Woodstock Primary Homes for Sale

Browse primary homes for sale in Woodstock Vermont below and contact me for more information about any specific properties.  You can also create an account with my site to save all of your favorite Vermont real estate listings.  

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: 6.57% last updated on May 25, 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
  • Bedrooms 3
  • Square Feet 1,013
  • Construction New Construction
  • Bathroom 2

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: 6.57% last updated on May 25, 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
  • Construction New Construction
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 934

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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

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%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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

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$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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

MLS Number 4951990

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

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6,403

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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 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

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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4165 Hartland Hill Road Woodstock VT 05091
Pending

MLS Number 4951099

  • Residential Single Family
  • Square Feet 1,654
  • Bathroom 2
  • Bedrooms 3
  • Construction Existing

OPEN HOUSE FRIDAY 1:00-3:30pm & SATURDAY 1:00-4:00pm.Classic New England Cape 3-4 Bedroom, 2 Bath, 1,654 sqft cape on a large corner lot with quiet side streets in Woodstock yet still walkable to everything the bustle of town has to offer. The home is also just steps away from access to the Mt. Peg Trail System offering year round hiking, biking, and cross-country skiing. Charming split rail fencing surrounds the level yard and mature gardens with a sloping hill down to a lovely creek. There is walk-in/walk-out access through the full sized basement heading up to the main level. The main level flows from the gracious living room to an Open Concept kitchen with lots of counterspace and dining space for a generous sized dining table. There is an additional large Sunroom with gorgeous southern exposure and views of the yard and the neighbors' classic, antique red barn. The main level has an additional 2 bedrooms (or one bedroom and an office/study) and a shared full bath. Upstairs features two more large bedrooms with lovely wide plank maple flooring and another shared full bath. Outside, there is a large exterior barn-like studio (used to be a one car garage) with a full lower level basement for storage. Windows and walls are insulated and it would be a great play area, artist studio, recreational room and storage for all the toys (bikes, skis, kayaks & more), with even work space for projects. Just on the edge of town and easy walking to everything! Won't last long!

Listed by John Bassette of Bassette Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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358 Cowdrey Path Woodstock VT 05071

Woodstock, VT358 Cowdrey Path

Price$639,000

Est. Mortgage: $/month

MLS Number 4949933

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,048

Charming move-in-ready house in a great location, privately situated in South Woodstock, just 7 mins to the Woodstock Green. Beautiful open floor plan between dining, kitchen and living room. Kitchen and dining have cherry floors and cabinets, granite countertops, lovely view out the kitchen sink window and sliding doors to the back deck for outdoor barbeques & playing in the back yard. The living room has sliding doors for lots of light, a gently vaulted ceiling and a wonderful gas fireplace that is visible from kitchen and dining areas. First floor den/office could also serve as a bedroom. Private powder bath on first floor. Upstairs is a master bedroom with walk-in closet and ensuite bath. Two other bedrooms share a hallway bath. Much of the basement has been finished and suitable as TV/game/play/den area. Neat, tiled-floor mud-laundry room with cubbies and hooks - is conveniently located on the way in from the attached 2-car garage. Recent upgrades include new garage door, garden shed, front porch update, all interior repainted, new carpet, landscaping/plantings. Very good mechanicals and easy to maintain house. Full-house, automatic propane backup generator. If you are looking for a move-in-ready house in a great location - this is it!

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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3256 South Road Woodstock VT 05091

Woodstock, VT3256 South Road

Price$600,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4948874

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Square Feet 1,888

Perfectly situated between the charming villages of Woodstock and South Woodstock, this beautifully renovated historic cape is a turn-key delight. Bright and sunny with a spacious, landscaped back yard, the home was comprehensively transformed in 2017 - from the roof to the systems and from the gorgeous kitchen to the marble primary bath. The three bedrooms, including one on the first floor, accommodate family and guests comfortably, and living and dining rooms provide wonderful spaces to gather. A thoughtfully designed upstairs den is ideal as an additional cozy sitting room or as a flexible space for extra company. Perfect as a full-time home, this meticulously maintained property is also wonderfully suited for more seasonal enjoyment. With a robust rental history, 3256 South Road has proven unsurprisingly attractive for area visitors. Close to skiing, lakes, Hanover, and the larger Upper Valley, this move-in ready home is a rare find in our marketplace.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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3752 Densmore Hill Road Woodstock VT 05091

MLS Number 4946242

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,000

23.46-acre equestrian property with a fenced field, woodland trails, moss covered stone walls and a year-round babbling brook. This property has been farmed since the 1800's with rich soils, pastureland, wood lot and perennial gardens. Mature blueberry, elderberry, raspberry, grape, peach pear, plum, mulberry, dogwood and kiwi produce edible fruit. Established flowering plants and herbs make a sanctuary for birds, and butterflies. The property just sings: A True Vermont Life. The Green Mountain Horse Association is two miles South and the village of Woodstock, golf course and Athletic club is an easy drive 1.5 miles North. Hardwood floors from trees harvested on the property take in the golden light from many windows. Dwellings include:1973 Gambrel shaped house and two-story barn, sheds, cabin in the woods, root cellar, sugar house, potting shed/chicken coop. The homestead has an acre of well-maintained garden beds which are ready to plant. Killington Skiing and Dartmouth Hospital are 25 minutes away.

