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

540 West Woodstock Road Woodstock VT 05091

MLS Number 4872920

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,692

A charming cape style home in a location convenient to access the amenities enjoyed by living in Woodstock! Constructed for use as his own residence a local builder known for high standards and attention to detail created an interior that will please! Truly unexpected quality in a manageably sized 1540 sq. ft. home! Nicely separated from this residence a detached classic New England style building houses a 7 room office complex and 2 privately entered 1 bedroom apartments! Income with excellent tenants in place! Situated at the rear of the .8 acre parcel the cape residence is in an elevated sunlit location. Entering the residence from a large deck leads into an open floor plan which encompasses living room, dining area and attractively appointed kitchen. Located off the kitchen a cozy den offers privacy and the ambience of a wood burning fireplace. A full bath completes the 1st floor. The entire 2nd floor is dedicated to a primary bedroom suite with full bath and walk in closet. On the lower level is a large 2nd bedroom, laundry room and entrance to a 1 car garage. In the front of the parcel the highly visible income property features a 7 room office complex that would satisfy any professional! Components include a private conference room with fireplace, reception/work station room, private executive office, 2 additional offices, break room, filing room and several 1/2 baths! Separately entered the 2 apartments are well finished. A residence with the bonus of income property!

Listed by John Wetmore, William Raveis Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$924,000

Est. Mortgage: $/month

MLS Number 4859269

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,824

NEW ROOF IN 2021. Meticulously maintained 5 bedroom, 4.5 bath, 4,824 sqft contemporary Saltbox situated on 5.1 acres just four minutes to Woodstock village. This includes a large and gracious lower level In-Law/Guest suite with a substantial kitchen, dining, and a generous bedroom that could double as a home office, rental, or guest quarters. There is a lovely 2002 Living/Great Room expansion with floor to ceiling windows with plenty of light and a substantial center fireplace for easy evening conversation. Additionally, the large modern kitchen has cherry cabinetry, lots of counter space, and a practical kitchen office area. The Family Room has an attractive Woodstock soapstone stove that comfortably heats the home. We round out the first floor with a practical mudroom, an extra den, a formal dining room, & custom wide-board milled cherry flooring throughout. Privately located, the first-floor master bedroom en-suite boasts a large walk-in closet and high ceilings with lots of windows that make the room sunny & bright. The second floor layout includes a second Master Bedroom suite with private bath and two additional large bedrooms with a common hallway full bath. Outside: Large wrap around deck, 2 car attached garage, sunny grounds, perennial gardens framing brick walkways, and adjacent to Mt Tom's hiking trails. Close to Suicide Six ski area too! There is view potential if you cut a few trees and it's just 2 miles to town! Be sure to see the 360 Matterport Virtual Tour!!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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4946 South Road Woodstock VT 05071

Woodstock, VT4946 South Road

Price$895,000

Est. Mortgage: $/month

Pending

MLS Number 4871947

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

Lilac Cottage is a most charming Gothic Revival home in South Woodstock Village. Lovingly restored with a new addition that can be used as an in law apt. or used completely by one family. A new 2 car garage with ample overhead storage is a very recent addition . The lawn is beautifully landscaped with stone walls and a lovely back deck . Walk to the Kedron Valley Inn 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 Carol Wood, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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339 Gully Road Woodstock VT 05091

Woodstock, VT339 Gully Road

Price$750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4860123

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,688

Price reduced $100,000! Motivated seller! Great location just minutes from Woodstock village on the quiet Gully road, located just a few miles from Woodstock's shops, restaurants, schools. Sited on 5.1 acres is this 4-bedroom, 2 1/2-bath home. The main living level features a foyer with 2 1/2 story vaulted ceiling and windows, an open concept kitchen/dining/living space and a 1/2 bath with an adjacent den room. The large wraparound deck just off the kitchen/great room is perfect for outdoor dining and gatherings. Upstairs is the primary bedroom with a walk-in closet, a full bath with separate tub and shower, and a small deck that leads to the wraparound deck below. 3 additional bedrooms, a full bath, and large laundry space complete the level. Beneath the house is an attached garage and workshop/storage area. Newer, high-efficiency propane heating furnace. The property also features two large outbuildings- one three-bay open garage/shed and a separate heated one-bay enclosed barn- for ample storage of vehicles, equipment, and toys. Super-fun treehouse sleeps 3+ in summer has power, sink and bar fridge - right off the back lawn. The property has a wonderful outdoor firepit area with level lawn, two brooks and walking trails/woods.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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81 Happy Valley Road Woodstock VT 05091

