Woodstock Homes Under $500K

Woodstock is the quintessential Vermont town. It has a lovely downtown, a beautiful green, shops, grocery stores, galleries, and outdoor activities like biking, hiking, skiing, and snowshoeing. There are plenty of homes in Woodstock in or close to the village or on quiet roads that give you access to all of the town’s charms.

If you’re looking for a home to move your family to, know that Woodstock schools are outstanding. The high school offers challenging academic programs that build critical thinking in all academic areas and the development of fundamental skills.

Pentangle Arts, located in the historic Woodstock Town Hall Theatre screens first-run Hollywood movies. The Woodstock Recreation Center offers comprehensive recreation programs, facilities, and services aimed at improving the quality of life for all.

With all the amenities and conveniences you’d find in a large city, charming Woodstock, VT could be the perfect place for your family, a vacation retreat, or rental 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.

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5070 South Road Woodstock VT 05071

Woodstock, VT5070 South Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4771226

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,936

Charming renovated antique cape in historic village of South Woodstock. There is an attached 20x24 heated workshop/studio that can be used for various purposes. Walk to the country store and the Kedron Valley Inn for dinner. Short drive to skiing as well as trails for hiking , horse back riding and fishing in the Kedron Brook.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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42 River Street Woodstock VT 05091

Woodstock, VT42 River Street

Price$499,000

Est. Mortgage: $/month

MLS Number 4692838

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,930

A riverfront Woodstock Village home is not often available for sale! The tastefully remodeled interior, of this centrally located residence, benefits from mesmerizing views of the ever changing coloring of the Ottauquechee River. Being located on a level village street enables comfortable walking to all of the amenities of Woodstock Village life. Three finished levels of living space present multiple possibilities for use by family and guests. A private stone terrace and lawn areas oriented towards the river provide unique platforms, for outside relaxation. With 3 bedrooms and 3 baths, this manageable size home is the ideal weekend retreat or equally a comfortable year round village residence!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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 Lincoln Street Woodstock VT 05091

Woodstock, VT20 Lincoln Street

Price$495,000

Est. Mortgage: $/month

MLS Number 4736345

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,784

This energy efficient Geo-Barn is within walking distance of Village amenities and sited on a level 'double' lot with views overlooking Mt. Tom and Billings Farm. The open 'post & beam floor plan provides spacious. light-filled gathering rooms on the main floor with two private decks, a separate bedroom and office enabling single level living. Two sunny bedrooms on the second floor and a 'guest space' on the walk-out lower level provide flexibility for larger or smaller space demands with a total finished area of about 2400 sq. ft. There is potential VRBO income from the 'lock-out' lower area. The 'double lot' has been surveyed for subdivision and the property is offered with the home on .51 acre at $595,000.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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1880 Curtis Hollow Road Woodstock VT 05091

MLS Number 4783272

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,604

Rustic Vermont hunting lodge with spectacular mountain views on 66.5 acres. This corner lot (Mecawee & Curtis Hollow) boasts a 4 bedroom home that has been a 2nd home getaway and recreational playground for the same family since the 1950's. Inside, the large kitchen with counter seating opens into the dining area which flows directly into the long living room that is accented with a huge stone fireplace at the end of the room. Off the kitchen is the master bedroom with ensuite bath and through the living room are 3 bed and bunk rooms and another full bath. There is an enclosed porch which leads out to a wooden deck that overlooks the rolling fields and takes in the amazing views to the Northeast. Roughly two thirds of the property is wooded with the VAST snowmobile trail cutting through it. There are multiple streams that run through and along the property as well as old stone walls. Across from the driveway is the entrance to the Coolidge State Forest and a few miles up Mecawee Rd. is the Mecawee Fishing Club. It is only 10 minutes to Woodstock Village and just 25 minutes to the Killington Mtn. base lodge. This is a unique property with endless possibilities that can be subdivided. A must see!

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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700 John Darling Road Woodstock VT 05071

Woodstock, VT700 John Darling Road

Price$450,000

Est. Mortgage: $/month

MLS Number 4764458

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,196

Tucked away at the end of a one mile Class IV road on 10 very private acres bordered by the Woodstock Town Forest in very desirable South Woodstock. No traffic noise, only the sounds of the birds and the stream that meanders through the woods behind the house. The house is powered by state-of-the-art solar so power failures are never an issue and you never get an electric bill. The open format layout of the first floor creates bright unobstructed living space perfect for everyday living and warm friendly space for entertaining. All the details on most buyers' check lists are here: attached garage, large mudroom, huge pantry, three baths, three bedrooms, master bedroom with updated en suite bath and the world's largest walk-in closet and full walkout basement. Recent upgrades include: updated kitchen and pantry, new high efficiency propane boiler, totally updated solar system, new Kohler generator, new deck and new Jotul woodstove. The location of the property is perfect with the South Woodstock General Store, the Kedron Valley Inn & Pub and GMHA all just minutes away plus convenient to skiing, golf, snowmobiling, health club, and all the amenities of Woodstock Village.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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132 Shurtleff Lane Woodstock VT 05091

Woodstock, VT132 Shurtleff Lane

Price$449,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4661648

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,738

Super location! This well maintained home is in move-in condition, newly painted exterior with multi level decks overlooking a private backyard. Open floor concept with an abundance of light, gracious room proportions and perfect flow for entertaining. Located just a quick into historic Woodstock Green for all of towns amenities. Set back off a quiet dirt road with well landscaped lawns and gardens. First floor has handsome birch hardwood floors with a bright kitchen accented with granite counters and large island. Off kitchen is both a formal dining room and Living Room anchored with a gas fireplace. Two bedrooms or office on adjacent end of home with shared bathroom. Second floor has 2 large master suites. Lower level is a massive finished space with capabilities to be used in multiple functions- great light with french doors leading outside. This residence is a must see for buyers looking to be close to the village but home nestled in a quiet setting.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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8 BORDER Lane Woodstock VT 05091

