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. 

1959 Cox District Road Woodstock VT 05091

Woodstock, VT1959 Cox District Road

Price$10,500,000

Est. Mortgage: $/month

MLS Number 4820913

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 9,515

Woodstock Farm is a modern architectural masterpiece and landmark work by award winning and internationally recognized architect Rick Joy. Based on a conceptual framework that draws from the simplest archetypical forms, this dramatic stone and shingle house and counterposed barn is set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close to ivy league Dartmouth College in Hanover, New Hampshire. Melding effortlessly into the Green Mountains, the property is sensationally experiential in nature and the design is executed with the sharpest attention to craft and detail. Drawing directly from the architectural vernacular of the rural northeast, the tension between the historical and contemporary is conveyed, to paraphrase the architect, through the massive character of the walls, through the qualities of light and dark, through spatial movement and through atmosphere. The four-bedroom main residence offers a 152-foot elongated gable house with massive end walls of quarried Lake Champlain bedrock and cedar cladding on the roof and side walls. Extraordinary, unique and exceptional in every way, Woodstock Farm presents the opportunity for a new owner to acquire an important piece of the history of modern architecture, an incomparable lifestyle, and a work of art.

Listed by Richard Higgerson of 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4809703

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 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 of LandVest, Inc/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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3114 Church Hill Road Woodstock VT 05091

Woodstock, VT3114 Church Hill Road

Price$2,740,000

Est. Mortgage: $/month

MLS Number 4820914

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 9,320

Between the storied Village of Woodstock, Vermont and the country cosmopolitan hamlet of equestrian-oriented South Woodstock a remarkable retreat can be found. The spectacular post and beam residence and barn/guest house are the result of a collaboration between two partners uniquely qualified and united in the passion to create something extraordinary. The architect designed main house is sited to take maximum advantage of the homes south elevation and provides a view of the barn, fenced pasture and paddock area. Employing old world craftsmanship, C.G. Nichols Builders brought over 35 years of custom residential construction experience to create a dramatic statement in wood, glass and stone. The connected open flow of the first floor plan is centered around the kitchen and its remarkable four season solar surround. The home features the finest quality materials and highest quality and most current construction standards. With approximately 6800 square feet, the 9-room main house offers four bedrooms, four and a half baths, open-concept kitchen, living and dining area, mudroom, entry and expansive first floor master bedroom suite and the main house is surrounded by bluestone terraces, dry laid stone walls, lush lawns and gardens. The detached barn and guest house provide everything one needs for the equestrian lifestyle and the nearby Green Mountain Horse Association is a short 2.5 mile hack away.

Listed by Richard Higgerson of 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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2574 Garvin Hill Road Woodstock VT 05091

Woodstock, VT2574 Garvin Hill Road

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4804667

  • 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. Subject to current use conservation program. 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

$
$
%
$/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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1532 Happy Valley Road Woodstock VT 05091

Woodstock, VT1532 Happy Valley Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 4760962

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

This secure Vermont retreat sits high on a hill on 55 protected acres. Architect designed, a premier builder, and built on the history and character of two fully reconstructed antique post & beam frames. Unquestionably one of the nicest homes in Woodstock. Five (5) bedrooms, four (4) bathrooms, & over 6,000 sq-ft of living space finished to an exacting level of detail. There is beautiful interior space, private guest quarters, four working fireplaces, & high-end master bathroom finishes. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas range, and a large Sub-Zero refrigerator. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors are quintessential Vermont architecture. The grounds have a duck pond, old stone walls, mature maple trees, a four-car garage, & an impressive 4-stall timber frame horse barn. A newer cedar shake roof & re-sided cedar shingle in 2019 complement all the modern conveniences of the 21st century - high speed internet, whole house generator, underground power. Most of the neighbor's holdings include protected land in VT Current Use. Happy Valley Road is on the exclusive easterly side of town with quick access to, and away from, the major metro hubs of Boston & New York City. Did we mention the two snowmobiles & 6-wheeled Polaris Ranger included in the sale? Enjoy snowmobile trails, wandering the estate, biking & sledding on your secure Vermont domain! Check out the house video!

Listed by John Bassette of 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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28-32 The Green Street Woodstock VT 05091

Woodstock, VT28-32 The Green Street

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4798172

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 10
  • Bedrooms 9

3 attached residences, on picturesque Woodstock Village Green! 2 elegantly proportioned brick townhouses, with an attached circa 1830 traditional clapboard home! The gracious interiors, of the brick townhouses, feature attractive antique detailing, high ceilings, multiple fireplaces. The western townhouse, 30 The Green, is fully renovated by quality craftsmen. Ground level is an open floor plan featuring stylish kitchen, dining area, living room with fireplace, and a half bath. A 2nd floor is dedicated to a large primary bedroom, with ensuite bath and walk-in closet! A 3rd floor has 2 comfortable guest bedrooms and full bath. The eastern townhouse, 28 The Green, presents antique detailing, exposed beams, wood flooring, 9 foot ceilings, 3 fireplaces and opportunity to renovate a traditional 3 level home, to suit one's taste. The traditional clapboard #32 The Green has a tastefully renovated contemporary interior with 3 bedrooms, 3 baths, and a finished lower level. Off street parking and a detached 2 car garage are useful amenities. These Woodstock Village landmark properties present a unique opportunity! The 3 bedroom residence at #30 is turn key and luxuriously appointed, for immediate residency. The antique residence at #28 is a very rare opportunity to renovate a traditional Woodstock Village Green residence to indulge new owner's preferences. The clapboard home at #32 is stylishly contemporary and comfortable! All 3 present level walking to Woodstock Village amenities!

