Greater Woodstock Area Homes Between $500K and $1 Million

The greater Woodstock, Vermont area (including the towns of Barnard, Bridgewater, Hartland, Pomfret, Reading, West Windsor, and Woodstock) offers diverse real estate opportunities. Whether you’re looking for a historic home, a home in town near shops and galleries and all the amenities you need, a family home, a secluded getaway with lots of land, a vacation home, or investment real estate, the greater Woodstock area has plenty of choices.

Apart from beautiful homes and real estate, the greater Woodstock area of Vermont hosts some great cultural institutions and events like the Hall Art Foundation in Reading, the Woodstock Film Series, and Taste of Woodstock. Summer and winter recreation opportunities abound at Suicide 6 ski area and Mount Ascutney. For horse lovers, the Green Mountain Horse Association (GMHA) in South Woodstock has activities and events all summer long.

Greater Woodstock VT Homes for Sale

The greater Woodstock VT area could be the perfect place for a family home, a vacation retreat, rental property or investment real estate. 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.

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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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$949,000

Est. Mortgage: $/month

MLS Number 4859269

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

Exquisitely 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 and a generous bedroom that could double as a home office, rental, or private guest quarters. There is a lovely Great Room 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 useful kitchen office area. The Family/TV room has an attractive Woodstock soapstone stove that comfortably heats the home. Round out the first floor with a practical mudroom, a sitting den, a formal dining room, & milled cherry flooring throughout. Privately located, the first-floor master bedroom en-suite boasts a Jacuzzi tub, large walk-in closet, and high ceilings with lots of windows that make the room sunny & bright. The second floor offers a second Master Bedroom en-suite, two additional bedrooms w/common bath, and a large storage area. Outside: Large wrap around deck, 2 car attached garage, sunny grounds, perennial gardens framing the brick walkways, and adjacent to Mt Tom's hiking trails & close to Suicide Six ski area. NEW ROOF going on the main section south side in August! Just 2-3 miles to town and the spacious living area make this an ideal family home. Be sure to view the 360 Matterport Virtual Tour!!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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4409 Route 106 Reading VT 05062

Reading, VT4409 Route 106

Price$895,000

Est. Mortgage: $/month

MLS Number 4863504

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,080

This traditional New England style home is sited on a plateau overlooking the surrounding hills and valleys with views ranging through east to south. The net metered solar array enjoys ideal exposure for full absorption of sunlight year round. The home offers a spacious primary dwelling with a connected, but private guest apartment each benefiting from 9' ceilings each with open floor plans illuminated with natural light. Energy efficiency and an outdoor lifestyle are the themes of this country property. The wood-fired hydronic boiler uses roughly 6 cord of wood in a heating season, which can be harvested from the land. A centrally located air-tight wood stove is a source of direct warmth distributed evenly throughout connecting the gathering rooms and second floor bedrooms with an open loft passage between them. Trails, gardens and a paved stone walk to a picnic area are wonderful amenities for active living. Privately located-not isolated just 4 miles from South Woodstock Village with Woodstock Village another 6 miles further. Mt. Ascutney State Park & miles of mountain biking are 10 minutes drive away.

Listed by Laird Bradley and Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

MLS Number 4871947

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

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: 2.8% last updated on Jul 29, 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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362 UPPER Road Bridgewater VT 05035

Bridgewater, VT362 UPPER Road

Price$835,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4741360

  • Residential Single Family
  • Construction Existing
  • Bedrooms 13
  • Bathroom 11
  • Square Feet 6,246

Perfectly suited for either residential or commercial use, this unique property is anchored around an antique cape farmhouse built when the township was founded. In an exceptional location, close to both the historic village of Woodstock and Killington Mountain Ski Resort, and within walking distance of the Long Trail Brewpub and the Bridgewater Corners Country Store; the beautifully landscaped four acre grounds feature an in-ground swimming pool with sheltered deck overlooking the Ottaquechee River Valley. The spacious, sunny, 6,200 square feet of living space is arranged into two sections connected by an enormous commercial grade kitchen. The larger section, continuously and profitably operated as October Country Inn since 1975, has 10 bedrooms, 11 baths, two large dining/meeting /game rooms, and a spacious living room. The other section, used as the innkeepers residence, has 3 bedrooms, 1 bath, office and private living area. A large semi-finished basement houses a commercial sized pantry, laundry area, large workshop and general storage. This property could easily be used as a private home for extended family, with room to grow into a special and affordable multi-generational family compound, or continued as a turn-key opportunity to step in and take over October Country Inn's long standing, excellent four decades long reputation for outstanding hospitality to the traveling public in the tradition of New England's country inns dating back over 200 years.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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299 Malagash Road Reading VT 05062

Reading, VT299 Malagash Road

Price$809,500

Est. Mortgage: $/month

Pending

MLS Number 4861892

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,600

C. 1800 brick cape sited on 38 acres overlooking its own vineyard and rolling southwest facing fields to a view of the church steeple in the nearby hamlet of S. Reading and distant hills beyond. The home has been extensively renovated including an expanded country kitchen with soapstone counters, Crown Point cabinets, and stainless appliances that is open to both the living room with fireplace and the dining room with wood stove. First floor master suite with custom walk-in shower, 2 additional bedrooms and 2 baths. Historic details throughout including hand hewn beams, and wide pine floors. Practical features include a recently added mudroom with half bath, a 4 season porch that opens onto the southwest-facing stone patio, a two story 18X42 barn / shop with humble living quarters above, a sugar house, and 1 bay garage. Grounds are complemented by stone walls, mature maple and apple trees, and the vineyard with 870 vines, a mix of 8 hardy northern varietals.

