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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42 River Street Woodstock VT 05091

Woodstock, VT42 River Street

Price$499,000

Est. Mortgage: $/month

MLS Number 4692838

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,930

A riverfront Woodstock Village home is not often available for sale! The tastefully remodeled interior, of this centrally located residence, benefits from mesmerizing views of the ever changing coloring of the Ottauquechee River. Being located on a level village street enables comfortable walking to all of the amenities of Woodstock Village life. Three finished levels of living space present multiple possibilities for use by family and guests. A private stone terrace and lawn areas oriented towards the river provide unique platforms, for outside relaxation. With 3 bedrooms and 3 baths, this manageable size home is the ideal weekend retreat or equally a comfortable year round village residence!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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12 Maple Street Woodstock VT 05091

Woodstock, VT12 Maple Street

Price$499,000

Est. Mortgage: $/month

MLS Number 4816179

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 5
  • Square Feet 2,344

Woodstock Village! A bright, spacious and well maintained 1900's colonial home with 5 bedrooms, 2 full baths. Located on a dead end, quiet neighborhood with an easy walk to the center of the Village for all of our amenities, a quick jump onto Mt Peg for a short hike, access to Vail Field for fun and sports. The spacious kitchen has granite counter tops and maple cabinets with an island- open floor plan to a sunlit filled sitting area and informal dining. The floors consist of a mixuture of tile, hardwood and carpet. Large dining that opens into the living room in the front of the house. Second floor has 5 bedrooms or one could be converted to an office. Enjoy the coverage porch overlooking a wonderful row of stunning Annabelle Hydrangeas bushes. Plenty of space for a vegetable garden, perennials and mature landscaping around the house. This home is located in the heart of Woodstock Village- super location. Come take a look.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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151 Happy Valley Road Woodstock VT 05091

Woodstock, VT151 Happy Valley Road

Price$479,000

Est. Mortgage: $/month

Pending

MLS Number 4819111

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,746

HOUSE and SALT WATER IN-GROUND POOL: This historically registered 3 bedroom, 2 bath, 1842 Cape sits on 1.48 acres in the quaint village of Taftsville. It is beautiful! Many new upgrades over the last five years including the addition of a 2nd full bathroom, central air conditioning, and new paved driveway - see the attached document for a complete list. The modern up to date kitchen with a 6 burner Kitchen-Aid gas stove, tin ceiling & back splashes, large French door refrigerator, soapstone counters, and enamel sinks. For cozy family dining eat-in the kitchen near the gas fireplace, or for entertaining move into the formal dining area or living room. The space is versatile to have the main level bedroom be a family/living room. A tucked away office gives you a private space to escape from life's busy days. History, character, and charm abound with all the modern conveniences of 21st century living. On those hot summer days, move out to the full privacy fenced, heated, saltwater in-ground pool. Nearly maintenance free and no harsh chemicals. A perfect place to barbecue & entertain from May to October. There is even brook frontage for the purist and space for kids & animals to play in the fully fenced rear yard. Only 5 minutes to downtown Woodstock and 15 minutes to the West Lebanon Shopping Plazas. Convenient location with quiet, small town living yet close to schools and great recreational areas. Come take a look today!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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$475,000

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: 2.88% last updated on Aug 6, 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

MLS Number 4783272

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • 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: 2.88% last updated on Aug 6, 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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700 John Darling Road Woodstock VT 05071

Woodstock, VT700 John Darling Road

Price$450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4764458

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,196

Tucked away at the end of a one mile Class IV road on 10 very private acres bordered by the Woodstock Town Forest in very desirable South Woodstock. No traffic noise, only the sounds of the birds and the stream that meanders through the woods behind the house. The house is powered by state-of-the-art solar so power failures are never an issue and you never get an electric bill. The open format layout of the first floor creates bright unobstructed living space perfect for everyday living and warm friendly space for entertaining. All the details on most buyers' check lists are here: attached garage, large mudroom, huge pantry, three baths, three bedrooms, master bedroom with updated en suite bath and the world's largest walk-in closet and full walkout basement. Recent upgrades include: updated kitchen and pantry, new high efficiency propane boiler, totally updated solar system, new Kohler generator, new deck and new Jotul woodstove. The location of the property is perfect with the South Woodstock General Store, the Kedron Valley Inn & Pub and GMHA all just minutes away plus convenient to skiing, golf, snowmobiling, health club, and all the amenities of Woodstock Village.

Listed by Stan Butler, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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: 2.88% last updated on Aug 6, 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: 2.88% last updated on Aug 6, 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

MLS Number 4814053

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

This very appealing 'Geo-barn' 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: 2.88% last updated on Aug 6, 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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450 College Hill Woodstock VT 05091

Woodstock, VT450 College Hill

Price$379,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4812157

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,024

This family home sits attractively on a large corner lot conveniently located within walking distance to everything Woodstock has to offer. It features on the 1st level, 3 bedrooms, 2 baths, hardwood floors throughout, a Living Room with a Vermont Castings gas stove, a spacious Kitchen opening to a large deck overlooking the backyard. On the lower level a finished basement including 11x 25 bonus room, an extra room, laundry room, 3/4 bath and lots of storage with light and a walkout door to the backyard. It has an attached one car garage. The yard is nicely landscaped and also has a storage shed in back large enough to fit a lawn tractor. The home has lots of great natural light. The location is walking distance to both Woodstock Union High School and Woodstock Elementary.

Listed by Dail Frates, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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294 Barberry Hill Road Woodstock VT 05091

Woodstock, VT294 Barberry Hill Road

Price$350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4809367

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,128

You'll love this 3 bedroom, 2.5 bath home, sitting on nearly 2 acres just minutes from the Village of Woodstock! Charming contemporary build was designed w/ space + privacy in mind. Enter the home from the oversized 2-car garage, into the mudroom w/ a built-in laundry area! As you're lead into the spacious family room, take in gorgeous views from the large bay window flooding the room w/ sunlight from floor to vaulted ceilings ft skylights! Relax in one of the many cozy areas while watching the fire from the wood-stove in the living area! The sunken living room and formal dining room that boast views of the flowing brook, is a separate area from the main house and great for entertaining, providing you plenty of space for the event of your choosing! Living area also ft's an additional fireplace! Need a mini-getaway? Sneak away to your private den off the central family room! Kitchen provides ample storage with numerous cabinetry and counter space! Master-suite will be your new oasis, complete w/ full bath + large walk-in closet! Enjoy walks to the top of Barberry Hill to the Billings property for great views. Hike up the Appalachian trail or ski at Suicide Six + Killington! Store wood, tools + toys in the large shed on-sight. Recent upgrades include all renovated bathrooms, brand new clapboard siding, + so much more! From the lovely front porch, to the serenity of the stream that runs through the back of the property- let this wonderful home become your personal retreat!

Listed by Hergenrother Realty Group and Daniel Preston, KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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299 Benedict Road Woodstock VT 05091

Woodstock, VT299 Benedict Road

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4809799

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,870

Listed by Seth Warren, Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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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 August 7, 2020.