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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25 Slayton Terrace Woodstock VT 05091

Woodstock, VT25 Slayton Terrace

Price$499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4870215

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,632
  • Bathroom 2

Overlooking Woodstock village and the Pomfret hills beyond, 25 Slayton Terrace sits on a quiet neighborhood street, just a quick stroll from downtown shops and restaurants, the Mt. Peg trailhead, and the Marsh Billings Rockefeller National Park. With three sunny bedrooms, ample living spaces, wood floors, a gracious covered porch, charming period details, and an open lawn, this 1920's cape lives beautifully in every season and is comfortable for gatherings, convivial or cozy. A new standing seam roof, Tesla battery backup, recently renovated upstairs bath, and a spray-foam insulated basement make this home ideal as a worry-free primary residence, or as an easy-keeping vacation property. For the buyer who values a tranquil village location and a well-maintained home, this lovely cape is not to be missed. NOTE: Tesla battery backup is leased and available to the purchaser for a nominal monthly fee through the GMP Tesla pilot program. Battery will be removed by GMP should the purchaser elect to discontinue the lease.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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273 Liberty Farm Road Woodstock VT 05091

Woodstock, VT273 Liberty Farm Road

Price$419,000

Est. Mortgage: $/month

Pending

MLS Number 4878999

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,736

This Vermont Log Home served as the company's model when they launched construction. Superbly landscaped with gardens for perennial's, herbs and a sustainable food resource. An enclosed screened porch and deck overlook the spring-fed pond with views to Biscuit Hill beyond the Ottauquechee River to the south. Extraordinary care and attention to detail are evident everywhere in the home and on the land. The original detached garage was converted into a workshop and a one bedroom studio apartment. A handsome authentic hand-crafted post & beam barn was constructed for use as a garage and storage. There are a garden shed and equipment shed providing shelter for outdoors activities. A solar array serves to off-set nearly all electrical use. Minutes from Woodstock Village and on the way to skiing in Killington on the westerly side of the town.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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40 Deer Ridge Way Woodstock VT 05091

Woodstock, VT40 Deer Ridge Way

Price$399,000

Est. Mortgage: $/month

Active With Contract

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: 3.09% last updated on Oct 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
Active With Contract

MLS Number 4841891

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

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: 3.09% last updated on Oct 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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37 South Street Woodstock VT 05091

Woodstock, VT37 South Street

Price$399,000

Est. Mortgage: $/month

Pending

MLS Number 4886138

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,660

Wonderful family home conveniently located in Woodstock Village. Walk the kids to the Woodstock Elementary School or to the playground and Vail Field across the street from the house. Watch ball games from the comfort of your front porch. The kitchen opens to a spacious dining area. There are two bathrooms on the main level, one off of the living room and one off of the kitchen. The living room has a wood burning stove. Upstairs are three bedrooms and a common area. There is a two bay detached heated garage with amble storage above. The property is just a block or two away from the Woodstock Inn, Norman Williams Library, shopping, and restaurants. Just down the road is the Woodstock Country Club's golf course and Athletic Club. There are numerous trails on Mt Peg and Mt Tom that are in walkable distance as well. A wonderful opportunity to live in the Village.

Listed by Daphne Lowe and Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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53 Pleasant Street Woodstock VT 05091

Woodstock, VT53 Pleasant Street

Price$379,000

Est. Mortgage: $/month

Active With Contract

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: 3.09% last updated on Oct 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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57 Townhouse Way Woodstock VT 05091
Pending

MLS Number 4887471

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Bathroom 3
  • Square Feet 2,268

Gorgeous "high end" townhouse located in Woodstock West. A very private and well kept community in Woodstock, Vermont. Only 24 units surrounded by plush lawns and mature plantings. All townhouses have 3 living levels. This larger unit has many upgrades including a new kitchen and new larger deck. Gorgeous wood floors though out and new carpet in lower level. As you enter the front door, a den with pocket doors is on the right. The seller currently has twin beds in there for guests. The hardwood floors and fireplace in Livingroom, make this room a very enjoyable place to relax with family and friends. The kitchen dining area has sliders leading to the deck and view of the private wooded backyard. Upstairs has 2 large bedrooms and a full bath. The lowest level has a very large entertainment center, full bath and laundry room with sliders that open to a flag stone patio. This neighborhood is a little piece of heaven. The town was voted "The prettiest small town in America." An historical town, known as a "Rockefeller" town. 20 minutes to Killington and 25 minutes to Dartmouth college and hospital.

Listed by Dorothea Mongulla, High End Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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479 Barberry Hill Road Woodstock VT 05091

Woodstock, VT479 Barberry Hill Road

Price$365,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4883875

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,248

Looking for a private retreat a half mile from the Woodstock High School and minutes from the center of Woodstock Village? Look no more. Offered is a one level energy efficient home with three bedrooms, sited on 1.45 acres with Southern Exposure and a brook on the perimeter. The bright, light filled home has all new windows (picture window in the Living Room is triple paned), wood floors and a full basement. Take in the views of the yard and gardens from the side deck. The back deck is wired for a hot tub and is also generously sized. Inside, is a laundry/mudroom, kitchen, dining, large living room and three bedrooms. The home is very easy to maintain. The level lot has plenty of space for gardening. Keep your gardening tools organized in the spacious garden shed. A wonderful property to call your own.

Listed by Daphne Lowe, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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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: 3.09% last updated on Oct 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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387 Carlton Hill Road Woodstock VT 05091

Woodstock, VT387 Carlton Hill Road

Price$295,000

Est. Mortgage: $/month

MLS Number 4888132

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,328

Pull right in to this cozy country retreat less than 2 miles from Woodstock Village. Enter through an attractive mud room with plenty of space to hang coats and take off boots. Proceed through French doors into the wide open living/dining room area. Prepare your favorite meals in the well-equipped kitchen featuring a Wolf stove and Sub-Zero refrigerator. A full bath on the first floor includes a side-by-side washer and dryer. Upstairs has 2 good sized bedrooms with a shared bath. A bonus bedroom is located off the porch. Conveniently located within walking distance to Woodstock Farmers Market. Ski Killington, only 25 minutes away. Convenience, comfort, and charm make this property highly desirable. Showings begin October 30, Open House on October 31, noon to 3.

Listed by Bobbi Dagger, Atlantic Real Estate Network

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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
Active With Contract

MLS Number 4840144

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

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: 3.09% last updated on Oct 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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2247 E Woodstock Road Woodstock VT 05091

Woodstock, VT2247 E Woodstock Road

Price$129,900

Est. Mortgage: $/month

Pending

MLS Number 4877002

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Square Feet 1,860
  • Bedrooms 5

3.24 acres of river front land in Woodstock! Structures in need of rehab or just take them down and start all over. Great location close to all amenities, shopping, skiing, river activities, Come take a look and bring your imagination!!

Listed by Linda Benoit, Highland Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 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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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 October 27, 2021.