Woodstock VT Real Estate

Woodstock has a year-round population of approximately 3,500 and is the area’s largest township. It consists of both fulltime working residents and their families, as well as retired, recreational and seasonal residents. A short weekend commute of 2 to 2 1/2 hours from Boston, where the majority of the second homeowners reside, the area also draws a significant number of visitors from other New England communities and New York City. Woodstock boasts a wide range of cultural activities sponsored by the local arts council, Pentangle.

The Woodstock Union High School and Middle School provide secondary education for the children from Woodstock and the surrounding towns of Barnard, Pomfret, Reading, Killington, Plymouth, and Bridgewater.

Parents who live in Hartland and West Windsor can also choose to send their children to Woodstock’s middle and high schools. Known for providing a first class college preparatory curriculum, Woodstock was recently honored at the Kennedy Center for Performing Arts for having the most outstanding arts, music, and theater department for any school of its size in the country.

Browse Woodstock VT Real Estate for Sale

Scroll down to browse real estate for sale in Woodstock, Vermont. Create an account to save your favorite Woodstock property listings and to receive email notifications when similar listings become available. Contact us to schedule a tour of your favorite properties or if you have any questions. 

2358 Long Hill Road Woodstock VT 05071

Price$5,500,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4,165

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. Landscape design by Shep Butler includes an orchard of 110 productive apple trees with varieties such as Macoun, Empire, Cortland, Spartan and Macintosh.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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1001 Atwood Lane Woodstock VT 05091

Price$3,250,000

Est. Mortgage: $/month

Pending

MLS Number 4762434

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,701

“The Hill” is a modest name for an exceptionally private 82+/- acre hill top meadow at a 1,780' foot elevation with breathtaking 270-degree views of the Green and White Mountain ranges. Located within 4.8 miles of Woodstock village, this is a property designed to enjoy country living and the outdoors. The c2002 custom cedar shingle 3-bedroom residence (2,688 square feet) was designed by AIA award winning Truexcullins, a firm known for high craftsmanship and sustainable, enduring architecture. Created to integrate with the natural surroundings, the spacious living areas take advantage of the stunning unobstructed views with large windows and high ceilings, and is finished with cedar plank walls and trim, antique pine floors, soapstone counters, fir trusses, exposed beams, and a 2-story fieldstone fireplace. Tucked away with its own views, privacy and rustic comfort is a 2-bedroom classic cabin (1,013 square feet) with a floor-to-ceiling stone fireplace. The grounds are a balance of meadows and woodlands laced with reconstructed stonewalls. There is a 1.5-mile maintained trail for walking and skiing, a 1/3-acre swimming pond with a fishing shack, a “Hobbit House” built into the side of a hill, and a lean-to with a fire pit sited on a prominent overlook. Adjacent is 300-acre town-owned land with reservoir, extensive trail network, and a 186-acre conserved property. The Hill overlooks Mt. Tom and the protected Marsh Billings Rockefeller National Park.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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1532 Happy Valley Road Woodstock VT 05091

Price$2,895,000

Est. Mortgage: $/month

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This contemporary cape with classic Vermont lines is built on the history and character of two fully reconstructed antique post & beam frames. Currently it is being completely re-sided with beautiful cedar shingles (photo #4). Architect designed and unquestionably one of the nicest homes in Woodstock. There is beautiful interior space, newly created guest quarters, four working stone fireplaces, high-end master bathroom finishes, and 55.76 acres of playground. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas stove, a large double door commercial refrigerator, and even space for a kitchen herb garden. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. The look and feel is classic Vermont charm with all the modern conveniences of the 21st century. Five (5) bedrooms, four (4) bathrooms, and over 6,000 sq-ft of living space are finished to an exacting level of detail. The grounds have a duck pond, ancient stone walls, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Enjoy distant valley views from the stone patio and Happy Valley Road is on the easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, skiing, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat from the busyness of life.

Listed by John Bassette of Bassette Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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2574 Garvin Hill Road Woodstock VT 05091

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4765394

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 6,545

"GARVIN HILL GETAWAY"- Newer custom built residence (that easily sleeps 15+) on 50 acres of farm pasture fields and woods with a fabulous long-range mountain view - just minutes from Woodstock village. Designed for family gatherings and entertaining friends, the residence also lives beautifully on one level. Wonderful open floor plan with high ceilings and large-proportioned rooms. The 1,200 sf great room / gathering area combines kitchen, dining and living room areas with stone fireplace that opens to an expansive wrap-around deck with its own indoor-outdoor entertaining space - with indoor and outdoor spaces all sharing the long-range mountain view over the pasture fields. A spacious first level master bedroom suite provides for 1-level living. Excellent mechanicals. An oversized 3-car garage - for all your motorized toys bikes, skis, kayaks and other outdoor gear - walks into a mud-laundry room and into the house. Minimal gardens and landscaping make for a low-maintenance, super-fun gathering house on 50 acres with big views, just minutes and easy access on public roads from Woodstock village.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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2352 Curtis Hollow Road Woodstock VT 05091

Price$2,300,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird C. Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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SAWYER Woodstock VT 05091

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4467517

  • Land
  • Acreage 282.81
  • Zoning RESIDENTIAL

An incomparable 282.81 acres of conserved woodstock land! The quality acreage to compliment the construction of an unparallel residential compound. This desirable location is within one half mile of historic woodstock village. The property benefits from long range views and managed woodlands.

