Woodstock VT Real Estate

Woodstock Vermont

Woodstock, Vermont is a beautiful historic area boasting the only national park in Vermont, three covered bridges, agricultural landscapes, and numerous inns/bed and breakfasts. Woodstock is a great small town with a great sense of community and a delightful historic downtown that's home to fabulous restaurants and charming shops and boutiques. Learn more about Woodstock!

Browse Real Estate in Woodstock

Scroll down to find all current real estate for sale in Woodstock, VT. Contact Martha Diebold Real Estate if you have questions or would like to learn more about a listing. Sign up to save your favorite listings and email updates when similar listings hit the market.

734 Curtis Hollow Road Woodstock VT 05091

Woodstock, VT734 Curtis Hollow Road

Price$479,000

Est. Mortgage: $/month

MLS Number 4937671

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,928

Options are endless with this well-crafted, three-bedroom home in Woodstock Vermont. Buy it as a primary residence, comfortable getaway home or rental income property, but buy it quickly because it won't be on the market long. The home is offered fully and tastefully furnished, with luxurious details like pro-grade appliances, granite countertop and hardwood floors. You'll find two full bathrooms, including a whirlpool tub downstairs and high-end laundry facilities upstairs. The spacious primary bedroom features a cozy gas fireplace and exit onto the back deck. Also exiting onto the back deck is an inviting sunroom, the perfect place to relax with morning coffee as you keep an eye on youngsters or pets in the large fenced-in backyard. A two-floor, three-car garage with ample storage and workshop space keeps all your vehicles, skis, bikes and kayaks out of the Vermont elements. The basement features more workshop space and a walkin, climate controlled wine cellar. Located just a short drive from Woodstock, Woodstock Union High School, and Killington Resort (9 miles to Skye Ship Gondola), this property is both private and convenient.

Listed by Bret Williamson of Killington Valley Real Estate

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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 Woodstock VT 05091

Woodstock, VT28-30 The Green

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4937336

  • Residential Single Family
  • Village Woodstock
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 3,892

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 4937127

  • Residential Single Family
  • Bedrooms 2
  • Square Feet 3,748
  • Bathroom 2
  • Construction Existing

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, tennis court and smokehouse, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite thoughtful renovation to meet the quality of the site: its woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering. No showings November 24-26

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

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%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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1782 South Road Woodstock VT 05091

Woodstock, VT1782 South Road

Price$549,000

Est. Mortgage: $/month

MLS Number 4936894

  • Residential Single Family
  • Square Feet 2,300
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

Here it is! Conveniently located just south of Woodstock Village, walking distance to Woodstock Inn's Athletic Club and the Mt Peg biking/hiking trails. This well maintained classic ranch style home has generous spaces for gathering. Enjoy views to the Pomfret Hills from the deck! Gleaming hardwood floor on the main level with Kitchen, Dining Room, Living Room, plus three bedrooms and a full bath. Natural light fills the home including the lower level, which is newly carpeted throughout. The lower level has a large family room with new LP gas fired stove, a large bedroom, 3/4 bath, laundry, storage and utility room. The lease for the two Tesla wall batteries is assumable through Green Mountain Power.

Listed by Geoff Eckler of Bassette Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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89 Academy Circle Woodstock VT 05071

Woodstock, VT89 Academy Circle

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4936765

  • Residential Single Family
  • Square Feet 4,139
  • Bedrooms 6
  • Construction Existing
  • Bathroom 4

Knoll Brook Bend is one of the premier landmark homes in the historic village of South Woodstock , Vt. Sitting up on a hill looking out over the village and bordered by the lovely Kedron Brook it is truly breathtaking. The original features have been left intact while updating the home with modern conveniences. The stone work and landscaping enhance the grounds in keeping with the Federal architectural style of the 1831 house. The living room with wall of bookcases and fireplace offers a beautiful place for entertaining . The large chef's kitchen makes cooking for a large or small crowd a joy . This is Village living at its best . Walk to the Kedron Inn for dinner at the Ransom Tavern , take a swim in the Kedron pond or pick up lunch at the country store. Only 5 minutes into Woodstock. Skiing at Six, and Killington minutes away . Green Mountain Horse Association is within walking distance to observe world class horse events . There are year round actives to enjoy whatever ones interests are from music to live theater and all types of arts events .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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42 Heritage Condos Way Woodstock VT 05091

MLS Number 4935979

  • Condo
  • Square Feet 865
  • Bedrooms 1
  • New Contruction Existing
  • Complex Heritage Condos

Carefree affordable living! Great location, minutes from Historic Woodstock Village and only 15 minutes to the Skyeship at Killington! Walking distance to the middle/high school, Union Arena Community Center (Ice Rink), the Thompson Senior Center and locally famous Woodstock Farmer's Market! This sought after lower unit has just been completely painted and is move in ready. The spacious living /dining room (23' x 10') has oversized sliding glass doors that open up to a private slate patio, perfect for relaxing, grilling up dinner or watching the wildlife. Dedicated parking spot just a few steps from your front door. Lovely landscaped grounds compliment the well planned and laid out buildings. Plus your own lockable storage space in the adjacent barn.

