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

326 Hall Circle Woodstock VT 05091

Woodstock, VT326 Hall Circle

Price$929,000

Est. Mortgage: $/month

MLS Number 4837802

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,949

This super timber framed home is privately sited to take advantage of sweep southerly views over hayfields and forest land protected by a development restriction as gift by Laurence & Mary Rockefeller to the National Park. Expansive open spaces provide a casual living environment on three floors. Gathering areas on the primary living level include an eat-in kitchen with gas cook-top & grill, new double ovens & new refrigerator. The inviting, sunny kitchen opens to a dining area warmed by a Vermont Castings wood stove. The great room is configured with a media area & a living room centered on the wood-burning fireplace. The third floor offers a private master bedroom with designer bathroom ensuite & a separate study/bedroom. The walk-out lower level has views over a stone patio & lawn to distant hills and valleys. Another handsome enamel coated Vermont Castings wood-stove warms the family room area on this level with two bedrooms & a spa bathroom that with Finnish dry sauna and a steam shower. A modern synthetic deck spans the length of the primary living level with another deck off the master bedroom. A woodland trail winds uphill through the property to a point just west of the ridgeline boundary of the Suicide Six Ski Area. Priced fully furnished & equipped with quality appointments for ease of occupancy during these challenging times.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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898 Barnard Road Woodstock VT 05091

Woodstock, VT898 Barnard Road

Price$899,000

Est. Mortgage: $/month

MLS Number 4843539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,608

Prime location in Woodstock. Located a minute to Woodstock Village and Marsh-Billings-Rockefeller National Park. First time offered since 1975. Circa 1771 "Hillside" is a special property on over 31+ acres with beautiful views everywhere you look. The sprawling 5 bedroom/ 4 bath Farmhouse is the perfect place to entertain family and friends. The home has a mudroom/pantry that leads you into a large eat in kitchen. Walk out to the screened porch to sit back and enjoy your morning coffee and soak in the sweet views. The main level of the home has the original hand hewn wood beams and consists of a formal dining room, living room with wood burning fireplace, cozy library with hearth and fireplace, first floor guest room, and full bath with clawfoot tub. Take the main staircase to the second level where you will find a spacious primary bedroom suite, and two more bedrooms one which is being used as an office currently. The third level has a guest bedroom, hangout room and bathroom. The home has a spacious floor plan with the option to turn one area back to an in law suite. As you head outside you will enjoy the very private backyard with stone patio and gazebo. Stroll down to the 3 level barn and let your imagination fly. The barn is 3 barns that were merged together. This could be a great place to have a home business, artist studio or renovate it as extra recreation or sleeping space. Close to Suicide Six. Schedule a tour of this Woodstock property today. It will not last.

Listed by Marni Rieger, KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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25 Lincoln Street Woodstock VT 05091

Woodstock, VT25 Lincoln Street

Price$895,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4841644

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

The Watkins Farmhouse was built in 1868 on a prominent knoll overlooking the Ottaquechee River Valley, the distant hills of Pomfret and nearby Mt. Tom. As such, this classic center hall colonial also enjoys a wonderful view over Woodstock Village and Billings Farm today. Spacious in size and offering the elegantly proportioned rooms of a classic period in American architecture, the 3,688 square feet that make up the interior of this home were completely renovated in 2018 by an award winning builder with an eye towards easy comfort and sensible function. Those extensive renovations included the addition of a wrap-around porch to capture the view and hillside breezes, a total renovation of the attached working barn. The house also received the installation of a state of the art kitchen, a hidden magnolia surround sound entertainment system in the living room and one of the most spectacular 3rd floor Master Bedroom/Spa Baths that we have seen. Soak in your tub as you look across the river at the hill of Pomfret and the valley below. The parcel of land is a surprisingly generous .66-acre village parcel with level areas for gardens, a beautiful stone patio. The house is part of a larger multi-unit development that will be completed in 2021. Virtual showings ONLY using our online assets prior to physical entry into the property.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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492 Westerdale Road Woodstock VT 05091

Woodstock, VT492 Westerdale Road

Price$775,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4838691

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,214

THE COMPLETE PACKAGE! This gorgeous country compound is beautifully sited on 5.2 acres which includes a spacious 3 bedroom / 4 bath Country Gambrel style home, two-stall horse barn with insulated tack room and fenced pasture abutting riding/walking trails, in-ground pool, a two-car garage which includes a separate entrance heated office space, and a private but convenient location within minutes of the village of Woodstock. The Country Gambrel offers a functional and fun layout to enjoy all the seasons. The spacious and open living/dining room is ideal for entertaining family and friends. The Great Room with cathedral ceiling and fireplace is the perfect place to gather on a cold winter's night. Enjoy relaxing, taking in the view, and star gazing on the farmers porch. The eat-in kitchen opens to the screened porch and deck that overlook the pool area. Tiled entryway, mudroom, half-bath and laundry complete the main level.. The second level offers a master bedroom suite as well as two additional bedrooms and bath. The exterior grounds are a beautiful composition of lush and level lawn space, stonewalls, perennials, pastures, and a fabulous in-ground pool with patio. Truly an exceptional property to experience all that Vermont living has to offer!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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12 High Street Woodstock VT 05091

