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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218 Mecawee Road Woodstock VT 05091

Woodstock, VT218 Mecawee Road

Price$499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822982

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1,331

A safe retreat in desirable Woodstock Vermont! Recently, a well respected local builder has carefully crafted his thoughtful interpretation of the small home concept. His long experience in building Vermont homes is obvious throughout this immaculate cape style home! An open floor plan creates a naturally bright and comfortable first floor living space. On this level, the living room, dining area and kitchen all have visually separate locations and yet all flow together creating the feeling of a being in a larger space. On the second floor, there are two nicely separated bedrooms, on either end of the cape, and a beautiful tiled bathroom. These bedrooms each have the bonus of highly functional built in clothing storage drawers that run the full length of a wall! Radiant floor heating for comfort, wood floors on both levels of the house for classic appeal and natural beauty and extensive windows for wonderful natural lighting are among the appealing interior features of this home. Dramatic stonewalls, a sunny patio and an attractive garage/workshop are among exterior features. This privately sited home is located on 5 acres of land that have appeal for their diversity. Adding to the sense of a safe retreat the location of this home is in a more rural neighborhood of Woodstock. This recently built home would serve equally well as a safe vacation retreat from the busy world or could be a comfortable year round residence, of a manageable size!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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35 Wayside Road Woodstock VT 05091

Woodstock, VT35 Wayside Road

Price$485,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4827275

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 3,680
  • Acreage 2.19

Bring your imagination to this historic building that has the systems in place to become an outstanding family home! Plenty of room in this mostly open space to create your dream house, with the newer baseboard and radiant heat flooring, 30+ gal/minute drilled water well, septic in place and 1.5 bathrooms. This would be a perfect set-up for a home business with accessory apartment, a single family home, or whatever combination you can dream up! The antique posts are made in the gunstock style (tapered top to bottom) with the lower half reinforced with steel beams. This building is a real gem, and the right owner will appreciate living in such a unique piece of history! Bring your plans and an open mind...Building has a Woodstock mailing address but is located in the Town of Pomfret.

Listed by Susan Hickey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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819 Pomfret Road Woodstock VT 05091

Woodstock, VT819 Pomfret Road

Price$479,000

Est. Mortgage: $/month

MLS Number 4836029

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,764

Stunning traditional cape style home nestled on an open lot with vistas to the West over looking hayfields and views North towards the Pomfret hillside. Immaculately maintained property with handsome hardwood floors throughout. Wood burning fireplace for cozy ambiance, large kitchen island with ample seating, storage and space for cooking. First floor bedroom with full bath located with two large closets and small efficient office. Second floor will convey 2 very large bedrooms with full bathroom. Both rooms with more space for storage in the eaves and filled with abundance of sunlight. Full basement for more storage although there is a free standing shed just off the deck for entertaining guests or family. Portable generator hookup- Great space for a vegetable gardens- as well as lovely perennial gardens on property. Located between Suicide Six Ski area and historic Woodstock Green. This is the perfect location to all of towns amenities, shops, theatre and restaurants. Championship golf, skiing, fly-fishing close by. Enjoy hikes on Mt. Tom and the Appalachian Trail- This home is great value for Woodstock and prime location. Come take a look!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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
Active With Contract

MLS Number 4783272

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • 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: 2.81% last updated on Oct 29, 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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321 Deerbrook Way Woodstock VT 05091

Woodstock, VT321 Deerbrook Way

Price$449,500

Est. Mortgage: $/month

MLS Number 4819539

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,856

Off a private gravel road is 321 Deerbrook. A superb location on the western side of Woodstock making skiing at Killington close by and shopping or recreation in Woodstock Village very convenient! The VAST trail crosses the property which is great for snowshoeing and hiking in the Spring. Have your morning coffee while watching the sunrise over the Valley and admiring the peaceful views over the Ottaquechee River. Built in 1987 with an open floor plan. The kitchen is centrally located with a cozy den to the left complete with a wood burning fireplace and a spacious living room to the right. Off the back of the house is a large deck. Upstairs are three bedrooms and two full baths. The southernly exposure and open land make gardening a breeze! A wonderful family home!

