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!

 

 

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 7

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 and Dail Frates, Snyder Donegan Real Estate Group

$
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%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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343 Spruce Way, Woodstock, VT 05091

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4710997

  • Residential Single Family
  • Listing Agent Name Danny Kogut
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5

This is one that you absolutely have to see! Pictures simply cannot capture the warmth, functionality and tranquility of this very special property. Located on a private dead-end road in the Cox District region of Woodstock just 8 minutes from the Village Green. The pristine long-range views can be appreciated from every room. Every inch of this lovely post and beam cape has been tastefully renovated to the highest standard with new chef's kitchen, bathrooms, systems, solar and generator. Each of the four bedrooms has it's own private bathroom. Lovely screened porch and deck overlooking stone walls, perennial beds and the view beyond. Brand new barn with separate farm road entrance, open pasture and a magnificent interior trail system. Walk out lower level with family room, office and guest accommodation. Spacious, private heated room above the attached three car garage for studio, recreation room or for home occupation. Excellent equine potential.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$1,650,000

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: 4.65% last updated on Sep 20, 2018
* 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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1096 Prosper Road, Woodstock, VT 05091

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4699235

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

Fabulous private timberframe residence on 34.29 acres with long-range south-facing views and direct walking access to the Marsh-Billings-Rockefeller National Park, which abuts to the east. The residence was completed in 2005 and boasts an oak timberframe and reclaimed barnboard floors. The great room has vaulted ceilings, two fireplaces, looks out at the long-range view and opens to the gourmet kitchen, beyond which is the mudroom and powder bath. With a four-bedroom septic in place, the house is currently designed as a three-bedroom residence, with each bedroom having an ensuite bath. Wonderful south-facing covered porch, side screen porch and detached 2-car garage. All expected modern mechanicals including backup generator, radiant heat throughout (except MBR), a fire sprinkler system, security system. Totally privately situation yet easy access - just 2 minutes to the Woodstock Farmers Market, 5 mins to Woodstock Green and 20 mins to the Killington Skyship.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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1018 Deerbrook Way, Woodstock, VT 05091

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number 4694036

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

1018 Deerbrook Way offers the perfect Vermont getaway with end-of-road privacy on 26 +/- acres, a FABULOUS long-range mountain view overlooking the swimming pond, and a beautifully constructed and well-maintained getaway residence. Constructed in 2009 with substantial recent upgrades including kitchen renovation, upgraded insulation, Hunter Douglas window treatments, new generator and more. All the amenities you are seeking in a second home - including an open floor plan, gourmet kitchen that opens to a vaulted ceiling great room with stone fireplace and exceptional views! Two pairs of french doors open from the great room out to the expansive south and west facing wrap-around deck that looks out over the pond to the long-range mountain views. First level master bedroom, three other bedrooms, three full baths and one half bath. The downstairs was recently fully renovated into a hang-out den/rec/TV/game room plus other spaces for workout equipment, and painting/writing studios/office space. Mechanicals include a two-car attached, heated garage, whole-house UNICO AC/heating system, full automatic backup generator and high-speed fiber optic internet - so you can get away but be fully wired when required. The property is located at the top/end of a private road and is just 15 minutes to Killington and 8 minutes to the Woodstock Green - so very easy access. This house is quite simply the perfect turnkey Vermont getaway house that has it all!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 The Green, Woodstock, VT 05091

Price$1,195,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4687193

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Village Woodstock
  • Construction Existing
  • Bathroom 5

"Ebenezer Fitch House" is one of the grand historic homes on the Woodstock Green. Located next to the covered bridge and overlooking the Ottauquechee River, it enjoys perhaps one of the best residential locations in Woodstock village.Although built in 1827, it has both an expansive formal living/dining room as well as an equally expansive family room with an antique fireplace; a primary bedroom suite; 1st floor laundry room (6.9x12); and an elevator! Enjoy having all of the village amenities just outside your front door plus gracious, cozy or spacious gathering spaces inside your home.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing

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 2-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 and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$1,645,000

