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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. 

4945 South Road Woodstock VT 05091

Woodstock, VT4945 South Road

Price$2,865,000

Est. Mortgage: $/month

MLS Number 5013744

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

The melding of the convenience of a premiere Village residence with the privacy and peace of a country estate is a rare balance. The John Arnold Cottle House achieves just such a balance. The three bedroom two story brick Federal home, built in 1811, has a prominent position on the main street in South Woodstock hamlet. It's setting belies the unique qualities the 2.7 acres offers. A drive to the lower level two car garage separates the main house and the renovated Kingley Barn, a two bedroom with loft guest house with a deck overlooking the Kedron Brook. There is a timber bridge crossing the Kedron Brook which accesses the open field and meadow and the two bay barn. The 450 feet of frontage on the Kedron Brook is an ideal tranquil retreat to enjoy the water element, firepit and surrounding environment with complete privacy. The John Arnold Cottle House has been fully renovated/restored with all of the best systems and finishes. The newer addition on the rear of the house has a gourmet kitchen, large brick fireplace, and relaxed living space.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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187 Dana Road Woodstock VT 05091

Woodstock, VT187 Dana Road

Price$695,000

Est. Mortgage: $/month

Open House

MLS Number 5013447

  • Residential Single Family
  • Next Open House: Sat 09/14 10:00 am. to 12:30 pm.
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3

This beautifully maintained home is perfectly situated on a quiet street just minutes from the middle/high school and the renowned Woodstock Farmer's Market. Step inside to discover a home that has been thoughtfully updated for modern comfort. Recent improvements include blown-in cellulose insulation and 2" exterior insulation, new windows throughout, a whole-house generator, and a newly added first-floor bathroom, ensuring a cozy and energy-efficient living environment year-round. One of the standout features of this property is the inviting three-season porch. Whether you're enjoying a quiet moment with a good book or hosting friends and family, this versatile space is sure to become your favorite spot in the house. In fact, this home has endless spaces for hosting! The open and welcoming kitchen/dining area is another perfect gathering space, while the living room, centered around a warm and charming gas fireplace, offers a cozy retreat for relaxing evenings. Additionally, the spacious family room provides even more room for entertaining or unwinding. Storage is never a concern here. A clean concrete basement and a one-car garage offer ample space for all of your hobbies. Located just minutes from downtown Woodstock, you'll enjoy the peacefulness of your quiet backyard while being close to shopping, dining, and entertainment. This property beautifully blends comfort, functionality, and convenience, making it the perfect place to call home. Showings delayed until 9/14.

Listed by Melissa Grey of KW Vermont-Stowe

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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378 Fletcher Hill Road Woodstock VT 05071

Woodstock, VT378 Fletcher Hill Road

Price$525,000

Est. Mortgage: $/month

MLS Number 5013286

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 1

Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away! The entrance to the property is via a level tree sided private driveway. By walking up a few steps from the driveway you enter the home into a bright kitchen. Adjacent to the kitchen is a Living room/dining room that features access to a balcony with views of distant hills. Well located within this space is a hearth with a wood pellet stove. At a further end of the main floor is an attractive room equally well suited to be a family room or a first floor bedroom. Completing the main floor is a full bath with both a shower and a tub. Accessed up stairs from the living room are two second floor bedrooms. One of these bedrooms features a private balcony, with hillside views. The full basement is entered either via an interior stairway or through a ground level door off the driveway. Within the basement is a laundry area, space used as a workshop and storage area. Mechanical systems are contemporary, with a newer furnace and hot water heater. Separated off the basement is a 15'x11' heated room currently used as living space. A comfortable home, in a great location within desirable Woodstock!

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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2394 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT2394 Fletcher Hill Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 5012999

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,944

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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2358 Long Hill Road Woodstock VT 05091

Woodstock, VT2358 Long Hill Road

Price$6,750,000

Est. Mortgage: $/month

MLS Number 5011268

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

Sited on 465 +/- private acres in South Woodstock, Birch Tree Farm was created as a retreat to bring family and friends together and to enjoy the great outdoors. The farm offers a variety of experiences, including pressing apples for cider, collecting eggs for breakfast, hiking to the cabin with 360 degree views, fishing or skating on the pond, enjoying miles of trails for walking, riding, or snowshoeing, and tapping trees for maple syrup. The relaxed vibe of the Lodge-style home, made of wood and stone, evokes a sense of mountain living, with design elements like exposed beams, a cathedral ceiling in the great room, a large stone wood burning fireplace, and floor-to-ceiling windows that frame expansive views of the mountains and the Ottauquechee Valley. Step out onto the wrap-around deck to take in an infinity pool, hot tub, stocked pond, and apple orchard. Landscape design by Shep Butler includes 10' hydrangea bushes, perennials gardens, stone walls, wild lupine in the meadow and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with seven stalls, an office/tack room, and a versatile upper level for entertaining & recreation, as well as accommodating an overflow of guests. Nine fenced pastures, two run-in sheds, a two-level storage barn, and a chicken coop enhance the farm with miles of trails connecting to GMHA. Showings begin 8-30-24

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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33 River Street Woodstock VT 05091

