Woodstock VT Real Estate

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

Homes for Sale in Woodstock

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2456 Cox District Road Woodstock VT 05091

MLS Number 4978162

  • Residential Single Family
  • Bedrooms 2
  • Square Feet 2,032
  • Bathroom 2
  • Construction Existing

A Beautiful Ranch located on a prestigious country road in Woodstock, Vermont. Once voted the prettiest small town in America. Almost 2 acres, this property has plush lawns and mature plantings. Private pond. Shed. Beautiful scenery out every window. Hard wood floors under upstairs carpet. Spacious finished basement with 3 rooms and full bathroom. Deck at front door and huge deck off Livingroom. It's a luxury in Vermont to have a garage attached to the house. Electric garage door opener.20 minutes to Killington Ski area. Enjoy country living at its' best. Farmers Market just down the street.

Listed by Dorothea Mongulla of High End Realty

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$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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506 Westerdale Road Woodstock VT 05091

Woodstock, VT506 Westerdale Road

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4976244

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,492

A great opportunity to acquire a small Woodstock horse farm nestled on 5+ private acres, with an updated 3 bedroom home, oversize detached 3 car garage with large storage room above or to be converted to offices/playroom,. This property also includes an Amish horse barn containing three 12x12 stalls, tack room, power and water, equipment shed, 2 fenced paddocks and even a riding ring. On main level is a handsome kitchen, with stainless steel appliances and granite counters, dining area that overlooks a deck and perennial gardens, dramatic living room, with hardwood floors, vaulted ceiling, exposed beams, and dramatic windows. Completing the 1st floor are 2 bedrooms and a bath with Travertine tiled shower. The upper level features a primary bedroom, with ensuite tiled bath, and den/office area. Partially finished basement has 30x23 family/exercise room. A wood deck wraps around the front of the house providing views of a rolling lawn down to the exclusive swimming pond. Trail system near by for the outdoor enthusiasts. Rolling yard accents this quaint home located on one of Woodstocks premiere roads. Just 5 minutes to Historic Woodstock Green. Okemo and Killington Ski areas within 30 minutes. Fly Fishing, championship golf and shopping all nearby. This property is being offered furnished with some exclusions. Come take a look!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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 4976148

  • Residential Single Family
  • Square Feet 1,500
  • Bathroom 2
  • Bedrooms 3
  • Construction Existing

Escape to the green mountains of Vermont! This 23.46 acres is ideally located just 2 miles south of Woodstock VT in the very desirable area of South Woodstock. As the saying goes- location, location, location! Also known as horse country this area of central VT is as scenic as it gets with large acreage properties very rarely becoming available. The Green MTN Horse Association, the So, Woodstock general store, The Kedron Valley Inn and the So. Chapel Church make up the small village of So. Woodstock. Down shift as you settle into country life where the pace is slower and life is a lot more beautiful. This is quintessential Vermont. Farmed since the 1800s and still being lovingly tended to, this land is abundant in natural resources including rich soil, pasture land, wood lot, water, perennial gardens, and mature fruit trees. Currently used as a sustainable homestead this property could easily make the transition to luxury mountain or equestrian property. Take your pick from multiple appealing home sites on this 23 acres. The diverse landscape includes meadow, forest, woodland trails, high elevation spots, brook, established gardens, fruit trees, moss covered stone walls, and a year round brook. The property also features a 1500 sq ft house and a 792 sq ft insulated barn/workshop as well as a small cabin, root cellar, sugar house, and chicken coop. Use the house while you build out your vision, parcel off 5 acres to offset costs, or live in to the turnkey house.

Listed by Derek Greene of Derek Greene

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$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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37 Atwood Avenue Woodstock VT 05091

Woodstock, VT37 Atwood Avenue

Price$379,000

Est. Mortgage: $/month

MLS Number 4975954

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 768

It's not just maple syrup that makes VT sweet! This efficient and stress-free home is move-in ready with newer systems including furnace, hot water heater, Tesla power wall and water purifier. The interior has been renovated throughout as well with fresh kitchen with solid surface counters, gas range, newer appliances and easy care vinyl plank flooring. The exterior features a deck to enjoy the local mountain views and a shed to store garden tools and toys. Move in and enjoy the short jaunt to the bustling village with quaint shops, covered bridges, hiking trails, cozy bistros and restaurants, and close proximity to premier skiing and the Dartmouth/Upper Valley regions. Delayed showings begin on 11/2/23.

