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.  

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$499,000

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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2525 Barnard Road Woodstock VT 05091

Woodstock, VT2525 Barnard Road

Price$1,875,000

Est. Mortgage: $/month

Pending

MLS Number 4935649

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Square Feet 3,552
  • Bedrooms 4

This classic 1850's farmhouse honors the timeless VT vernacular while having been meticulously renovated and updated with a crisp modern aesthetic. The rooms are bright, spacious, and flow seamlessly to comfortably accommodate family and friends. The first level great room is anchored by a beautiful fieldstone fireplace suited with a woodstove. The generous, well-appointed kitchen. Wolf range, Danby marble counters and custom built-ins. TV room with pellet stove, potential guest suite/office and mudroom further complete the first level. The generous primary suite and two bedrooms are located on the second level. A double guest room with spa bathroom is located on the third level. Four stall barn with tack room, power and water to accommodate horses, hobbies or to host parties! The grounds are comprised of 28+ac of rolling fields and woods with an interior trail system for hiking, biking and snowshoeing. There are magnificent, established perennial beds, extensive landscaping and a stone terraced area for outdoor entertaining around the firepit. The scenic valley view will capture dramatic sunsets. There's even a pond for a cool dip on a hot day, and the active N. Bridgewater Brook abounds the north property line. Solar panels, and a leased Tesla storage battery provide peace of mind in the event of a power interruption. Conveniently located just 5 minutes from the Woodstock Village Green. 10 min to skiing at Saskadena Six;10 min to Silver Lake; 20 min to Killington Mtn.

Listed by Danny Kogut 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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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

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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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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

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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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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

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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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178 Willow Brook Road Woodstock VT 05091-3734

Woodstock, VT178 Willow Brook Road

Price$1,195,000

Est. Mortgage: $/month

Pending

MLS Number 4933482

  • Residential Single Family
  • Square Feet 3,312
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

OPEN HOUSE - NOVEMBER 19th SATURDAY 1-3:00pm. Beautiful contemporary timber frame 4 bedroom, 3.5 bathroom, 3,300sqft home with an attached 2 car garage on 2.44 acres. Generous no-cost furniture package is available! Privately sited on a lovely rolling hill with stone retaining wall, garden space, & gorgeous southerly views of the Vermont countryside. This property offers an ideal Woodstock location with a 1 mile walk to the heart of town, and even less to the Woodstock Middle/High School. The property directly abuts the protected King Farm and the Marsh Billings Rockefeller National Historic Park trail network to the Pogue, Billings, & Faulkner Park. The main level open floorplan living/dining space has beautiful 20ft plus cathedral ceilings with exposed beams and the kitchen features great counter space, practical storage pantry & updated appliances, along with a main level master bedroom with en-suite bathroom, separate laundry room, and half bath. The upper level has a lovely open loft/office space with southern pine floors, and there are two bedrooms with cathedral ceilings & large closets, and a common shared full bathroom. The lowest level features a large family room, an additional bedroom, & full bathroom for complete guest quarters; along with a heated workshop for projects & extra clean overflow heated basement space. The house has an expansive newer solar array feeding back to the grid and a dual TESLA battery system which serves as a whole house generator.

Listed by John Bassette 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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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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10 Linden Hill Woodstock VT 05091

Woodstock, VT10 Linden Hill

Price$980,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4932889

  • Residential Single Family
  • Square Feet 2,970
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

A light-filled Village Victorian-era home located in an established neighborhood with great character and charm is located within an easy walk to Woodstock Village. The windowed front porch, bordered by perennial gardens, is a great space to relax at the end of the day. The renovated kitchen opens to a spacious family room and is terrific for entertaining. The spacious dining room has a propane wood stove. A comfortable den with built-in bookcases is located just off the dining room. Upstairs are three bedrooms and two bathrooms. Listen to the activity on Vail Field from a sunny second-level deck that allows for views across the valley. Ample finished space in the basement can serve as a guest room, office, or playroom. Stone steps access the level backyard at the end of the driveway. Leased Tesla batteries provide comfort and peace of mind when/if the power is lost. The Li Hi neighborhood, Chill on the Hill, is one to be appreciated! The seller is a licensed Realtor.

