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.

132 Shurtleff Lane Woodstock VT 05091

Price$499,900

Est. Mortgage: $/month

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: 4.07% last updated on May 16, 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

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: 4.07% last updated on May 16, 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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5763 West Woodstock Road Woodstock VT 05091

MLS Number 4727726

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 6
  • Square Feet 3,180

This is an operating Bed and Breakfast that could revert to residential use as a second home, a ski home, or a rental property. The property enjoys proximity to downhill skiing, cross country skiing, golf, spa facilities, and a wonderful, historic Village. Perfect for gatherings for groups for celebrations and reunions.

Listed by Wendy Beach, Hearthside Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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195 Roberts Road Woodstock VT 05091

Price$469,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4691800

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,656

With 6.8 acres of mostly open pasture land, a well designed barn, desirable South and West exposure and close proximity to Mount Tom and the riding trails there is potential for this Woodstock property to be a small horse farm, or perhaps even the site for an organic farming operation! The well built home features a cathedral ceiling, wood burning fireplaces, pastoral views and the option for providing separate in-law accommodation! Conveniently located, in a quiet neighborhood, all the amenities of Woodstock Village are just short drive away!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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 2
  • Square Feet 1,792

Lovely home 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: 4.07% last updated on May 16, 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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358 Cowdrey Path Woodstock VT 05071

Price$439,000

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 and 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: 4.07% last updated on May 16, 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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168 Barberry Hill Road Road Woodstock VT 05091

MLS Number 4720375

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,740

Fantastic location for a family with a busy lifestyle or a single level living arrangement for an owner with additional space for guests on rental potential downstairs. Walking distance to schools, trails, ice/community arena, The Thompson Senior Center, and the Farmer's Market. Large deck overlooking beautiful stone work with perennial gardens. Spacious rooms, all season porch, family room w/ wood stove, and a living room with a wood burning fireplace. New propane heating system. Fresh, Light, Comfortable , Convenient, and Functional.

Listed by Lynne Bertram, Lynne Bertram Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

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: 4.07% last updated on May 16, 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 4715423

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

A well known local builder thoughtfully remodeled this home, as his own residence. The practical floor plan features a bright interior and primary rooms with generous dimensions. The first floor is anchored by a large eat-in kitchen, with ample workspace, on one end, and a wood floored living room, with stone faced fireplace, on the other end. In between these gathering places is an extended den/family room that opens to a covered porch. On the second floor, is an oversized primary bedroom suite, with dressing area, en-suite bath and walk-in closet. A second large bedroom is privately located at the opposite end of the hall. Located in between is an office or a child's bedroom. The 5 acre lot features a large, level and sun lit lawn surrounding the home and space for keeping animals or gardening. The detached garage has served well for both car storage and as a carpenter's workshop. An old sugarhouse presents the opportunity for a second, detached workshop or perhaps an artist's studio! A well designed living space, in a location convenient for access to skiing at Killington, or for enjoying all the amenities to be found in Woodstock!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

1021 Randall Road Woodstock VT 05091

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/3 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 & 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 formerly was a municipal landfill (closed in the 1960's). Sale is subject to new owner assuming a preexisting lease from July 25th to Sept 25th.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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1 HIGH Street Woodstock VT 05091

Price$389,000

Est. Mortgage: $/month

MLS Number 4720654

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 5
  • Square Feet 2,170

This beautifully renovated multi-use property offers an unique opportunity to live and/or work in-town while collecting an income from a rental unit. There are two units. The ground floor unit has three bedrooms, a welcoming eat-in kitchen with brand new stainless steel appliances and soapstone countertops and a roomy sun-filled living room. All of the rooms could easily be used as office space. The second floor unit has two bedrooms, an eat-in kitchen and a cozy living room. Both units have a proven record of reliable income. This property is steps from restaurants and shopping in town and just down the street from Mount Peg hiking trails..

Listed by Jennifer Falvey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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69 South Street Woodstock VT 05091

Price$369,000

Est. Mortgage: $/month

MLS Number 4729023

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

Charming in-village residence, walk-to-town, near Vail field, Mt. Peg hiking trails, The Woodstock Inn Golf Course and Athletic Club and more. The circa 1890 house features two entrances - from the covered porch walk directly into the nicely updated kitchen, and a second entrance enters the mud/laundry room and through the half bath. A spacious dining room (with gas stove) has a glass sliding door for easy access to a flat backyard space. Downstairs also has a cozy living room. Four bedrooms and one full bath are on the 2nd level. Pleasant views looking out over the Golf Course to Mt. Peg. One car attached garage with storage above, and plenty of additional parking space located in the driveway.

Listed by Andrew Holson and John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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 May 22, 2019.