Listed by Seth Warren, Seth Warren Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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1111 Randall Road Woodstock VT 05091

Woodstock, VT1111 Randall Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4867287

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,686

This 5BR, 3.5BA home is located less than 3 miles from the Village of Woodstock on 25+/- private acres with a pond and a mountain view. Some of the many fine features include: recently renovated kitchen with an open floor plan to the dining/living room, master bedroom suite on the main level, a large private deck overlooking a large backyard and perennial gardens.

Listed by Herb Hart, Quechee Lakes Real Estate Center

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$795,000

Est. Mortgage: $/month

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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865 Kimball Farm Road West Windsor VT 05037
Pending

MLS Number 4871701

  • Residential Single Family
  • Village Brownsville
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

END OF DEAD END ROAD PRIVACY on 20+ acres on the mountain-side of Mnt. Ascutney. Surrounded and abutting 2,000 acres of State and Town preserved forest and trails in every direction. Classic style 3 bedroom, 3.5 bath single level living with a private in-ground pool facing directly up the mountainside! The Mt Ascutney Trail system let's you ride directly from the farm (on your horse/bike/hike), with miles of amazing trails right to the top of the mountain. You can even hop right on the VAST snowmobile trail system at the end of the driveway! There is a large wide pine floored living room w/cathedral ceiling and a gracious fireplace, and the spacious country kitchen has plenty of cabinets with a top of the line Hearthstone woodstove. The master bedroom has stunning views of the mountain with a private en-suite bathroom. Two other bedrooms and a full bath are just off a cozy Family Room den. The basement offers a large fitness room, a full bathroom, & separate laundry room. Additionally there is a covered porch & decks, garage, barn w/stalls, & run-in shed. The home is surrounded by cottage gardens, perennial beds, beautiful views & privacy, for a perfect mountain garden landscape. The newer barn is appr 38x60 w/200 amp service, a tack room, six spacious matted stalls, & storage for 1,000+ hay bales. Alternatively, turn the barn into living quarters. There is extensive split rail fencing & lovely rolling meadows. 12 miles to Woodstock, 20 miles to Okemo, 28 miles to Killington.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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5 Stanton Street Woodstock VT 05091

Woodstock, VT5 Stanton Street

Price$775,000

Est. Mortgage: $/month

Pending

MLS Number 4862204

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 2,928

Stanton Street Schoolhouse (circa 1840) is an architectural gem nestled in the heart of picturesque Woodstock Village! The captivating interior boasts a spacious main level that includes a farmhouse kitchen, two living rooms, dining room, an office/study, and mudroom laundry that are detailed with striking 10 ½ foot ceilings, 6 over 6 windows, hardwood floors, and exposed antique beams. The second level offers a splendid primary bedroom, 2 full baths, and 4 additional bedrooms! The wrap-around covered porch, backyard patio, and built-in firepit are perfect for entertaining and relaxing. Lovely level yard, stone walls and garden space complete this picture-perfect village property! Looking for walkability this property scores a perfect score. Dining, shops, the arts and recreation are just outside your door. Take a look and fall in love!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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2986 Webster Hill Road Barnard VT 05031
Active With Contract

MLS Number 4863804

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,784

Perched on a knoll just above a year round meandering stream in a very private setting of Barnard, this meticulously maintained home is everything a country home should be. The grounds are professionally landscaped with lush lawn areas populated with flowering trees and shrubs, stone walls and gardens. A large stone patio off the living room provides a perfect setting for relaxing and entertaining and a second stone patio off the walkout basement bedroom is certainly a bonus for guests. Recent improvements to the house are too numerous to list and include a complete kitchen renovation including all new appliances, exceptional master bath renovation, new gas furnace, new automatic whole house generator, air conditioning and so much more. There is a one-car attached garage plus a two-car detached garage with overhead storage. The property is a short drive to Barnard Village and Silver Lake, Suicide Six Ski Area and all the amenities of Teago including the Grange Theater, the newly renovated Teago General Store, Artistree Art Center and just a couple miles more to all the amenities of Woodstock.

Listed by Stan Butler, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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13 RIVER Street Woodstock VT 05091

Woodstock, VT13 RIVER Street

Price$725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4774015

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

This historic Woodstock Village home is a short stroll over the Elm Street Bridge from all amenities. The 1850 structure was conceived originally as a 'farm cottage'. The home was restored and re-imagined in a comprehensive renovation in the early 1980's with Arts & Crafts period design elements. Right-sized for today's small house movement the home is beautifully landscaped with a spacious yard providing ample room for outdoor entertaining and gardens. A detached antique barn offers potential for use as a studio or recreational activities. Rare opportunity to own a Village home offering modern systems with delightfully diverse spaces.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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 August 2, 2021.