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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43 Pleasant Street Woodstock VT 05091

Woodstock, VT43 Pleasant Street

Price$500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4505862

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 4,146

This stately Victorian Home is conveniently located in close proximity to all that Woodstock Village life has to offer. Just a short stroll to the fabulous shops, restaurants, theatre and happenings on the Village Green. The gracious foyer entry has a sweeping oak staircase with period detail intact. The beautifully maintained, sun filled rooms are of generous proportion. Commercial grade kitchen for the chef in your house. There is a private, attached 1 bedroom apartment with separate entry that currently generates a handsome income stream. Pleasant, fenced outdoor space with stone footpaths and established gardens. Excellent family home, or ideally located for an in-home-occupation, or a great investment opportunity. Convenient to recreation, skiing, I-91, DHMC, VA, and Dartmouth.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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$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: 3.65% last updated on Jan 16, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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: 3.65% last updated on Jan 16, 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: 3.65% last updated on Jan 16, 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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93 Town Farm Road Woodstock VT 05071

Woodstock, VT93 Town Farm Road

Price$449,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4788380

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,596

Perfect location in the quaint neighborhood village of South Woodstock! Located on a town-maintained dead-end road and overlooking the venerable Green Mountain Horse Association grounds, this well-built classic cape is a perfect spot for enjoying the equestrian lifestyle of South Woodstock! From the garage, one enters into the laundry/mud room enhanced by local VT slate flooring. The dining area has wonderful custom wainscotting and features a delightful fireplace with wall sconces above. The kitchen is currently ADA-modified and features custom built cabinetry and great light. The living room/office/first-floor bedroom has polished wood floors and ample closet space with an accessible 3/4 bathroom. The deck from this room has raised garden beds for your convenience! Upstairs in the managable home are 2 additional bedrooms, one with its own walk-in closet and half bath. Addiional attic room could be finished for expansion. This home has attractive foundation plantings and some delightful tree specimens. The property also benefits from a 3000 sq ft "apple barn" which may be repurposed. Lovely local views of the Kedron Valley!

Listed by Susan Hickey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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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: 3.65% last updated on Jan 16, 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: 3.65% last updated on Jan 16, 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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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: 3.65% last updated on Jan 16, 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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Tucker Road Woodstock VT 05091

Woodstock, VTTucker Road

Price$339,469

Est. Mortgage: $/month

MLS Number 4706368

  • Residential Single Family
  • Construction Pre-Construction
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,760

New home situated at the end of the road with small stream. This Westchester model will be at hill's edge, southeast facing and a daylight basement. Lot could be kept wooded or opened up for more sun. Adjacent to a field and close proximity to the National Park and Town. Main floor master with guest rooms up. Come enjoy this new, efficient home! Photos of home are concepts!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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173 Peterkin Hill Road Woodstock VT 05091

Woodstock, VT173 Peterkin Hill Road

Price$339,000

Est. Mortgage: $/month

MLS Number 4762468

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,368

Lovely home with 10+ acres, large yard and a stream 4 miles from downtown Woodstock. Open floor plan flows from great room with fireplace and cathedral ceilings to dining room and updated kitchen with cherry cabinets, granite counters and breakfast bar out onto the deck overlooking the large yard. 3 bedrooms and 2 baths plus two rooms used as offices. Practical mudroom / entry area from the attached garage. Set back from a quiet dirt road but very convenient to downtown Woodstock.

Listed by Seth Warren, Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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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 January 22, 2020.