Woodstock VT Real Estate

Woodstock, Vermont real estate offers residents the opportunity to live in a beautiful community surrounded by natural beauty. The area boasts excellent schools and a less hectic lifestyle. From antique farmhouses to updated homes to wooded acreage, discover a variety of properties in Woodstock. Browse the latest Woodstock, Vermont real estate listings below. You may also be interested in viewing real estate listings in other Vermont towns.

Homes for Sale in Woodstock

Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. Register to save your favorite listings and get email notifications when similar properties become available.

3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

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

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: 5.81% last updated on Jun 23, 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

4946 South Street Woodstock VT 05071

Woodstock, VT4946 South Street

Price$1,100,000

Est. Mortgage: $/month

MLS Number 4917030

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,440

Lilac Cottage: A charming Gothic Revival home in South Woodstock Village. Recently restored with a new addition that can be used as an in-law apartment or used completely by one family- stunning hand hewn beams that accent lofted ceiling capturing lovely light, there are french doors out to back gardens and handsome kitchen that opens to living/dining room. The lawn is beautifully landscaped with stone walls and perennial gardens. Enjoy two outdoor gathering spaces with a new back deck or under the charming covered front porch. A new 2 car garage with ample overhead storage is a very recent addition. This home boasts large spaces for entertaining family and guests. Gracious formal living room off a very large dining room. Hardwood floors and lots of antique character throughout this home. Enjoy the Kedron Valley Inn for a swim in the the pond or for dinner on the front porch, or gather at the country store for coffee and visits with neighbors. The Kedron Brook is across the road and Green Mountain Horse Association is a short walk away. There are endless miles of country roads and trails for hiking, biking , horseback riding and cross country skiing. This is the best of a country village lifestyle.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

1157 West Woodstock Road Woodstock VT 05091

MLS Number 4916726

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Square Feet 2,760
  • Bathroom 3

Gorgeous fully restored farmhouse with modern amenities and original charm! This sunny and pristine four-bedroom home is conveniently situated in west Woodstock village - just a short drive from Killington, Hanover, and DHMC and within the desirable Windsor Central School District. Comprehensively and meticulously renovated in 2017 from roof to basement, this property boasts all new electrical and plumbing, high-quality polyethylene foam insulation, a new standing seam roof and all new appliances, fixtures, and flooring throughout. Turn-key, convenient, and low maintenance, this home is ideal for primary homebuyers, vacation enthusiasts, and investment shoppers alike. From the soapstone countertops and the exposed beams to the spacious deck and easy-keeping yard, you'll find something to enjoy in every season. Offering flexible upstairs spaces and expansion opportunities, the layout gracefully accommodates both intimate gatherings and larger crowds. With luxe farmhouse design influences and an unbeatably convenient location, this property is a rarity in the Woodstock marketplace! Showings begin 6/28/2022. No showings shall be held 7/1/2022-7/4/2022.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

Catamount Lane Woodstock VT 05091

Woodstock, VTCatamount Lane

Price$340,000

Est. Mortgage: $/month

MLS Number 4916325

  • Land
  • Acreage 17.2
  • Zoning Residential

17+ 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. Additional Acreage available MLS#4916323, MLS#4916241

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

Catamount Lane Woodstock VT 05091

Woodstock, VTCatamount Lane

Price$640,000

Est. Mortgage: $/month

MLS Number 4916323

  • Land
  • Acreage 32
  • Zoning Residential

32 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. Additional Acreage available MLS#4916325, MLS#4916241

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Lane Woodstock VT 05091

Woodstock, VT370 Catamount Lane

Price$900,000

Est. Mortgage: $/month

MLS Number 4916241

  • Land
  • Acreage 49.2
  • Zoning Residential

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: 5.81% last updated on Jun 23, 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

48 River Street Woodstock VT 05091

MLS Number 4914354

  • Condo
  • New Contruction Existing
  • Year Built 1890
  • Bedrooms 1
  • Square Feet 950

