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 an investment property.

It’s also what Woodstock offers beyond beautiful homes that makes 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 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.

25 The Lane Woodstock VT 05091

Price$999,999

Est. Mortgage: $/month

Active With Contract

MLS Number 4663484

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 4,866

EXCEPTIONAL 14 ACRE PROPERTY, MINUTES FROM WOODSTOCK VILLAGE. Beautifully constructed with custom details like gorgeous millwork, Brazilian cherry floors, nine-foot ceilings, gracious family rooms, and a massive granite fireplace, this spacious home is perfectly equipped to accommodate your family and friends in comfort and luxury. Two ponds, a contemporary barn, an antique barn on a fieldstone foundation, an open-air cottage, an automatic generator, an oversized two-car garage, and a finished lower-level family room make this home the perfectly equipped Vermont retreat. A screened breakfast room opens off the gourmet kitchen, and a generously proportioned mahogany-floored porch runs the length of the house - the ideal spot for breezy summer days spent admiring the long-range views to Killington. The first-floor master suite offers his and hers walk-in closets, a steam shower, and a claw-foot tub, and each of the three ample guest bedrooms enjoys an en suite bath. With flexible spaces and the potential for additional square footage, this home checks all the boxes!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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20 RIVER STREET Woodstock VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4707913

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

A superbly renovated FEDERAL-STYLE FARMHOUSE sited overlooking a sloping lawn fronting on a tranquil stretch of the Ottauquechee River. Viewed from River Street, the front porch retains the appearance of the long time configueration as a 'twin home', before the two sides were graciously reconnected in a return to the original design and layout. The floor plan features spacious main level rooms with Master Suite, Eat-in-Country kitchen, living-dining room a secluded study and wonderful 'river room'. The second floor offers 4 bedrooms and two mirrored bathrooms. Privately situated and tastefully landscaped with native plants and shrubs. A classic Village home within walking distance of all popular amenities and activities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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739 Westerdale Road Woodstock VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4728514

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,960

Constructed in 2003, this custom home on just under 11 acres of beautifully manicured land was designed with the vernacular architectural style of Vermont barns in mind and enjoys a location that is convenient to Woodstock Village and nearby Killington and Okemo ski resorts. The center of the open interior floor plan house is a magnificent Great Room with oversized windows, high ceilings, cherry floors and a granite hearth with gas stove. The Great Room opens onto a mahogany deck that overlooks established perennial gardens, stonewalls, a brook fed pond stocked with trout and mountain views to the south. A chef's kitchen with granite counters, cherry cabinetry, a generous center island work space and stainless appliances opens onto an inviting south facing sunroom with a vaulted ceiling and oversized windows. Three bedrooms and two baths on the second floor long with 1600 sqft of additional space ready for finish in the lower level & heated, attached, direct entry 3 car garage.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 Church Street Woodstock VT 05091

Price$945,000

Est. Mortgage: $/month

MLS Number 4698660

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,909

EXTRAORDINARY RIVERFRONT HOME IN WOODSTOCK VILLAGE! Incomparably situated on nearly an acre of gorgeous lawns with direct river access and views of Mt. Tom, this historic village home has been impeccably updated and maintained. An open and airy kitchen boasts a gorgeous La Cornue range and a new Sub-Zero refrigerator - ideal for entertaining. Central air conditioning, a generator, and a new standing-seam roof make the antique home comfortable in every season. Large upstairs room provides flexible space for guest accommodation, a home office, or a play room. Walk to everything in New England's most beautiful village from this matchless Woodstock home.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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1040 Dunham Hill Road Woodstock VT 05091

Price$925,000

Est. Mortgage: $/month

MLS Number 4705269

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,282

Price Reduction! Incredible, breath-taking views of Killington and the Green Mountains from every room in this home. Every detail of this custom built Post and Beam masterpiece was carefully thought through by the owner/builder, a timber frame master craftsman. With an open floor plan, the main level of this magnificent home has a fabulous well equipped chef's kitchen with energy efficient appliances, plenty of cupboards for storage, a lovely dining space, and an expansive Great Room with field stone fireplace and soaring cathedral ceilings. The first floor master bedroom suite has spectacular views from its own private deck, cathedral ceilings, and master bath with walk-in shower, soaking tub, and double sinks. Two large second floor bedrooms provide plenty of space for a growing family, or hosting family and friends. The mostly finished basement is waiting for your finishing touches and pricing includes a generous allowance to wrap up the details and flooring choices. Top quality materials throughout this home with advanced systems and radiant heat. Separated from the main living spaces by a generous mudroom/laundry area, is a finished and over-sized 2 car garage to complete the package. A fantastic opportunity to enjoy the beautiful Vermont scenery only 2-3 minutes to the Fitness Center and 5 minutes to Woodstock Village. A great place to enjoy Vermont as a vacation retreat. Come see what this impressive home has to offer!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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125 Hoadley Road Woodstock VT 05091

