Woodstock VT Homes for Sale

View current real estate listings for homes in Woodstock, Vermont below. You’ll find a variety of homes including farmhouses, private country estates, classic Capes, newly renovated houses, and well maintained properties. Residents enjoy a high quality of life and plenty of beautiful Vermont countryside in the heart of the Green Mountains.

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If you have any questions or would like to schedule a private showing, give us a call at 802.457.2244. Our team at Bassette Real Estate Group is ready to help you find your dream home!

4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$5,200,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5

4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America's most beautiful villages.

Listed by Richard Higgerson, 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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336 Stone Bridge Way Woodstock VT 05091

Woodstock, VT336 Stone Bridge Way

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4887084

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,824

Room for all, close to town, very private: Stone Bridge is a capacious and thoughtfully-built 2002 5824sf Craftsman Style home set at the end of a private way, with a guest house on a separate lot. The two parcels total 22.65+/- acres. Stone Bridge Way is off of Densmore Hill Road, well-located between Woodstock and South Woodstock Villages in the heart of horse and gravel cycling country. Lovely views to Killington: the western exposure makes for dramatic sunsets from the wide stone patio. Comfortable in all seasons, the spaces flow from open kitchen to living and dining areas warmed by a fireplace (with a conveniently located bar off the living area). Main level primary suite, second-floor primary, plus two bedrooms with shared bath and guest suite. The lower level offers a sports pub, gym and indoor spa. Plenty of space for toys alongside the garage. The guesthouse is privately sited away from the main house, with two bedrooms, two baths, fireplaced living room, dining room, kitchen and study. The site is elevated and largely open around the houses, with woodlands on the other side of the private drive. Site quality, location, and amenities make for a great compound offering.

Listed by T Story Jenks and Ruth Sudduth, LandVest,Inc/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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4884374

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

Listed by T Story Jenks and Dia Jenks, LandVest,Inc/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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66 Hollow Road Woodstock VT 05091

Woodstock, VT66 Hollow Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4885504

  • Residential Single Family
  • Bedrooms 6
  • Square Feet 4,350
  • Construction Existing
  • Bathroom 4

John Curtis, a veteran of the American Revolution, received a land grant to establish a homestead in the new State of Vermont circa 1780. The fields & pastures carved out of a wilderness sustained his family for 5 generations. Stonewalls & tumbled dams remain as evidence of the industry & effort of early pioneers. The Hollow Farm consists of the striking 6 bedroom/4 bath Homestead House & the 3 Bedroom/2 bath Brook House sited in the middle of the 91-acre property. The new Homestead created in 1988 around the stone fireplace & native timber framed original home. The southwesterly exposure illuminates the spacious gathering rooms & private spaces through the enormous round windows. The interior layout reflects casual country lifestyle with an open floor plan spiraling around the central kitchen complex, which opens out on to a wide, elevated terrace, decks & balcony's on each level. Common rooms & quiet corners are visually connected & access by open stairways. The architectural form expresses the Vermont farmhouse on a grand scale with a cupola & splendid views of the surrounding fields & mountains. The property adjoins Coolidge State Forest at a place where a magical waterfall & sweet swimming hole are formed over exposed bedrock. The maintained road ends a mile or so beyond the old farmstead & continues on with miles of trails leading to South Woodstock, Plymouth & Reading townships. Nearby are Woodstock Village, the ski resorts of Killington & Okemo & public waters.

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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4884402

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 37.8 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award-winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-level bank barn has a wide center aisle, 3 box stalls and heat throughout on the first level; hayloft and office with high-speed internet on the second level; and storage on the third level. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Daily pleasures range from a plum fresh picked eaten at the outdoor table overlooking the perennial garden Virtual tour of the home and the barn available.

Listed by T Story Jenks and Dia Jenks, LandVest,Inc/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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17 Mountain Avenue Woodstock VT 05091

Woodstock, VT17 Mountain Avenue

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4856827

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 3,123
  • Construction Existing
  • Bathroom 5

This circa 1825 story and a half Cape is sited on one of the most lovely and largest parcels of land in Woodstock Village landscaped with shrubs and perennials providing a succession of colorful flowers throughout the summer. The floor plan provides a gracious combination of gathering rooms with privacy afforded for quiet pursuits. A short stroll from the Village Green and Faulkner Park this superbly located home offers views of Mt. Tom and abuts the Marsh-Billings-Rockefeller National Park. A historic gem.

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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28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4754916

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

One of a kind! Woodstock Village! A professional designer's well conceived compound. The stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. The length of the tranquil landscaped rear grounds, lush with spectacular gardens and leading to accessible Ottauquechee River frontage, is an unexpected surprise! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the main level, a spacious kitchen, with full size informal dining area, opens in 3 directions, to either a fire-placed living room, a dramatic formal dining room or a large 16'x10.5' screened porch. On the second floor are 2 guest bedrooms, full bath, and a primary bedroom, with ensuite bath. On the 3rd level, a large unfinished attic presents endless potential! The detached guest house is perfect! On the ground level is a living room, with vaulted ceiling, a kitchen with a panty, a mud room and a bedroom with 3/4 bath. A second floor loft bedroom is 21' long! Separately, the free standing 36'x24' studio/workshop has potential only limited by your imagination! Truly an ideal property for combining residential use with a home occupation! The front view of the property has the expected classic New England appeal that typifies the residences of Woodstock Village. While the long private rear lawn, with professionally designed gardens, and accessible river frontage is an unexpected surprise!

