Woodstock Homes Between $500K and $1 Million

Woodstock, Vermont offers buyers myriad choices of beautiful and unique properties. A historic home in quaint Woodstock Village within walking distance to all the amenities you need, a secluded home with lots of land and views of the Green Mountains, a vacation home, or investment property.

It’s also what Woodstock offers beyond beautiful homes that make it special. For lovers of outdoors, there are miles of trails for hiking, biking, and horseback riding, and snowmobiling. Rivers in and around Woodstock offer fishing and kayaking.

For art lovers, there are galleries and theaters in town. For foodies, there are topnotch restaurants, many featuring farm-to-table cuisines.  Woodstock, Vermont is one of the loveliest towns in the Upper Valley. The area offers even more of the great amenities and attractions you'll find in Woodstock.

Woodstock VT Homes for Sale

Woodstock, VT could be the perfect place for a family home, a vacation retreat, rental or investment property. Explore the homes below, then give Bassette Real Estate Group a call at 802-457-2244. Our agents and buyer brokers would love to help you find your perfect new home in Woodstock.

View all Homes for Sale in Woodstock

370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$895,000

Est. Mortgage: $/month

MLS Number 4897046

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,016
  • Bathroom 3
  • Bedrooms 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 Bassette Real Estate Group

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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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, Wade I Treadway Real Estate

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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1 Border Lane Woodstock VT 05091

Woodstock, VT1 Border Lane

Price$599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4912025

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

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, William Raveis Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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880 College HIll Road Woodstock VT 05091

Woodstock, VT880 College HIll Road

Price$599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4930353

  • Residential Single Family
  • Square Feet 1,768
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Super location! Nestled on a knoll just outside of the village of historic Woodstock. Quiet setting anchored by large old Maple trees for great foliage color and shade during warm days. The property offers over 3 gracious acres of both open land for those looking for a large garden and perennials for those gardening enthusiasts and woods with a variation of tree species. The large circular driveway accesses a two bay garage and an extra carport as well as a storage shed. Enjoy a cool glass of lemonade on the back porch overlooking a large private backyard or the second covered porch off the front facing south. The home includes multiple gathering spaces for entertaining family and friends. Enjoy a large sun-lit family room and a more intimate living room accented with a warm propane fireplace for those cold winter days. Master bedroom is en-suite with 2 extra guest bedrooms and bathroom. Large kitchen with dining available. This property has a newer furnace with central air and whole house generator - Easy access to all of towns amenities: shopping, dining, hiking and movies. Championship golf, skiing and fly-fishing all close by. Rare opportunity to own a home with one floor living so close to the village but still privately tucked away ... come take a look!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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3903 Densmore Hill Road Woodstock VT 05091
Active With Contract

MLS Number 4929494

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 2,232
  • Construction Existing
  • Bathroom 2

Crisp, bright 3 story cape just minutes from the Woodstock Green on a quiet road with privacy. Open concept with cathedral ceiling, spacious living room, dining area, updated kitchen with granite counters, hardwood floors, propane stove and new deck overlooking fenced yard to a lovely view. First floor bedroom with full bath. Second floor offers 2 bedrooms with full bathroom. Lower level provides family room, office alcove, laundry and space for additional accommodation, a second propane stove and direct outside access. Attached garage, hard wired generator, mini split AC, water softener and gazebo add to the convenience, security and comfort of this home. Showings begin Saturday, September 17, 10-2PM.

Listed by Scott Monahan and Danny Kogut, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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588 Kendall Road Woodstock VT 05091

Woodstock, VT588 Kendall Road

Price$575,000

Est. Mortgage: $/month

MLS Number 4929954

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

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

Listed by John Wetmore, William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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238 Cowdrey Path Woodstock VT 05071

Woodstock, VT238 Cowdrey Path

Price$555,000

Est. Mortgage: $/month

Pending

MLS Number 4922371

  • Residential Single Family
  • Square Feet 1,748
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

You're sure to fall in love with this classic log style home perched on a knoll with pleasant valley views. Located on a quiet dead-end road, steps away from the Kedron Valley Inn in South Woodstock, and a five-minute drive to the Woodstock Village Green. The rooms are spacious, with plenty of natural light throughout. The home transitions seamlessly between interior to exterior spaces with two private terraces and an oversized deck for outdoor entertaining. The living room is anchored by a a woodburning fireplace. Best of all there is a beautiful-screened porch overlooking the grounds to the view. The lower level holds great potential for expansion. There is a great detached multi-purpose barn/ garage. Access to trail system for hiking, snowshoeing and snowmobiling. Close proximity to skiing, restaurants, recreation.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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35 Stimets Road Woodstock VT 05091

Woodstock, VT35 Stimets Road

Price$550,000

Est. Mortgage: $/month

MLS Number 4907062

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,076
  • Construction Existing

PERFECT LOCATION! Just a three minute drive to downtown Woodstock. This 1.42 acre property has been owned and thoroughly maintained over the past 40 years. Gorgeous Landscaping and a beautiful artists studio behind. Attached 2 car garage/barn with multiple areas for a workshop. Stained glass embellishments throughout. Original hardwood flooring and ample amounts of natural sunlight. With a screened in porch for those beautiful evenings. First floor has two bedrooms and a full bathroom. Second floor has additional 2 bedrooms with a full bath while, the 3rd floor is a fully finished attic with a Jack and Jill on-suite. Currently used as a two family home but could be easily converted back into a single family. This home is a once in a lifetime opportunity!" Only 5 minutes to Suicide Six ski area. Property Survey (2012) and Septic Inspection (2022) available. Delayed showings starting Sunday, May 1 at the open house from 11am-2pm.

Listed by Morriah Adams and Kate Barry, EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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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 October 5, 2022 12:52 AM EDT.