Greater Woodstock Area Luxury Homes Between $1 and $2 Million

The greater Woodstock area of Vermont, consisting of the towns Barnard, Bridgewater, Hartland, Pomfret, Reading, West Windsor, and Woodstock, boasts exceptional real estate valued over 1 million dollars. Many of these luxury homes, estates, compounds, and upscale farms have gorgeous views of the Green Mountains and the surrounding area.

A private luxury home in the greater Woodstock, Vermont area offers peace, quiet, and tranquility while still being just a short trip to all the amenities you could want or need.

There are plenty of things to see and do in the greater Woodstock area. For example, Feast & Field, a unique farmers’ market, music jam, and community gathering in Barnard, fine dining at Simon Pearce restaurant in Quechee, summer and winter sports at Suicide 6 in Pomfret or Mount Ascutney in West Windsor.

Greater Woodstock Luxury Real Estate $1M to $2M

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

974 Cemetery Hill Road West Windsor VT 05089

West Windsor, VT974 Cemetery Hill Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4764706

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,884

White Fox Farm's c. 1790 yellow clapboard farmhouse and attached red barn is set just outside the village of Brownsville on a quiet country road where it seems like more horses go by than cars. The 39 acres scale of the farm is manageable with the key Vermont features: a pond, pastures and big views of Mt. Ascutney. The five-bedroom house underwent a major renovation in 2012. The kitchen with its hand hewn beams was enlarged to include a sitting area with views over the field, and outfitted with top-flight appliances for a cook that likes to prepare meals while surrounded by family and friends. Pssst…there is a secret room, believed to be part of the Underground Railway. There are fireplaces in the living room, the two master bedrooms, the birthing room (now used as an office), dining room and paneled family room. The third level is a great place for innovative thoughts (the owner launched a business here) with a two-room study with built in book shelves and a ¾ bath. Throughout the house there is a sense of fine craftsmanship that has stood the test of time in form and function. White Fox Farm is integral to the Green Mountain Horse Association community as the 83-mile marker for the hundred-mile ride.

Listed by T Story Jenks and Dia Jenks, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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23 Cowdrey Path Woodstock VT 05071

Woodstock, VT23 Cowdrey Path

Price$1,900,000

Est. Mortgage: $/month

MLS Number 4850633

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,584

Douglas Fir post and beam home and fully operational auto mechanics garage with 4 lifts. Property is selling as a home and fully operational business and is commercially zoned. This is a rare opportunity to live and work all in one place, or have space for your hobby on wheels. The house features an open floor plan on the main level. Large windows and two sliders to the deck let light poor into the kitchen and living room. The Master Suite on the main level has two large walk in closets and a full bathroom with a jacuzzi soaking tub. The upstairs loft area would make a lovely office/hobby space or could easily be transformed into a private third bedroom if desired. The lower level is fully finished with a second bedroom, full bathroom, and utility room. There are also several closets for storage! Outside you will find an on demand generator, an above ground pool and a heated shed for storage or a small workspace. The auto mechanics garage has two commercial garage doors that open up to three vehicle lifts inside. A fourth lift is located under the new addition to the right of the building. There are three office rooms in the building as well. All garage equipment/tools will be included in the sale. Email for interior garage photos and more information about the business.

Listed by Shenia Covey, C.G. Shepherd Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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32 Horton Hill Road Hartland VT 05048

Hartland, VT32 Horton Hill Road

Price$1,800,000

Est. Mortgage: $/month

Pending

MLS Number 4806321

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 6,600

The Hartwell House is one of Hartland's finest residences. The home, in a traditional Vermont vernacular style, sits on a secluded hilltop with stunning long-range views across the Connecticut River Valley, and far beyond. The seamless integration of design, ingenuity and craftsmanship, antique elements (including two-200 -year-old hand hewn barn frames), and state of the art functionality make this unique property the perfect primary or part-time home. One of the regions most revered builders, Dana Ennis, impeccably designed and constructed Hartwell House as his family home using the finest materials available. The generous, light filled spaces flow beautifully, and imbue warmth, showcasing the picture-perfect exterior surroundings with oversized windows throughout. The spacious Great Room is anchored by a massive floor to ceiling field stone fireplace backed by a soothing waterfall. The chef's kitchen has top of the line appliances, and a brick fireplace; the perfect place to congregate. The study features mahogany wainscot and lovely built-ins. The house is further completed with a walk out, finished lower level with game room, rec room, exercise space and wine cellar. The 10 kw solar array with battery bank will reduce energy bills. The property includes thirty-two acres, a solar heated in ground pool, two ponds, two barns, spectacular grounds, gardens and trails. Easy access to I-91, Historic Woodstock, Hanover, skiing, recreation.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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7 Laber Road Bridgewater VT 05035

