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
  • Listing Agent Name Gretchjen Smith
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

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: 4.45% last updated on Jan 17, 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 Prospect Street, Woodstock, VT 05091

Price$499,000

Est. Mortgage: $/month

MLS Number 4722128

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Village Woodstock
  • Construction Existing
  • Bathroom 3

INCREDIBLE WOODSTOCK VILLAGE OPPORTUNITY! Built in 2012, this gorgeous three-bedroom home enjoys a spacious 1.36 acre lot within walking distance of downtown Woodstock village. With fine fits and finishes, light-filled rooms, a large yard, and an incomparable location, this village property lives wonderfully as a primary home. Efficient systems and a strong rental history also make this property incredibly attractive as a vacation property. Look no further - this is where you want to be.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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$479,000

Est. Mortgage: $/month

MLS Number 4691800

  • Residential Single Family
  • Listing Agent Name John Wetmore
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

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: 4.45% last updated on Jan 17, 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
  • Listing Agent Name Wendy Beach
  • Construction Existing
  • Bathroom 8
  • Bedrooms 6

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: 4.45% last updated on Jan 17, 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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530 Gabert Road, Woodstock, VT 05091

Price$450,000

Est. Mortgage: $/month

Pending

MLS Number 4676586

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2

GORGEOUS NEW CONSTRUCTION, CONVENIENT BUT PRIVATE! Just ten minutes from Woodstock Village and fifteen minutes from the Killington Skyeship Gondola, this exceptionally well-crafted and energy-efficient home is built with ease of ownership in mind. Gorgeous fits and finishes, an automatic generator, a two-car garage, and two bedrooms plus a spacious office/den/flex space make this home ideal for comfortably accommodating you and yours in all seasons. Enjoy sun-drenched westerly views from the gracious second-floor porch and walk to an expansive network of trails for hiking, biking, snowshoeing and nordic skiing. Located two houses from the end of a well-maintained but lightly traveled town road, the home is privately situated amidst extensive acreages. This is an uncommon opportunity to own a handsome, worry-free home in a classic Vermont paradise.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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 4628208

  • Residential Single Family
  • Listing Agent Name John Wetmore
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3

An absolutely turn key home, in a convenient and desirable Woodstock location! Well situated for access to either the world class equestrian activities of South Woodstock or for the numerous amenities of historic Woodstock Village. The immaculate interior is bright and inviting. The cape style residence features an open concept kitchen/dining/living room with an attractive cathedral ceiling and hard wood floors. The well conceived floor plan provides the practical advantage of the primary rooms of kitchen, living room, dining room, bedroom and full bath being located on the ground level. On the second floor is a large den that dramatically overlooks the living room. On this level is also a private bedroom and a bath. On the lower level is an expansive family room that opens to a generous size office/studio. Additional interior amenities of note are a tiled mud room, two well placed cast iron gas fired stoves, granite counter tops, and wall mounted air conditioning. The attached garage opens directly to the mud room, for those days of inclement weather. The owner has the property well fenced, to provide a large safe area for dogs to play. A traditional New England style home, with a well designed floor plan, in a desirable Woodstock location!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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
  • Listing Agent Name Lynne Bertram
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

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: 4.45% last updated on Jan 17, 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
  • Listing Agent Name Mary Mayhew
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

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: 4.45% last updated on Jan 17, 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$399,000

Est. Mortgage: $/month

MLS Number 4720654

  • Residential Single Family
  • Listing Agent Name Jennifer Falvey
  • Construction Existing
  • Bathroom 2
  • Bedrooms 5

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: 4.45% last updated on Jan 17, 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
  • Listing Agent Name John Wetmore
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

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: 4.45% last updated on Jan 17, 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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Woodstock, VT 05091

Price$396,810

Est. Mortgage: $/month

MLS Number 4690082

  • Residential Single Family
  • Listing Agent Name Eric Johnston
  • Construction Pre-Construction
  • Bathroom 3
  • Bedrooms 3

New three-bedroom home to be built on .93 acre lot in a great location in West Woodstock. Westchester brand home, conventional stick framed with detail to modern efficiency trends and finishes. Purchaser has choices of finishes, colors and details. All pictures are renderings of other finished projects. Close to Thompson Center, Woodstock Junior/Senior High School, Union Arena and the Woodstock Farmers Market. Just a short distance back to the center of town.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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
  • Listing Agent Name Andrew Holson
  • Village Woodstock
  • Construction Existing
  • Bathroom 2

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: 4.45% last updated on Jan 17, 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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Copyright 2019 Northern 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 19, 2019.