Greater Woodstock Area Homes Under $500K

Centrally located in the heart of the Green Mountains, the greater Woodstock, Vermont area encompasses the towns of Barnard, Bridgewater, Hartland, Pomfret, Reading, West Windsor, and Woodstock. The real estate options here are nearly endless, with homes in town, family homes, secluded real estate, and vacation homes.

The area is also rich in family activities. Artistree in Pomfret offers courses in music, theater in the arts for all ages. Silver Lake State Park in Barnard is a great place for swimming, boating, and fishing. Pentangle Arts shows first run movies in Woodstock Town Hall.

It’s not all fun and games, of course. The schools in the greater Woodstock area are some of the best in the state. Amenities and conveniences like grocery stores, hardware stores, and pharmacies, are plentiful.

If you’re looking for a family home, a vacation home, or investment property, it’s worth exploring greater Woodstock VT real estate. Take a look at the listings below and then contact us. The agents and buyer brokers at Bassette Real Estate Group are happy to show you around this special area.

3052 Brownsville Hartland Road West Windsor VT 05037

MLS Number 4943977

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 2,012
  • Bedrooms 2

Whether you are thinking about a second home to visit in all 4 seasons, or a great place to live full time, this one may just be it. These owners built it, cared for it, and have made it into a space for all to enjoy both inside and out. The deck style offers a finished basement with one bedroom, and one other office or sleeping space(if you need), with laundry and 3/4 bath. There is ample mudroom space also. On the main living level, you will enjoy custom woodwork skills, a Primary suite, a living room with an expansion of sunlight and wrap around deck, and a kitchen/dining area where I promise you all will gather. Stepping outside(see photos), the fun continues with a beautiful in-ground pool, patio, pool house, and endless gardens. Come see. Showings begin Saturday, 2/25/23.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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2305 South Road Woodstock VT 05091

Woodstock, VT2305 South Road

Price$499,000

Est. Mortgage: $/month

Pending

MLS Number 4921126

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 3
  • Square Feet 1,748

Gambrel style Cape sited on a corner parcel of 4+- acres of open land bordered by the Kedron Brook. Updated eat-in kitchen and baths, living room with built-ins, dining room, hardwood floors, and spacious mudroom. Upstairs en-suite primary bedroom and two additional bedrooms. Complete with detached carriage barn/garage and spacious deck. Only two miles to the village green and minutes to Mt. Peg for hiking, biking, and cross-country skiing.

Listed by Scott Monahan and Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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1101 Tattle Street Reading VT 05062

Reading, VT1101 Tattle Street

Price$495,950

Est. Mortgage: $/month

Pending

MLS Number 4945249

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Square Feet 4,044
  • Bedrooms 5

True horse property and ready for you to bring it back to what it once was!!!! 39.22 acres hosts an original 1795 farmhouse with so much character!!! 5 bedrooms, fireplaced living room, lovely sun-mudroom and so much more!!! 110x60 indoor arena and stable with 10 stalls and tack/viewing area. Additional shop/barn with 5 additional stall, carriage house and shed for storage. This property is a real gem!!!

Listed by Dick Thackston, R.H. Thackston & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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28 Garcia Lane Hartland VT 05048

Hartland, VT28 Garcia Lane

Price$459,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4930486

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,008
  • Construction Existing

Perfect country setting in Hartland Vermont. This two bedroom home sits on a hill with field, trees, and trails. Seasonal view of Mount Ascutney, more trees could be cleared to open up the view. If you want a year round cozy home, or a vacation home in Vermont, this is it. Two car garage plus a large outbuilding. Heating options are wood stove, electric, and newly installed propane heater. Full sunshine throughout the day would be perfect for solar energy. Brand new roof on the house and garage. Enjoy the peaceful tranquility sitting on the deck taking in the sunrise and sunsets each day. Close to Interstate 91, 25 minutes to Dartmouth.

Listed by Erika Smith, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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3685 VT Route 106 Reading VT 05062

Reading, VT3685 VT Route 106

Price$450,000

Est. Mortgage: $/month

MLS Number 4934376

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 4
  • Square Feet 3,678

Opportunity to work from home! Nicely renovated - 2 bedroom, 1 bath apartment with deck & separate 1 car garage. Below is a 50 seat restaurant most recently the Hammondsville Tavern formerly known as Keeper's Cafe, a Reading landmark for locals and tourists alike. This commercial space has lots of on site parking & good exposure for your business endeavors. Located just 5 minutes south of Green Mt Horse Assoc. on Route 106, easy access to Woodstock and surrounding towns. Come see all that it has to offer!

Listed by Dana Waters and Paula Waters, Dark Horse Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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7471 US Route 4 Bridgewater VT 05034

Bridgewater, VT7471 US Route 4

Price$449,500

Est. Mortgage: $/month

MLS Number 4938392

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,268

Conveniently located in Bridgewater in the center of the Village mid-way between Woodstock & Killington Ski Area. The property is currently configured as three income producing units. However, there's an outstanding opportunity for creative changes. The main house could be restored to single family use and the detached rear unit could supplement the cost of ownership. Additionally, the location lends itself to the entrepreneur or service provider with high visibility ideal for a home occupation. Come and see the possibilities. 48 hour notice to tenants is required.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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2943 Cox District Road Woodstock VT 05091

Woodstock, VT2943 Cox District Road

Price$449,000

Est. Mortgage: $/month

MLS Number 4943992

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Square Feet 979
  • Bedrooms 3

