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

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

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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57 River Street Woodstock VT 05091

Woodstock, VT57 River Street

Price$995,000

Est. Mortgage: $/month

MLS Number 4791575

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,075

Beautiful Woodstock home located in the heart of the village. The backyard adjoins Mountain Ave, the most prestigious street in Woodstock. Known as "The Prettiest Small Town in America." A Rockefeller town, renowned for it's rich history. This is a renovated 1826 home. The seller has updated and finished the property in the most remarkable way. His keen sense for detail, makes this property extremely unique. This home is filled with light, creating a very happy and peaceful atmosphere, and is move in ready. If you have been dreaming about purchasing a home in Vermont, then this is the one for you. 20 minutes to Killington, Okemo and to Dartmouth hospital. Call now to view this property!!!

Listed by Dorothea Mongulla, High End Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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

MLS Number 4781136

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

Premier location, location, location - on Cloudland Road just up from River Road and a pleasant walk to Billings Farm and downtown Woodstock for amazing bike riding, walking, and running right out the door. 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 less than three mins from the Village of Woodstock. This one is all about move-in-ready, and location location location.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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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206 Meoki Way Woodstock VT 05091

Woodstock, VT206 Meoki Way

Price$929,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4799170

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,484

Wonderful, award-winning 4 BR, 4 BA newer construction VT barn house on 5.5 acres, located less than a mile from Woodstock Village Green. Winner of 3 top awards from the VT Assoc of Home Builders in 2012 including Best in Energy Efficiency, Best in Environmental Excellence, and Best Single Family Home. The Ambrose-built home is architecturally designed to maximize natural light throughout the living space. The interior decor blends reclaimed 150-year-old Vermont beams with totally modern amenities. It has large windows, eight foot doors, nine foot ceilings and an atrium open all the way to the cupola 35 feet above the first floor that floods light down through the interior spaces. A wood burning stove and first floor radiant heat keep it warm and cozy. Random width hard wood ash floors. Classic covered porch has views over a neighboring pond. The present owners did extensive renovations over the past 3 years including a new gourmet kitchen, appliances, upgraded bathrooms, and completely finished the lower level into finished living space with an additional bath. The exterior is designed for low maintenance. Extensive use of closed cell foam and blown cellulose insulation all contributed to making this a highly efficient home. Tesla vehicle charger is in place. The residence is being offered turn-key and fully furnished. All of the furnishings were purchased less than three years ago by the present owners, and are perfectly suited for the home.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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

Active With Contract

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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: 3.5% last updated on Mar 26, 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: 3.5% last updated on Mar 26, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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: 3.5% last updated on Mar 26, 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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32 The Green Street Woodstock VT 05091

Woodstock, VT32 The Green Street

Price$549,900

Est. Mortgage: $/month

MLS Number 4766737

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

Prominently situated, at #32 the Woodstock Village Green, is a circa 1803 traditional style home, with a tastefully renovated contemporary interior! From the covered front porch a resident can enjoy the relaxing pleasure of viewing the beautiful brick Woodstock Town Hall, the impressive neighboring stone church, or the passing activity of village life. From this central location the residents conveniently walk to the numerous Woodstock amenities of shopping, dining and cultural events. The stylish interior living space encompasses 3 levels! The ground floor is entered from either the front porch or through a rear entrance, with a foyer. A more open floor plan features a bright kitchen with adjacent dining area, a comfortable living room, a den, the entry foyer and a 3/4 bath. On the upper floor is the primary bedroom, with en suite full bath, 2 additional bedrooms and a 3/4 bath. The lower level is dedicated to fun! The lower level family room and bar area are either accessed from an interior stairway or through an exterior door that opens to a below street level courtyard. The owners have achieved an impressive history of rental income, with this desirable property!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 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 March 29, 2020.