Woodstock, VT8 BORDER Lane

Price$449,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4746811

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,373

A hidden gem! This serene home is filled with southerly light year round and has been comprehensively renovated with many new components: thermal windows, heating system, baths, kitchen, foam insulation, detached garage and extensively landscaped with a pan-Asian aesthetic. The residence is very privately sited on 5 acres of open and forested land in Woodstock Village and Town boundary. A massive 'butte' of exposed granite contributes to the great character of the property. Landscaped with perennials, water and exposed ledge and stones accented with mature northern hardwoods and conifer the land has delightful diversity. Single level living areas are accessed via a walk-out lower level entry at grade. Looking to downsize without compromise? This home should be on your list!

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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3903 Densmore Hill Road Woodstock VT 05091

MLS Number 4744616

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,792

Lovely 3 story cape nestled on a knoll overlooking a meadow with short range views. Super location situated between Woodstock and the Hamlet of South Woodstock and GMHA. Easy access to all of towns amenities, shopping, and skiing. This residence is immaculately maintained. Hardwood floors throughout. First floor includes a bedroom with full bath, open floor concept with generous size living room with cathedral ceilings creating a spacious feel- opening into dining and kitchen. Attached garage into mudroom for easy access. Second floor provides a loft and another guest bedroom with a full bathroom. Lower level functions as either a bedroom, family room and/or office. Easy access to outdoors with exterior exit. The house features: generator, A/C in LR and Master Bedroom, 2 gas stoves for ambiance, gazebo with electricity for afternoon lunches and quiet serenity for the true Vermont experience. Come take a look-

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

358 Cowdrey Path Woodstock VT 05071

Woodstock, VT358 Cowdrey Path

Price$419,000

Est. Mortgage: $/month

MLS Number 4746546

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,148

Charming move-in-ready house in a great location, privately situated in South Woodstock, just 7 mins to the Woodstock Green. Beautiful open floorplan between dining, kitchen and living room. Kitchen and dining have cherry floors and cabinets, granite countertops, lovely view out the kitchen sink window and sliding doors to the back deck for outdoor barbeques & playing in the back yard. The living room has sliding doors for lots of light, a gently vaulted ceiling and a wonderful gas fireplace that is visible from kitchen and dining areas. First floor den/office could also serve as a bedroom. Private powder bath on first floor. Upstairs is a master bedroom with walk-in closet and ensuite bath. Two other bedrooms share a hallway bath. Much of the basement has been finished off into a rec room area (that is presently used as a music practice and recording studio!). Neat, tiled-floor mud-laundry room with cubbies and hooks - is conveniently located on way in from the attached 2-car garage. Very good mechanicals and easy to maintain house. If you are looking for a move-in-ready house in a great location - this is it! Must see!

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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80 Blankey Cottage Lane Woodstock VT 05091
Active With Contract

MLS Number 4723058

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,772

This charming 4 bedroom/2 bath updated bungalow cottage with 1.5 acres on a quiet side street is within minutes of downtown Woodstock! Recent renovations and upgrades include a wonderful Great Room/kitchen addition, updated windows, shed dormer, peerless boiler, and 14kw propane generator. There is a lovely deck off the Great Room to enjoy outdoor entertaining and an open and private yard with plentiful space to enjoy both recreating and gardening. In addition this property has a two car garage and garden shed. Excellent opportunity for either a primary residence or vacation home!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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1021 Randall Road Woodstock VT 05091

Woodstock, VT1021 Randall Road

Price$395,000

Est. Mortgage: $/month

MLS Number 4750011

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,531

This well maintained recently built 3,500 sqft. 3 bedroom & office/2.5 bath classic New England style home is just 5 minutes to Woodstock Village & located on a peaceful dead-end road where you can enjoy views of distant hills during the day or starlit skies at night. There are rustic post & beam features, cathedral ceilings, & spacious, bright, light-filled rooms. The large expansive living space make this home perfect for entertaining family & friends. The kitchen (21x12) has quality cherry cabinets for plenty of storage, newer stainless steel appliances, and a huge entertaining island for more prep space. The open floor-plan Living Room (24x21) has a central fireplace for those cold winter nights, wide pine flooring, & built in bookcases will make you want to grab a book and escape for a bit. There is a pleasant dining area for intimate family gatherings. Everyone will enjoy the giant Family/Game Room (24x23), with pool table & foosball included. It's everything someone needs to visit Vermont & relax with friends. You can spread out onto the deck for views of the pond and enjoy the open land and stone walls that add character to this classic Vermont home. Ten minutes to GMHA, Suicide Six, or the Woodstock Country Club and a whole house propane generator is included & a full basement for additional storage. This home is located on land that was formerly a municipal landfill for a few years in the mid 60's (closed in the late 1960's).

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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5274 West Woodstock Road Woodstock VT 05091

MLS Number 4778694

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,058

Enjoy all the conveniences this property has to offer. Only 5 miles from downtown Woodstock and a short drive to many ski areas and local attractions. The expanded layout with recent upgrades includes the kitchen with granite countertops and ample space for cooking. Large living spaces on the first floor with stone fireplace to stay warm! Second level offers two bedroom, half bath, laundry and master suite with custom walk in closet and 3/4 bathroom and beautiful wood floors. Enjoy the back deck overlooking your 5 acres of manicured open pasture. The Ottauquechee River is across the street. The one car detached garage has plenty of space for storage or a workshop. There is even a cute sugarhouse that has running water and power!

Listed by Holly Hall, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

Save 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 November 12, 2019.