Woodstock

Explore the latest real estate for sale in Woodstock, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

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
  • County Windsor
  • Property Type Single Family
  • 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: 6.29% last updated on Sep 22, 2022
* 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

1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4913355

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Carol Wood and Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 10
  • Bathroom 15

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: 6.29% last updated on Sep 22, 2022
* 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

486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4925674

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SHOWINGS WILL START SUNDAY AUGUST 21.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$3,250,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • 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 Richard Higgerson and Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

19 the Green Woodstock VT 05091

Woodstock, VT19 the Green

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4928047

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

THE OTIS SKINNER HOUSE - Once owned by famed stage actor Otis Skinner, this historic Woodstock village home has been lovingly and comprehensively updated by its current owners. The spacious gourmet kitchen is a home chef's dream with a stunning Lacanche range, dual dishwashers, a brand new Sub-Zero refrigerator, ample counter space, and abundant storage. Redesigned and renovated in 2011 around a central windowed "tower," the home overlooks the Ottauquechee River and the covered bridge; Pella casements welcome in stunning sunset views and the sounds of water journeying to the Connecticut. With at least six flexible bedroom spaces - including a third-floor guest suite - a formal office, and multiple common spaces, this home accommodates a houseful as comfortably as it provides a cozy home for just a few. From the copper roof to the central air on the second and third floors to excellent heating systems, 19 the Green is well designed to greet every New England season. Beautifully situated on Woodstock's fabled Green and a short stroll from shops and restaurants, the Otis Skinner house enjoys the best of two worlds - the home may be situated at the heart of the village, but it truly lives on the burbling banks of the Ottauquechee.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

17 Mountain Avenue Woodstock VT 05091

Woodstock, VT17 Mountain Avenue

Price$1,900,000

Est. Mortgage: $/month

MLS Number 4929946

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

On a crisp Fall afternoon, enjoy an artisans' fair on beautiful Woodstock's Village green, then walk home through the covered bridge to one of the village's loveliest homes. Set on a quiet lane, this handsome antique Cape offers spacious living for you and every member of your family. Decorate the sweet small side cottage to your taste, with options of having it as your home office. Walk over to play on Vail Field or the Woodstock Recreation Center. And during the school year, enjoy the stroll over to the elementary school, with easy access to the middle school, and high school. Lots of year round sports for anyone to enjoy such as skiing at the historic Saskadena Six ski area, cross country skiing and golfing through the Woodstock Inn, skating at the Union Arena, mountain biking trails, hiking Mt. Tom and other leisurely areas. Walk to the library, the post office, the market or the White Cottage for an ice cream cone or dip in the river. Best of all, don't leave home at all! Invite your friends in for a simple summer brunch on the attractive sun porch. Look out over the immaculately manicured lawns behind the house - over two acres for gardening, to play or simply enjoy. In winter, gather around a cheerful blaze in the fireplace of the elegant living room for a cup of hot chocolate after dinner. You may search near and far but you'll soon discover - there isn't another home as elegant and versatile as 17 Mountain Avenue anywhere else in all of Woodstock.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

Biscuit Hill Woodstock VT 05091

Woodstock, VTBiscuit Hill

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4868865

  • Land
  • County Windsor
  • Square Feet 19,768,399
  • Acreage 453.82

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: 6.29% last updated on Sep 22, 2022
* 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

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
  • County Windsor
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 9

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: 6.29% last updated on Sep 22, 2022
* 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

458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4713272

  • Land
  • County Windsor
  • Square Feet 199,069
  • 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: 6.29% last updated on Sep 22, 2022
* 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

458 Woodstock Road Woodstock VT 05091

MLS Number 4713229

  • Commercial
  • County Windsor
  • 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: 6.29% last updated on Sep 22, 2022
* 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

33 Central Street Woodstock VT 05091

Woodstock, VT33 Central Street

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4923096

  • Multifamily
  • County Windsor
  • Bathroom 4
  • Square Feet 6,741
  • 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: 6.29% last updated on Sep 22, 2022
* 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

