Woodstock VT Real Estate

Woodstock, Vermont real estate offers residents the opportunity to live in a beautiful community surrounded by natural beauty. The area boasts excellent schools and a less hectic lifestyle. From antique farmhouses to updated homes to wooded acreage, discover a variety of properties in Woodstock. Browse the latest Woodstock, Vermont real estate listings below. You may also be interested in viewing real estate listings in other Vermont towns.

Homes for Sale in Woodstock

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3752 Densmore Hill Road Woodstock VT 05091

MLS Number 4955400

  • Land
  • Acreage 23.46
  • Utilities Phone
  • Zoning residential

23.46-acre equestrian property with a fenced field, woodland trails, moss covered stone walls and a year-round babbling brook. This property farmed since the 1800's with rich soils, pastureland, wood lot and perennial gardens. Located in the heart of horse country. Green Mountain Horse Association up the street. A serene property that gives you the true Vermont lifestyle. Make your visit to GMHA a lasting one. Located in South Woodstock just up the street from beautiful Woodstock, voted at one time "The prettiest small town in America." Located east of Killington and west of Dartmouth college and hospital.

Listed by Dorothea Mongulla of High End Realty

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 River Street Woodstock VT 05091

Woodstock, VT26 River Street

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4954906

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,719

One of Woodstock's most beautiful Greek Revival homes sited on a landscaped village lot that rolls gently down to the Ottauquechee River. The riverfront lawn is sheltered from activity on the Green and enjoys views of the iconic covered Middle Bridge. This authentic antique house is configured with the gable end facing the street and a series of westerly side entry doors. The facades are a template of aesthetic tastes with original classic architectural form modified in the late 19th Century with Carpenter Gothic elements in keeping with the Victorian style. The central country-kitchen is the common gateway to the home with more formal spaces and bedrooms located in the front portion of the residence. The original barn has evolved into a family great room/library with a wood-burning fireplace and opening onto the elevated deck overlooking the river. There are two 1st floor bedrooms with shared a bathroom and upstairs there are 2 private bedrooms and a study adapted to bedroom use that opens out to an old-fashion sleeping porch. A long bunkroom accessed off a back stairway sleeps a crowd during holidays and other occasions. This is an opportunity to acquire a rare gem of a home on the river.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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2646 Curtis Hollow Road Woodstock VT 05071

MLS Number 4954660

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,352

Delano Birches Farm , built in 1834, has been lovingly cared for by the present owners for 36 years. The approach is down a country lane bordered by stone walls and mature trees. The owners added a bright open family /dining room and large primary bedroom with bath. This classic country home is filled with charm . There are two stone fireplaces as well as original wood floors. The grounds include a lovely year round pond , gardens as well as a brick patio for entertaining. Only minutes from Killington for skiing and historic Woodstock village for shops and restaurants. The area offers sports and entertainment for all seasons .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

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%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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170 Grove Hill Road Woodstock VT 05091

Woodstock, VT170 Grove Hill Road

Price$2,650,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4954334

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,759

Welcome to Grove Hill Farm, a quintessentially Vermont home that is one of the original dwellings in Woodstock! This stunning property has been lovingly stewarded through the ages by several families, and has been upgraded accordingly while maintaining the charm and character of its beginnings. The home has open kitchen/dining with incredible views over a stone patio and across its pond to Killington beyond! The kitchen has been renovated and features a cozy nook where you can enjoy your morning beverage while taking in the view. There is a 1st floor primary ensuite bedroom w/ fireplace, a laundry in the walk-in closet, and new bathroom. The living room is anchored by a large wood-burning fireplace and several seating areas including a bay window capturing the view. Powder room, mud room and den/office complete the 1st floor. Upstairs are 3 light-filled bedrooms with full bath. The surprise is a second "bunk room" area with sitting room and 3/4 bath! The barn can hold 3 vehicles with room to build 2 horse stalls that opens into the fenced pasture. The grounds have extensive perennials and an orchard. The property is in conservation with the VT Land trust, assuring undisturbed views in perpetuity. However, the covenant allows for a second homesite in the event the owner wishes to build a guest house. This property is completely unique in the Woodstock market! Peace and tranquility await, yet just minutes to both the Woodstock green and the quaint hamlet of South Woodstock.

