Woodstock Luxury Homes Over $1 Million

Woodstock, Vermont boasts exceptional properties valued at over 1 million dollars. Many of these beautiful homes, estates, compounds, and upscale farms have gorgeous views of the Green Mountains and the surrounding area.

A private luxury home in Woodstock offers peace, quiet, and tranquility while still being just a short trip to all that Woodstock offers. This includes fine dining, golfing, hiking, fishing, and other outdoor activities, cultural events at Pentangle Arts in Woodstock Town Hall Theater, and a deep sense of community. Other venues and amenities are close by in the Upper Valley.

A luxury estate in Woodstock offers you all the culture and conveniences you would expect in and around places like Boston or New York City but in a small town, beautiful setting.

Whatever type of property you are looking for in Woodstock, VT—a vacation retreat, a family compound, a country estate, a gentleman’s farm or an investment property, Bassette Real Estate Group’s knowledgeable and experienced brokers and buyer brokers can help you find your ideal luxury home. Contact us today!

1959 Cox District Road Woodstock VT 05091

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4429915

  • Residential Single Family
  • Listing Agent Name Richard Higgerson
  • Construction Existing
  • Bathroom 6
  • Bedrooms 9

A modern architectural masterpiece and important work by award winning and internationally recognized architect Rick Joy, Woodstock Farm presents a dramatic shingle and stone house and barn set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close proximity to Dartmouth College in Hanover, New Hampshire. The high concept contemporary design is executed with the sharpest attention to craft and draws on the vernacular of the rural northeast. The main residence offers a 152-foot elongated gable house with massive end walls of Lake Champlain bedrock and cedar cladding on the roof and side walls. Set at a subtle angle to the barn, the north facade of the main house engages the purity of the setting and looks out onto a large, deep, spring fed swimming pond and the rolling pastureland, hills and mixed northern hardwood forests that comprise the property.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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2358 Long Hill Road Woodstock VT 05071

Price$5,500,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 foot Old Baldy Mountain with 360-degree views and a small private cabin at the summit.

Listed by T Story Jenks and Ruth Sudduth, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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535 Peace Mountain Way Woodstock VT 05091

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4659067

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5

"PEACE MOUNTAIN" is a private estate with breathtaking views of the Ottauquechee River Valley. Custom built in 2008, Peace Mountain is a spectacular Arts & Crafts shingle style home situated on 183 acres with a vaulted ceiling yoga/recreation room and scenic trails for hiking, snowmobiling, mountain biking and cross country skiing for year round recreation. It is designed for gracious living and offers total peace and tranquility. Spacious gathering rooms open out to a wide veranda surrounding three sides of the home with a beautiful stone fireplace and grilling area for 3 season use. The property includes five river stone fireplaces as well as a wood-fired pizza oven in the kitchen to enjoy in winter evenings. Peace Mountain was designed for an active family and extended family and includes a climate controlled hardwood yoga studio/basketball court, rock climbing wall with spectacular views and an expansive storage area for outdoor recreation equipment. Convenient to the Killington Ski area, Dartmouth College and is located four miles from the Woodstock Village. Off private road leading to the house is direct access to VAST snowmobile trails to east and west. Multiple building sites served by underground utilities. Located at the end of a paved private road engineered for New England's rugged weather. The Peace Mountain Ranch is an exceptional property and is ideal for a residence, yoga retreat, corporate retreat, or family gathering compound.

Listed by John Snyder and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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327 Fletcher Schoolhouse Road Woodstock VT 05071

MLS Number 4644250

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

Bybrook Farm is a picturesque country estate , built in 1797, and completely restored with historic integrity and deluxe amenities, including custom hand planed cabinetry and finishes , reclaimed wood floors , hand hewn beams and decorative painting by renowned artist Kevin Paulsen. Sited on 26 acres, with an exquisite brook that meanders throughout the property and leads to a picturesque spring fed pond .Gorgeous and varied regional views. A rare combination of brook, pond, rolling hills, forest, mature gardens, and original stone walls, complete with charming farmhouse , classic wooden bridge and quintessential Vermont red barns. A moments stroll to historic hamlet of South Woodstock and nationally acclaimed Green Mt. Horse Association equestrian center . The best of serene country living with easy access to downtown Woodstock and nearby equestrian, golfing , tennis, skiing, restaurants, spa and fitness facilities. 5 bedrooms in the Main House, and Guest House and 2 separate kitchens provide for cozy relaxation or entertaining friends and relatives. Settle in on the stone terraces or open air porches that overlook the rushing brook ; swim , fish or relax by the serene pond; take a nature walk in the forest ; ice skate on the pond ; snow shoe or cross country ski right out your back door. Enjoy the best of spring wildflowers , summer sunshine , fall foliage and winter wonderland in this unique property. Fun for two or twenty , with separate spaces for all to enjoy !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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486 Benedict Road Woodstock VT 05071

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4734913

  • Residential Single Family
  • Listing Agent Name Terry Davis
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6

Circa 1820 stone cape with 10' ceilings has been elegantly restored while keeping the authentic charm and architectural beauty. Chefs can enjoy the gourmet kitchen, which has quality stainless steel appliances, brick flooring, a walk-in pantry, along with a fireplace keeping a true country feeling. Beautiful windows and hand painted murals adorn the formal dining room. A small cozy family room located off of the kitchen features a fireplace, built-in cabinets, and French Doors leading to the stone patio. The rustic living room has vaulted ceilings, hand-hewn beams, with a large fireplace; perfect for entertaining. Presently the house is used as a 4-bedroom, featuring 5 bathrooms, and 5 wood burning fireplaces. The reclaimed barn of the same era has been beautifully restored serving as a 3-bedroom guesthouse. Open floor concept with a two-story stone fireplace, full kitchen, den, and large sleeping loft. The walk-out basement has two bedrooms, full bathroom, utility room, and a recreation room with French Doors. Completing the package is a rustic 5-stall barn with multiple fenced pastures. Green Mountain Horse Association and riding trails are just up the road. With over 6,000 square feet of living space there is plenty of privacy for everyone. Square footage includes both buildings. A truly idyllic Vermont property!