33 Central Street Woodstock VT 05091
Active With Contract

MLS Number 4922122

  • Commercial
  • County Windsor
  • Square Feet 5,913
  • 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: 6.29% last updated on Sep 22, 2022
* 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

28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4754916

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 4

One of a kind, in Woodstock Village! A professional designer's well conceived compound. A stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. An unexpected surprise is the length of the landscaped rear grounds which lead to accessible Ottauquechee River frontage! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the ground 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 2nd floor are 2 guest bedrooms, a 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 2nd floor loft bedroom is 21' long! A detached 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. A long private rear lawn, with accessible river frontage is an unexpected surprise! A property equally suited to be a wonderful year round residence, with a quality guest house, or a vacation retreat!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4791944

  • Multifamily
  • County Windsor
  • Bathroom 2
  • Square Feet 3,488
  • Acreage 0.61

One of a kind, in Woodstock Village! A professional designer's well conceived compound. A stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. An unexpected surprise is the length of the landscaped rear grounds which lead to accessible Ottauquechee River frontage! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the ground 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 2nd floor are 2 guest bedrooms, a 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 2nd floor loft bedroom is 21' long! A detached 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. A long private rear lawn, with accessible river frontage is an unexpected surprise! A property equally suited to be a wonderful year round residence, with a quality guest house, or a vacation retreat!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4889125

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Fifty pristine, peaceful, and private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock's famous amenities - less than 10 minutes to The Woodstock Inn & Resort's Athletic Center, 18 hole championship golf course, x- c skiing - hiking - biking trail system, fantastic dining, shopping, galleries and more! Or explore your own land which features numerous hiking trails, stone walls, and a stream. Parcels of this size & quality are scarce; this one's location also has a perfect balance of privacy & convenience. The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont!

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

3 BOND Street Woodstock VT 05091

Woodstock, VT3 BOND Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4924310

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 6

#3 BOND STREET is a classical example of the Greek and Colonial Revival architectural movement in the United States. Built in 1836 by Henry Lawrence, a piano manufacturer, the property transferred a year later to Oel and Sophia Billings who resided in the home they called 'The Maples' with their nine children. Their daughter Elizabeth lived in the home after her parents moved to #16 the Green and she later shared it with her brother Frederick, until he could acquire and renovate the George Perkins Marsh Mansion. The home was later the long time residence of Frank and Lucy MacKenzie. Her kindness and support of animals in service to people is remembered by naming the regional animal shelter in her honor. The residence is currently configured as three apartments, but retains the original floor plan. Evident throughout the home are elegant moldings, trim and architectural elements of the bygone era, including a greenhouse used on the north side for orchids and spacious interior porch leading to the private back yard on the northeasterly side where it provided cool shelter on summer days. A remarkable property with a special heritage as home to many who made Woodstock what it is today.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

3436 Church Hill Road Woodstock VT 05071

Woodstock, VT3436 Church Hill Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4918981

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

Set back off a quiet country road with stone walls sits this Cape Cod home on thirteen acres. A peaceful setting for those seeking privacy in South Woodstock. The fenced-in backyard is perfect for summer barbecues and long swims in the pool. Enjoy a cocktail on the covered porch while the sun sets. A mix of rolling pasture allows for gardening and equine friends. The main level of the home features hardwood oak flooring, a large living room with fireplace, an eat-in kitchen overlooking the backyard, dining room, laundry room, half bath and a bedroom suite. The upper level provides pine flooring, an additional bedroom, bonus room and bath. There is a separate guest apartment with its own entrance over the garage. The attached and detached garages offer a workshop and plenty of space for toys, vehicles and storage. Solar panels cover most of the electric overhead. Lovely landscape surrounds the yard with lilacs, roses and shrubs. Less than five minutes to Green Mountain Horse Association with easy proximity to golf, skiing and Woodstock center. Showings begin Saturday, July 9th.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

