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South Woodstock VT Real Estate

South Woodstock is located five miles south of Woodstock. It is home to expansive meadows and gently rolling hills, which make the area an especially popular equestrian community and home to the internationally renown event facility, Green Mountain Horse Association. Upon entering South Woodstock, you are greeted by the old-fashioned South Woodstock Country Store and post office. Both spots are a good place to meet the locals year round.

The highly regarded Kedron Valley Inn and Restaurant is also located in this village center. The entire village boasts stylish Federal and Greek Revival buildings and a number of handsome brick houses.

Browse Real Estate in South Woodstock

Search South Woodstock real estate for sale below. Contact us if you have any questions or if you would like to schedule a showing. Create an account to save your favorite South Woodstock properties and to receive email notifications when similar listings become available. 

2358 Long Hill, Woodstock, VT 05071

Price$6,900,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Bedrooms 5
  • Bathroom 4
  • Construction Existing

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 foot Old Baldy Mountain with 360-degree views and a small private cabin at the summit.

Listed by T Story Jenks and Ruth Sudduth of LandVest, Inc/Woodstock

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Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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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327 Fletcher Schoolhouse Road, Woodstock, VT 05071

Price$2,925,000

Est. Mortgage: $/month

MLS Number 4644250

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Bedrooms 5
  • Bathroom 4
  • Construction Existing

Bybrook Farm is a picturesque country estate , built in 1797, and completely restored with historic integrity and deluxe amenities, including custom hand planed cabinetry and finishes , reclaimed wood floors , hand hewn beams and decorative painting by renowned artist Kevin Paulsen. Sited on 26 acres, with an exquisite brook that meanders throughout the property and leads to a picturesque spring fed pond .Gorgeous and varied regional views. A rare combination of brook, pond, rolling hills, forest, mature gardens, and original stone walls, complete with charming farmhouse , classic wooden bridge and quintessential Vermont red barns. A moments stroll to historic hamlet of South Woodstock and nationally acclaimed Green Mt. Horse Association equestrian center . The best of serene country living with easy access to downtown Woodstock and nearby equestrian, golfing , tennis, skiing, restaurants, spa and fitness facilities. 5 bedrooms in the Main House, and Guest House and 2 separate kitchens provide for cozy relaxation or entertaining friends and relatives. Settle in on the stone terraces or open air porches that overlook the rushing brook ; swim , fish or relax by the serene pond; take a nature walk in the forest ; ice skate on the pond ; snow shoe or cross country ski right out your back door. Enjoy the best of spring wildflowers , summer sunshine , fall foliage and winter wonderland in this unique property. Fun for two or twenty , with separate spaces for all to enjoy !

Listed by Carol Wood of Williamson Group Sotheby's International Realty

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Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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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6310 Bryant Road, Hartland, VT 05071

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4693928

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing

"HUBBARD FARM” - Fully renovated, classic, historic hilltop farm property on +/- 130 acres with long-range mountain views of Killington, a swimming pond, tennis court, open meadows and a 3-mile private trail network - much of which is enrolled in the Vermont Current Use Program. The recently and beautifully fully renovated residence has hip, contemporary styling, a large gourmet kitchen, two den/family rooms, a private dining room, expansive wrap around porch oriented to take in the view, downstairs recreation room, 5 fireplaces, radiant heat throughout, MBR with bath and steam shower, and other fully renovated bedrooms and baths. Russound speaker sound system throughout the first floor and porch. Large breezeway leads to the huge historic post-and-beam barn that presently serves as a garage. Located approximately 7 minutes from the village green in Woodstock, Vermont - with end of road privacy - this property has access only from Woodstock, a South Woodstock mailing address and emergency services, but is legally located in the town of Hartland. Truly a special property and residence with all the features most desirable in a Vermont getaway, relocation or retirement home.

