Woodstock VT Historic Homes

View a list of historic homes for sale in Woodstock Vermont below and contact me if you would like more information about individual properties.  You can also create an account for free to save all of your favorite Vermont real estate listings.  

894 Rose Hill Road Woodstock VT 05091

Price$129,000

Est. Mortgage: $/month

MLS Number 4774874

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,726

Vintage 1840's home with distinctive architectural appeal ready for a step back to the stature it once had. This colonial styled Cape sits on a corner lot with a large barn and a playhouse. Two lots compose the boundaries at the westerly base of Rose Hill. Walking distance to the Farmers Market, near the Middle and High School, and a short distance to the Village of Woodstock. A great opportunity, being sold as-is.

Listed by Eric Johnston of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

23 The Green Woodstock VT 05091

Price$1,200,000

Est. Mortgage: $/month

MLS Number 4774840

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,465

This gracious home , circa 1803, located on The Green in historic Woodstock has had a most colorful history. Situated along the Ottauquechee River and looking up toward Mt. Tom , Vermont's only national park , it stands out as one of Woodstock's most adored properties. A major remodeling took place in the first half of the 1900's with designs by noted architect David Adler and seemingly paying tribute to former occupant a Mr. Leet who was renowned for making gingerbread thus giving the house the name , Gingerbread House ! The lovely porches front and back , gorgeous landscaping filled with a profusion of lilacs with paths leading across the gracious lawns down to the river makes this property perfect for entertaining .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

13 RIVER Street Woodstock VT 05091

Price$698,000

Est. Mortgage: $/month

MLS Number 4774015

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

This historic Woodstock Village home is a short stroll over the Elm Street Bridge from all amenities. The 1850 structure was conceived originally as a 'farm cottage'. The home was restored and re-imagined in a comprehensive renovation in the early 1980's with Arts & Crafts period design elements. Right-sized for today's small house movement the home is beautifully landscaped with a spacious yard providing ample room for outdoor entertaining and gardens. A detached antique barn offers potential for use as a studio or recreational activities. Rare opportunity to own a Village home offering modern systems with delightfully diverse spaces.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

5 Linden Hill Woodstock VT 05091

Price$725,000

Est. Mortgage: $/month

MLS Number 4772701

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 4,250

An exceedingly rare opportunity for Woodstock Village: antique 1850's house converted to 4 units in early 1970s and then renovated to a fine functional and aesthetic condition in 2000 while still preserving its 4 unit status. The largest apartment (8 rooms, 4 BR, 3 1/2 BA) occupies three levels of the original house, and enjoys rooms of generous proportion, high level detailing and fixtures, and fine interior finishes. Apartments either side (one of 5 rooms, 2 BR, 1 BA; the other of 3 rooms, 1 BR, 1 BA) have interconnected passage with the main apartment to allow substantial quarters of three discrete spaces for family or friends, or the passages may be closed off for independent use. A 4th apartment (4 rooms, 2 BR, 1 BA) has separate entry off terraced private lawns in the rear. All apartments have private entries, complete kitchens, wood burning fireplaces, separate utility capability, and share use of a generous common parking area. Walk to Village Center and all its many amenities!

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

5070 South Road Woodstock VT 05071

Price$519,000

Est. Mortgage: $/month

MLS Number 4771226

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,936

Charming renovated antique cape in historic village of South Woodstock. There is an attached 20x24 heated workshop/studio that can be used for various purposes. Walk to the country store and the Kedron Valley Inn for dinner. Short drive to skiing as well as trails for hiking , horse back riding and fishing in the Kedron Brook.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

