Woodstock VT Real Estate

Woodstock Vermont

Woodstock, Vermont is a beautiful historic area boasting the only national park in Vermont, three covered bridges, agricultural landscapes, and numerous inns/bed and breakfasts. Woodstock is a great small town with a great sense of community and a delightful historic downtown that's home to fabulous restaurants and charming shops and boutiques. Learn more about Woodstock!

Browse Real Estate in Woodstock

Scroll down to find all current real estate for sale in Woodstock, VT. Contact Martha Diebold Real Estate if you have questions or would like to learn more about a listing. Sign up to save your favorite listings and email updates when similar listings hit the market.

16 College Hill Road Woodstock VT 05091

Woodstock, VT16 College Hill Road

Price$1,895,000

Est. Mortgage: $/month

MLS Number 4919158

  • Residential Single Family
  • Bathroom 5
  • Bedrooms 5
  • Construction Existing
  • Square Feet 4,449

This five-bedroom Neo-Colonial overlooks western Woodstock Village and Mount Tom from an iconic columnated verandah. Thoroughly updated and expanded by meticulous owners - including a family room addition in 2014, a remodeled kitchen and basement in 2015, a 6500 square foot veranda in 2016, and a circular driveway in 2021. Careful preservation and restoration of the antique elements lends an old-world elegance; new electrical, insulation, roofs, and heating systems provide worry-free convenience. On an uncommonly spacious village lot, just over an acre, the land offers plenty of room for your needs - a pool, a play structure, or a barn. The wide wraparound porch, landscaped patios, and abundant perennials make spring, summer, and fall a joy to experience. In the winter, relax by the wood-burning and propane fireplaces and enjoy the seasonal view of the Mount Tom star. With a flexible bedroom spaces and a discreet in-law or guest suite, this home accommodates friends and family with ease. Within close walking distance of downtown Woodstock, this extraordinary property is as rare as it is delightful.

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: 5.7% last updated on Jun 30, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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46-48 River Street Woodstock VT 05091

MLS Number 4918856

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 900

Super location in the heart of Woodstock Village. Nestled on the bank of the Ottaquechee River. Easy walk to all of towns amenities and Mtn Tom for a short hike. This one bedroom condo features hardwood floors, large full bathroom and eat-in kitchen. Lots of natural light especially in the afternoon. Low list price for those who would like to come in an do some upgrades to the kitchen and bathroom. There is one assigned parking space. Seller is a licensed real estate agent in VT. Easy to show.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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
  • Square Feet 4,502
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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11 College Hill Woodstock VT 05091

Woodstock, VT11 College Hill

Price$1,275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4918360

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,305

Highbank Cottage- A truly lovely estate nestled on the banks of the Ottaquechee River overlooking a clear view of Mtn Tom. Stunning, private backyard with beautiful landscaping and perennial gardens. Stroll down to the river or enjoy an evening under the stars at the cozy fire pit. This antique gambrel features handsome hardwood floors, first floor master bedroom suite, propane fireplace in the Living Rm with lofted ceilings for a spacious feel. The intimate dining room has ample space for a long harvest table for many guests looking out to Mtn Tom. The 2nd floor incorporates 3 more guest bedrooms and full bath. The lower level features a large office with propane stove for chilly fall days, summer kitchen and screened in porch to cozy up in the afternoon reading a book. The 'Barn' includes a 2 bay heated garage, stunning apt with bedroom/sitting area and 1.5 baths. High vaulted ceilings with beadboard walls to capture the true 'cottage' feel. Lower level has a large workshop and more storage or could be converted to a workout room. Enjoy fishing on the Ottaquechee or take a trip floating on tubes down the River on a hot summer day. All of town amenities, shops and theatre right out your back door. Suicide Six, Okemo and Killington near-by as well as championship golf, tennis and mountain biking. Very few properties in the village offer a view and river access with large apt for either friends/family or rental income. Come take a look- Its adorable!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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
  • Square Feet 10,206
  • Bedrooms 10
  • Bathroom 15
  • Construction Existing