Listed by Susan Hickey of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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31 Parkview Way Woodstock VT 05091

MLS Number 4953780

  • Residential Single Family
  • Construction New Construction
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,013

2023 Single Wide Mobile home will be delivered for a end of July closing. Buyers application for Park approval under Documents. Pets are allowed. Home floor plan under doc's also available. 2 bedroom one on each end of the home. Main bedroom with in-suite full bath. Central Livingroom, dining area and Kitchen. Laundry area ready for your washer and dryer. Close to shopping and downtown Woodstock. Easy access to the Woodstock High School.

Listed by Deb Roberts and Jenna Luce of RE/MAX Upper Valley

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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32 Parkview Way Woodstock VT 05091

MLS Number 4953777

  • Residential Single Family
  • Square Feet 934
  • Bedrooms 2
  • Bathroom 2
  • Construction New Construction

2023 Single Wide Mobile home will be delivered for a end of June closing. Buyers application for Park approval under Documents. Pets are allowed. Home floor plan under doc's also available. 2 bedroom one on each end of the home. Main bedroom with in-suite full bath. Central Livingroom, dining area and Kitchen. Laundry area ready for your washer and dryer. Close to shopping and downtown Woodstock. Easy access to the Woodstock High School.

Listed by Deb Roberts and Jenna Luce of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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282 Fletcher Hill Road Woodstock VT 05071

Woodstock, VT282 Fletcher Hill Road

Price$1,950,000

Est. Mortgage: $/month

MLS Number 4953523

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,329

This classic Yankee Barn home is sited on a plateau protected from the north providing sweeping views over South Woodstock to Mt. Ascutney and beyond. The expansive glass windows and sliding doors open onto wide deck & an adjacent covered porch to enjoy the seasonal fine weather. A handsome multi-purpose horse barn and equipment shed are generously sized for recreational equestrian & farm use with open fields & pastures offering supplemental grazing areas. The open post & beam great room is spacious with gathering spaces framing the field stone fireplace with a secluded study or occasional bedroom adjacent. A private loft and bedrooms are on the upper level. Designed for comfortable country living & to take best advantage of the extraordinary world surrounding you. Flowering trees, shrubs and a luminus birch grove accent the elegant natural landscaping. Located in the heart of horse country.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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2356 Fletcher Hill Road Woodstock VT 05091
Pending

MLS Number 4953395

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,893

You'll check all the boxes with this charming, beautifully maintained, classic log home located just ten minutes west of The Woodstock Green. Conveniently sited on a tranquil, partially wooded and level two acre lot, this home has so much to offer, all within an efficient footprint. Galley kitchen with pine cabinetry, stainless steel appliances and slate counters. The bright, spacious living/dining room features a cathedral ceiling, lots of windows and steps directly out to a huge, private wrap around deck overlooking a level lawn with mature plantings. The main level is further completed by a bedroom, and 3/4 bathroom. The second level is an open loft bedroom overlooking the living room. The walk out lower level has a large, finished room (perfectly suited for guest accommodation, family room, gym or home office), a full bathroom, and utility room with laundry. There is a detached one-car garage with a work bench for gardening and hobbies. Close proximity to Killington Sky Lift, recreation, restaurants and shops of Woodstock. Perfect primary or second home opportunity.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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2622 South Road Woodstock VT 05091

Woodstock, VT2622 South Road

Price$330,000

Est. Mortgage: $/month

Pending

MLS Number 4951990

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,068
  • Bathroom 1

Welcome to your dream A-frame home in the serene and picturesque town of Woodstock, Vermont. This one-of-a-kind property offers a rare opportunity to own a stunning and unique A-frame style home in a tranquil, friendly neighborhood. As you enter the home, you'll be greeted by the open floor plan that is perfect for entertaining family and friends. The living room is adorned with large windows that let in an abundance of natural light and stunning views of the surrounding landscape. The master bedroom and full bath are both located on the first floor. The charming spiral staircase is a standout feature of the home, leading up to the second floor where you will find two cozy bedrooms. Step outside onto the first or second-floor deck to take in the fresh air and breathtaking views of the lush greenery that surrounds you. The over half an acre of land provides ample space for outdoor activities, gardening, and dining. This home is perfect for those seeking a peaceful retreat while still being close to all the amenities that Woodstock has to offer. With its ideal location and unique features, this A-frame home is truly a gem that won't be on the market for long. Don't miss your chance to own a piece of paradise in Woodstock, Vermont.