Listed by Dorothea Mongulla of High End Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 4945641

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

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 8,921

High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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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
  • Construction Existing
  • Bedrooms 8
  • Bathroom 5
  • Square Feet 3,748

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4935033

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

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: 6.57% last updated on May 25, 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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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
  • Bathroom 10
  • Square Feet 11,470

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: 6.57% last updated on May 25, 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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433 Cowdrey Path Woodstock VT 05071

Woodstock, VT433 Cowdrey Path

Price$995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4932619

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,507

Splendid contemporary cape and separate barn guest apartment idyllically nestled on an open and sunny hillside in the heart of South Woodstock horse country. The light and airy interior boasts an open concept gourmet kitchen with dining/living area that opens to both a wonderful screened porch and deck. In addition, there is a warm and spacious family room to gather for games or a movie. The primary bedroom ensuite is detailed with a stunning vaulted ceiling with exposed beams, a newly updated bath, and a lovely balcony overlooking a quintessential Vermont landscape. The additional two bedrooms share a full bath. An upstairs laundry room is an added convenience. As a bonus there is a wonderful barn with a separate guest apartment complete with kitchen and bath! The lower level of the barn has parking for one car as well as ample storage area which could easily be converted back to the original horse stall. New buderus boiler and standing seam roof are at the top of an extensive list of substantial upgrades and improvements to this property. Enjoy the convenience of being just around the corner from the South Woodstock Country Store, the Kedron Valley Inn, Green Mountain Horse Association (GMHA) and just a short ride to the village of Woodstock. A truly special and versatile property!

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4932341

  • Residential Single Family
  • Square Feet 1,456
  • Bathroom 2
  • Construction Existing
  • Bedrooms 2

This extraordinary 115 acre property, located in the towns of Woodstock & Hartland, offers the perfect mosaic of qualities that buyers are looking for. The acreage is unencumbered and presents the perfect opportunity for a family estate, future development or equestrian opportunities with grass covered hillsides, trail systems and the GMHA just 3 miles away. The diverse topography of the property with trails throughout has an easily accessible summit offering a unique homesite location with spectacular unobstructed panoramic long range views that can be captured from sunrise to sunset. For the winter sports enthusiast, you have it all right here. The extensive trail systems can be combined for snowmobiles, nordic or alpine skiing. The level of stewardship is evident from the maintenance of the extensive trail systems, existing structures and grounds to the main pond that is deep and well stocked. The structures include a very comfortable two story cottage with long vista views, a large barn/garage, two stall horse barn with run-in and a split rail fenced area. There is also a three sided oversize pole barn currently being used for equipment storage located at the end of one of the trails. The property is accessed off a municipal road via (3) gated entry points. A gazebo at the summit takes in nearly 360 degree long range views providing the idyllic setting for a substantial residence. The properties captivating views and trailed woodlands stand ready to implant your vision.

Listed by Roger Danyew of Diamond Realty

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$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • Square Feet 6,799

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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5250 West Woodstock Road Woodstock VT 05091

Woodstock, VT5250 West Woodstock Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4918791

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 5,348

The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes' drive of the Killington and Okemo ski resorts, respectively. Known locally as the Robinson Farm, after the family that build the handsome home and legendary barn shortly after the turn of the 20th Century. The property has been converted by the present owners into a gracious and authentic rural farm environment for vacations, weddings, and other events large and small. The historic 1905 Farmhouse Inn offers accommodation in the 7 Guest Rooms, all with private baths and gracious gathering rooms on the first floor. A 2-bedroom Innkeeper's quarters provides private living space. The Red Barn was constructed in the style of a 'bank barn' with grade level entry points to the different levels of the barn where they served a variety of agricultural purposes. The massive timber frame is exposed on all levels with the upper two having been adapted for the event venue hosting up to 150 guests. The White Barn accommodates 50 guests for smaller ceremonies and other events with a wide deck providing a place of seasonal outdoor dining. 13 acres of open land and convenient location offer the potential to create a farm-to-table restaurant, direct-to-consumer shop selling local and regional goods or an immersive Agri-tourism guest experience. Less hospitality-oriented uses as a gentleman's farm or niche farm producing or marketing local goods are great options as well.

Listed by Rachel Arsenault and Laird Bradley of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$3,550,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Square Feet 10,206
  • Bedrooms 10
  • Bathroom 15

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

  • Residential Single Family
  • Square Feet 600
  • Bathroom 1
  • Construction Existing
  • Bedrooms 2

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Square Feet 5,142
  • Bedrooms 6
  • Construction Existing
  • Bathroom 8

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Carol Wood and Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.57% last updated on May 25, 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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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 May 28, 2023 6:39 PM EDT