11 College Hill Woodstock VT 05091

Woodstock, VT11 College Hill

Price$1,275,000

Est. Mortgage: $/month

MLS Number 4918360

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 4

Highbank Cottage- A truly lovely estate nestled on the banks of the Ottaquechee River overlooking a clear view of Mtn Tom. Stunning, private backyard with beautiful landscaping and perennial gardens. Stroll down to the river or enjoy an evening under the stars at the cozy fire pit. This antique gambrel features handsome hardwood floors, first floor master bedroom suite, propane fireplace in the Living Rm with lofted ceilings for a spacious feel. The intimate dining room has ample space for a long harvest table for many guests looking out to Mtn Tom. The 2nd floor incorporates 3 more guest bedrooms and full bath. The lower level features a large office with propane stove for chilly fall days, summer kitchen and screened in porch to cozy up in the afternoon reading a book. The 'Barn' includes a 2 bay heated garage, stunning apt with bedroom/sitting area and 1.5 baths. High vaulted ceilings with beadboard walls to capture the true 'cottage' feel. Lower level has a large workshop and more storage or could be converted to a workout room. Enjoy fishing on the Ottaquechee or take a trip floating on tubes down the River on a hot summer day. All of town amenities, shops and theatre right out your back door. Suicide Six, Okemo and Killington near-by as well as championship golf, tennis and mountain biking. Very few properties in the village offer a view and river access with large apt for either friends/family or rental income. Come take a look- Its adorable!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

134 Spruce Way Woodstock VT 05091

Woodstock, VT134 Spruce Way

Price$1,175,000

Est. Mortgage: $/month

MLS Number 4927608

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Privately located in the desirable Cox District region of Woodstock, just five minutes from The Farmers Market and fifteen minutes from Killington's Sky Ship, this beautifully-crafted, meticulous cape has everything you could possibly want. The sizable living room with custom built-ins is anchored by a handsome fireplace with insert, and brick and wood surround. From here, step out to a lovely private screened room overlooking established perennial beds. The well-appointed kitchen has custom cabinetry and soapstone counters, and the adjoining dining area's focus is a brick fireplace with a woodstove. There is one ensuite bedroom on the first level, and a primary sizeable ensuite on the second level, an additional bedroom and bathroom, plus an exercise/playroom with office space. Pristine, restored pine floors run throughout both levels. At the back of the house is an additional bright spacious room with separate entry room, which is perfect for a home occupation, painting, playroom or yoga studio. Attached two-car garage steps into the mudroom for easy unloading. The ten-acre property has a backup generator, fire pit, and excellent trail access and includes many updates and improvements.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

MLS Number 4890993

  • Commercial
  • County Windsor
  • Square Feet 7,804
  • 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: 6.29% last updated on Sep 22, 2022
* 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

370 Catamount Lane Woodstock VT 05091

Woodstock, VT370 Catamount Lane

Price$900,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4916241

  • Land
  • County Windsor
  • Square Feet 2,143,152
  • Acreage 49.2

Nearly fifty acres of pristine land in Woodstock Vermont, ready to build your dream estate. The mixed mature woodland hosts walking trails, a stream, a potential pond site, and several potential house sites with magnificent, sweeping, long-range westerly views. The end-of-road location ensures privacy and tranquility, yet is only six minutes from Woodstock Village and the Woodstock Inn & Resort's Athletic and Golf complex. Ten minutes from Green Mountain Horse Association. Power and high-speed internet at the road. Acreage that combines this level of size, quality, and convenience is becoming preciously rare in greater Woodstock.

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$895,000

Est. Mortgage: $/month

MLS Number 4897046

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Pristine, peaceful, with 5 private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock's famous amenities - less than 10 minutes to The Woodstock Inn & Resort's Athletic Center, 18 hole championship golf course, x- c skiing - hiking - biking trail system, fantastic dining, shopping, galleries and more! The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont! Additional land available - total of 50 acres.

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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

234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 1

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: 6.29% last updated on Sep 22, 2022
* 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

Broker Reciprocity

Copyright 2022 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 September 29, 2022 9:39 PM EDT.