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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97 & 99 Darling Road Woodstock VT 05071

Price$1,575,000

Est. Mortgage: $/month

MLS Number 4767586

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,749

High Riding's 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson's (NYC Mayor Fiorello LaGuardia's “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible. The “Studio” at 97 Darling Road, a 2,384 square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio. The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a swimming pond. There are over 800 sugar maples- tapped for maple syrup, apple trees, well maintained pastures, forest, private riding and hiking trails and a 3-stall stable.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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4 The Green Woodstock VT 05091

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4702840

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 10
  • Square Feet 6,800

This elegant 1827 stone federal-style former residence is located on a quiet corner of the Woodstock Green and is one of village's historic properties. A complete renovation of the 6,800 square feet in 2010 brought back the impressive period finishes, and provided space for 5-6 office suites (3 kitchenettes) and a 4-bedroom 3rd floor apartment. The zoning, overall floor plan, large rooms, and high ceilings open the possibility for a single or multi-family property. Ten private parking spaces are located at the back of the building accessed from Mechanics Street. The building is zoned Central Commercial and has town water & sewer. 94% occupancy.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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4 The Green Woodstock VT 05091

MLS Number 4700265

  • Commercial
  • Year Built 1827
  • Acreage 0.29
  • Area Business District

This elegant 1827 stone federal-style former residence is located on a quiet corner of the Woodstock Green and is one of village's historic properties. A complete renovation of the 6,800 square feet in 2010 brought back the impressive period finishes, and provided space for 5-6 office suites (3 kitchenettes) and a 4-bedroom 3rd floor apartment. The zoning, overall floor plan, large rooms, and high ceilings open the possibility for a single or multi-family property. Ten private parking spaces are located at the back of the building accessed from Mechanics Street. The building is zoned Central Commercial and has town water & sewer. 94% occupancy.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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779 PETERKIN HILL Road Woodstock VT 05091

Price$1,475,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4655908

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,370

Superbly sited overlooking the Ottauquechee River Valley this outstanding reproduction of the region's classic Colonial style offers sweeping views over Woodstock to the National Park and beyond. A broad, covered porch wraps around the westerly and north exposures of the home providing a gracious place to enjoy the old-time pleasure of simple relaxation. Versatile living spaces feature 4 bedrooms in the main residence, including a private 1-bedroom Guest Suite and separate 1 bedroom Guest Apartment over the barn. Master bedroom suite is warmed by a fireplace. Entertaining revolves around a spacious, open concept kitchen-dining and living room that provide direct access to a stone patio and covered porch. A lower, walk-out level is configured for a recreational activities and potential media room. Completely private within minutes of the Village Green.

Listed by Laird C. Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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10 College Hill Road Woodstock VT 05091

Price$1,385,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4759904

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,214

10 College Hill is a welcoming house perfect for entertaining friends and family, including 5 bedrooms, in-village, beautifully maintained, move-in condition with lovely gardens, patios, a screen porch and a first level master suite. Just a two-minute walk to the village green, 10 College Hill is set back from the traffic of Rt 4, on a quiet 1.05 acre parcel with lovely gardens in a private back yard. The original residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the National Archives, Jefferson Memorial, master plans for Dartmouth, Yale and Johns Hopkins. Under the guidance of Duo Dickinson, AIA, the traditional “servants kitchen” was renovated into a wonderful gourmet kitchen, with a breakfast area that looks out to the private patio and gardens. In 2012, under the direction of David Beilman, AIA, a fabulous first level master bedroom suite with separate full bath and walk-in closet areas were added as well as a 2-car garage with a covered, radiant-heated brick walkway. The formal dining and living rooms each have wood-burning fireplaces. A powder bath is off the spacious foyer-entry. Upstairs are four other bedrooms: two bedrooms with en-suite baths and two other bedrooms that share a hall bath, plus a small but elegant office. Air conditioning in all five bedrooms. Beautiful landscaping, gardens and a fieldstone back patio offer indoor outdoor space for both quietude and gatherings.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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458 Woodstock Woodstock VT 05091

Price$1,290,000

Est. Mortgage: $/month

MLS Number 4713272

  • Land
  • Acreage 4.57

It has been said that the highest and best use of this property would be a combination of constructing residential units, in the private rear acreage, and commercial development, of the highly visible road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village. A portion of the property was affected by a breached fuel storage tank. All clean-up work has been completed, with no residual evidence of petroleum distillates. The site has the Brownsfield Redevelopment Program approval. Full documentation is readily available. The 4.57 acres provide a visible opportunity for a multi-use development, in desirable Woodstock! Location, Location, Location!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 2019 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 September 20, 2019.