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Woodstock VT Real Estate

Woodstock is located in Windsor County in the southeastern part of Vermont. It has a population of approximately 3,200 and a household median income of approximately $57,000.  Neighboring towns include Bridgewater and Pomfret. Woodstock has 1 elementary school, 1 middle school and 1 high school. Browse available Woodstock VT real estate below. 

Woodstock Real Estate & Homes for Sale

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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

$
$
%
$/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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1782 South Road Woodstock VT 05091

Woodstock, VT1782 South Road

Price$549,000

Est. Mortgage: $/month

MLS Number 4936894

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

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

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42 Heritage Condos Way Woodstock VT 05091

MLS Number 4935979

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

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

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4935033

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

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

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

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

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

Listed by Christopher Lang of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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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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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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated December 5, 2022 1:54 AM EST.