A Woodstock home, with a practical floor plan, in a peaceful country setting! The location is great! Just a few minutes of walking brings access to the trailhead of the well known Woodstock Aqueduct Recreation Trail, for year round enjoyment. The Woodstock High School/Middle School is conveniently just a few minutes drive away. With over 2 acres of sunny open land, there is the opportunity for gardening, space for pets and for endless recreational fun! The home is centrally sited on this attractive parcel of land, with ancient stonewalls defining the rear boundary and large open fields to the left and right. The main floor of the home features 3 bedrooms, a kitchen, a living/dining room and a full bath. Off the living room is a large front deck for enjoying abundant sunshine. To the rear of the home a large covered patio with a substantial roof, is accessed off the kitchen. The full walk out basement, with a den and a laundry area, presents obvious opportunity for further expanding the living area within the home. Both the home's location, in a popular residential area of the Woodstock community, and the quality of the land parcel would justify improvements made to the residence.

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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115 Bud's Way Woodstock VT 05091

Woodstock, VT115 Bud's Way

Price$425,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4940583

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,016

PRICE REDUCTION. Spacious ranch on 1.32 private acres at the end of a cul-de-sac within minutes drive to center of Woodstock. Walk to the Woodstock Farmer's Market and the Woodstock Middle & High School. There are three bedrooms total and a portion of the home could be used as an In-Law space (two kitchens) if you want to claim one of the bedrooms. There is a large, sunny family room with a Vermont Castings woodstove, beautiful exposed beams and access to the two sided porch through two glass sliders. The two potential living areas have separate entrances or the home can be easily used as a larger single family residence with a private master bedroom suite (take out the kitchen). There is plenty of space for dining and bedroom flexibility to each unit and separate bathrooms. There are newer and separate gas & oil boilers, and two 100 amp electric panels. The lower level has a 24' x 13' one car garage and a large unfinished basement for storage with an additional washer/dryer hookup. The property has split rail fencing - great for containing family pets or young children or keeping your garden safe from wildlife. There is a classic, Vermont barn already framed for 3 distinct spaces with double barn doors, poured cement floor, windows for light, water from the main house, and a back exit. Perfect for small animals like chickens, goats, sheep or potential to convert to a large workshop or home workspace or studio. Just a 600 yard walk to the High School!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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52 Seems Road West Windsor VT 05037

West Windsor, VT52 Seems Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4946335

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 1
  • Construction Existing
  • Square Feet 1,670

Rare large in-village lot with sunny southern exposure, pleasant view of Mt Ascutney, large back yard with two sheds, and a second parcel between Seems and Rt 44. Home has been well cared for but needs interior updating. Walk-out basement with garage bay and both wood and oil furnaces. Connected to public sewer and fiber internet available. Right in the heart of the village but just far enough up Seems Rd from Rt 44 to buffer noise and traffic.

Listed by Seth Warren, Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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$349,000

Est. Mortgage: $/month

Pending

MLS Number 4934148

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 812

A newly renovated Woodstock Village cottage, with the advantage of solar powered energy efficiency! This sunlit property presents pleasant long views in a private peaceful setting. In addition to the substantial solar panel that is connected to an energy storing Tesla battery, the property benefits from the valuable infrastructure components of a connection to both the municipal sewer system and to the Woodstock Aqueduct Water Company. The attractive interior renovation features wood flooring throughout! A large enclosed porch serves the dual function of both a practical mud room entrance in the winter and a beautiful sitting area year round. When entering from the porch into the kitchen the warm feeling emanating from the cottage's wood paneled interior is immediately apparent. A butcher block counter top and brand new kitchen appliances accentuate the kitchen. Adjacent is a living/dining room, with well placed windows. A generously sized bedroom with wood burning stove, vaulted ceiling and comfortable sitting area is more substantial than would be expected in a small home. A full bath with laundry completes the home. This appealing cottage could become your affordable primary home or a Woodstock vacation retreat, of 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: 6.42% last updated on Mar 23, 2023
* 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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58 Valley View Road Bridgewater VT 05035

MLS Number 4943599

  • Residential Single Family
  • Square Feet 1,373
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Spacious 3-bedroom, 2-bathroom, main floor condo with high ceilings, natural light, separate entrance, and parking. Conveniently located between Woodstock, Ludlow, and Killington/Rutland. Recent upgrades include new water heater, freshly painted interior, along with several exterior improvements. Commons space includes a shared deck, gazebo, and a storage room, along with 2 parking spaces per unit. The property is situated between Okemo and Killington ski areas, and close to multiple lakes, rivers, golf courses, or hiking trails for all of your outdoor activities. An easy commute for employment, shopping, eateries, or entertainment.

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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58 Valley View Road Bridgewater VT 05035

MLS Number 4943124

  • Residential Single Family
  • Square Feet 1,078
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1

Recently updated 2nd floor, 2-bedroom condo, conveniently located between Woodstock, Ludlow, and Killington/Rutland. Upgrades include, freshly painted interior, new laundry room outfitted with washer and dryer, refurbished bathroom, new dish washer, along with exterior upgrades, just to name a few. This turnkey unit is furnished with radiant heat, sky lights for additional natural lighting, a small balcony and nice views throughout. Commons space includes a shared deck, gazebo, and a storage room, along with 2 parking spaces per unit. The property is situated between Okemo and Killington ski areas, and close to multiple lakes, rivers, golf courses, or hiking trails for all of your outdoor activities. An easy commute for employment, shopping, eateries, or entertainment.

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 1, 2023 3:08 AM EDT