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: 5.7% last updated on Jun 30, 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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4946 South Street Woodstock VT 05071

Woodstock, VT4946 South Street

Price$1,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4917030

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,440

Lilac Cottage: A charming Gothic Revival home in South Woodstock Village. Recently restored with a new addition that can be used as an in-law apartment or used completely by one family- stunning hand hewn beams that accent lofted ceiling capturing lovely light, there are french doors out to back gardens and handsome kitchen that opens to living/dining room. The lawn is beautifully landscaped with stone walls and perennial gardens. Enjoy two outdoor gathering spaces with a new back deck or under the charming covered front porch. A new 2 car garage with ample overhead storage is a very recent addition. This home boasts large spaces for entertaining family and guests. Gracious formal living room off a very large dining room. Hardwood floors and lots of antique character throughout this home. Enjoy the Kedron Valley Inn for a swim in the the pond or for dinner on the front porch, or gather at the country store for coffee and visits with neighbors. The Kedron Brook is across the road and Green Mountain Horse Association is a short walk away. There are endless miles of country roads and trails for hiking, biking , horseback riding and cross country skiing. This is the best of a country village lifestyle.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

1157 West Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4916726

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,760
  • Construction Existing

Gorgeous fully restored farmhouse with modern amenities and original charm! This sunny and pristine four-bedroom home is conveniently situated in west Woodstock village - just a short drive from Killington, Hanover, and DHMC and within the desirable Windsor Central School District. Comprehensively and meticulously renovated in 2017 from roof to basement, this property boasts all new electrical and plumbing, high-quality polyethylene foam insulation, a new standing seam roof and all new appliances, fixtures, and flooring throughout. Turn-key, convenient, and low maintenance, this home is ideal for primary homebuyers, vacation enthusiasts, and investment shoppers alike. From the soapstone countertops and the exposed beams to the spacious deck and easy-keeping yard, you'll find something to enjoy in every season. Offering flexible upstairs spaces and expansion opportunities, the layout gracefully accommodates both intimate gatherings and larger crowds. With luxe farmhouse design influences and an unbeatably convenient location, this property is a rarity in the Woodstock marketplace! Showings begin 6/28/2022. No showings shall be held 7/1/2022-7/4/2022.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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Catamount Lane Woodstock VT 05091

Woodstock, VTCatamount Lane

Price$340,000

Est. Mortgage: $/month

MLS Number 4916325

  • Land
  • Acreage 17.2
  • Zoning Residential

17+ acres of pristine land in Woodstock Vermont, ready to build your dream estate. The mixed mature woodland hosts walking trails, a stream, a potential pond site, and several potential house sites with magnificent, sweeping, long-range westerly views. The end-of-road location ensures privacy and tranquility, yet is only six minutes from Woodstock Village and the Woodstock Inn & Resort's Athletic and Golf complex. Ten minutes from Green Mountain Horse Association. Power and high-speed internet at the road. Acreage that combines this level of size, quality, and convenience is becoming preciously rare in greater Woodstock. Additional Acreage available MLS#4916323, MLS#4916241

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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Catamount Lane Woodstock VT 05091

Woodstock, VTCatamount Lane

Price$640,000

Est. Mortgage: $/month

MLS Number 4916323

  • Land
  • Acreage 32
  • Zoning Residential

32 acres of pristine land in Woodstock Vermont, ready to build your dream estate. The mixed mature woodland hosts walking trails, a stream, a potential pond site, and several potential house sites with magnificent, sweeping, long-range westerly views. The end-of-road location ensures privacy and tranquility, yet is only six minutes from Woodstock Village and the Woodstock Inn & Resort's Athletic and Golf complex. Ten minutes from Green Mountain Horse Association. Power and high-speed internet at the road. Acreage that combines this level of size, quality, and convenience is becoming preciously rare in greater Woodstock. Additional Acreage available MLS#4916325, MLS#4916241

Listed by Geoff Eckler of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 July 7, 2022.