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

20 RIVER Street Woodstock VT 05091

Woodstock, VT20 RIVER Street

Price$995,000

Est. Mortgage: $/month

Active With Contract

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: 3.24% last updated on May 21, 2020
* 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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4662 Cloudland Road Woodstock VT 05091

Woodstock, VT4662 Cloudland Road

Price$985,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4781136

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,452

Premier location just 1 mile to Woodstock village on Cloudland Road just up from River Road and a pleasant walk to the village. High speed fiber-optic internet and good cellphone signal. Privately situated in a well-landscaped setting is this immaculately maintained newer construction 3,154 sf 3 bedroom cape with vaulted ceiling mini-great room open to lovely gourmet kitchen with custom-made cherry cabinets. A charming dining area is next to kitchen. Half bath and mudroom at entrance. 1st level MBR with ensuite bath, two bedrooms a sitting room and full bath upstairs. Partially finished basement has a workout/TV area and office. Just across the driveway from the cape is a barn-garage with two bays of garage with overhead doors, a third covered bay for vehicles and equipment, and upstairs is a 1,298 sf fully finished in-law apartment with vaulted ceiling, kitchen, bath, dining, sitting area and bedroom with ensuite bath - all with its own entrance and two-level private deck area. Property has a brook flowing through it and is well landscaped with stonewalls, a charming patio, flower gardens and a garden shed with chicken coop. Excellent mechanicals in both buildings. Beautifully maintained, privately and peacefully sited on approximately 5 acres - exceptionally located 1 mile from the Village of Woodstock. High speed internet and good cellphone signal.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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 Linden Hill Woodstock VT 05091

Woodstock, VT5 Linden Hill

Price$725,000

Est. Mortgage: $/month

MLS Number 4772701

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 4,250

An exceedingly rare opportunity for Woodstock Village: antique 1850's house converted to 4 units in early 1970s and then renovated to a fine functional and aesthetic condition in 2000 while still preserving its 4 unit status. The largest apartment (8 rooms, 4 BR, 3 1/2 BA) occupies three levels of the original house, and enjoys rooms of generous proportion, high level detailing and fixtures, and fine interior finishes. Apartments either side (one of 5 rooms, 2 BR, 1 BA; the other of 3 rooms, 1 BR, 1 BA) have interconnected passage with the main apartment to allow substantial quarters of three discrete spaces for family or friends, or the passages may be closed off for independent use. A 4th apartment (4 rooms, 2 BR, 1 BA) has separate entry off terraced private lawns in the rear. All apartments have private entries, complete kitchens, wood burning fireplaces, separate utility capability, and share use of a generous common parking area. Walk to Village Center and all its many amenities!

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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5070 South Road Woodstock VT 05071

Woodstock, VT5070 South Road

Price$700,000

Est. Mortgage: $/month

MLS Number 4771226

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,800

Completely renovated antique cape located in the historic village of South Woodstock . This classic cape dating to 1850 is being totally renovated with state of the art new kitchen, downstairs master bedroom with new bathroom. Upstairs two bedrooms with new shared bathroom. Open floor plan living room/dining room with french doors leading out to a very private well landscaped back garden/lawn. A special opportunity to own an antique home with all new systems .

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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 4786056

  • 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: 3.24% last updated on May 21, 2020
* 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$698,000

Est. Mortgage: $/month

MLS Number 4774015

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 3
  • Bedrooms 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: 3.24% last updated on May 21, 2020
* 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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457 Peterkin Hill Road Woodstock VT 05071

Woodstock, VT457 Peterkin Hill Road

Price$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4774508

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,360

Stunning long range mountain views on nearly 40 acres of mostly open level field/pasture and woods with a stream on a very desirable road with substantial neighboring properties in Woodstock just 11 mins to the Woodstock Green. An authentic three bedroom log cabin with open kitchen-dining-living area and covered porch all look out at the really amazing long-range mountain view. A sun porch, three bedrooms and two baths with a full concrete basement complete the log cabin itself. Nearby is a post-and-beam barn-office space, insulated and heated with overhead door, plus a separate large garden shed for storage of all kinds of outdoor toys, equipment, gardening supplies. The mostly level / gently sloping fields create a big playground, an area for gardens or animals, and/or a second building site with easy access further back on the property, which would also share the stunning long-range mountain view. Very rare opportunity to buy this kind of land and view with a charming and very livable log cabin, with lots of potential for renovations or new construction in a great location in Woodstock at an attractive entry price point.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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$669,000

Est. Mortgage: $/month

MLS Number 4798290

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

Excellent multi purpose- In-Village opportunity. 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 potential for 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: 3.24% last updated on May 21, 2020
* 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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6656 South Road Woodstock VT 05071

Woodstock, VT6656 South Road

Price$650,000

Est. Mortgage: $/month

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located on the southerly side of South Woodstock across from the Green Mt. Horse Association, with direct access to miles of horse riding trails. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, lovely gardens and playground.The homestead includes a guest apartment periodically rented, and additional potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

Woodstock, VT326 Hall Circle

Price$599,000

Est. Mortgage: $/month

Pending

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: 3.24% last updated on May 21, 2020
* 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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154 Deer Brook Way Woodstock VT 05091

Woodstock, VT154 Deer Brook Way

Price$575,000

Est. Mortgage: $/month

MLS Number 4656716

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,184

Beautifully detailed colonial built in 2004 with dramatic views is an excellent value priced under the town assessment. Open , easy flow with lots of natural light . Rolling meadows ,lovely grounds with mature landscaping and views to the south and west. Basement has ample room with high ceilings for workout space , workshop or whatever the buyer chooses. Short distance to Killington for world class skiing. Less than 10 minutes to historic Woodstock Village, named one of the most beautiful small towns in America.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

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: 3.24% last updated on May 21, 2020
* 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 2020 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 May 24, 2020.