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Woodstock VT Real Estate

Woodstock Real Estate & Homes for Sale

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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. 

60 Pleasant Street Woodstock VT 05091

Woodstock, VT60 Pleasant Street

Price$950,000

Est. Mortgage: $/month

MLS Number 4969539

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3

Incredible opportunity to own a piece of Woodstock History that has not been up for sale in over 50 years. The Woodstock Train Station, which first welcomed passengers in the late 1800s, is a main stay in the community and is one of the first buildings to greet people as they arrive in town. It has great visibility on Rte 4 and is just across the way from the recently developed East End Park and Riverfront. The building has seen several transformations over the years but currently sits empty. Buildout is underway to have a 2 bedroom apartment on the 2nd floor and commercial space on the main level. It is basically a clean slate for someone to come in and create their own vision and next chapter for the property. Recent upgrades include all new electric, plumbing, windows, and a new roof, and both the town sewer and water lines have been replaced. This historic building has endless potential in a premier location and comes with plenty of parking out back. Sale of the property is contingent on approved subdivision.

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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708 E Woodstock Road Woodstock VT 05091

Woodstock, VT708 E Woodstock Road

Price$599,000

Est. Mortgage: $/month

MLS Number 4969496

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Bathroom 1
  • Square Feet 1,034

This charming home is the perfect place to relax and unwind and is less than a mile from the heart of Woodstock with shops and restaurants. Wake up to stunning views of the mountains, then spend your days exploring the nearby hiking trails. In the evenings, enjoy a glass of wine on the deck in the secluded garden. 25 minutes to Dartmouth College 30 minutes to Dartmouth Hitchcock Medical Center 20 minutes to VA hospital 23 minutes to Killington Skyship Base Lodge 6 minutes to the Athletic Club for golf, mountain bike trails, indoor/outdoor tennis and an expansive Nordic ski trail system. Recent upgrades include new electrical and plumbing, a new bathroom, new kitchen with quartz countertops, new appliances including an electric heat pump water heater, spray foam insulation and new windows throughout. The septic will need to be replaced, but all plans and permits are in place and a credit will be issued for the installation cost. Showings by appointment. Seller is a licensed agent.

Listed by Karen DeMas of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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2018 Church Hill Road Woodstock VT 05091

Woodstock, VT2018 Church Hill Road

Price$2,275,000

Est. Mortgage: $/month

MLS Number 4969169

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 4,610
  • Bathroom 4

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the spring-fed swimming pond. Designed for gracious country living the eat-in kitchen and generous great room are accented by a fieldstone fireplace and vaulted ceilings. The primary bedroom suite and two guest bedrooms are located on the main living level with a walk-out level offering an additional bedroom with media and exercise areas. A 'bonus room' used as a studio is available for many alternative pursuits. Fifty acres of private woodland and open meadows is laced with trails enabling access to nature year round. A small stable is a resource to take advantage of South Woodstock's network of horse trials and miles of gravel roads. A private retreat within minutes of Woodstock's Village Green or the South Woodstock and the Green Mountain Horse Association. The best of all possible worlds.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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39 South Street Woodstock VT 05091

Woodstock, VT39 South Street

Price$550,000

Est. Mortgage: $/month

MLS Number 4968624

  • Residential Single Family
  • Square Feet 1,020
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2

Located a quarter mile from the Village Green, this peaceful home does not rely on any fossil fuel energy to run. Outfitted with energy efficient mini splits for heat and air conditioning, an electric car charger, and energy-star rated appliances, this cozy two-bedroom two bath home is looking for a new owner. Located across the street from the historic Vail Field. Enjoy a local baseball game from the wrap-around front porch. Showings begin at the Open House Saturday, September 9, from 12 - 3 PM and Sunday, September 10, from 12 PM - 2 PM.

Listed by Holly Hall and Fran Collins of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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72 Frenchs Road Woodstock VT 05091

Woodstock, VT72 Frenchs Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4968402

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4

Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the grand living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a Primary with ensuite bath and a quaint sitting room. In addition to the main house, there is a detached garage with an apartment above and a 1 bedroom cottage set back on the premises. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away.

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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268 Willow Brook Road Woodstock VT 05091

Woodstock, VT268 Willow Brook Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 4968234

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,148

This elegant residence is an Award Winning Lindal Cedar Home. Private sited on the edge of Woodstock Village it is within walking distance of the abutting King Farm and the Woodstock Recreational Center. Constructed of massive laminated beams enabling the home to offer expansive light-filled gathering rooms on three levels. A combination chef's kitchen opens into a solarium for casual entertaining adjacent to classic formal dining area with indoor grill for celebrations and holidays. The gracious foyer opens in to a Great Room with wood burning fireplace and direct access by French Doors onto the south facing patio. The south and westerly common areas are located a discrete distance from 3 main level bedrooms two full bathrooms. An open stairway and loft overlooking the Great Room leads to the primary bedroom suite and a quiet study. The lower walkout with a second wood-burning fireplace and 3/4 bathroom is presently configured as a media and gameroom. Two attached garages provide ample space for 3 vehicles and outdoor recreational equipment. Convenient with a country environment this is a home for all seasons.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5798 South Road Woodstock VT 05071

Woodstock, VT5798 South Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4968227

