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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1522 Curtis Hollow Road Woodstock VT 05091

MLS Number 4743887

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,816

Well maintained custom Colonial being sold for the first time. Situated on a peaceful country road with access to abundant land and forest. Spacious and pleasing floor plan, open kitchen appointed with granite tops, custom cabinetry and slate flooring. The living room has 18-foot ceilings creating a view from the upper loft. The ground floor master bedroom suite is accented with a large full bath with both step in shower and a jetted tub and plenty of closet space. Three bedrooms and two more bathrooms are upstairs and a bonus room for guests, crafts or recreation. The large basement could also be partitioned if needed. For extra storage or recreation/farming there is a 28x38 pole barn. The land has a gradual slope which could be cleared for agricultural use. This property is currently subject to and benefits from a current use plan. Come enjoy the covered porch, hear the stream while relaxing and absorbing the local views.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l 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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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

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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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275 Iver Johnson Way Woodstock VT 05091

Woodstock, VT275 Iver Johnson Way

Price$479,000

Est. Mortgage: $/month

MLS Number 4797143

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,796

A complete, professional renovation, from the roof to the basement!! Newly created is the often sought, but seldom found, turn key residence! On the exterior is a new roof, new exterior painting, a new deck to view your large pond, all new electric service and jetted septic. Inside the sun filled residence is all new wiring and lighting, all new plumbing, all new flooring, new bathrooms, new furnace, 3 wood burning fireplaces and a beautifully appointed new kitchen! An oversized attached 2 car garage is a desirable amenity. Either entering from the attached garage or through the front door it is immediately apparent the interior is bright and welcoming. A spacious entry room, with attached half bath, leads to the south facing kitchen. Adjacent to the kitchen is a sun filled dining area with stylish wood burning fireplace on 1 side and comfortable bench seating on the opposite wall. Opening from the dining area is a living room with another wood burning fireplace and doors that lead to a south facing deck overlooking the pond. Completing the ground floor are 2 bedrooms, a full bath and an office/study. The opportunity presented for single level living, with all the principal rooms on the main level, is very practical. The surprising lower level features a laundry room, bedroom, a family room, a den with a wood burning fireplace, a study/office, a utility room and a heated workshop/storage room. A turn key home to serve equally well as a full time residence or vacation retreat!

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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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: 3.5% 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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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: 3.5% 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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117 Evergreen Court Woodstock VT 05091

Woodstock, VT117 Evergreen Court

Price$399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4797598

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,720

Log cabin with river view less than a mile to the Woodstock Village Green. This cabin has had many recent updates. With open charm and space, enjoy sitting in the living room with cathedral ceilings and views west over the Ottauquechee River at sunset. Covered porches, open yard, and large garage, all add to the charm of country living next to the village. The lower walkout living space is ready for your finishing touches completing the third bedroom and a recreation area. Come enjoy this surprising oasis.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l 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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3903 Densmore Hill Road Woodstock VT 05091

MLS Number 4792333

  • 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- Motivated Seller

Listed by Gretchjen Smith, 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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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: 3.5% 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

69 South Street Woodstock VT 05091

Woodstock, VT69 South Street

Price$349,000

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 Dan Noble, 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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2943 Cox District Road Woodstock VT 05091

Woodstock, VT2943 Cox District Road

Price$225,000

Est. Mortgage: $/month

MLS Number 4724970

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 4
  • Square Feet 1,014

Price reduction!!! Four bedroom home in Woodstock Vermont is ready for move in. The owner is eager to sell. This house has a deck off the main living area. The kitchen has a back door that opens to the covered patio and 2 plus acre and very private yard. Upstairs on the main level are three bedrooms and one bath plus the kitchen and living area. Downstairs is the walkout basement and another bedroom. Laundry hookups, water heater and oil furnace are downstairs also. The house is very clean with all new paint and floors. Metal roof, stone walls, outbuilding and more add to the value of this bargain priced home. Convenient to town and route 4, this great private parcel is only a little over a mile to the Woodstock High School. The kids can bike to school! Nestled in its own private oasis of stone walls, woods, and a big green lawn, this homestead is the perfect spot for gardening, beekeeping, chickens, kids playing, kayak storage, and lots of quiet. Don't miss this affordable chance to be part of the Woodstock community. Located on beautiful Cox District Road.

Listed by Jackie Jameson, Jameson Real Estate Agency

$
$
%
$/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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2663 Route 4 Road Woodstock VT 05091

Woodstock, VT2663 Route 4 Road

Price$205,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4778665

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 2,000

This property is in a commercial zone but can be used as residential. There is a Right of Way off of Route 4 to the property and a Right of Way to the Ottauquechee River. The buildings have historic value and a very interesting history. A great opportunity to have a business and to live on site . The structures offer a variety of use possibilities. There is ample space for extensive parking. Only minutes from Woodstock Village and less than 20 minutes to the lower gondola for skiing at Killington.

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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1097 West Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4795824

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,392

The beauty and detail of this Classic Woodstock home is showcased throughout. A completely renovated and thoughtfully re-imagined Circa 1790 vintage home is move in ready . Its timeless character, with modern vintage charm makes this house a forever home. Nestled within picturesque Woodstock Vermont. The home is near the Farmers Market and within the most coveted school district Vermont has to offer. The brilliantly reappointed antique marvel is complete with a private back yard and a brook! Head inside through the inviting bright and airy living room, with hand-hewn exposed beams and original wide plank floors. The rustic farmhouse of yesterday, revived with whimsical country chic abandon. A completely reappointed kitchen- highlight new custom concrete counter-tops, farm chic cabinetry and state of the art stainless-steel appliances! First floor living at its best, with its very own sun drenched bedroom and full bathroom show casing a vintage claw foot tub, bright white subway tile and shower! Two additional spacious bedrooms reside on the second floor with an equally marvelous shared bath. Modern amenities complimented by nostalgic flair. Enjoy your morning coffee on the brand-new back deck, perfect for entertaining, barbecuing, and relaxation! Includes a brand new furnace! The wonders of Woodstock, showcased with historic charm and detail are endless. This house will not last long- schedule your showing today!

Listed by Hergenrother Realty Group and Daniel Preston, KW Vermont

$
$
%
$/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.