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.

7 Highland Avenue Woodstock VT 05091

Woodstock, VT7 Highland Avenue

Price$499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4836992

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,352

Fabulous three bedroom Cape in a canopy of trees with views of Marsh-Billings-Rockefeller National Historical Park. End of road location. Custom built in 2003 with cherry floors, maple cabinets, recessed lights, granite vanity tops, spacious open living space with kitchen and dining and a two-car garage. The finished lower living space features a gas fireplace and lovely built-ins plus a walk-out to the second balcony. Walk to Village for amenities or hike Mt. Peg right out your back door.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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6182 Tyson Road Reading VT 05062

Reading, VT6182 Tyson Road

Price$498,000

Est. Mortgage: $/month

MLS Number 4822425

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 5
  • Square Feet 4,387

Spectacular views of Okemo from almost every room! This well-built Adirondack home would make a great primary home, outstanding vacation retreat, or maybe a home business. Beautiful kitchen has plenty of counter space, stainless appliances, as well as a fully equipped butler's pantry. The 2 story living room has a soaring stone fireplace and French doors that lead to the expansive front porch. The second level has a wrap-around balcony and 2 large bedrooms that could both be master suites. The third bedroom has a private entry and is part of a family suite with its' own kitchen, living, and laundry. The lower level has a massive game room with billiards, large full bar, exercise area, sauna, and woodstove. The 3 bay plus garage is self-contained with a ¾ bath, heating system, compressed air stations, and workshop. Stone walls border the property and it abuts 9,000 acres of Vermont State forest. Only 5 mins to the lakes region, 10 mins to Okemo, 25 mins to Killington or Woodstock, and the VAST snowmobile trail system is right down the road by Colby Pond. Don't miss out on this property.

Listed by Katherine Burns, William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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91 Densmore Hill Road Hartland VT 05048

Hartland, VT91 Densmore Hill Road

Price$495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4807262

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,704

Berry Brook- a stone cottage covered in blooming hydrangea and ten acres of magical woods where you can experience many joys of country living. Custom wide stone steps lead from the formal lawn and flower beds down to an wide open meadow with apple trees, blueberry bushes, and fragrant flowering bushes. A path winds through the woods down to an enchanting little brook. Indoors is also a pleasure - an abundance of light streams through the large Anderson windows all along the southern face of the cottage, lending a warm glow to the original wide pine country flooring. A recent addition- a the large screen porch which invites nature in.. You can take an afternoon nap listening to the chirping of small birds and the wind playing in the trees, or entertain with friends. Upstairs are two large airy bedrooms with big windows and a smaller middle bedroom. Off the screen porch is a deck ,with clematis climbing the railings, big enough for tables and chairs and a good sized barbecue for family gatherings..in the back garden are three custom built waist-high raised beds for home grown vegetables. There's nothing like picking your salad greens right out of your garden ...another country pleasure. There's a large two car garage , with one side used as a work workshop. The cottage its located on a quiet country road but only 6 miles to historic Woodstock, shopping, restaurants and amenities, Skiing, walking trails, fly fishing, health club and golfing.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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35 Wayside Road Woodstock VT 05091

Woodstock, VT35 Wayside Road

Price$485,000

Est. Mortgage: $/month

Active With Contract

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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448 Dana Road Pomfret VT 05053

Pomfret, VT448 Dana Road

Price$482,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4828318

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,183

Lovely antique cape nestled on an old country road - quiet location among the hilltops of North Pomfret. Enjoy your morning coffee under your covered porch watching the sunrise. Multiple large barns for storage, horses with multiple stalls, workshop or in-home occupation. Good size sugar house for those sugaring enthusiasts. Large open space for large gardens and outdoor entertaining. This home is quite large with several additions done over the years. Spacious family room with vaulted ceilings with outdoor patio off the back. Country kitchen with island adjacent to a formal dining room that leads into living room anchored by a handsome wood burning fireplace. The master bedroom is quite roomy ensuite with its own bathroom. Upstairs consists of 3 more bedrooms, bonus room to be used as an office or tv room or finish off another bonus space for an extra office/craft room. There is an open loft area above Family room currently being used as an exercise area. Almost of the floors in this cape are wood with soft tones... lots of original moldings and characteristics throughout. Close proximity to Hanover and Upper Valley. Suicide Six just 10 minutes as well as championship golf, fly-fishing and trails for hiking. Wonderful home nestled in a quaint setting just outside historic Woodstock.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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819 Pomfret Road Woodstock VT 05091