Listed by John Wetmore of 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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2352 Curtis Hollow Road Woodstock VT 05091

Woodstock, VT2352 Curtis Hollow Road

Price$1,975,000

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: 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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41 Pleasant Street Woodstock VT 05091

Woodstock, VT41 Pleasant Street

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4809479

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 11
  • Bedrooms 9

"Why not the best?" An exquisite home built with magnificent taste. The wallpaper (Bradbury & Bradbury) in one bedroom, was $10,000.00. When one walks through this amazing property, one stands in awe. Every bedroom has a full bathroom. A perfect place for family and friends, complete with your own bar. Original woodwork, including pocket doors. Custom carpeting. Original stain glass windows. All current and previous owners maintained and improved property. Private living quarters on right side of house.This is a Rockefeller town, once voted "Most beautiful small town." 20 minutes to Killington and Dartmouth. Sidewalks to small stores and restaurants. Mt Peg and Mt Tom trails bordering village. Theater and Health Club including golf course in town.Beautiful historical property priced to sell. Most furnishings included. Move in ready!!! Can be permitted as private residential property with zoning permit. Being sold to use as residential but currently commercial.

Listed by Dorothea Mongulla of High End 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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97 & 99 Darling Road Woodstock VT 05071

Woodstock, VT97 & 99 Darling Road

Price$1,575,000

Est. Mortgage: $/month

Pending

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: 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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SAWYER Woodstock VT 05091

Woodstock, VTSAWYER Road

Price$1,499,000

Est. Mortgage: $/month

Active With Contract

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: 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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28-30 The Green Street Woodstock VT 05091

Woodstock, VT28-30 The Green Street

Price$1,450,000

Est. Mortgage: $/month

MLS Number 4796400

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6

Prominently situated, on the picturesque Woodstock Village Green! This elegantly proportioned brick townhouse is comprised of 2 distinct residences! Complimenting the stately brick exterior are gracious interiors, with attractive antique detailing, high ceilings and multiple fireplaces. Located in the western portion of the townhouse, #30 The Green has been totally renovated by quality local craftsmen. The ground level has an open floor plan featuring a stylish kitchen, a dining area, a living room with wood burning fireplace, and a half bath. The 2nd floor is entirely dedicated to a large primary bedroom, with ensuite bath and walk-in closet! On the 3rd floor are 2 comfortable guest bedrooms and a full bath. Located in the eastern portion of the townhouse, #28 The Green presents antique detailing, exposed beams, wood flooring, 9 foot high ceilings, 3 fireplaces and the opportunity to renovate a traditional 3 level home, to suit one's taste. Off street parking, with a detached 2 car garage, is a useful amenity of the townhouse. This Woodstock Village landmark property presents a unique opportunity! The 3 bedroom residence located at #30 is turn key and luxuriously comfortable, for immediate residency. The antique residence at #28 is a very rare opportunity to renovate a traditional Woodstock Village Green residence to indulge a new owner's preferences. The location is excellent! Level surface walking to all of the numerous amenities of Woodstock Village awaits the new owner!

Listed by John Wetmore of 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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22 Prospect Street Woodstock VT 05091

Woodstock, VT22 Prospect Street

Price$1,399,900

Est. Mortgage: $/month

MLS Number 4820298

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

This is a rare opportunity to own over four acres within the town of Woodstock. This immaculately updated expanded Cape puts you walking distance to schools, shops, restaurants, golf, and hiking. At home, sit back and relax while you enjoy quintessential Vermont views of Mount Tom and your own landscaped pond from the wrap-around deck or star-gaze from the perfectly situated spa. The cook's kitchen has granite/soapstone countertops, stainless steel appliances, a breakfast nook, and a sitting area with a mount for a television and a propane stove. The dining room has beautiful built-ins and pastoral views. The living room has vaulted ceilings and a wood-burning fireplace. The first-floor master bedroom suite has mountain views, a large dressing room, an office, and a spa-quality bathroom with amenities including a bubbler-tub and multi-nozzled shower. Upstairs there is an ensuite bedroom and two family rooms, one is a TV room and the other is a game room. On the walk-out basement level, there are two ensuite bedrooms, a full kitchen, pantry, and two offices, and a sauna. The lovely landscaped grounds are surrounded by woodlands affording privacy not often found in town.

Listed by Jennifer Falvey of 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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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 11, 2020.