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Woodstock VT Real Estate

Once named the “Prettiest Small Town in America” Woodstock is the shire town of Windsor County, Vermont. Its picturesque village has won awards for its beautiful scenery and streetscapes making it a year-round destination. The town of Woodstock hosts several annual events and festivals including December’s Wassail Weekend in which the town transforms into a winter wonderland with lights, decorations, and charm. Woodstock is home to a welcoming, tight-knit community that embraces the town’s unique character. 

Search the latest real estate in Woodstock, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ‚ÄčRegister to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Bathroom 8
  • Square Feet 5,142
  • Construction Existing
  • Bedrooms 6

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$4,350,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Bathroom 5
  • Bedrooms 7
  • Square Feet 5,306

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 of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

244 Happy Valley Road Woodstock VT 05091

Woodstock, VT244 Happy Valley Road

Price$2,100,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4896882

  • Residential Single Family
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 3,456
  • Construction Existing

This very charming home is located in the historic hamlet of Taftsville. The tree lined driveway leads to a custom designed house built in 2002 by a top local design/ builder team using top quality materials. The lovely open grounds include meadows , fruit trees , fenced paddock, as well as a very large pond . Also there are 5 miles of trails for riding , walking , snowshoeing. The gardens include lovely spaces for entertaining. The finished lower area is complete with bathroom . A great space for family activities. The home is light filled with pastoral views from every window.Price includes all furnishings as well as tractor ,riding mower and many other high end pieces of equipment . This is as "turn key" as it gets right dow to the Waterford wine glasses !

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

67 Grassy Lane Woodstock VT 05091

Woodstock, VT67 Grassy Lane

Price$1,895,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4895867

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 4
  • Construction Existing
  • Square Feet 3,438

This historic Vermont home has been thoroughly renovated and expanded to offer boundless curb appeal. Sited on 10 acres surrounded by stone walls, open fields, a pond, and a stream, this rare gem is located in one of the most desirable areas of Woodstock just minutes from the Village. The interior has a spectacular great room with southern exposure, high ceilings, a gorgeous fireplace, and floor-to-ceiling windows that invite beautiful natural light into the newly renovated space, all of which opens into the kitchen and dining area. The house, while designed as a 3-bedroom septic, features 5 bedroom spaces and 4 baths that were updated in 2012 and a spacious and convenient mudroom with 3 large storage closets. There is an attached 2-car garage as well as a separate 2-stall horse barn and sugar shack. With a skating pond on the property, a network of nearby trails, and access to Marsh-Billings-Rockefeller National Park, this is truly a special place to be enjoyed in all seasons.

Listed by Dail Frates of Snyder Donegan Real Estate Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Biscuit Hill Woodstock VT 05091

Woodstock, VTBiscuit Hill

Price$1,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4868865

  • Land
  • Acreage 453.82
  • Utilities None
  • Zoning residential

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

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

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5 Pine Street Woodstock VT 05091

Woodstock, VT5 Pine Street

Price$1,775,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4891594

  • Residential Single Family
  • Village Woodstock
  • Bedrooms 5
  • Bathroom 6
  • Construction Existing

Situated on a quiet road in a sought after Village neighborhood, this 5* VT Efficiency home is walking distance to downtown Woodstock. It has 4 ensuite bedrooms, 3 on the 2nd floor and the Primary suite on the 1st floor complete with a steam shower, spa and gas fire place. There is a 5th bedroom and 3/4 bath on the lower level which also plays host to a large open and newly renovated family and game room. An oversized mudroom takes you upstairs and also has access to the two car garage. The 1st floor boasts an open kitchen, dining and living room with stone fire place, cathedral ceiling and beautiful wood floors throughout. Down the hall are a TV room/den with gas fireplace and a 3/4 bath. Off the kitchen, French doors lead to a screened in porch which opens onto a multi level deck perfect for a morning cup of coffee, grilling up dinner, or a glass of wine on a warm summer night. Across the way are the Rec Center playing fields and playground and down the road is the Woodstock Country Club. This turnkey home is ideal as a primary or second home getaway. Don't miss out on this rare in-town property. Showings begin on 11/26/21.

Listed by Dan Noble of Snyder Donegan Real Estate Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000The price has recently decreased

MLS Number 4713229

  • Commercial
  • Village Woodstock
  • Acreage 4.57

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! The parcel is zoned to present multiple opportunities for successful commercial or residential development! Location, Location, Location!