This is a 3 unit condo building perched on the Ottaquechee River with new landscaping. Walk to town or across the street to the Recreation Center. This unit is a 1 bedroom, 1 bath residence. It has only 1 assigned parking space. Located on the second/third floor. Lovely honey- colored hardwood floor in the bedroom with lots of light. Kitchen and bath need a little upgrade but overall a super condo located in the heart of Historic Woodstock Village. Condo fees are 300/month and include trash, lawncare, plowing and town water. Please note there is a deed restriction that buyer must use the condo as a primary residence. Seller is a licensed real estate agent in the State of Vt.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

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

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: 5.81% last updated on Jun 23, 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

1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

MLS Number 4913355

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 7,590
  • Construction Existing

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: 5.81% last updated on Jun 23, 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 Church Street Woodstock VT 05091
Active With Contract

MLS Number 4912759

  • Condo
  • New Contruction Existing
  • Complex Village Condominiums
  • Square Feet 1,059
  • Bedrooms 2

This simply superb recently updated Woodstock Village condo will capture your heart! The completely renovated eat-in kitchen is a beautiful and intelligent design blend of custom cabinetry and tile, quartz countertops, and new Bosch appliances all of which are framed by a ceiling accented with hand-hewn beams and cherry hardwood flooring. A newly renovated bathroom offers a splendid tiled walk-in shower and under-tile floor heating! The new laundry unit is tucked into a new custom combination bookshelf/cabinet in the guest room. A warm and inviting living room is detailed with a wood-burning fireplace and lovely built-in shelving. The private deck with views of Mt Tom and the Ottauquechee River is the perfect spot for relaxing and outdoor entertaining. A lush, level, and expansive lawn with river frontage offers even more outdoor space to unwind with friends and family! All of this within walking distance to dining, shopping, and theatre. The perfect "pied-a-terre" or primary residence!

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

1 Border Lane Woodstock VT 05091

Woodstock, VT1 Border Lane

Price$629,000

Est. Mortgage: $/month

MLS Number 4912025

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,368

A highly desirable Woodstock location! Conveniently situated only a few minutes from the Woodstock Village Green, in a lush pastoral setting, is a bright 3 bedroom home. The land component of the property is truly high quality, with ample lawn area for entertaining or recreation, pleasant meadow views and a sunny exposure. All the convenience of single level living is provided in this home of a manageable size! A well conceived floor plan features a large living room/dining area with a fireplace and a dramatic bow window, a kitchen with an area for breakfast dining, a well designed sunroom, 3 bedrooms with wood flooring and 1.5 baths. The sunny back patio presents a private sitting area with tranquil views of a large meadow. The interior of the home feels comfortable and well built. The land is idyllic! Neighboring homes are substantial. All of these attributes combine to offer a property that is equally appealing as a manageable vacation home or a comfortable year round residence!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

57 Townhouse Way Woodstock VT 05091
Active With Contract

MLS Number 4911780

  • Condo
  • New Contruction Existing
  • Bedrooms 3
  • Construction Masonry,Wood Frame
  • Year Built 1978

A desirable Woodstock West Townhouse, with 3 levels of living space! The quiet setting features landscaped grounds and pleasing woodland views. A well maintained home of a manageable size! On the main level is a den with the ambiance of a wood burning fireplace, a conveniently located half bath and a bright kitchen with a practical adjacent dining area. The sun filled kitchen is well appointed with an island work surface, good cabinet space, an attached pantry and even a wine cooler! A large deck extends off from the kitchen for the pleasure of leisurely outside dining or for morning coffee communing with nature. On the upper level are 2 generously sized bedrooms and a well appointed bathroom with double sinks and beautiful shower. The front bedroom could easily become a spacious in home office space. On the lower level is a laundry room, attractive bath with shower, and a multipurpose family room, with a wood burning stove. This lower level is easily visualized as presenting a primary bedroom with private bath. Wonderful guest quarters! The location of the townhouse is particularly convenient for access to the Woodstock Middle School and the High School. Beloved Woodstock Farmer's Market is just a short drive away! Townhouse dues are $355/month and include snow removal, lawn mowing, trash removal, master insurance policy and exterior maintenance/repairs on the building. A property well suited for use as a primary residence or as a quiet vacation retreat! Showings begin 5/28.

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

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 June 27, 2022.