Woodstock, VT33 River Street

Price$1,695,000

Est. Mortgage: $/month

MLS Number 5009557

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hiking on Mtn Tom in your backyard. Situated on a very large lot featuring an in-ground pool accented with arbor and pool house. Lovely perennial gardens and large backyard for those seeking a vegetable garden or room for entertaining friends and family. This 4000+ sq. ft residence has generous room proportions, lots of natural sunlight and plenty of nooks for those seeking a quiet place to read a book. Handsome original wide pine floors throughout. This home was fully renovated with updated wiring, plumbing and insulation but still maintains the antique charm of a true Vt farmhouse. Original doors, 2 refurbished sunrooms, 2 covered porches overlooking the river, studio, family room and formal living room accented with a wood burning stove. Large kitchen with soapstone counters with Wolfe Gas range, ample room for cooking. Large dining area for entertaining and a first floor bedroom en suite. 2nd FL offers large primary bedroom suite with cozy sunroom overlooking the pool with views to Mtn Tom. Don't miss the 3rd floor with 2 small offices and lots of storage. The attached barn has capacity for lots of storage and options for multiple use. Walk over beautiful covered bridge to access restaurants, movie theatre and shops. Snow shoeing, championship golf, fly fishing and skiing all minutes away!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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105 Happy Valley Road Woodstock VT 05091

Woodstock, VT105 Happy Valley Road

Price$695,000

Est. Mortgage: $/month

MLS Number 5008819

  • Residential Single Family
  • Full Bath 1
  • Village Taftsville
  • Construction Existing
  • Bedrooms 3

**PUBLIC & BROKER OPEN HOUSE THIS SATURDAY, AUGUST 31 FROM 2:00PM-4:00PM. ** A Quintessential Historic Village Home in Woodstock's coveted Taftsville Village, the "Levi D. Hall House" was built in 1848 by D. Taft & Sons and has been a loved and well maintained family home by the same family for nearly 70 years. The properties provenance is included and traces back to the original owner. Walk along the stone pathway from the driveway to the covered front porch and enter into beautiful, natural light and lovely wide-board pine floors in pristine condition throughout the home. The classic country kitchen has direct access to the garage with nicely separated bonus office space. The kitchen walls are of sturdy, whitewashed pine board and there are painted country cabinets in a cheerful mustard color. The high ceiling has exposed original beams and a gas fireplace adds warmth to your colder Vermont days. In the Dining and Living Rooms you are greeted with clean, white walls, period trim and lighting, high ceilings and an abundance of natural light. The first floor bedroom/full bath suite has a private dressing area with large closet space and built-in cabinetry. Moving upstairs, there are two attractive bedrooms on either side of a quaint landing. Both bedrooms have wide pine floors and nice light. New furnace in 2023 and the grounds boast mature perennial beds, a lovely setting, and there is great storage above the barn/garage. Must see and be sure to view the Unbranded Tour link.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5008434

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 6
  • Bathroom 8

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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1 Border Lane Woodstock VT 05091

Woodstock, VT1 Border Lane

Price$675,000

Est. Mortgage: $/month

MLS Number 5006149

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

Location, location location! Situated on a very desirable road within Woodstock Village, this 3 bedroom Ranch sits on just over 1 acre of open lawn surrounded by mature trees. The yard is tastefully landscaped and there is a beautiful patio out back, ideal for a morning cup of coffee, grilling dinner, or a nice glass of wine. As you enter through the front door, the bedrooms and a bath are off to the right. To the left, the long eat-in kitchen flows into to the dining area which connects to the living room. There is patio access, a large bow window and a gas fireplace to keep warm in the wintertime. At the end of the living room is a lovely sunroom that could also be a great office. Rounding out the first floor is a half bath, and access to the attached garage and full basement. Local shops and restaurants are within walking distance and you are just minutes from the Woodstock Country Club and Saskadena 6.

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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944 College Hill Road Woodstock VT 05091

Woodstock, VT944 College Hill Road

Price$759,000

Est. Mortgage: $/month

MLS Number 5004968

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

PRIVATE- Cape Cod Home less than a mile to Historic Woodstock Village! This generous sized home consisting of 2616 squ ft. sits on 3.62 secluded acres. Built in 1988 and first time on the market- this home has been well maintained with an abundance of light, generous proportioned rooms with handsome hardwood floors. First floor consists of kitchen with quartz counters and soft neutral toned tiled backsplash, small eat-in area for informal dining, a pantry and easy access to the attached garage. Enjoy large family gatherings with use of a formal dining room, family room/study accented with a propane stove to cozy up on a rainy day with a good book and spacious formal living room. A large Primary Bedroom with en suite bathroom and large walk-in closet with extra drawers for storage for buyers seeking a first floor bedroom. Second floor has 3 more spacious bedrooms with a full bathroom. Enjoy a large covered patio off the back of this residence for entertaining friends and family. Plenty of room in the 2 bay attached garage adjacent to the first floor laundry/mudroom. There is ample flat space in the vast yard for those garden enthusiasts to expand the perennial gardens, fruit trees and vegetable gardens or kicking around a soccer ball. This property also conveys a good size shed for storage of bikes, kayaks etc. Central Air Conditioning, generator hook-up, full basement with newer mechanics- this is a low maintenance home. Easy stroll or bike ride into town!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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 2024 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 12, 2024 10:43 AM EDT