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.

Woodstock VT Luxury Real Estate

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!

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1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

MLS Number 4913355

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 7,590
  • Construction Existing

SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Construction Existing
  • Square Feet 5,142
  • Bathroom 8
  • Bedrooms 6

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 Carol Wood and Danny Kogut, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$4,350,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Bathroom 5
  • Bedrooms 7
  • Square Feet 5,306

4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America's most beautiful villages.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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, LandVest,Inc/Woodstock

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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5 Pine Street Woodstock VT 05091

Woodstock, VT5 Pine Street

Price$1,775,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4891594

  • Residential Single Family
  • Village Woodstock
  • Bedrooms 5
  • Bathroom 6
  • Construction Existing

Situated on a quiet road in a sought after Village neighborhood, this 5* VT Efficiency home is walking distance to downtown Woodstock. It has 4 ensuite bedrooms, 3 on the 2nd floor and the Primary suite on the 1st floor complete with a steam shower, spa and gas fire place. There is a 5th bedroom and 3/4 bath on the lower level which also plays host to a large open and newly renovated family and game room. An oversized mudroom takes you upstairs and also has access to the two car garage. The 1st floor boasts an open kitchen, dining and living room with stone fire place, cathedral ceiling and beautiful wood floors throughout. Down the hall are a TV room/den with gas fireplace and a 3/4 bath. Off the kitchen, French doors lead to a screened in porch which opens onto a multi level deck perfect for a morning cup of coffee, grilling up dinner, or a glass of wine on a warm summer night. Across the way are the Rec Center playing fields and playground and down the road is the Woodstock Country Club. This turnkey home is ideal as a primary or second home getaway. Don't miss out on this rare in-town property. Showings begin on 11/26/21.

Listed by Dan Noble, Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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370 Catamount Road Woodstock VT 05091

Woodstock, VT370 Catamount Road

Price$1,395,000

Est. Mortgage: $/month

MLS Number 4889125

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 3
  • Square Feet 2,016

Fifty pristine, peaceful, and private acres at the end of a town-maintained road. Magnificent westerly views of the Green Mountains including Killington. This 1989 custom home with three bedrooms and multiple gathering places can accommodate all the family and friends. Conveniently located to all of Woodstock's famous amenities - less than 10 minutes to The Woodstock Inn & Resort's Athletic Center, 18 hole championship golf course, x- c skiing - hiking - biking trail system, fantastic dining, shopping, galleries and more! Or explore your own land which features numerous hiking trails, stone walls, and a stream. Parcels of this size & quality are scarce; this one's location also has a perfect balance of privacy & convenience. The home boasts bright and sunny open concept kitchen/living area; first floor bedroom with private bath, and plenty of spaces for work or leisure. Second floor has two additional bedrooms, bath, and office/ sitting area. In addition to the turn-key home, there is a fully framed and weather-tight wing awaiting finishing touches, as well as a completed oversized 34 x 15 high bay garage; perfect for XXL toys like a boat or camper. There is also an additional 800 sf of covered storage space; simply add garage doors to fully enclose. Truly a one-of-a-kind property in the best part of Vermont!

Listed by Bassette Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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15 Pleasant Street Woodstock VT 05091

Woodstock, VT15 Pleasant Street

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4905121

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

15 PLEASANT STREET - Elegant, tastefully renovated Greek Revival in ideal Woodstock Village location. This spacious home has been thoroughly updated and expanded over the years- most recently by the highly respected Hank Savelberg Construction Co.- and combines modern convenience with the craftsmanship and exquisite detail of the original home. The interior spaces are bright, well-appointed, and well-maintained. The kitchen has a large south facing dining/eat-in area, while the living room/formal dining area is anchored by a warm and inviting stone fireplace. A more intimate wood paneled library with a second fireplace adjoins. The lovely great porch on the front of the house is perfect for entertaining, enjoying a good book, or simply taking in the seasonal staples of Woodstock Village such as the annual Wassail Holiday Parade. With five bedrooms, four baths, and a separate office, there is plenty of room for everyone. Three of the bedrooms and the office are on the second floor, two bedrooms on the third floor. Walk to restaurants in minutes, stroll the Village Green, or take in the groomed beautiful trails of Marsh-Billings-Rockefeller National Historic Park. SHOWINGS START 4/19/22

Listed by David Donegan, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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28 Pleasant Street Woodstock VT 05091

Woodstock, VT28 Pleasant Street

Price$1,299,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4754916

  • Residential Single Family
  • Village Woodstock
  • Square Feet 3,488
  • Bedrooms 5
  • Construction Existing

One of a kind! Woodstock Village! A professional designer's well conceived compound. The stylish main residence is complimented with both a delightful detached 2 bedroom guest house and a large 36x24 studio/workshop. The length of the tranquil landscaped rear grounds, lush with spectacular gardens and leading to accessible Ottauquechee River frontage, is an unexpected surprise! In the main residence, the principal rooms feature generous dimensions and careful attention to detail. On the main level, a spacious kitchen, with full size informal dining area, opens in 3 directions, to either a fire-placed living room, a dramatic formal dining room or a large 16'x10.5' screened porch. On the second floor are 2 guest bedrooms, full bath, and a primary bedroom, with ensuite bath. On the 3rd level, a large unfinished attic presents endless potential! The detached guest house is perfect! On the ground level is a living room, with vaulted ceiling, a kitchen with a panty, a mud room and a bedroom with 3/4 bath. A second floor loft bedroom is 21' long! Separately, the free standing 36'x24' studio/workshop has potential only limited by your imagination! Truly an ideal property for combining residential use with a home occupation! The front view of the property has the expected classic New England appeal that typifies the residences of Woodstock Village. While the long private rear lawn, with professionally designed gardens, and accessible river frontage is an unexpected surprise!

Listed by John Wetmore, William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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13 The Green Woodstock VT 05091

Woodstock, VT13 The Green

Price$1,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4911613

  • Residential Single Family
  • Bathroom 4
  • Bedrooms 4
  • Construction Existing
  • Square Feet 2,831

Beautiful historic home overlooking the Ottaquechee River- Built in 1812 and originated and functioned as a schoolhouse. Considered to many one of the prettiest homes in Woodstock. Nestled next to the cover bridge just off the Green with perennial gardens and new stone patio. The detailed craftsmanship both inside and outside of this home are stunning. Large spacious rooms with handsome crown moldings boast these elegant spaces. Enjoy the propane fireplace in the cozy nook off the kitchen overlooking the river. First floor consists of a den, large dining area and a grand living room anchored by a handsome wood burning fireplace- honey colored hardwood floors throughout. Second floor has 2 large bedrooms with tall ceilings, an office and master suite. 3rd floor incorporates a large room that has been used as the 'bunkroom' or could be a playroom. Additionally, a large 18x16 unfinished space to be used for storage or built- out for another purpose. Two large porches both anchored in the front of the home with ample space for entertaining and another porch in the back of the house overlooking the river. Easy stroll to restaurants, library, shops and Mtn Tom trails for walking or snowshoeing. Quick drive to Suicide Six, championship golf, fly-fishing or mountain biking. Stunning home with lots of history!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

MLS Number 4917030

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • 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, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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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 June 28, 2022.