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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540 West Woodstock Road Woodstock VT 05091

MLS Number 4872920

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,692

A charming cape style home in a location convenient to access the amenities enjoyed by living in Woodstock! Constructed for use as his own residence a local builder known for high standards and attention to detail created an interior that will please! Truly unexpected quality in a manageably sized 1540 sq. ft. home! Nicely separated from this residence a detached classic New England style building houses a 7 room office complex and 2 privately entered 1 bedroom apartments! Income with excellent tenants in place! Situated at the rear of the .8 acre parcel the cape residence is in an elevated sunlit location. Entering the residence from a large deck leads into an open floor plan which encompasses living room, dining area and attractively appointed kitchen. Located off the kitchen a cozy den offers privacy and the ambience of a wood burning fireplace. A full bath completes the 1st floor. The entire 2nd floor is dedicated to a primary bedroom suite with full bath and walk in closet. On the lower level is a large 2nd bedroom, laundry room and entrance to a 1 car garage. In the front of the parcel the highly visible income property features a 7 room office complex that would satisfy any professional! Components include a private conference room with fireplace, reception/work station room, private executive office, 2 additional offices, break room, filing room and several 1/2 baths! Separately entered the 2 apartments are well finished. A residence with the bonus of income property!

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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$924,000

Est. Mortgage: $/month

MLS Number 4859269

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,824

NEW ROOF IN 2021. Meticulously maintained 5 bedroom, 4.5 bath, 4,824 sqft contemporary Saltbox situated on 5.1 acres just four minutes to Woodstock village. This includes a large and gracious lower level In-Law/Guest suite with a substantial kitchen, dining, and a generous bedroom that could double as a home office, rental, or guest quarters. There is a lovely 2002 Living/Great Room expansion with floor to ceiling windows with plenty of light and a substantial center fireplace for easy evening conversation. Additionally, the large modern kitchen has cherry cabinetry, lots of counter space, and a practical kitchen office area. The Family Room has an attractive Woodstock soapstone stove that comfortably heats the home. We round out the first floor with a practical mudroom, an extra den, a formal dining room, & custom wide-board milled cherry flooring throughout. Privately located, the first-floor master bedroom en-suite boasts a large walk-in closet and high ceilings with lots of windows that make the room sunny & bright. The second floor layout includes a second Master Bedroom suite with private bath and two additional large bedrooms with a common hallway full bath. Outside: Large wrap around deck, 2 car attached garage, sunny grounds, perennial gardens framing brick walkways, and adjacent to Mt Tom's hiking trails. Close to Suicide Six ski area too! There is view potential if you cut a few trees and it's just 2 miles to town! Be sure to see the 360 Matterport Virtual Tour!!

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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4946 South Road Woodstock VT 05071

Woodstock, VT4946 South Road

Price$895,000

Est. Mortgage: $/month

Pending

MLS Number 4871947

  • Residential Single Family
  • Square Feet 3,440
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

Lilac Cottage is a most charming Gothic Revival home in South Woodstock Village. Lovingly restored with a new addition that can be used as an in law apt. or used completely by one family. A new 2 car garage with ample overhead storage is a very recent addition . The lawn is beautifully landscaped with stone walls and a lovely back deck . Walk to the Kedron Valley Inn for dinner on the front porch , or gather at the country store for coffee and visits with neighbors. The Kedron Brook is across the road and Green Mountain Horse Association is a short walk away. There are endless miles of country roads and trails for hiking, biking , horseback riding and cross country skiing. This is the best of a country village lifestyle .

Listed by 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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339 Gully Road Woodstock VT 05091

Woodstock, VT339 Gully Road

Price$750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4860123

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,688

Price reduced $100,000! Motivated seller! Great location just minutes from Woodstock village on the quiet Gully road, located just a few miles from Woodstock's shops, restaurants, schools. Sited on 5.1 acres is this 4-bedroom, 2 1/2-bath home. The main living level features a foyer with 2 1/2 story vaulted ceiling and windows, an open concept kitchen/dining/living space and a 1/2 bath with an adjacent den room. The large wraparound deck just off the kitchen/great room is perfect for outdoor dining and gatherings. Upstairs is the primary bedroom with a walk-in closet, a full bath with separate tub and shower, and a small deck that leads to the wraparound deck below. 3 additional bedrooms, a full bath, and large laundry space complete the level. Beneath the house is an attached garage and workshop/storage area. Newer, high-efficiency propane heating furnace. The property also features two large outbuildings- one three-bay open garage/shed and a separate heated one-bay enclosed barn- for ample storage of vehicles, equipment, and toys. Super-fun treehouse sleeps 3+ in summer has power, sink and bar fridge - right off the back lawn. The property has a wonderful outdoor firepit area with level lawn, two brooks and walking trails/woods.

Listed by John Snyder, Snyder Donegan 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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81 Happy Valley Road Woodstock VT 05091

Woodstock, VT81 Happy Valley Road

Price$725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4877228

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 4,679

This gorgeous, historic Greek Revival Farmhouse located in the heart of the charming Taftsville community has been lovingly stewarded for over two centuries, while honoring and preserving the beautiful, period detail. The sun filled, spacious rooms flow perfectly for daily living and entertaining. The private, en suite bedrooms are ideal for accommodating a house full. The charming country kitchen is of generous proportion, and commercially suited to cook for the masses. Step out to a lovely, secluded terrace garden, and lawn. The antique barn is perfect for storage and workshop. Neighborhood access to a wonderful trail system. Stroll down to the covered bridge and walk or bike along the banks of the Ottauquechee River. This impeccable property is turn key! The property is currently being operated as The Apple Butter Inn (and available as a going concern, fully suited at $740,000). The property can be easily transitioned back to a grand single family home, or single family with a rental unit, guest, or in law accommodation. Limited availability for showings.

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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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.