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. 

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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

Active With Contract

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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

Pending

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

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%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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$1,700,000

Est. Mortgage: $/month

MLS Number 4809479

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

"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

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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Happy Valley Road Woodstock VT 05091

Woodstock, VTHappy Valley Road

Price$1,600,000

Est. Mortgage: $/month

Pending

MLS Number 4833262

  • Land
  • Acreage 86.11
  • Zoning RR5

Pastoral setting with 86+/- acres two miles from the village of Woodstock in the highly coveted Happy Valley neighborhood on the eastern edge of town. Incudes frontage along Hartland Hill and Happy Valley Roads. Comprised of thee parcels: 76.5+/- acres, 7+/- acres and a 2.5+/- acres. The last parcel includes a 3 bedroom 2 bathroom 1800's cape in need of restoration. The bulk of the land has been held by the same family since 1972. The composition of fields, forest, trails, stream, wetlands, old stone walls and views is classic Vermont in every direction. This is the last significant parcel in this corner of Woodstock that hasn't been consolidated into a larger holding. Broker interest.

Listed by Christopher Lang of LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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2039 Randall Road Woodstock VT 05091

Woodstock, VT2039 Randall Road

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822404

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,800

A hidden gem at the magical “end of the road ” this classic 1840s stone Cape was constructed by Scots craftsmen of hewn stone quarried in nearby South Woodstock. Gently rolling meadows and northern hardwoods surround the homestead which is less than four miles from the public gathering space at the Village Green in Woodstock, often called the “prettiest town in America.” The National Register of Historic Places refers to this part of Windsor County as “the stone house belt of Vermont.” There is simply nothing quite like a stone house cool in summers and snug in harsh winter storms. The well-chosen farm site spreads out across 34 acres of southerly oriented landscape shaped by generations to provide sustenance and shelter. A deep, spring-fed pond serves as a refreshing swimming spot in the summer and perfect skating rink in the winter. The property includes an assemblage of outbuildings that appear like they were placed by a master painter within a frame. Under the current three-decade plus stewardship of a well-known local architect and his family, a purity of form has been retained during periodic renovations providing 21st Century comforts and updated mechanical systems, while honoring the history and embracing the quintessential Vermont vernacular of the house and setting.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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675 College Hill Road Woodstock VT 05091

Woodstock, VT675 College Hill Road

Price$1,385,000

Est. Mortgage: $/month

MLS Number 4833519

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

This newly constructed, Ambrose design/build home is privately situated on 20+ acres just a short walk to the Woodstock Village Green and includes a separate 3.5-bedroom, 1.5-bath, 1,500-square foot farmhouse/guest house (currently rented for $1,700/mo) plus an historic barn, 4-bay shed-garage and swimming pond. The beautifully crafted main residence, built in 2016, features an open floor plan main living level with high ceilings and large windows which flood the kitchen/living/dining area with natural light. The main level also enjoys a generous pantry, mudroom with adjoining laundry, bedroom and 1/2 bath (to which a shower could easily be added). Upstairs is the master bedroom featuring a walk-in closet and full bath with a clawfoot tub, shower and double vanity, and two additional bedrooms and full bath. The finished lower level offers a wonderful rec/hangout room and another full bath. The house also features rooftop solar panels and is certified for excellence in energy-efficient design and construction through Efficiency Vermont. Well-maintained and beautifully landscaped grounds with a mix of lawn, gardens, a swimming pond, and woods, all of which can be enjoyed from the comfort of the covered wraparound porch. Newer, state-approved 7-bedroom septic, and a total of 4,200 sf between both homes. This is a prime opportunity for a private spot within walking distance of all of the many amenities Woodstock Village life has to offer.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500

Est. Mortgage: $/month

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 of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

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: 2.8% last updated on Oct 22, 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 October 26, 2020.