Listed by John Wetmore of William Raveis Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4713272

  • Land
  • Acreage 4.57
  • Utilities Telephone Available

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! The parcel is zoned to present multiple opportunities for successful commercial or residential development! Location, Location, Location!

Listed by John Wetmore of William Raveis Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$1,395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4889125

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 3
  • Square Feet 2,016

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

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Pleasant Street Woodstock VT 05091

Woodstock, VT15 Pleasant Street

Price$1,395,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4905121

  • Residential Single Family
  • Village Woodstock
  • Bedrooms 5
  • Bathroom 4
  • Construction Existing

15 PLEASANT STREET - Elegant, tastefully renovated Greek Revival in ideal Woodstock Village location. This spacious home has been thoroughly updated and expanded over the years- most recently by the highly respected Hank Savelberg Construction Co.- and combines modern convenience with the craftsmanship and exquisite detail of the original home. The interior spaces are bright, well-appointed, and well-maintained. The kitchen has a large south facing dining/eat-in area, while the living room/formal dining area is anchored by a warm and inviting stone fireplace. A more intimate wood paneled library with a second fireplace adjoins. The lovely great porch on the front of the house is perfect for entertaining, enjoying a good book, or simply taking in the seasonal staples of Woodstock Village such as the annual Wassail Holiday Parade. With five bedrooms, four baths, and a separate office, there is plenty of room for everyone. Three of the bedrooms and the office are on the second floor, two bedrooms on the third floor. Walk to restaurants in minutes, stroll the Village Green, or take in the groomed beautiful trails of Marsh-Billings-Rockefeller National Historic Park. SHOWINGS START 4/19/22

Listed by David Donegan of Snyder Donegan Real Estate Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4754916

  • Residential Single Family
  • Village Woodstock
  • Square Feet 3,488
  • Bedrooms 5
  • Construction Existing

One of a kind! Woodstock Village! A professional designer's well conceived compound. The stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. The length of the tranquil landscaped rear grounds, lush with spectacular gardens and leading to accessible Ottauquechee River frontage, is an unexpected surprise! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the main level, a spacious kitchen, with full size informal dining area, opens in 3 directions, to either a fire-placed living room, a dramatic formal dining room or a large 16'x10.5' screened porch. On the second floor are 2 guest bedrooms, full bath, and a primary bedroom, with ensuite bath. On the 3rd level, a large unfinished attic presents endless potential! The detached guest house is perfect! On the ground level is a living room, with vaulted ceiling, a kitchen with a panty, a mud room and a bedroom with 3/4 bath. A second floor loft bedroom is 21' long! Separately, the free standing 36'x24' studio/workshop has potential only limited by your imagination! Truly an ideal property for combining residential use with a home occupation! The front view of the property has the expected classic New England appeal that typifies the residences of Woodstock Village. While the long private rear lawn, with professionally designed gardens, and accessible river frontage is an unexpected surprise!

Listed by John Wetmore of William Raveis Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4791944

  • Multifamily
  • Village Woodstock
  • Units 3
  • Bathroom 2
  • Square Feet 3,488

One of a kind! Woodstock Village! A professional designer's well conceived compound. The stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. The length of the tranquil landscaped rear grounds, lush with spectacular gardens and leading to accessible Ottauquechee River frontage, is an unexpected surprise! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the main level, a spacious kitchen, with full size informal dining area, opens in 3 directions, to either a fire-placed living room, a dramatic formal dining room or a large 16'x10.5' screened porch. On the second floor are 2 guest bedrooms, full bath, and a primary bedroom, with ensuite bath. On the 3rd level, a large unfinished attic presents endless potential! The detached guest house is perfect! On the ground level is a living room, with vaulted ceiling, a kitchen with a panty, a mud room and a bedroom with 3/4 bath. A second floor loft bedroom is 21' long! Separately, the free standing 36'x24' studio/workshop has potential only limited by your imagination! Truly an ideal property for combining residential use with a home occupation! The front view of the property has the expected classic New England appeal that typifies the residences of Woodstock Village. While the long private rear lawn, with professionally designed gardens, and accessible river frontage is an unexpected surprise!

Listed by John Wetmore of William Raveis Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 24, 2022.

 

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