the municipal sewer system. The demand for Woodstock rental housing is steady and rental rates are at historically high levels. The barn style residence has a multipurpose garage/workshop space on the ground level. A convenient adjacent office area makes this space ideal for use by a contractor, tradesman or hobbyist requiring a workshop. A 2nd floor apartment can either be separately entered through a graceful covered porch or from within the garage. The 1 bedroom apartment features a kitchen, living room, bedroom and full bath with laundry. The 2nd residence is a classic New England 3 bedroom home. The ground floor features a simple kitchen with a pantry, dining area and a large living room with spacious built in book case. Attractive wood floors, well placed windows and a covered front porch add appeal. On the 2nd floor are 3 bedrooms and a bath. A simple comfortable home, with attractive features. Great components create a great location, with great zoning, with great infrastructure and with great rental income potential! The value of the components is real!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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433 Cowdrey Path Woodstock VT 05071

Woodstock, VT433 Cowdrey Path

Price$995,000

Est. Mortgage: $/month

MLS Number 4932619

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,507

Splendid contemporary cape and separate barn guest apartment idyllically nestled on an open and sunny hillside surrounded by conserved land in the heart of South Woodstock horse country. The light and airy interior boasts an open concept gourmet kitchen with dining/living area that opens to both a wonderful screened porch and deck. In addition, there is a warm and spacious family room to gather for games or a movie. The primary bedroom ensuite is detailed with a stunning vaulted ceiling with exposed beams, a newly updated bath, and a lovely balcony overlooking a quintessential Vermont landscape. The additional two bedrooms share a full bath. An upstairs laundry room is an added convenience. As a bonus there is a wonderful barn with a separate guest apartment complete with kitchen and bath! The lower level of the barn has parking for one car as well as ample storage area which could easily be converted back to the original horse stall. New buderus boiler and standing seam roof are at the top of an extensive list of substantial upgrades and improvements to this property. Enjoy the convenience of being just around the corner from the South Woodstock Country Store, the Kedron Valley Inn, Green Mountain Horse Association (GMHA) and just a short ride to the village of Woodstock. A truly special and versatile property!

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$3,300,000

Est. Mortgage: $/month

MLS Number 4932341

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,456

This extraordinary 115 acre property, located in the towns of Woodstock & Hartland, offers the perfect mosaic of qualities that buyers are looking for. The acreage is unencumbered and presents the perfect opportunity for a family estate, future development or equestrian opportunities with grass covered hillsides, trail systems and the GMHA just 3 miles away. The diverse topography of the property with trails throughout has an easily accessible summit offering a unique homesite location with spectacular unobstructed panoramic long range views that can be captured from sunrise to sunset. For the winter sports enthusiast, you have it all right here. The extensive trail systems can be combined for snowmobiles, nordic or alpine skiing. The level of stewardship is evident from the maintenance of the extensive trail systems, existing structures and grounds to the main pond that is deep and well stocked. The structures include a very comfortable two story cottage with long vista views, a large barn/garage, two stall horse barn with run-in and a split rail fenced area. There is also a three sided oversize pole barn currently being used for equipment storage located at the end of one of the trails. The property is accessed off a municipal road via (3) gated entry points. A gazebo at the summit takes in nearly 360 degree long range views providing the idyllic setting for a substantial residence. The properties captivating views and trailed woodlands stand ready to implant your vision.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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588 Kendall Road Woodstock VT 05091

Woodstock, VT588 Kendall Road

Price$539,000

Est. Mortgage: $/month

MLS Number 4929954

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,904

While relaxing on the gracious front porch of this classic New England home the mesmerizing sound of the nearby cascading brook can transport your cares away! Located in equestrian oriented South Woodstock, this home presents generous interior space to entertain the friends and family who will surely come to enjoy all that Woodstock offers. The principal rooms feel large and welcoming. Yet, throughout the house private areas are easily found. As is typical in traditional New England homes, there are well placed windows and beautiful wood flooring. Upon entering the home this striking flooring is immediately displayed, in a practical entry room, which then opens to a bright kitchen, with eat-in dining area. Adjacent to the kitchen is a dining room. A large double living room provides comfortable gathering spaces, with a fireplace in 1 room and windows viewing out to a large front porch in the other. Completing the ground floor are a 1/2 bath and a bedroom. On the 2nd floor are 4 well placed bedrooms, all with beautiful wood floors. Adjacent to a full bath is a den/sitting room. Well separated, at the opposite end from the bedrooms, is an office area with space for 3 workstations. Conveniently, this workspace has interior stairs leading directly down to the kitchen. Both the desirable South Woodstock location and the spacious interior floor plan of this classic Vermont style home make it equally suited to be a convenient year round residence or a wonderful vacation retreat!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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853 Rose Hill Road Woodstock VT 05091