Listed by Daphne Lowe 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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853 Rose Hill Road Woodstock VT 05091

Woodstock, VT853 Rose Hill Road

Price$549,000

Est. Mortgage: $/month

MLS Number 4932868

  • Residential Single Family
  • Square Feet 2,604
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing

The opportunity presented by this unique Woodstock property provides much to consider! The entire 1.3 acre parcel is zoned Light Commercial Light Industrial enabling commercial venture use. There is a highly visible level lawn area directly on Route 4 that is diagonally opposite the beloved Woodstock Farmer's Market. The 2 detached residences which are accessed off desirable Rose Hill each benefit from connection to the municipal sewer system. The demand for Woodstock rental housing is steady and rental rates are at historically high levels. The barn style residence has a multipurpose garage/workshop space on the ground level. A convenient adjacent office area makes this space ideal for use by a contractor, tradesman or hobbyist requiring a workshop. A 2nd floor apartment can either be separately entered through a graceful covered porch or from within the garage. The 1 bedroom apartment features a kitchen, living room, bedroom and full bath with laundry. The 2nd residence is a classic New England 3 bedroom home. The ground floor features a simple kitchen with a pantry, dining area and a large living room with spacious built in book case. Attractive wood floors, well placed windows and a covered front porch add appeal. On the 2nd floor are 3 bedrooms and a bath. A simple comfortable home, with attractive features. Great components create a great location, with great zoning, with great infrastructure and with great rental income potential! The value of the components is real!

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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433 Cowdrey Path Woodstock VT 05071

Woodstock, VT433 Cowdrey Path

Price$995,000

Est. Mortgage: $/month

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 surrounded by conserved land 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: 6.49% 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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311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$3,300,000

Est. Mortgage: $/month

MLS Number 4932341

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

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. 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

$
$
%
$/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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592 Quinn Road Woodstock VT 05091

Woodstock, VT592 Quinn Road

Price$2,975,000

Est. Mortgage: $/month

Pending

MLS Number 4932110

  • Residential Single Family
  • Square Feet 4,700
  • Bathroom 7
  • Construction Existing
  • Bedrooms 6

This charmingly restored turn of the century Dutch Colonial 6-bedroom farmhouse is sited on 573 acres backing up to the 22,000 acre Coolidge State Forest. Long Hill Farm has the dramatic big mountain setting. The house expands to fit many guests while still intimate for a quiet weekend away. The wraparound porches take in the breeze and views to the gardens, meadows and mountains. The property and adjoining lands are threaded by miles of wide trails, connecting to the GMHA and VAST networks, providing four season access to a remarkable landscape of big trees, old orchards, and sweeping meadows. A log cabin provides a rustic retreat in the back woods. A classic end-of-the-road setting, Long Hill Farm feels miles from anywhere, yet is five minutes to pizza, ten to the Farmer's Market and 15 to Killington Skyship tram.

Listed by T Story Jenks and Ruth Sudduth 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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588 Kendall Road Woodstock VT 05091

Woodstock, VT588 Kendall Road

Price$539,000

Est. Mortgage: $/month

MLS Number 4929954

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Bedrooms 5
  • Square Feet 2,904

While relaxing on the gracious front porch of this classic New England home the mesmerizing sound of the nearby cascading brook can transport your cares away! Located in equestrian oriented South Woodstock, this home presents generous interior space to entertain the friends and family who will surely come to enjoy all that Woodstock offers. The principal rooms feel large and welcoming. Yet, throughout the house private areas are easily found. As is typical in traditional New England homes, there are well placed windows and beautiful wood flooring. Upon entering the home this striking flooring is immediately displayed, in a practical entry room, which then opens to a bright kitchen, with eat-in dining area. Adjacent to the kitchen is a dining room. A large double living room provides comfortable gathering spaces, with a fireplace in 1 room and windows viewing out to a large front porch in the other. Completing the ground floor are a 1/2 bath and a bedroom. On the 2nd floor are 4 well placed bedrooms, all with beautiful wood floors. Adjacent to a full bath is a den/sitting room. Well separated, at the opposite end from the bedrooms, is an office area with space for 3 workstations. Conveniently, this workspace has interior stairs leading directly down to the kitchen. Both the desirable South Woodstock location and the spacious interior floor plan of this classic Vermont style home make it equally suited to be a convenient year round residence or a wonderful vacation retreat!