Est. Mortgage: $/month

MLS Number 4675093

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

“Spring Hill Farm” located in the heart of Vermont's equestrian region. The renowned Green Mountain Horse Association and all the events are just up the road. This amazing property offers a 3,040 sq. ft. vintage 1820 stone cape, which has been elegantly restored while keeping the authentic charm and architectural beauty. The gourmet kitchen has stainless steal appliances, brick flooring, and pantry, along with a fireplace keeping a true country feeling. The formal dining room walls have hand painted murals, and the large gathering room, perfect for entertaining, has vaulted ceilings with hand- hewn beams and built-ins. The house is set up with 4 bedrooms, 5 bathrooms, along with 5 wood burning fireplaces. The views of the barns and pastures can be had from most every room. Included is a 3,000 sq. ft. reclaimed barn of the same era that has been beautifully restored serving as a 3-bedroom guesthouse. The guest barn has a 2 story stone fireplace, wide pine floors, full kitchen, and a generous loft with a ¾ bathroom. On the lower lever are 2 additional bedrooms, a full bathroom, and a recreational room. To complete the package is a 5-stall barn with multiple fenced pastures. With over 6,000 sq. ft. of living space there is plenty of privacy for everyone. A truly idyllic piece of Vermont! The town office has the house listed as a 3 bedroom and the guest barn as a 2 bedroom; currently the house is set up with 4 sleeping areas and 3 in the guest barn.

Listed by Terry Davis, Engel & Volkers Okemo-Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$1,250,000

Est. Mortgage: $/month

MLS Number 4665720

  • 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. This 5* VT Efficiency home was built with all the latest green technology available. From the radiant heated floors, energy efficient lighting, heavy insulation, high efficiency boiler and appliances, 8” stud construction, and passive siting with deciduous trees, this home needs very little energy to create a comfortable living situation. With the upcoming installation of solar panels, heat pumps and Tesla battery pack acting as a generator you couldn't ask for a more efficient and comfortable home. Open concept living with reclaimed barn board flooring, a stone fireplace, dining, kitchen and screen porch. The master suite with steam shower, spa bath and gas fireplace is located on the first floor as well as a guest bath and TV den with a gas fireplace. On the second floor are two additional en suite bedrooms, and family room with a full bath; the second floor can be closed off to save energy. The finished basement has a den, recreation room, full bath, and a ski/mudroom, which is attached to the two-car garage. The bedroom count can be increased from 3 to 5 bedrooms by converting the den and family rooms. The layout allows natural lighting throughout, and privacy for all including guests. All within a short stroll to the green or Mt Peg for hiking.

Listed by Terry Davis, Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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21 Mountain Avenue, Woodstock, VT 05091

Price$1,275,000

Est. Mortgage: $/month

MLS Number 4665864

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

RARE MNT. AVENUE LOCATION combines the convenience of Village life in a lovely setting within a four-minute walk to vibrant downtown Woodstock. This gracious, historic 1849 Brick Gothic Revival Cape on 1.14 acres abuts Mount Tom & the Marsh-Billings-Rockefeller National Historic Park. This 3,500+ sq. ft. well-maintained home is surrounded by established gardens and offers 5 bedrooms, 4 baths, hardwood floors, original windows & other distinctive historic features. The modern kitchen includes a 6-burner gas range, convection wall oven, built in refrigerator, butcher block counter-tops & plenty of cupboards for storage. Adjacent to the kitchen, the family room provides an inviting eating area and cold winter nights are made more comfortable by the warmth of a Vermont Castings woodstove. The fenced brick courtyard off the kitchen adds additional living space in warm weather months. Larger gatherings are accommodated in the formal dining room with decorative fireplace & charming built-in cabinets. The bright, spacious living room has built-in bookshelves to store your games & family photos and is a perfect place for entertaining. A private master bedroom suite has its own bath, walk-in closet, & lovely views of the back lawn; and the other three to four bedrooms & bathrooms offer comfortable space to host extended family & friends. Large in town lot along a tree lined street gives privacy & solitude from Village events. This is a rare and coveted home in the heart of Woodstock!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 3 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, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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: 4.65% last updated on Sep 20, 2018
* 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

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