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4935033

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Square Feet 2,555
  • Bedrooms 5

Exposed beams and wide board wood floors accentuate the classic interior of this 5 bedroom Woodstock home! Pastoral views, large terraced lawns and massive stonewalls define the striking exterior landscape! When you enter through the classic front entrance a memorable first impression is created with the wood floors and exposed beams that are found throughout the main level. To the left is a living room with wood stove and attractive book case. To the right is a ground floor primary bedroom with ensuite bath. The rear of the main level is dedicated to a bright kitchen with classic wood cabinetry and a well complementing dining room area. Up a traditional front stairway are 2 bedrooms on the left side and a bath. On the right is a large bedroom with ensuite bath. When exiting the home from the kitchen a large covered porch leads to an attached oversized 2 car garage with plenty of space for a workbench and sports equipment storage! Separately entered from this covered porch, in a wing connecting the main house to the garage, is a bedroom with bath. The location of this detached 5th bedroom could easily become an office area conveniently nearby to but yet separated from the home. Additionally, a detached barn, with a full cement foundation, provides practical storage underneath and large 30x19 workshop/studio space above. For many years, this archetypical Vermont property was a bed and breakfast. By updating the baths and adding appliances it will become truly a memorable home!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Square Feet 11,470
  • Bathroom 10

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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6 Highland Avenue Woodstock VT 05091

Woodstock, VT6 Highland Avenue

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4934148

  • Residential Single Family
  • Construction Existing
  • Square Feet 812
  • Bedrooms 1
  • Bathroom 1

A newly renovated Woodstock Village cottage, with the advantage of solar powered energy efficiency! This sunlit property presents pleasant long views in a private peaceful setting. In addition to the substantial solar panel that is connected to an energy storing Tesla battery, the property benefits from the valuable infrastructure components of a connection to both the municipal sewer system and to the Woodstock Aqueduct Water Company. The attractive interior renovation features wood flooring throughout! A large enclosed porch serves the dual function of both a practical mud room entrance in the winter and a beautiful sitting area year round. When entering from the porch into the kitchen the warm feeling emanating from the cottage's wood paneled interior is immediately apparent. A butcher block counter top and brand new kitchen appliances accentuate the kitchen. Adjacent is a living/dining room, with well placed windows. A generously sized bedroom with wood burning stove, vaulted ceiling and comfortable sitting area is more substantial than would be expected in a small home. A full bath with laundry completes the home. This appealing cottage could become your affordable primary home or a Woodstock vacation retreat, of manageable size. This location is equally wonderful for the proximity of the numerous amenities of village life, or for enjoying the peaceful solitude of the nearby trails that meander through the Mount Peg town forest! A property with obvious upside potential!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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26 The Green Woodstock VT 05091

Woodstock, VT26 The Green

Price$2,150,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4933190

  • Residential Single Family
  • Construction Existing
  • Square Feet 4,864
  • Bedrooms 4
  • Bathroom 5

The Historic Daughter's of the American Revolution (DAR) Mansion was constructed in 1807 by Tilley Parker to serve as housing for Vermont's early legislature & tavern. A master preservationist undertook a complete restoration of the original dwelling in 1995 with an architecturally sympathetic addition using original materials combined with elements crafted using authentic hand tools. The result blends the patina of an antique structure with an aesthetically elegant kitchen, baths & modern mechanical systems offering the best of yesterday & today. Living & dining rooms feature wide board floors, antique brick fireplaces, crown moldings & chair rails, all enclosed by airy 9+ foot high ceilings. The library is warmed by a 3rd fireplace, flanked by hand-made mahogany bookshelves & raised paneling for a gracious comfortable retreat. Generous country kitchen is outfitted with professional style appliances, granite surfaces & custom cherry cabinets & opens into a comfortable family gathering room framed floor to ceiling with windows flooding the space with warm natural light throughout the year. Upstairs accommodations include 2 guest bedrooms, each with fireplace & private bath, as well as a master bedroom suite with dressing area, bath accented by marble & tile and a spacious bedroom with elevated tray ceiling. Two finished rooms on the lower level with bathroom provide space for seasonal gatherings or a media/exercise room. Walk to all Village amenities!

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 December 5, 2022 3:54 AM EST.