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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19 the Green Woodstock VT 05091

Woodstock, VT19 the Green

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4928047

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 4,454
  • Construction Existing

THE OTIS SKINNER HOUSE - Once owned by famed stage actor Otis Skinner, this historic Woodstock village home has been lovingly and comprehensively updated by its current owners. The spacious gourmet kitchen is a home chef's dream with a stunning Lacanche range, dual dishwashers, a brand new Sub-Zero refrigerator, ample counter space, and abundant storage. Redesigned and renovated in 2011 around a central windowed "tower," the home overlooks the Ottauquechee River and the covered bridge; Pella casements welcome in stunning sunset views and the sounds of water journeying to the Connecticut. With at least six flexible bedroom spaces - including a third-floor guest suite - a formal office, and multiple common spaces, this home accommodates a houseful as comfortably as it provides a cozy home for just a few. From the copper roof to the central air on the second and third floors to excellent heating systems, 19 the Green is well designed to greet every New England season. Beautifully situated on Woodstock's fabled Green and a short stroll from shops and restaurants, the Otis Skinner house enjoys the best of two worlds - the home may be situated at the heart of the village, but it truly lives on the burbling banks of the Ottauquechee.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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$
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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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3 BOND Street Woodstock VT 05091

Woodstock, VT3 BOND Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4924310

  • Residential Single Family
  • Village Woodstock
  • Bedrooms 7
  • Square Feet 6,472
  • Construction Existing

#3 BOND STREET is a classical example of the Greek and Colonial Revival architectural movement in the United States. Built in 1836 by Henry Lawrence, a piano manufacturer, the property transferred a year later to Oel and Sophia Billings who resided in the home they called 'The Maples' with their nine children. Their daughter Elizabeth lived in the home after her parents moved to #16 the Green and she later shared it with her brother Frederick, until he could acquire and renovate the George Perkins Marsh Mansion. The home was later the long time residence of Frank and Lucy MacKenzie. Her kindness and support of animals in service to people is remembered by naming the regional animal shelter in her honor. The residence is currently configured as three apartments, but retains the original floor plan. Evident throughout the home are elegant moldings, trim and architectural elements of the bygone era, including a greenhouse used on the north side for orchids and spacious interior porch leading to the private back yard on the northeasterly side where it provided cool shelter on summer days. A remarkable property with a special heritage as home to many who made Woodstock what it is today.

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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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 5,412

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

$
$
%
$/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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2305 South Road Woodstock VT 05091

Woodstock, VT2305 South Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4921126

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Square Feet 1,748
  • Bedrooms 3

Gambrel style Cape sited on a corner parcel of 4+- acres of open land bordered by the Kedron Brook. Updated eat-in kitchen and baths, living room with built-ins, dining room, hardwood floors, and spacious mudroom. Upstairs en-suite primary bedroom and two additional bedrooms. Complete with detached carriage barn/garage and spacious deck. Only two miles to the village green and minutes to Mt. Peg for hiking, biking, and cross-country skiing.

Listed by Scott Monahan and Danny Kogut 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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3436 Church Hill Road Woodstock VT 05071

Woodstock, VT3436 Church Hill Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4918981

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,894

Set back off a quiet country road with stone walls sits this Cape Cod home on thirteen acres. A peaceful setting for those seeking privacy in South Woodstock. The fenced-in backyard is perfect for summer barbecues and long swims in the pool. Enjoy a cocktail on the covered porch while the sun sets. A mix of rolling pasture allows for gardening and equine friends. The main level of the home features hardwood oak flooring, a large living room with fireplace, an eat-in kitchen overlooking the backyard, dining room, laundry room, half bath and a bedroom suite. The upper level provides pine flooring, an additional bedroom, bonus room and bath. There is a separate guest apartment with its own entrance over the garage. The attached and detached garages offer a workshop and plenty of space for toys, vehicles and storage. Solar panels cover most of the electric overhead. Lovely landscape surrounds the yard with lilacs, roses and shrubs. Less than five minutes to Green Mountain Horse Association with easy proximity to golf, skiing and Woodstock center. Showings begin Saturday, July 9th.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l 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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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
  • Bedrooms 9
  • Construction Existing
  • Bathroom 9
  • Square Feet 4,502

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: 6.49% 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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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

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

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: 6.49% 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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234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

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

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: 6.49% 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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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 7, 2022 3:53 AM EST.