Listed by Daphne Lowe, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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2 High Street Woodstock VT 05091

Woodstock, VT2 High Street

Price$447,500

Est. Mortgage: $/month

MLS Number 4807011

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 1,600

Super location in the heart of historic Woodstock Village. This 4BR, 3 BA residence has lots of antique characteristics throughout the home. Hardwood floors, high ceilings and many upgrades. There is a one bay attached garage. Small lot for low maintenance accented by a handsome stone step entry to a cozy front porch for those wanting to enjoy the 'leisure walking' of pedestrians. Walk to all shopping, restaurants and amenities this lovely town has to offer. Hiking trails out the back door onto Mt Peg or short walk to Mt Tom and Billings National Forest.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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27 Maple Street Woodstock VT 05091

Woodstock, VT27 Maple Street

Price$439,000

Est. Mortgage: $/month

MLS Number 4825598

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

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: 2.81% last updated on Oct 29, 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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1157 West Woodstock Road Woodstock VT 05091

MLS Number 4825106

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,760

Gorgeous fully restored farmhouse with modern amenities and original charm! This airy and flexible four-bedroom home is conveniently situated in west Woodstock village within the desirable Windsor Central School District and moments from Killington, Hanover, and DHMC. This beautiful home was completely gutted in 2017 and renovated to a high standard from roof to basement, including all new electric and plumbing, high-quality polyethylene foam insulation, new standing seam roof and all new appliances, fixtures, and flooring throughout. This home is ideal for primary homebuyers, vacation enthusiasts, and investment shoppers alike. From the soapstone countertops and the exposed beams to the spacious deck and easy-keeping yard, this home is a delight in every season. Offering flexible upstairs spaces - including a nursery or office - the layout will easily accommodate family and guests. With luxe design influences and a wonderfully convenient location, this property is a rarity in the Woodstock marketplace!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1122 Peterkin Hill Road Woodstock VT 05091

MLS Number 4808425

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 2
  • 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: 2.81% last updated on Oct 29, 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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530 BRYANT Road Woodstock VT 05091

Woodstock, VT530 BRYANT Road

Price$397,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4814053

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 867

This very appealing barn-style open floor plan home is sited privately on a level and rolling 12 acre parcel mid-way between the South Woodstock and Woodstock Village centers. Nearby Green Mt. Association horse trails make the location ideal for equestrian's. The home is energy efficient with expansive windows that bring the outside 'in' aesthetically without compromising comfort. The sweeping westerly views can be enjoyed from a wide covered porch and the meadow setting surrounding the dwelling. A 'right sized' small, but not too tiny house.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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 4830804

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,095

This 1972 Farmhouse is situated on 5 acres of land, just 15 minutes from Killington, VT! Enjoy all that Woodstock has to offer with its delightful boutique shopping, delicious Farm to Table restaurants and numerous indoor/outdoor Recreational opportunities. This lovely home boasts beautiful natural light and woodwork throughout. A gourmet kitchen with breakfast bar and center island, mudroom with built-in storage, a large living area with stone fireplace and access to the back deck plus so much more! The second level includes two bedrooms with a large Master Bedroom en-suite, complete with full bath, dressing area and large walk-in closet. You'll also enjoy the convenience of the half bath and second level laundry area. Outside you'll find plenty of storage between the detached garage and old sugar house, with a well manicured and sun lit lawn that is perfect for animals and gardening.

Listed by Kate Jarvis and Rachel Arsenault, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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74 South Brook Way Woodstock VT 05091

Woodstock, VT74 South Brook Way

Price$359,000

Est. Mortgage: $/month

MLS Number 4826798

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,232

Sunny, one-level living! Just two miles from the village green, less than a mile from the Woodstock Fitness Center, and five minutes from South Woodstock and GMHA, this bright three-bedroom home is the perfect spot for anyone looking to enjoy the benefits of village living with a bit more elbow room. Well-situated on an open, park-like acre, this easy-keeping property has been well cared for and updated, with a whole-house generator, a sun porch, and a renovated kitchen. An attached, oversized two-car garage, central air conditioning, and a huge open basement make this home incredibly comfortable in every season. Enjoy listening to the babbling brook from the new screened porch or take a quick bike ride into town. In the Woodstock school district, this low-maintenance home is close to everything while feeling delightfully private - the perfect spot for both primary and secondary homeowners!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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 TourAsk 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 October 31, 2020.