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

433 Cowdrey Path Woodstock VT 05071

Woodstock, VT433 Cowdrey Path

Price$995,000

Est. Mortgage: $/month

MLS Number 4932619

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

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

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

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

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: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4935033

  • Residential Single Family
  • Square Feet 2,555
  • Bedrooms 5
  • Construction Existing
  • Bathroom 5

Exposed beams and wide board wood floors accentuate the classic interior of this 5 bedroom Woodstock home! Pastoral views, large terraced lawns and massive stonewalls define the striking exterior landscape! When you enter through the classic front entrance a memorable first impression is created with the wood floors and exposed beams that are found throughout the main level. To the left is a living room with wood stove and attractive book case. To the right is a ground floor primary bedroom with ensuite bath. The rear of the main level is dedicated to a bright kitchen with classic wood cabinetry and a well complementing dining room area. Up a traditional front stairway are 2 bedrooms on the left side and a bath. On the right is a large bedroom with ensuite bath. When exiting the home from the kitchen a large covered porch leads to an attached oversized 2 car garage with plenty of space for a workbench and sports equipment storage! Separately entered from this covered porch, in a wing connecting the main house to the garage, is a bedroom with bath. The location of this detached 5th bedroom could easily become an office area conveniently nearby to but yet separated from the home. Additionally, a detached barn, with a full cement foundation, provides practical storage underneath and large 30x19 workshop/studio space above. For many years, this archetypical Vermont property was a bed and breakfast. By updating the baths and adding appliances it will become truly a memorable home!

Listed by John Wetmore, William Raveis Woodstock

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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3752 Densmore Hill Road Woodstock VT 05091

MLS Number 4946242

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Acreage 23.46

Beautiful 23.46 acre property including: House, 2 story Barn, Horse sheds, Cabin, Root cellar, sugar house, potting shed/chicken coop and fenced in pastures. Babbling brook. Fabulous wood floors throughout house. Walk in closet. Large enclosed back deck. Barn- top floor was converted into a Yoga studio. This is a fabulous property that gives you a true Vermont life. Green Mt Horse association up the street and Woodstock Village down the street as well as a golf course and Health Club with pool and tennis courts. Killington skiing and Dartmouth Hospital 25 minutes away. Delayed showings until April 6.

Listed by Dorothea Mongulla, High End Realty

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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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37 South Street Woodstock VT 05091

Woodstock, VT37 South Street

Price$550,000

Est. Mortgage: $/month

Pending

MLS Number 4946384

  • Residential Single Family
  • Square Feet 1,660
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

Broker Open House Saturday, March 25th 10am-noon. Fabulous Woodstock Village location. This charming colonial puts you steps from everything the Village of Woodstock has to offer: The Woodstock Inn, hiking Mount Tom and Mount Peg, golf, skating, shopping, restaurants and more. Spend sunny days sitting on the front porch overlooking Vail Field with its playground, tennis, pickle ball and ball fields. Inside you'll find the Dining Room to the left and the Living Room to the right of the front hall foyer. The generous sized living room with its cozy wood stove, is the perfect place to gather and watch the games on TV. The kitchen opens to a roomy dining room which is perfect for dinner parties. Both bathrooms are on the first floor. Upstairs you'll find two bedrooms to the left, a walk-through studio/office and then the third bedroom just beyond. In addition to the main house, there is a two-car garage, part of which is currently set up as a workroom, and upstairs there is a bonus room ready to become whatever you choose.

Listed by Jennifer Falvey, KW Vermont Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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853 Rose Hill Road Woodstock VT 05091

Woodstock, VT853 Rose Hill Road

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4932868

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

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

Listed by John Wetmore, William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Mountain Avenue Woodstock VT 05091

Woodstock, VT5 Mountain Avenue

Price$525,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4944553

  • Residential Single Family
  • Bedrooms 1
  • Square Feet 645
  • Bathroom 1
  • Construction Existing

A beautiful first-floor sunlit condo right in the heart of Woodstock! This unique location is only one block from the Village Green and a short stroll to farmers' markets, coffee shops, restaurants, and retail shops. Fully renovated, this unit has been thoughtfully brought back to its splendor with high-end energy efficient windows (preserving the classic moldings), all new lighting, all new appliances, and new paint throughout. Enjoy the benefit of a private garage and ample storage space. The elegant furnishings are also available. Enjoy a beautiful large private location on Mountain Avenue with mature trees and direct access to the river.

Listed by Holly Hall, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 April 1, 2023 3:08 AM EDT