Woodstock, VT819 Pomfret Road

Price$479,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4836029

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,764

Stunning traditional cape style home nestled on an open lot with vistas to the West over looking hayfields and views North towards the Pomfret hillside. Immaculately maintained property with handsome hardwood floors throughout. Wood burning fireplace for cozy ambiance, large kitchen island with ample seating, storage and space for cooking. First floor bedroom with full bath located with two large closets and small efficient office. Second floor will convey 2 very large bedrooms with full bathroom. Both rooms with more space for storage in the eaves and filled with abundance of sunlight. Full basement for more storage although there is a free standing shed just off the deck for entertaining guests or family. Portable generator hookup- Great space for a vegetable gardens- as well as lovely perennial gardens on property. Located between Suicide Six Ski area and historic Woodstock Green. This is the perfect location to all of towns amenities, shops, theatre and restaurants. Championship golf, skiing, fly-fishing close by. Enjoy hikes on Mt. Tom and the Appalachian Trail- This home is great value for Woodstock and prime location. Come take a look!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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16 Balhart Ridge Road Hartland VT 05048

Hartland, VT16 Balhart Ridge Road

Price$475,000

Est. Mortgage: $/month

MLS Number 4811941

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 4,743

“Wintergreen” - a Frank L. Wright inspired 4700 sqft home with 3+ bedrooms, 2½ baths on 3.8 acres surrounded by majestic evergreens and black birch trees overlooking Vermont's Connecticut River Valley. Carved into solid bedrock, the foundation sits on large veins of semi-precious quartz, at the top of a ridge overlooking hills, valleys and a stunning view of Ascutney Mtn. High ceilings, large rooms with expansive windows combined with light from all directions create a unique, customizable home on three levels, each +- 1800 sqft. The top floor is a tree-tops 2 bedroom penthouse with a large roofed porch to watch hawks and eagles circling at eye level. Ideal in-law setup. The main floor is a living and entertaining delight with large master suite. The ground level has a grand public entryway and is brightly lit with substantial windows. Its flexible floorplan offers multiple uses: artist studio/gallery, theater/family/workout rooms or just a great home business opportunity. 18th century pine doors from historic houses are used throughout. In a landscape composed of fields of native ferns, the home is well insulated from the R40 foundation to the R30, 2x8 wall construction that affords a modest heating expense. Stone removed from the foundation has been used in the naturalized landscape. Quiet, private location yet very close to all of the amenities of the Upper Valley - just minutes to Hartland, I91, -S to CT/NYC, -N to I89 and the entire Dartmouth Hospital/College community.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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
Active With Contract

MLS Number 4783272

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • 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: 2.72% last updated on Nov 25, 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$449,500

Est. Mortgage: $/month

Active With Contract

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: 2.72% last updated on Nov 25, 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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101 Westmont Way Woodstock VT 05091

Woodstock, VT101 Westmont Way

Price$449,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4837894

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,346

A truly comfortable 4 bedroom home, in a setting which benefits from a beautiful large level lawn area. Ground floor rooms are designed with extensive windows to allow full enjoyment of the pastoral views! A more open floor plan presents easy transitioning from a generously sized dining area on one end of the home to a spacious living room on the opposite end. For working from home, a large office area, with wood burning fireplace, has great appeal! The dining room can accommodate a full size dining table. From the dining room is an easy transition through sliding glass doors to an outside deck, for barbecuing or outside eating. A pellet burning wood stove is well placed on this end of the home. Midway, on the ground floor, is a kitchen with breakfast seating at a counter and expansive views of lawn. The 26 foot living room is dramatic! A vaulted ceiling, beautiful wood work, a wall of sliding glass doors that open to the spacious lawn and a wood burning fireplace all contribute to create a room for enjoyment in every season! Adjacent to the living room is an office designed to present options for multiple work areas. The fire chamber of the brick fireplace is open on both the living room side and on the office side of the ground floor. The 2nd floor features a large primary bedroom. 3 additional bedrooms open off an open walkway. A full bath and 1/2 bath are well situated. A full basement, with large workshop area, opens to a 2 car garage. Your comfortable Woodstock retreat!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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
  • Bedrooms 4
  • Bathroom 3
  • 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: 2.72% last updated on Nov 25, 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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72 Adams Road Barnard VT 05031

Barnard, VT72 Adams Road

Price$445,000

Est. Mortgage: $/month

MLS Number 4761896

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 2,110

Located in the heart of the village is the original boarding house of Nettie Adams. A circa 1900 Cape on a level 2-acre parcel. The house has 5 bedrooms, 3 bathrooms with a new 6-bedroom septic system. The country kitchen and family room have been renovated while keeping many of the original character and charm. Attached is a two-car garage with a workshop, and a storage room for firewood. The wrap around porch is perfect for morning coffee or relaxing at the end of the day. The rustic outbuilding was used as a one-bedroom cottage in years past but is now used as storage. Located across from Silver Lake and the Barnard General Store.

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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 December 2, 2020.