Woodstock, VT81 Happy Valley Road

Price$725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4877228

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 4,679

This gorgeous, historic Greek Revival Farmhouse located in the heart of the charming Taftsville community has been lovingly stewarded for over two centuries, while honoring and preserving the beautiful, period detail. The sun filled, spacious rooms flow perfectly for daily living and entertaining. The private, en suite bedrooms are ideal for accommodating a house full. The charming country kitchen is of generous proportion, and commercially suited to cook for the masses. Step out to a lovely, secluded terrace garden, and lawn. The antique barn is perfect for storage and workshop. Neighborhood access to a wonderful trail system. Stroll down to the covered bridge and walk or bike along the banks of the Ottauquechee River. This impeccable property is turn key! The property is currently being operated as The Apple Butter Inn (and available as a going concern, fully suited at $740,000). The property can be easily transitioned back to a grand single family home, or single family with a rental unit, guest, or in law accommodation. Limited availability for showings.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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31 South Street Woodstock VT 05091

Woodstock, VT31 South Street

Price$649,000

Est. Mortgage: $/month

MLS Number 4886759

  • Residential Single Family
  • Square Feet 2,359
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

Just a stroll from the heart of Woodstock village, this spacious antique home is the perfect haven for you and yours. High ceilings, exposed beams, gorgeous light, and cozy gathering spaces lend a European aesthetic to this historic cape, while new systems (roof, boiler, windows) make this a worry-free home in every season. With separate suites of rooms at each end of the house, this four to five-bedroom property comfortably accommodates multiple families and guests. Two doors down from Woodstock's acclaimed elementary school, and right across the street from new tennis and pickle ball courts, there simply isn't a better village location. Sold fully and beautifully furnished, this turnkey home is ready to welcome you to Woodstock.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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348 Gabert Road Woodstock VT 05091

Woodstock, VT348 Gabert Road

Price$599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4876532

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,188

Charming and wonderfully sited three-bedroom ranch style home on 21 beautiful acres of rolling fields and forest on a quiet dead-end road, convenient to Woodstock. Enjoy sunny afternoons and take in the delightful views from the large west facing deck in the shade of magnificent old maples, surrounded by perennial flowers, stone walls, and apple trees. New “Energy Star” fridge and dishwasher; new systems include high efficiency, heat pump fired water heater, well pump, Tesla Powerwall (assumable lease with GMP), and upgraded oil-fired baseboard heat. Propane stove in the living room. Sunny master bedroom has two large closets. Walk-out basement has ample space for storage, and could easily be finished for additional living space. Oak hardwood and laminate flooring. Attractive garden shed for equipment and storage. This home is on the market for the very first time and has been lovingly cared for by the same family since its construction.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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1222 West Woodstock Road Woodstock VT 05091
Pending

MLS Number 4876534

  • Residential Single Family
  • Construction Existing
  • Square Feet 4,985
  • Bathroom 4
  • Bedrooms 7

Large, stately, rambling West Woodstock home with attached studio apartment has easy vehicular access and ample parking. Enjoy morning coffee in the private, fenced side yard before heading to the spacious workshop-garage to tinker. Unusual home has multiple spaces for any activity or hobby. Main portion of the house contains two kitchens (one is recently remodeled with high-end cabinetry and appliances), two living rooms, a library, a hot tub room, 5-6 large bedrooms, and three baths. The studio apartment includes an additional ¾ bath, kitchenette, balcony, and its own laundry. Ideally suited to become a three+ family ski house, with many common and private spaces for all. Could also be converted into three fully separate apartments, or possibly a B&B. The home is filled with antique touches: lavish trim and woodwork, a fabulous staircase, and plentiful built-in cabinets, drawers, and shelves. The studio is tenant occupied, so 48-hour notice is legally required to see it. Main portion of the house is available to view with less notice.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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3961 Hartland Hill Road Woodstock VT 05091
Pending

