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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35 Wayside Road Woodstock VT 05091

Woodstock, VT35 Wayside Road

Price$485,000

Est. Mortgage: $/month

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

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$
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$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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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321 Deerbrook Way Woodstock VT 05091

Woodstock, VT321 Deerbrook Way

Price$449,500

Est. Mortgage: $/month

Pending

MLS Number 4819539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 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: 2.77% last updated on Jan 21, 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

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: 2.77% last updated on Jan 21, 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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1157 West Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4825106

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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 subject to existing Lease

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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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5274 West Woodstock Road Woodstock VT 05091
Active With Contract

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: 2.77% last updated on Jan 21, 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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49 Valley View Road Woodstock VT 05091

Woodstock, VT49 Valley View Road

Price$350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822840

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,860

Move in ready! This 1 ½ story cape style home started as a barn in 1800, and was converted to a home in mid 1900. The house is outfitted with a heated sunroom, two main floor bedrooms, full bathroom with laundry, and two additional rooms on the second level. The deck offers expanded living space with views to the yard. An attached one car garage under has direct access, storage space, work shop, and mechanicals. A nice level yard; perfect for family fun, with established perennial, vegetable, and berry gardens. The garden shed has electric, water, and dry storage. Located 1 mile from Woodstock Village, and an easy commute to the Upper Valley, or Interstate.

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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: 2.77% last updated on Jan 21, 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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74 South Brook Way Woodstock VT 05091

Woodstock, VT74 South Brook Way

Price$349,000

Est. Mortgage: $/month

Active With Contract

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: 2.77% last updated on Jan 21, 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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2286 Church Hill Road Woodstock VT 05091

Woodstock, VT2286 Church Hill Road

Price$343,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4833862

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 2
  • Square Feet 2,832

Perfect rehab/rebuild opportunity on desirable Church Hill Road, sited on 6.77 country acres just two miles from beautiful downtown Woodstock. On-site septic, drilled private well, and a well-designed driveway approach to the home/building site. Existing northeasterly views and potential for expanded views with further landscaping. The home- formerly a local dance hall in its prime- features a lovely stone hearth/fireplace and wood stove which could become the focal point of a redesign or rebuild. This is a terrific lot with loads of potential in a highly sought-after locale.

Listed by David Donegan, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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$339,469

Est. Mortgage: $/month

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: 2.77% last updated on Jan 21, 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. Low condo dues. Posh weekend crash pad? Full-time unique home? Business use? This distinctively beautiful condo sparks creativity and is awaiting new dreams.

Listed by Geoff Eckler, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 21, 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.

Save 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 January 26, 2021.