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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4 The Green Woodstock VT 05091

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4702840

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Construction Existing
  • Bathroom 7
  • Bedrooms 10

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, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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779 PETERKIN HILL Road Woodstock VT 05091

Price$1,475,000

Est. Mortgage: $/month

MLS Number 4655908

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Superbly sited overlooking the Ottauquechee River Valley this outstanding reproduction of the region's classic Colonial style offers sweeping views over Woodstock to the National Park and beyond. A broad, covered porch wraps around the westerly and north exposures of the home providing a gracious place to enjoy the old-time pleasure of simple relaxation. Versatile living spaces feature 4 bedrooms in the main residence, including a private 1-bedroom Guest Suite and separate 1 bedroom Guest Apartment over the barn. Master bedroom suite is warmed by a fireplace. Entertaining revolves around a spacious, open concept kitchen-dining and living room that provide direct access to a stone patio and covered porch. A lower, walk-out level is configured for a recreational activities and potential media room. Completely private within minutes of the Village Green.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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268 Willow Brook Road Woodstock VT 05091

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4684497

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

Walk to Woodstock Village from this privately situated, custom-built Lindal cedar timberframe home - a perfect getaway entertaining gathering house. Windows and french doors bring in Vermont sunlight. Interesting architectural lines and a 5/4 cedar shake roof. Large gourmet kitchen with granite countertops, an abundance of storage / cabinets, center island with range top, double ovens, Bosch dishwasher, Subzero fridge and classic woodstove for warming up hands and house! Indoor barbeque for year-round grilling. Kitchen expands into fantastic sun porch with glass roof and walls - for year-round sunlight indoors. The dining area and living room areas - with woodburning fireplace - have french doors that open to a 1200 square foot, south-facing patio for wonderful gathering/entertaining! First floor bedrooms and baths provide for one level living. Or go upstairs and enjoy the MBR and ensuite large MBR bath with jacuzzi tub beneath a second floor sunroom. Additional BRs and baths are perfect for family or friends up for the weekend or holidays. The lower level - with 2nd woodburning fireplace - is a large TV/Game/Workout/Rec room with adjoining full bath and french doors that lead outside. Also access to 3rd bay of attached garage on the lower level. Mud-laundry is between main two-car attached garage and kitchen, perfect for dropping off clothes and ski gear. Walk to town, but enjoy space and privacy in this Vermont getaway gathering home!

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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798 Thomas Hill Road Woodstock VT 05091

Price$1,295,000

Est. Mortgage: $/month

MLS Number 4715651

  • Residential Single Family
  • Listing Agent Name Dan Noble
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6

A classic Vermont cape and guest barn sit attractively on a country road just minutes from downtown Woodstock abutting King Farm and Mount Tom National Park. The house features 4 en-suite bedrooms, an eat-in kitchen, family, living, and dining rooms, two gas fireplaces, a classic screened in covered porch, beautiful stone terrace area and a beautifully landscaped private yard. The guesthouse features it's own garage and 2 bedrooms with two baths. The living area with gas fire place and kitchen are extraordinary and are perfect for entertaining. The guest barn also has an attached summer porch as well as large stone patio area which are both nicely landscaped.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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5 Pine Street Woodstock VT 05091

Price$1,229,500

Est. Mortgage: $/month

MLS Number 4736511

  • Residential Single Family
  • Listing Agent Name Terry Davis
  • Village Woodstock
  • Construction Existing
  • Bathroom 6

Traditional Modern Style Village home located on a quiet dead-end street. Peace and quiet all within a short stroll to the village. Walk to town for morning coffee, or start your day with a hike on Mt Peg. If golf is more your style the Woodstock Golf Course is just up the road. Skiing anyone? A perfect ski house with plenty of room for everyone. This 5* VT Efficiency home built with all the latest green technology available. The house is designed for multiple levels of living, with the capability of closing off the unused portions when not in use. With radiant heated floors, energy efficient lighting, heavy insulation, high efficiency boiler, 8” stud construction, and passive siting with deciduous trees, this home uses very little energy to create a comfortable living space. Open concept living with a stone fireplace, dining, kitchen and screen porch. The master suite with steam shower, spa bath, and gas fireplace are located on the first floor, as well as a guest bath and TV den with a gas fireplace. On the second floor are three additional en suite bedrooms. The basement is outfitted with family/recreation room, 3/4 bath w/laundry, bedroom, utility room, and a ski/mudroom, which is attached to the two-car garage. End the day on the two-tiered deck for a barbecue and a drink. The best of modern, efficient, village living!

Listed by Terry Davis, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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

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Copyright 2019 Northern 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 February 17, 2019.