Price$885,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4631074

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,793

A handsome timber frame house situated on 78 acres of open and wooded land protected by conservation easement., designed to take advantage of privacy,quiet, an overflowing spring-fed pond and year round brook. Splendid solar exposure for great natural light .Living Room/Dining Room and Kitchen all open to each other and provide wonderful access to 4 decks opening to the pond, brook, and lovely perennial gardens. Kitchen features high quality appliances , custom cherry cabinets, with island/bar to provide a great gathering space while cooking and entertaining. Main level bedroom with bath , spectacular 2nd level master suite with cathedral ceiling, sitting room, balcony, walk-in closets and luxurious bath. Lower level consists of bedroom suite with sitting room and kitchenette. Exceptional grounds include trails for hiking, horseback riding, 24x28 barn could easily accommodate horses for this property which is in the center of the spectacular Green Mt. Horse Assoc. trail system. Just a short stroll to the village of South Woodstock and a 5 minute drive to the Woodstock Green. Convenient to skiing, spa, fitness center and recreation.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Price$749,000

Est. Mortgage: $/month

MLS Number 4721629

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,349

This exciting property offers 4 bedrooms, 3.5 baths, and is a scant 3 miles to Woodstock village and minutes to skiing. There is a two-stall horse barn with fenced pasture on this 5.2 acre level lot with power, water, and insulated tack room abutting riding/walking trails. This home features easy transitions between indoor and outdoor spaces and is perfect for entertaining: a screened lounge, country porch, patios and decks surround an in-ground pool. Professional landscaping has maintained the mature perennial beds. The spacious master bedroom takes full advantage of the beautiful pastoral view and has a Jacuzzi tub and walk-in closet. The generous, yet cozy, family room has a fireplace, pine floors and natural light from the many windows. The efficient kitchen has dual ovens & stone counter tops. Plenty of storage throughout, plus mudroom with laundry. Work from home? The detached two car garage has a heated office with separate entrance, plus a workshop. Built in 1981 with addition/renovations 1996. Broker owned.

Listed by Geoff Eckler, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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229 Blankey Cottage Lane Woodstock VT 05091

MLS Number 4706007

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4,084

Best of both worlds!! Located just 1 mile from Woodstock Village, yet on 3.38 private acres at the end of a town maintained road with spectacular views of Killington and Green Mtns. The first floor is handicap accessible and consists of an open kitchen with center island and an eat-in dining area, large living room with stone fire place, beautiful sun room with views and 3 bedrooms. The master suite, with 3/4 bath, has spacious walk-in closets and opens onto the lovely 48 foot deck running along the backside of the house. The two additional bedrooms share a full hallway bath and first floor laundry is close by. First floor also has a mudroom, 1/2 bath and opens into heated 2 car garage. There is a partially finished lower level basement that opens onto the backyard and has a plummed bathroom and extra storage room. Lastly, there is a detached garage/workshop with a second floor for storage or potential living space.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Price$699,000

Est. Mortgage: $/month

MLS Number 4698305

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 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: 4.17% last updated on Apr 18, 2019
* 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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353 Cabot Road Woodstock VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4737344

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,542

A very comfortable Woodstock home, beautifully sited, on 18 acres, to enjoy long views and substantial sun light! The practical floor plan features a primary bedroom suite, with ensuite bath and walk in closet, on the first floor. For convenience, in Winter weather, direct access from an oversize garage leads into a long mud room. The living room is designed for entertaining! This central gathering area is anchored on one end, by a dramatic stone fireplace, features wood beams overhead, and ever changing pastoral views over a large open field, toward distant hills. The first floor is completed with a view oriented dining room, a well designed kitchen and a formal entry foyer. On the second floor are 3 bedrooms, full bath and a den. A full basement provides multiple areas for workshop space and has a fully finished office space, with a private walk out entrance. An inground swimming pool provides Summer entertainment. The diverse land is comprised of both acres of open land and a sugarbush with a sugarhouse structure. A beloved family homestead that is waiting for its next generation of occupants.

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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326 Hall Circle Woodstock VT 05091

Price$689,000

Est. Mortgage: $/month

MLS Number 4691364

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,949

Privately sited and superbly maintained, this timber-framed New England style home offers incredible southerly views over the Ottauquechee River Valley. You can enjoy watching the lights of Woodstock Village a mile distant from every room. The home was constructed by one the areas finest post and beam builders using traditional mortise and tenon joinery on display throughout. Spacious common areas all open onto patios and decks on each level of the residence. Generously sized bedrooms and well-appointed baths provide private space for family and guests. This wonderful and quiet country setting is just minutes from restaurants, recreation offerings at Suicide Six Ski area, Woodstock's Golf Course, Athletic Club and all resort amenities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 A VisitAsk A QuestionMore Details

10 North Street Woodstock VT 05091

Price$655,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4685781

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,872

AN EXTRAORDINARY WOODSTOCK OPPORTUNITY - walk to everything in Woodstock village and enjoy the Marsh-Billings-Rockefeller National Park trails on Mt. Tom from your own back yard! This four-bedroom, three-and-a-half bath antique cape was renovated and expanded in 2007 and includes a sunny great room and a two-car garage. The uncommonly expansive lot - nearly an acre - abuts the Marsh-Billings-Rockefeller National Park, making it ideal for hikers, walkers, cross-country skiers, snowshoers, families, retirees, dog-owners, and general outdoor enthusiasts. The house has been thoughtfully enlarged and updated with an emphasis on light-filled rooms and gracious spaces for gathering and relaxing. The generous family room enjoys views of the grounds and the protected park land beyond, and the spacious kitchen opens onto a delightful screened porch and stone patio. With ample space to accommodate friends and family and an incomparable location, this Woodstock village home is as rare as it is wonderful. Don't miss it!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 A VisitAsk A QuestionMore Details

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Copyright 2019 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 April 25, 2019.