Woodstock, VT853 Rose Hill Road

Price$549,000

Est. Mortgage: $/month

MLS Number 4928424

  • Multifamily
  • Units 2
  • Bathroom 1
  • Acreage 1.3
  • Square Feet 2,604

The opportunity presented by this unique Woodstock property provides much to consider! The entire 1.3 acre parcel is zoned Light Commercial Light Industrial enabling commercial venture use. There is a highly visible level lawn area directly on Route 4 that is diagonally opposite the beloved Woodstock Farmer's Market. The 2 detached residences which are accessed off desirable Rose Hill each benefit from connection to the municipal sewer system. The demand for Woodstock rental housing is steady and rental rates are at historically high levels. The barn style residence has a multipurpose garage/workshop space on the ground level. A convenient adjacent office area makes this space ideal for use by a contractor, tradesman or hobbyist requiring a workshop. A 2nd floor apartment can either be separately entered through a graceful covered porch or from within the garage. The 1 bedroom apartment features a kitchen, living room, bedroom and full bath with laundry. The 2nd residence is a classic New England 3 bedroom home. The ground floor features a simple kitchen with a pantry, dining area and a large living room with spacious built in book case. Attractive wood floors, well placed windows and a covered front porch add appeal. On the 2nd floor are 3 bedrooms and a bath. A simple comfortable home, with attractive features. Great components create a great location, with great zoning, with great infrastructure and with great rental income potential! The value of the components is real!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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

40 Park View Way Woodstock VT 05091

Woodstock, VT40 Park View Way

Price$70,000

Est. Mortgage: $/month

Pending

MLS Number 4925444

  • Mobile
  • Listing Agent Name Rachel Arsenault
  • Year Built 2006
  • Bedrooms 3
  • Square Feet 1064

Fully renovated manufactured home in Woodstock's Riverside Park. Large primary suite with full bath. Two additional bedrooms and a full bath offer plenty of additional living or office space. Open concept layout compliments the tons of natural light. Located just minutes from the village of Woodstock, 25 minutes to Killington, and 35 minutes to Lebanon, NH,

Listed by Rachel Arsenault of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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33 Central Street Woodstock VT 05091

Woodstock, VT33 Central Street

Price$1,400,000

Est. Mortgage: $/month

MLS Number 4923096

  • Multifamily
  • Village Woodstock
  • Units 6
  • Bathroom 4
  • Acreage 0.03

Constructed in 1880, as a significant commercial focal point in bustling Woodstock Village, the prime location of this appealing Woodstock Village landmark has truly stood the test of time! The attractive brick building features 4 levels of desirable space, in a combination of premier commercial storefronts and much in demand residential components. A large main floor commercial space presents over 1900 sq. feet, with high visibility to those passing by, through large display windows. For many years, this main level was home to the favorite breakfast restaurant in the village. Successful retail stores are neighbors to the property, on both sides, and that presence contributes to attracting potential customers. A 2nd commercial space is accessed by stairs leading down from the busy sidewalk. As with the main commercial space, effective display windows entice customers to visit this lower level storefront. This lower level space could be combined with a main floor enterprise or could house a stand alone venture. Accessed through an entrance separate from the commercial space are 4 spacious apartments located on the 2nd and 3rd floors of the building. On the 2nd floor is a 1 bedroom apartment and a 2 bedroom apartment. On the 3rd floor is a 1 bedroom and a 2 bedroom apartment. All apartments have high ceilings, well placed windows and an excellent rental history. Woodstock Village has been a vacation destination of choice for generations. Entrepreneurial Opportunity awaits!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Square Feet 5,412
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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5250 West Woodstock Road Woodstock VT 05091

Woodstock, VT5250 West Woodstock Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4918791

  • Residential Single Family
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing
  • Square Feet 4,502

The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes' drive of the Killington and Okemo ski resorts, respectively. Known locally as the Robinson Farm, after the family that build the handsome home and legendary barn shortly after the turn of the 20th Century. The property has been converted by the present owners into a gracious and authentic rural farm environment for vacations, weddings, and other events large and small. The historic 1905 Farmhouse Inn offers accommodation in the 7 Guest Rooms, all with private baths and gracious gathering rooms on the first floor. A 2-bedroom Innkeeper's quarters provides private living space. The Red Barn was constructed in the style of a 'bank barn' with grade level entry points to the different levels of the barn where they served a variety of agricultural purposes. The massive timber frame is exposed on all levels with the upper two having been adapted for the event venue hosting up to 150 guests. The White Barn accommodates 50 guests for smaller ceremonies and other events with a wide deck providing a place of seasonal outdoor dining. 13 acres of open land and convenient location offer the potential to create a farm-to-table restaurant, direct-to-consumer shop selling local and regional goods or an immersive Agri-tourism guest experience. Less hospitality-oriented uses as a gentleman's farm or niche farm producing or marketing local goods are great options as well.

Listed by Rachel Arsenault and Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 15
  • Square Feet 10,206

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 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 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 January 30, 2023 12:55 PM EST.