Woodstock, VT12 High Street

Price$699,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4835346

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,423

EXCEPTIONAL VILLAGE PROPERTY! Wonderful opportunity to own a terrific turn-key home in the heart of Woodstock Village. This 3 bedroom home, each with ensuite baths, was designed to enjoy easy access to the vibrant village life of Woodstock with it's wonderful restaurants, shops, arts/theatre, and abundant recreational activities. The open concept main living area is beautifully accented with a gorgeous updated and newly applianced kitchen, hardwood cherry floors, cathedral ceiling, and a picturesque view of Mount Tom and village life! The two additional bedroom suites for family/guests are both ample and private. The backyard and deck are perfect for relaxing, entertaining, and space to garden or take in the village street scape from the front deck. Intelligently designed mechanical systems that include radiant heat, central air, and state of the art Tesla Battery System will keep you comfortable and will give you peace of mind throughout all the seasons. The added bonus of the attached and heated 2 car garage with 4 additional off street village parking spaces makes this truly a unique village property!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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16 Lincoln Street Woodstock VT 05091

Woodstock, VT16 Lincoln Street

Price$625,000

Est. Mortgage: $/month

MLS Number 4834696

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,000

Pristine, fully refinished Cape in a desirable location just a short walk to the lovely downtown area of Woodstock. Wood burning fireplace in the living room. all new appliances and granite in the well designed kitchen. 3 bedrooms plus lots of space in the nicely finished lower level. Nice fenced-in area for your dog. This is a great house. Come take a look.Furnishings negotiable.

Listed by Barbara West, Quechee Associates, Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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45 Pleasant Street Woodstock VT 05091

Woodstock, VT45 Pleasant Street

Price$599,000

Est. Mortgage: $/month

MLS Number 4798290

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,554

Excellent In-Village opportunity. Conveniently located in the East end of Woodstock Village, This well maintained c1900 colonial home, most recently utilized as a suite of law offices can easily be transformed back to a private residence, or a multi family with abiloity to accommodate a home business with excellent street presence, lovely wrap around porch and plenty of parking. Also available for long term commercial lease.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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3332 South Woodstock VT 05091

Woodstock, VT3332 South

Price$575,000

Est. Mortgage: $/month

MLS Number 4826681

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,508

FOLDING HILLS is a well maintained vintage 1960 ranch style mini farm waiting for a face lift. There are presently 2 bedrooms, however the new septic system is for 3 bedrooms. There is a 2 car attached garage, a garage door access and space for one car in the spacious basement / workshop. There are multiple out buildings for storage, animals, more cars, trucks and tractors and a heated office. There are fenced paddocks and pastures, apple trees and a field bordering the Kedron Brook. There is a fabulous HOUSE SITE to develop up on the hill behind the house. Sunny exposure, with view possibilities to the north east and the south. The road is roughed in and the septic site has perc'd. This is a unique building site halfway between South Woodstock and Woodstock Village.

Listed by Lynne Bertram, Lynne Bertram Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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28 The Green Street Woodstock VT 05091

Woodstock, VT28 The Green Street

Price$549,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4698305

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,037

An elegantly proportioned brick townhouse, of genteel style and character, situated on the picturesque Woodstock Village Green! A gracious 3 story interior, with attractive antique detailing, 9 foot high ceilings, exposed beams, wood floors and multiple fireplaces. On the ground floor is the kitchen, a dining room with fireplace, a living room with fireplace, a classic entry hall and a half bath. On the second floor is a great room with fireplace, 2 bedrooms and a full bath. On the third floor is the primary bedroom suite, with walk-in closet and full bath. The front exterior of the residence features a formal covered entry. The rear exterior of the residence features an elevated brick patio. An useful amenity is off street parking. There is additional parking and storage in a detached garage. An opportunity to acquire a charming village townhouse residence, ideally located on the Woodstock Village Green!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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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4980 South Road Woodstock VT 05071

Woodstock, VT4980 South Road

Price$529,000

Est. Mortgage: $/month

MLS Number 4787330

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,180

Classic brick federal located in the charming village of South Woodstock. Easy walk to the country store , post office , and Kedron Valley Inn for dinner in the newly renovated Ransom Tavern. The Kedron Brook is across the street and Green Mountain Horse Association is just down the road . Lots of trails for hiking and biking and several ski mountains minutes away . Historic Woodstock is 5 miles and Dartmouth, with renowned medical facility ,is 25 minutes away. The extra large lot offers lots of space for gardening with a lovely back patio. The 2 car detached garage includes space for a work area . A great opportunity to own a bit of history !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 2021
* 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 2021 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 January 26, 2021.