Listed by Melissa Robinson of Coldwell Banker LIFESTYLES - Hanover

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$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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1747 Long Hill Road Woodstock VT 05091

Woodstock, VT1747 Long Hill Road

Price$495,000

Est. Mortgage: $/month

MLS Number 4972644

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 868

An idyllic 10 acres of land that is privately situated in the midst of several of the premier estates of South Woodstock! The interior of this acreage is very accessible, with meandering trails leading through the parcel to invite your casual exploration on foot or on horseback. Upon entering the property from Long Hill Road a private driveway leads up to a sunlit clearing in which is situated a classic old log cabin. This simple cabin has served the owners well for many decades as a much enjoyed "camp" where they escaped to life in a simpler form. The location of this parcel could certainly justify the construction of a truly substantial home. The obvious appeal of the land, with the ancient stonewalls, the woodland trails and the sunlit open spaces could suggest securing the land for immediate enjoyment while planning for a future use. Location, location, location!

Listed by John Wetmore of William Raveis Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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1747 Long Hill Road Woodstock VT 05091

Woodstock, VT1747 Long Hill Road

Price$495,000

Est. Mortgage: $/month

MLS Number 4972595

  • Land
  • Acreage 9.96
  • PricePerSqFt 49698.8
  • Zoning Residential

An idyllic 10 acres of land that is privately situated in the midst of several of the premier estates of South Woodstock! The interior of this acreage is very accessible, with meandering trails leading through the parcel to invite your casual exploration on foot or on horseback. Upon entering the property from Long Hill Road a private driveway leads up to a sunlit clearing in which is situated a classic old log cabin. This simple cabin has served the owners well for many decades as a much enjoyed "camp" where they escaped to life in a simpler form. The location of this parcel could certainly justify the construction of a truly substantial home. The obvious appeal of the land, with the ancient stonewalls, the woodland trails and the sunlit open spaces could suggest securing the land for immediate enjoyment while planning for a future use. Location, location, location!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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13B River Street Woodstock VT 05091

Woodstock, VT13B River Street

Price$1,929,000

Est. Mortgage: $/month

Pending

MLS Number 4972497

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

This is a rare opportunity to purchase a newer construction residence (2021) built to the highest quality standards by renowned local architectural design/build firm ACS Design. Located right in the village, yet set back from the road and abutting the National Park - you can walk to everything. The house interior offers an open floor plan, vaulted ceiling great room with handsome stone fireplace, built-ins and lovely views, and opens to a private dining room and the gourmet kitchen. A laundry room and mud-entry connects the garage/covered porch with the kitchen for easy access. The residence lives on one level with a 1st level primary bedroom with en suite bath and walk-in closet. Upstairs is a sitting room office with natural light from large windows and skylights, as well as two spacious bedrooms, both with ensuite baths. The garage upstairs is finished and heated - which could be used as an office, a rec/game room, or workout room. Excellent HVAC systems include both radiant heated floors and discretely placed heat-pumps, which offer a second source of heating in the "shoulder seasons", and whole-house air conditioning. The property is beautifully landscaped with extensive outdoor living spaces: a large stone patio out front, a grilling/dining patio on the side with an outdoor shower and space for hot tub and grill, and a 3-sided wrap-around porch that welcomes you home and greets visitors in all seasons. SEE PROPERTY WEBSITE. ** DELAYED OCCUPANCY - Please inquire

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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513 Deerbrook Way Woodstock VT 05091

Woodstock, VT513 Deerbrook Way

Price$1,295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4972415

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,668

This classic New England Colonial home is perched on a hillside to take advantage of the pleasant views of the distant hills and to benefit from its southern exposure. The home was professionally designed and custom built by the highly-regarded Vermont Vernacular Builders. Respect for the architectural vocabulary of Vermont is apparent in the form, scale, and proportion of this gracious, sun-filled, four bedroom home. There are wide board floors throughout the entire home with ceramic tile, appropriately, in the mudroom, kitchen and baths. You will be charmed by the exposed ceiling beams in the cozy den and in the spacious eat-in chefs kitchen. The large butler pantry has plenty of storage and leads to a formal dining room. The home boasts a gas insert in the fireplaced living room and a wood stove warming the den, which provides plenty of room for entertaining or just relaxing at home in the evenings. This beautiful home is privately located on over 8 acres yet is just a few miles away from the amenities of historic Woodstock Village: dining, shopping, and cultural events. Experience world class skiing less than eight miles away to the west at Killington Skyeship Base Lodge. Exterior features include an oversized garage/barn with storage above that could be converted to an additional dwelling unit or guest accommodation. There is also a beautiful in-ground swimming pool and a large deck overlooking the mountains. Seller is licensed agent.

Listed by Kathy Mahoney of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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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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

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$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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
  • Bathroom 4
  • Square Feet 4,610

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: 7.29% last updated on Nov 22, 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$499,000

Est. Mortgage: $/month

Pending

MLS Number 4968624

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

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, hook up for 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.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 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 a 2 bedroom apartment and a 2 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: 7.29% last updated on Nov 22, 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 November 29, 2023 3:38 AM EST