Listed by Livian Vermont of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4951694

  • Residential Single Family
  • Bathroom 5
  • Square Feet 6,403
  • Bedrooms 4
  • Construction Existing

Designed by AIA award-winning architect Lewis Davis, of the New York firm Davis Brody Bond in 1976, whose work ranged from modernist skyscrapers to the renovation of the Reading Room at the New York Public Library, High Birch's sleek white design is striking in Vermont's green hills. Davis firmly believed in the power of architecture to enrich people's lives, and that ethos is evident in every aspect of this magnificent property. A drive wends its way through rolling meadows with stunning views to provide a sense of sanctuary, only 2.5 miles from Woodstock village. One of the standout features of High Birch is the abundance of natural light that floods in through the tall windows, illuminating the interior and framing breathtaking views of the surrounding mountains. The split-level design creates intimate spaces perfect for reading, reflection, or simply taking in nature. During winter, the entire family can gather around the fireplace, while the stone terrace becomes the perfect venue for outdoor entertaining during summer. Recent renovations by Studio Nexus added a contemporary touch to the kitchen, living room, bathrooms, and offices while still preserving the essence of Lewis Davis' original intent. The kitchen was designed by Deane. The home comes fully furnished, ready for you to move in and make it your own. There is a two car attached garage, storage barn and high speed internet. It is 6 miles to Saskadena and 34 miles to Killington for skiing. SHOWINGS BEGIN MAY 12

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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9 School Street Woodstock VT 05091

Woodstock, VT9 School Street

Price$895,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4951081

  • Land
  • Acreage 0.33
  • Zoning res

Stunning Antique Barn located in the heart of Woodstock village: The Car Barn is a three-level, 6,000 squ. ft. building sitting on .33 acres that has stored a collection of antique cars for over fifty years. However, it awaits conversion into your Signature residence with cathedral ceilings, a large open floor plan, 4+ bedrooms, and the kitchen of your dreams. There is a deeded ROW from Woodstock Green to access the property or a possible curb cut from School Street. For the discerning developer, the town has the property zoned for up to 3 residences- however, the ROW from the Green will only permit two dwellings. Town water, and sewer are connected. The first floor currently consists of a large open room with tall ceilings and a large entry door; at the Eastern end of the first floor, there are two large shop spaces, a storage room, and a bathroom. The top floor is a vast open space for storage or potential bedrooms. The ground-level garage has five double bays that can hold many toys, automobiles, boats, trailers, lawn equipment, etc. This property boasts lots of southern exposure for natural light and a huge yard for entertaining or gardens. Large maple trees and lilac bushes accent the property. The barn is a leisurely stroll to Woodstock Village shops and just 3 miles to Suicide Six for those skiing enthusiasts. The trailheads to Mtn Tom is just a short walk away. This Barn is a rare investment opportunity to own a signature property in America's prettiest town.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 TourAsk A QuestionMore Details

9 School Street Woodstock VT 05091

Woodstock, VT9 School Street

Price$895,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4951094

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Lot Description City Lot,Open
  • Acreage 0.33

Stunning Antique Barn located in the heart of Woodstock village: The Car Barn is a three-level, 6,000 squ. ft. building sitting on .33 acres that has stored a collection of antique cars for over fifty years. However, it awaits conversion into your Signature residence with cathedral ceilings, a large open floor plan, 4+ bedrooms, and the kitchen of your dreams. There is a deeded ROW from Woodstock Green to access the property or a possible curb cut from School Street. For the discerning developer, the town has the property zoned for up to 3 residences- however, the ROW from the Green will only permit two dwellings. Town water, and sewer are connected. The first floor currently consists of a large open room with tall ceilings and a large entry door; at the Eastern end of the first floor, there are two large shop spaces, a storage room, and a bathroom. The top floor is a vast open space for storage or potential bedrooms. The ground-level garage has five double bays that can hold many toys, automobiles, boats, trailers, lawn equipment, etc. This property boasts lots of southern exposure for natural light and a huge yard for entertaining or gardens. Large maple trees and lilac bushes accent the property. The barn is a leisurely stroll to Woodstock Village shops and just 3 miles to Suicide Six for those skiing enthusiasts. The trailheads to Mtn Tom is just a short walk away. This Barn is a rare investment opportunity to own a signature property in America's prettiest town.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 TourAsk A QuestionMore Details

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Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 June 5, 2023 3:54 PM EDT