Listed by John Snyder and Andrew Holson of Snyder Donegan Real Estate Group

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Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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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486 Benedict Road, Woodstock, VT 05071

Price$1,645,000

Est. Mortgage: $/month

MLS Number 4675093

  • Residential Single Family
  • Listing Agent Name Terry Davis
  • Bedrooms 6
  • Bathroom 7
  • Construction Existing

“Spring Hill Farm” located in the heart of Vermont's equestrian region. The renowned Green Mountain Horse Association and all the events are just up the road. This amazing property offers a 3,040 sq. ft. vintage 1820 stone cape, which has been elegantly restored while keeping the authentic charm and architectural beauty. The gourmet kitchen has stainless steal appliances, brick flooring, and pantry, along with a fireplace keeping a true country feeling. The formal dining room walls have hand painted murals, and the large gathering room, perfect for entertaining, has vaulted ceilings with hand- hewn beams and built-ins. The house is set up with 4 bedrooms, 5 bathrooms, along with 5 wood burning fireplaces. The views of the barns and pastures can be had from most every room. Included is a 3,000 sq. ft. reclaimed barn of the same era that has been beautifully restored serving as a 3-bedroom guesthouse. The guest barn has a 2 story stone fireplace, wide pine floors, full kitchen, and a generous loft with a ¾ bathroom. On the lower lever are 2 additional bedrooms, a full bathroom, and a recreational room. To complete the package is a 5-stall barn with multiple fenced pastures. With over 6,000 sq. ft. of living space there is plenty of privacy for everyone. A truly idyllic piece of Vermont! The town office has the house listed as a 3 bedroom and the guest barn as a 2 bedroom; currently the house is set up with 4 sleeping areas and 3 in the guest barn.

Listed by Terry Davis of Engel & Volkers Okemo-Woodstock

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Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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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6656 South Road, Woodstock, VT 05071

Price$750,000

Est. Mortgage: $/month

MLS Number 4704059

  • Residential Single Family
  • Listing Agent Name Gretchjen Smith
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

This pre-Civil War farmstead is located on the southerly side of South Woodstock across from the Green Mt. Horse Association and with access to miles of horse riding trails. This property offers very good potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. A handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, gardens and playground. Fiber optic cable access expands the possibilities to include IT endeavors and other enterprises requiring the ultimate in high-speed internet connectivity. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields and forested land enrolled in Current Use invite traditional Vermont pursuits. The homestead includes a guest apartment periodically rented and additional 'possibility' spaces for income and creative uses.

Listed by Gretchjen Smith of Williamson Group Sotheby's International Realty

{$office->Name}

Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

6656A South, Woodstock, VT 05071

Price$175,000

Est. Mortgage: $/month

MLS Number 4706312

  • Land
  • Listing Agent Name Gretchjen Smith
  • Acreage 45
  • Zoning residential

This parcel is part of a larger farm. Enrolled in current use and benefits tax breaks. There is a very large meadow that can be used as pasture that abuts a small stream. Easy access to pasture from the South Road- or build up high and take advantage of views with some clearing. There is a right of way deeded to the upper portion of the land with a driveway already in place- Rare opportunity to own a large parcel of land in the highly coveted town of South Woodstock. GMHA trails nearby with easy accessibilty.

Listed by Gretchjen Smith of Williamson Group Sotheby's International Realty

{$office->Name}

Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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 A VisitAsk A QuestionMore Details

45 Downer Forest, Strafford, VT 05071

Price$89,000

Est. Mortgage: $/month

MLS Number 4452958

  • Land
  • Listing Agent Name Holly Hall
  • Acreage 13.38
  • Area Rural, Village
  • Zoning none

Beautiful land, convient location to Strafford town. Listen to the babbling brook or take in the peaceful land surrondings

Listed by Holly Hall of Ann Swanson Real Estate

{$office->Name}

Williamson Group Sotheby's International Realty
24 Elm Street
Woodstock VT, 05091
Office: 802-457-2000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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