4548 West Woodstock Road Woodstock VT 05091

MLS Number 4767264

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,677

"Deer Brook Farm" - Minutes from Woodstock Village and fifteen miles from Killington, this fully restored five-bedroom Colonial Farmhouse with attached two-bedroom apartment sits on nearly five acres, comprising established perennial beds, mature fruit trees, open meadow, and wooded hillside. Steeped in local history, the property was originally known as the Kole Family Farm. The entire home has been expertly restored under the guidance of the current owners, who imbued the period details with a comfortable elegance. The sunny and graciously proportioned rooms are ideal for hosting friends and family with ease, and state of the art systems - including a Buderus boiler and fiber-optic internet - ensure every comfort. The spacious dining room opens onto a private terrace; double French doors lead to a grand living room, complete with a handsome wood-burning fireplace. Each of the five bedrooms boasts an en suite bath and new Mitsubishi heat pumps. The attached two-bedroom, two-bath apartment with private deck is ideal as a long- or short-term rental unit, private guest accommodations, or as an in-law apartment. The post and beam barn can be adapted to support a gentleman's farm, a more formal garage, or a vaulted studio/workshop space. Currently operated as a multi-award-winning hospitality property, Deer Brook Farm offers the uncommon advantages of a traditionally licensed B&B with the additional value of AirBnB-style bookings. Also available fully furnished!

Listed by Danny Kogut and Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

32 The Green Woodstock VT 05091

Price$599,000

Est. Mortgage: $/month

MLS Number 4766737

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

Prominently situated, at #32 the Woodstock Village Green, is a circa 1803 traditional style home, with a tastefully renovated contemporary interior! From the covered front porch a resident can enjoy the relaxing pleasure of viewing the beautiful brick Woodstock Town Hall, the impressive neighboring stone church, or the passing activity of village life. From this central location the residents conveniently walk to the numerous Woodstock amenities of shopping, dining and cultural events. The stylish interior living space encompasses 3 levels! The ground floor is entered from either the front porch or through a rear entrance, with a foyer. A more open floor plan features a bright kitchen with adjacent dining area, a comfortable living room, a den, the entry foyer and a 3/4 bath. On the upper floor is the primary bedroom, with en suite full bath, 2 additional bedrooms and a 3/4 bath. The lower level is dedicated to fun! The lower level family room and bar area are either accessed from an interior stairway or through an exterior door that opens to a below street level courtyard. The owners have achieved an impressive history of rental income, with this desirable property!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

6656 South Road Woodstock VT 05071

Price$650,000

Est. Mortgage: $/month

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located on the southerly side of South Woodstock across from the Green Mt. Horse Association, with direct access to miles of horse riding trails. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, lovely gardens and playground.The homestead includes a guest apartment periodically rented, and additional potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

2352 Curtis Hollow Road Woodstock VT 05091

Price$2,300,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

1682 Barnard Road Woodstock VT 05091

Price$339,000

Est. Mortgage: $/month

MLS Number 4753374

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,010

This lovely antique Gambrel home located just 2 miles north of The Woodstock Village Green, near the site of the first ski tow in the US, was totally renovated in 1987, offering modern systems in a light, airy architectural style blending open gathering areas with private spaces. Well proportioned living room with exposed beams and wood burning brick fireplace and wainscot surround. The glass sun porch is perfect for summer entertaining. Spacious mudroom and private sauna. Works wonderfully as a primary or second home. Established gardens & a sunny yard sheltered by mature trees. Private & easily accessible home close to everything. Well cared for with many updates.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

1135 West Woodstock Road Woodstock VT 05091

MLS Number 4740005

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,080

An affordable Woodstock residence, with many attributes! On the ground floor, are the desirable features of a large primary bedroom with walk in closet, a bright eat-in kitchen with attractive built in cabinets and exposed beams, a remodeled full bath, a living room that opens to a large south facing deck, a laundry room and a half bath! On the second floor are 2 additional bedrooms! There are beautiful wood floors throughout the home. A door off the living room leads to a surprising 440 square foot bonus space, with the obvious potential for use as a workshop, studio, storage space or a home occupation! Further enhancing the property are the connection to the municipal sewer and Woodstock Aqueduct Company water. The large rear yard area has a stream meandering through and offers areas for exploration and plantings. This is a residence of an easily managed size, with the advantage of single level living! The land has sun light, interesting aspects and useable space. A property with much more to offer than meets the eye!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

