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.

View all Homes for Sale in Woodstock

4587 South Road Woodstock VT 05071

Woodstock, VT4587 South Road

Price$475,000

Est. Mortgage: $/month

MLS Number 4854293

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,839

Fully renovated from top to bottom in 2021 this 2 bedroom 2 bath home is turnkey. The first floor has a brand new kitchen with all new appliances, cabinets and counter tops. There are also new wood floors throughout and all new windows and doors (interior & exterior). The living room and dining room both have French Doors opening onto the full length insulated and heated porch. The bathroom is also completely new with a beautifully tiled shower and includes a new washer and dryer. All wiring, lights and switches have been replaced. Upstairs, the two bedrooms and renovated bath have new windows and the floors have all been redone. On the outside, the house has all new siding and a brand new roof. There is an antique barn next to the house with parking and ample storage. The large level yard has mature trees and offers great space for gardening and recreational activities. Located in the quaint Village of South Woodstock, you are a very short distance to the Kedron Valley Inn/Ransom Tavern and the South Woodstock Country Store. GMHA is just down the road and Woodstock is only 5 miles away. Snowmobile trails and the Kedron swimming pond are at your fingertips. Village life at its best. A must see!

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$471,405

Est. Mortgage: $/month

Active With Contract

MLS Number 4706368

  • Residential Single Family
  • Construction Pre-Construction
  • Bedrooms 3
  • Bathroom 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: 3.04% last updated on Apr 15, 2021
* 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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27 Maple Street Woodstock VT 05091

Woodstock, VT27 Maple Street

Price$439,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4825598

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2

A large home well located in one of Woodstock's favorite neighborhoods! Come enjoy level surface walking as you stroll to the numerous amenities for which Woodstock Village is beloved! For generations, children in this neighborhood have walked to the Elementary School and the Vail Field Playground. A pleasant side yard, with unexpected length and width, is bordered by the picturesque Kedron Brook. Across the brook is the Woodstock Country Club golf course. The floor plan of the residence presents flexible options for enjoying the interior. Passing through the front door you enter into a comfortable living room, with a practical office area at the further end. That office area opens to a dining area with an inviting country kitchen adjoining. These 3 rooms are obviously the heart of a well loved home! This kitchen is truly a delight! Just off the dining room a set of French doors open to a ground floor in-law apartment complete with sitting room, bedroom, full bath and kitchen. This apartment area could function equally well as a private yet convenient in-home office space! The 2nd floor can be accessed by either a front or a rear staircase and contains 4 bedrooms and a full bath. The primary bedroom is just off the front stair case and has a sitting room attached. The other family bedrooms are each unique and equally comfortable. To the rear of the home is a deck with a hot tub. To one side of the home is a fire pit area. Having neighbors provides a sense of well being!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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1104 West Woodstock Road Woodstock VT 05091

MLS Number 4841891

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,630

Well maintained and West Woodstock Village Home. Formal dining room with hardwood floors, large living room with nice light, eat-in kitchen with adjacent pantry and large mudroom. This property also features a rear addition connected to the house featuring a separate entrance, two large office/work spaces,finished basement, large barn and a great level yard for gardens or play. Near the Woodstock Farmers Market, the Middle and High School plus the Union Arena. Closing after May 31 or sooner subject to existing Lease

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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1122 Peterkin Hill Road Woodstock VT 05091
Active With Contract

MLS Number 4808425

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,100

The location doesn't get much better than this! One of Woodstock's premiere roads, this cottage is tucked behind a handsome old stonewall and surrounded by a small meadow filled with sun and fern groves. Very private and quiet. Lots of sugar maples available to tap for those sugaring enthusiasts. Need more living space, add on! A large garage with both an upper and lower storage area or workshop. The cottage is an open concept for easy entertaining... with slider doors onto a back deck for the afternoon sun or late night barbecue with friends. There is a small bedroom/office on the first floor just off the LR. Upstairs is a large bedroom/loft with skylights providing lots of ample light into this space... Easy access to both historic Woodstock or the hamlet of South Woodstock. Skiing, snowmobiling, fishing and golf just minutes away. This cottage is the perfect hide-away retreat!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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442 East Woodstock Road Woodstock VT 05091

MLS Number 4840144

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,190

Looking for a hip, contemporary space in a cool mixed use condo? There is only one such space in Woodstock, and it has never been on the market before!! Airy, tranquil, and quiet; this two-bedroom condo is situated on the top floor of Gallery Place, the home of the famous Worthy Kitchen. Bask in sweeping views of the surrounding Vermont landscape through the enormous Palladian window. Large main living area with soaring vaulted ceiling and storage loft. New kitchen with granite counters, and new bath with walk-in shower. Have lots of gear? The spacious entry (separated from the main living area) can amply accommodate bikes, skis, or even kayaks. Previously a gallery, this unit still has public safety features (emergency lighting, fire safety system, etc.) to allow corporate retreat/housing or other commercial uses. Walking distance to all the shops, restaurants, entertainment, and recreation that the beautiful, historic village of Woodstock offers, including the new East End Park and River Trails! Posh weekend crash pad? Full-time unique home? Business use? This distinctively beautiful condo sparks creativity and is awaiting new dreams.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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37 Atwood Avenue Woodstock VT 05091

Woodstock, VT37 Atwood Avenue

Price$285,000

Est. Mortgage: $/month

Pending

MLS Number 4838142

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 768

Enjoy the walk to Woodstock from this bright, well maintained two-bedroom home. All of the utilities have been upgraded and replaced; new furnace, new hot water heater, Tesla power wall, water purifier and more! The owner has expanded the decks, helping you enjoy the view of Billings Farm even more! The new shed and paved driveway are great bonuses to have! Come and move right in, and enjoy the stress free living!

Listed by Audrey Micca, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 South Road Woodstock VT 05091

Woodstock, VT1880 South Road

Price$215,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4853544

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,574

Close to Woodstock Village! This 3 BR, 2 BA home features newly refinished hardwood floors, open floor plan with a large deck off kitchen for easy access and super space for entertaining. There is a master suite with bathroom on first floor. Second floor consists of a guest bedroom, family room and bonus room that could be used for multiple uses- including an office. This property has a surprising amount of usable space - Enjoy the small yard for playing games, lounging and entertaining. Trail system close by for walking, biking and snowshoeing. Just minutes from historic Woodstock Green, shopping and restaurants, championship golf, skiing and fly-fishing just minutes away. This is a great little house- super rental income if you are interested in a investment- come take a look!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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6 Highland Avenue Woodstock VT 05091

Woodstock, VT6 Highland Avenue

Price$199,000

Est. Mortgage: $/month

Pending

MLS Number 4851865

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 680

Offered for sale, for the first time in over 50 years, is a charming Woodstock Village cottage! This sunlit property presents pleasant long views from a private and peaceful setting. Perhaps this simple cottage becomes an interim place to stay while you plan your transition to construction of a more substantial residence, on this desirable piece of village land. The property benefits from the valuable infrastructure components of connection to both the municipal sewer system and to the Woodstock Aqueduct Water Company. The existing cottage could become your affordable primary home or a Woodstock vacation retreat, of a manageable size. This location is equally wonderful for the proximity of the numerous amenities of village life, or for enjoying the peaceful solitude of the nearby trails that meander through the Mount Peg town forest! A property with obvious upside potential!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 TourAsk A QuestionMore Details

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Copyright 2021 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 April 18, 2021.