MLS Number 4886800

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,646
  • Construction Existing

This charming, expanded Cape sits just outside the Village of Woodstock. Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting within a mile or less of village shops, schools, dining and recreation. There is potential for one-level living with first floor bedroom and full bath nearby. The kitchen features granite countertops, an island with seating, tile floors and plentiful cabinets and updated appliances. The Lovely Dining Room with hand-hewn beams and gas fireplace, Living Room with Wood Burning Fireplace, a cheery office and wonderful Sunroom with gas stove and entry to large deck complete the first floor of the main house. There are two spacious bedrooms with room for seating and plentiful storage and another full bath on the second floor. The two-bedroom apartment with its own one-car garage, driveway, entrance and laundry can be accessed from the house if desired for flexibility of use. Whether you need room for guests, an in-law suite or would like rental income-the choice is yours in this versatile home. Recently added Automatic Generator and Mini-Splits insure comfort year round. The yard has established perennials and is bordered by a year-round brook with a foot bridge for accessing the nearby trails on Mount Peg. With the convenience of village amenities nearby and the gorgeous country setting -this home truly has the Best of Both Worlds.

Listed by Tambrey Vutech, KW Vermont Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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140 SOUTH BROOK Way Woodstock VT 05091

Woodstock, VT140 SOUTH BROOK Way

Price$589,000

Est. Mortgage: $/month

MLS Number 4885523

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,376

This striking contemporary post & beam home and 'guest' barn are located mid-way between the Villages of Woodstock & South Woodstock. The open and airy floor plan takes full advantage of the views of surrounding hills throughout the home. The private deck and hot tub overlook South brook shaded by mature hemlock trees that flows down to the Kedron Brook. A detached recreational barn has amply space on the main level for a variety of hobbies and the open upper level is a heated and insulated 'bunkroom'. A quiet spot close to area amenities, including restaurants, shopping, ski areas and the Green Mt. Horse Association.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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21 Golf Pond Extension Woodstock VT 05091

Woodstock, VT21 Golf Pond Extension

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869941

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,731

Fantastic location in the heart of Woodstock village! Nestled on Golf Pond with lovely landscaping and private deck facing South. Very quiet setting with walking distance to both the village, golf course and trails to Mt Peg. Warm toned hardwood floors throughout this residence, propane fireplace in the LR for those looking to curl up with a book, plenty of sunlit filled rooms with open floor concept for easy entertaining with friends and family. Half bath/laundry on first floor along with a mudroom. Second floor presents 3 bedrooms and 2 full baths... Lovely setting with pond- Walk to town to all restaurants, minutes from skiing, golf and fly-fising. Come take a look- very good rental property for a buyer looking to offset expenses.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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704 Austin Road Woodstock VT 05091

Woodstock, VT704 Austin Road

Price$529,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4884314

  • Residential Single Family
  • Square Feet 1,686
  • Bathroom 2
  • Construction Existing
  • Bedrooms 3

The serenity of Vermont living combined with the convenience of a 5 minute drive to the Village of Woodstock awaits with this wonderful property. The beautifully renovated 3 bedroom, 2 bath ranch style home is situated on over 3 lovely acres and is light filled throughout both levels. The owners have made many upgrades including newer kitchen, bathrooms, extensive basement changes including the addition of larger windows, expanded mudroom, electrical and plumbing to name a few. The main level offers 2 bedrooms, a full bathroom, an open concept living/dining/kitchen space and oversized mudroom. The basement provides an additional bedroom, 3/4 bath (partially finished and ready for a buyer's final touches), recreation room, multiple office areas, exercise room and laundry. There is newer blown-in insulation, newer doors and windows and a Buderus boiler for increased home efficiency. Enjoy sunsets from the spacious back deck overlooking the pond, walks or hiking from the front door or ski for the day at Suicide Six ski resort which is just minutes away. Woodstock, Vermont has been rated one of the best small towns in America and this property is a wonderful way to enjoy all that Woodstock and the surrounding areas have to offer. Just over 30 minutes to Killington and an easy 2 hour drive to Boston makes this property ideal as a vacation home as well. Schedule a tour today!

Listed by Zoe Hathorn Washburn, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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 October 27, 2021.