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

40 Deer Ridge Way Woodstock VT 05091

Woodstock, VT40 Deer Ridge Way

Price$399,000

Est. Mortgage: $/month

MLS Number 4870524

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,671

A surprisingly spacious Woodstock home, in a highly desirable location! The quiet sunlit yard benefits from wonderful privacy, with useful open space for gardens or recreation. With the Woodstock Middle School/High School and shopping at the beloved Farmer's Market just a short drive away, homes in this area of Woodstock are highly sought after! On the main level of this comfortable home are 3 bedrooms, a large living room with an attractive soap stone wood burning stove, a bright dining area, a kitchen, a laundry room and a full bath. The finished lower level of the home presents endless opportunities! Obvious possibilities are office work spaces, workshop/hobby areas, media rooms or just plain recreation fun! A 3/4 bath is conveniently centered among these 5 lower level rooms. The property benefits from high speed internet. A well sited detached 2 car garage, with cement floor, presents extra storage room for bikes, kayaks or garden tools. A home well suited for convenient year round living, in an often sought area of Woodstock! A location equally well suited for use a private vacation home retreat!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

1104 West Woodstock Road Woodstock VT 05091

MLS Number 4841891

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

Freshly cleaned and ready to show!! Well maintained West Woodstock Village home with a spacious dining room featuring hardwood floors and built ins, large living room with nice light, eat-in kitchen with adjacent pantry and large mudroom. Three bedrooms up with an additional rear staircase. This property also features a 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.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

53 Pleasant Street Woodstock VT 05091

Woodstock, VT53 Pleasant Street

Price$379,000

Est. Mortgage: $/month

MLS Number 4859590

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,964

Excellent opportunity for single, two family, or hybrid home/business located directly across from the beautiful, new East End Park. Let your imagination soar. This "blank canvas" is ready to put your ideas to action. The property is currently being used as a one bedroom, single family on first level, consisting of spacious living room, full kitchen, one bedroom with sliders, two bathrooms (one with with laundry). Plenty of parking! Building will require some TLC. Sold "as is".

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

65 South Street Woodstock VT 05091

Woodstock, VT65 South Street

Price$375,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4864662

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,356

Charming antique cape in the heart of Woodstock village! This sunny three bedroom, two bath darling is within easy walking distance of restaurants, the golf club, the elementary school, the Mt. Peg trails, and Marsh Billings Rockefeller National Park. Lovely as a year-round property or as a Vermont retreat, this home overlooks the impeccable Woodstock Inn golf course and is a two minute stroll from Vail Field and the village tennis and pickle ball courts. Well-situated on a large lot and convenient to the picturesque hamlet of South Woodstock, this historic home was once configured as two apartments and maintains some of the conveniences of that layout - ideal for an in-law suite or a home business. With a bedroom and bathroom on the first floor, two covered porches, and mature perennials, this is the perfect spot from which to enjoy the amenities of Woodstock village and the Upper Valley beyond.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

2626 E Woodstock Road Woodstock VT 05091

Woodstock, VT2626 E Woodstock Road

Price$299,000

Est. Mortgage: $/month

MLS Number 4863510

  • Residential Single Family
  • Village Taftsville
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Farmhouse-style home being sold with the opportunity of designing the finishing touches as a like-new home. This home has a great vision and a foundation of work already completed. This home features cherry cabinets, fir shaker style doors, new windows and new exterior doors, new finished slab floor with radiant heat with an insulated base and hard pine flooring. The structure is completely foam insulated, new on-demand Viessmann boiler, modern structural laminated beams in place and framed with fir beams to be exposed. The yard is open with established blueberry bushes, an asparagus bed with plenty of room for recreation and a garden. Located in Taftsville, with the lot abutting both Butternut Lane and East Woodstock Road. Easy walking access to the Taftsville covered bridge and the walking /biking of River Road. Five a minute drive to Woodstock Green and 20 minutes to most points in the Upper Valley.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

442 East Woodstock Road Woodstock VT 05091

MLS Number 4840144

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

Former office space/yoga studio has been converted into an apartment in highly desirable location. 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, and more. 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! Condo fees cover heat, hot water, insurance, lawn mowing, trash removal and snow plowing--that is correct--care free living in Vermont! Apartment could easily serve either as a weekend get-away or full-time home.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

6711 South Road Woodstock VT 05071

Woodstock, VT6711 South Road

Price$225,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4863608

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,124

Lovely Kedron Brook abuts this level one acre lot upon which sits a simple three bedroom one bath Ranch home for simple country living. The brook is year round with rushing water in the springtime and gentle flow in the summer allowing for leisurely dipping on those hot summer days. An ELOMA was performed on the property elevating the home out of the flood zone. There is an outdoor expansive deck great for barbecues or sun worshipping. A firepit brookside gives you the feeling of camping while still at home. The home flow combines open kitchen, dining and living so while entertaining, everyone can still chat. A pantry is great for storing goods for baking, canning, or cleaning. A short hallway brings you to three modest bedrooms with shared bathroom. Don't need three bedrooms? One or two can act as office space. The basement contains your mechanicals as well as your washer and dryer. Good storage or workout space is within its use. Easy access to north and south via route 106 makes traveling to Springfield and picturesque Woodstock Village or via Route 4 to Rutland or White River Junction, an easy commute. Showings start June 3, 2021

Listed by Leila Tarantelli, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

Broker Reciprocity

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 August 2, 2021.