57 River Street Woodstock VT 05091

Price$1,150,000

Est. Mortgage: $/month

MLS Number 4738167

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

200 years ago this classic cape home was built in a prime Woodstock Village location. The value of that location, opening on to Mountain Avenue, is as desirable now, as it was 200 years ago! In 1820, a well proportioned floor plan was the appeal of a cape. Today, the comfortable flow, of the interior, and the practical floor plan, of this home, are perfect, as well. The current owner is passionately a steward of this property. The cape has been totally renovated, with extraordinary attention to detail, and quality new amenities! The kitchen focuses on a beehive style brick oven designed for authentic wood fired cooking. Other chef's pleasures are radiant floor heating, heated stone counter top, professional quality appliances and beautiful cabinetry. A den opens off the kitchen, with exposed wood beams, wide board floors and built in secretary. The den opens to a living room, with well placed wood stove, comfortable seating area and south facing bay window. A formal dining room, with wood burning fireplace, completes the 1st floor principal rooms. Conveniently off the kitchen is a 1/2 bath, with stone vanity. On the 2nd floor are 2 larger bedrooms, on either end of an open hallway, a bath with soaking tub and shower and 2 smaller bedrooms. An option exists to use 1 smaller bedroom as an office and the other as laundry. Outside, the large covered porch has views of mature gardens, a level lawn, and of distant hills. A detached sauna building is just steps away! A quality home!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

20 RIVER STREET Woodstock VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4707913

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

A superbly renovated FEDERAL-STYLE FARMHOUSE sited overlooking a sloping lawn fronting on a tranquil stretch of the Ottauquechee River. Viewed from River Street, the front porch retains the appearance of the long time configueration as a 'twin home', before the two sides were graciously reconnected in a return to the original design and layout. The floor plan features spacious main level rooms with Master Suite, Eat-in-Country kitchen, living-dining room a secluded study and wonderful 'river room'. The second floor offers 4 bedrooms and two mirrored bathrooms. Privately situated and tastefully landscaped with native plants and shrubs. A classic Village home within walking distance of all popular amenities and activities.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

4 The Green Woodstock VT 05091

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4702840

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 10
  • Square Feet 6,800

This elegant 1827 stone federal-style former residence is located on a quiet corner of the Woodstock Green and is one of village's historic properties. A complete renovation of the 6,800 square feet in 2010 brought back the impressive period finishes, and provided space for 5-6 office suites (3 kitchenettes) and a 4-bedroom 3rd floor apartment. The zoning, overall floor plan, large rooms, and high ceilings open the possibility for a single or multi-family property. Ten private parking spaces are located at the back of the building accessed from Mechanics Street. The building is zoned Central Commercial and has town water & sewer. 94% occupancy.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

5 Church Street Woodstock VT 05091

Price$899,000

Est. Mortgage: $/month

MLS Number 4698660

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,909

EXTRAORDINARY RIVERFRONT HOME IN WOODSTOCK VILLAGE! Incomparably situated on nearly an acre of gorgeous lawns with direct river access and views of Mt. Tom, this historic village home has been impeccably updated and maintained. An open and airy kitchen boasts a gorgeous La Cornue range and a new Sub-Zero refrigerator - ideal for entertaining. Central air conditioning, a generator, and a new standing-seam roof make the antique home comfortable in every season. Large upstairs room provides flexible space for guest accommodation, a home office, or a play room. Walk to everything in New England's most beautiful village from this matchless Woodstock home.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

28 The Green Street Woodstock VT 05091

Price$599,000

Est. Mortgage: $/month

MLS Number 4698305

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,037

An elegantly proportioned brick townhouse, of genteel style and character, situated on the picturesque Woodstock Village Green! A gracious 3 story interior, with attractive antique detailing, 9 foot high ceilings, exposed beams, wood floors and multiple fireplaces. On the ground floor is the kitchen, a dining room with fireplace, a living room with fireplace, a classic entry hall and a half bath. On the second floor is a great room with fireplace, 2 bedrooms and a full bath. On the third floor is the primary bedroom suite, with walk-in closet and full bath. The front exterior of the residence features a formal covered entry. The rear exterior of the residence features an elevated brick patio. An useful amenity is off street parking. There is additional parking and storage in a detached garage. An opportunity to acquire a charming village townhouse residence, ideally located on the Woodstock Village Green!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2019 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 September 19, 2019.