  • Residential Single Family
  • Square Feet 4,510
  • Bedrooms 5
  • Construction Existing
  • Bathroom 7

For nearly two centuries the iconic Kedron Valley Farm has served as the gateway to the village of South Woodstock. Prominently sited on a knoll with lovely valley views in every direction, this warm and inviting post and beam home has been fully rejuvenated, honoring the classic period detail. The main house is ideal for entertaining with bright, generous rooms, and cozy spaces. The living room runs front to back, centered by a fireplace with pine surround and exposed beams. The kitchen is well suited with Thermador appliances, quartz counters and custom mahogany cabinetry. The spacious private primary suite features exposed beams, cathedral ceiling, new tandem bathrooms connected by a walk thru shower, plenty of closet space, laundry and AC. There are four additional guest suites, a TV and reading room w fireplace and built-ins, and clever loft spaces with offices. The charming, separate three-bedroom carriage house is perfect for guests, family or as an income producing rental unit. The property is anchored by a spectacular 4-story bank barn with six horse stalls, fenced paddocks and a run-in shed complete with power and water. The grounds are gorgeous with a beautiful brick terrace, level verdant lawns, grand, 175 year old maple trees, established perennial beds, a private swimming pond, apple orchard, and a fenced har-tru surfaced tennis court sited discreetly at the rear of the property. Seven minutes to Woodstock Village Green. Broker interest.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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2876 Hartland Hill Road Woodstock VT 05091

Woodstock, VT2876 Hartland Hill Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4967464

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing
  • Square Feet 3,350

This property is the quintessential classic Vermont farmhouse featuring the "big house, little house, backhouse, barn" concept. Conveniently located only 1.4 miles from the center of Woodstock village the home is surrounded by lovely gardens the Happy Valley brook and open meadows. The magnificent post and beam barn's upper level serves as parking space for multiple cars and abundant storage. The lower level has several stalls for animals that lead out to a paddock. The house has recently been completely renovated while retaining the lovely antique features . The rooms are filled with natural light and there is access to outdoor spaces throughout . The window from the fabulous "cook's kitchen" looks out to the open meadows beyond. The stone fireplace in the large family room is perfect for cozy fires on snowy winter days with amazing views from the French doors that open to a spacious deck perfect for entertaining. Living room with cathedral beamed ceiling and fireplace leads to a covered porch surrounded by perennial gardens. The bedroom floor plan provides privacy for multiple people. Close by is the Woodstock Inn Sports Center and Golf Club. Skiing at Killington and Woodstock's own Saskadena Six are minutes away . Two and half hours to Boston and 5 hours to NYC.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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2127 E Woodstock Road Woodstock VT 05091

Woodstock, VT2127 E Woodstock Road

Price$479,000

Est. Mortgage: $/month

Pending

MLS Number 4967184

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Square Feet 1,757
  • Bathroom 2

Discover the essence of Vermont living in this exquisite 2-bedroom, 2-bath home, with spacious bonus room w/bath; from its rustic charm to modern elegance, this property seamlessly combines natural beauty with contemporary comfort. Seeking a vacation retreat with STR income? This is it! Renovated kitchen with hard marble countertops and gleaming, energy-efficient appliances. The living room boasts wood floors & exposed beams, including classic Vermont charm with built in shelves. The bedrooms on the first level are designed for comfort and convenience, offering walk-in closets & direct access to the deck creating a seamless flow between the indoor & outdoor living with views overlooking the Ottauquechee River. The lower level offers a bonus room w/adjoining bath & rec room - complete with walkout to amble level yard offering space for various recreational activities, making it an ideal spot for both relaxation and entertainment. The home is thoughtfully designed with energy-efficient improvements. These upgrades not only contribute to eco-friendliness but cost savings. Only 5 minutes away from downtown Woodstock, under 10 minutes to Quechee Gorge, you'll enjoy convenience without sacrificing tranquility. Embrace all seasons - 30 minutes to Killington Resort & minutes to Saskadena Six Ski Area. Whether it's snowy winter days or warm summer nights, this home is your gateway to the best Vermont has to offer. Home Warranty Included.

Listed by Isabella Luhrs of BHG Masiello Keene

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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98 Riverbend Way Woodstock VT 05091

Woodstock, VT98 Riverbend Way

Price$100,000

Est. Mortgage: $/month

Pending

MLS Number 4967118

  • Mobile
  • Listing Agent Name Mia Parsons
  • Year Built 1997
  • Bedrooms 2
  • Square Feet 1270

A wonderful opportunity in the amazing community of Woodstock, Vermont. Only 10 minutes to the charming Woodstock village. This mobile home has plenty of space with two bedrooms located at either end of the home, two full bathrooms, a large living room and a beautiful, spacious kitchen. The large array of windows in the kitchen/dining area allows sunlight to pours through. The beautiful sliding barndoor allows for privacy as it separates primary bedroom, laundry, and kitchen area from the living room and second bedroom. Ideal outdoor space for plant lovers or to sit by the fire pit with friends. Killington Mountain is just 25 minutes away; skiing, hiking, kayaking, snowshoeing is within easy reach. Showings begin at Open House on Saturday, August 26 from 12:00 pm to 2:00 pm.

Listed by Mia Parsons of Douglas Elliman of Vermont LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

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 September 27, 2023 3:56 PM EDT