Bridgewater, VT7 Laber Road

Price$1,699,000

Est. Mortgage: $/month

MLS Number 4839222

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 4,906

Looking for a grand yet refined Vermont home? Look no further than Stonewall Manor! Situated on close to 30 acres in Bridgewater, you'll be pleasantly surprised by the space provided in this home. Arts & Crafts style allows home to grow as you enter, looking quaint & not massive, from the front elevation. 2 elevator shafts & stair chair offers wheelchair accessibility & can accommodate all needs. 2-car garage comfortably fits 3 cars & features man cave, complete with a living area, wood stove, bath & laundry room! Stonewall Manor features 5 living rooms, 7 bathrooms, 3 full kitchens (all complete w/ granite counter tops & Bosch appliances), 3 laundry centers, & secret passages between rooms. Additional option to rent out the two private 2-bedroom apartments! Stonewall Manor was designed to fully integrate w/ surrounding land & take advantage of all the property has to offer. Front of home is stunning in the morning light, while the back is beautiful in the afternoon with the way the sun hits & reflects off the house. 4th story cupola features historic 225 yr old bar end from the original Bridgewater Boarding house, & oversees glorious surrounding views of mountains, w/ peaks over 4,000 ft- including trail map view of Killington! Stunning great room features three story windows that allow for sunlight to pour in & heat the whole house during the colder VT winter months. Exceptional property w/ so much to offer- you need to see it to truly believe all of its features!

Listed by Hergenrother Realty Group and Daniel Preston, KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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145 South Puckerbrush Road Reading VT 05153

Reading, VT145 South Puckerbrush Road

Price$1,620,000

Est. Mortgage: $/month

MLS Number 4851788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,800

Lovely antique center chimney Cape c.1792 tastefully renovated to retain the warmth & charm that only an old home can offer while incorporating the conveniences of the 21st Century. 3 BR 2 Bath, Kitchen with VT Soapstone counters, gas range, ceramic tile flooring, Dining Room, Family Room, Sunroom, 1st floor Master w Bath; 2nd floor has 2 rooms, full bath and a Loft Study. Southern exposure, set on 104 acres on quiet dirt road with views to Ascutney, pond, mature plantings, gardens & fields bordered by stone walls, 2 horse barns, run in shed & 3 car garage. Also, 'The Sugarhouse' a stunning 2BR 2B post & beam house & a 2 car garage w workshop. On the GMHA hundred mile route. Protected by Vermont Land Trust. Beautiful property, must see to appreciate.

Listed by Dana Waters and Paula Waters, Dark Horse Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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477 Thistle Hill Road Pomfret VT 05053

Pomfret, VT477 Thistle Hill Road

Price$1,600,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4820067

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 6
  • Square Feet 5,691

Thistle Hill offers the ultimate combination of vernacular exterior form contrasted with stylish, modern and organically inspired interior spaces in a setting and location that offers privacy and a sense of protection as well as convenience to recreation and civilization. Snugly nestled into the North Pomfret hills, just a few miles from both Hanover, NH, home of Ivy-league Dartmouth College and Woodstock, VT, “the prettiest village in New England” and sharing a border with the federally protected Appalachian Trail Corridor, Thistle Hill enjoys a commanding view across the Pomfret hills and over the property's clean, spring fed pond at beginning of the approach to the private drive. The banked, terraced and cascading gardens surrounding the house are simply magnificent. Created with the deft hand and an artist's touch, the borders, beds and ground cover as well as the stone walls and paths that mark and define the property create a private sanctuary for humans and wildlife alike, with birds of every species trading across the valley in the air above. The screen room, steps from the front door and suspended over the hillside offers the most tranquil location from which to enjoy this aspect of the landscape.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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89 Silver and Knob Hill Road West Windsor VT 05037

MLS Number 4851737

  • Residential Single Family
  • Construction New Construction
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,200

NEW CONSTRUCTION 2021! Situated on 26.19 acres of woods and rolling grassy meadows and a great opportunity to develop a gentleman horse farm in the heart of horse country. This newly built country estate boasts 4,200+ sqft, 3-4 bedrooms, 2.5 baths, hand-plastered walls, fiber optic high-speed internet, a 2-car garage, and a stunning 18-foot beamed cathedral ceiling with a soaring New England stone fireplace in the Family Room. There is a fully equipped country kitchen with custom walnut cabinetry, Kitchen Aid appliances, a 48-inch WOLF dual-fuel double oven range, and elegant Equinox VT Soapstone countertops provides generous counter space for your next dinner party. This home has a gracious open flowing floor plan, and the large first-floor private master bedroom suite has a spa-like bathroom (all baths have marble countertops). Quality Andersen series windows, Hardwood and title flooring, a 48-foot mahogany porch, and a private office in wainscoted Alderwood. Oversized Andersen Patio doors extend out to the rear lawn & lovely, stonewalled grounds. There is a full basement, abundant attic storage, and the drilled well delivers over 50gpm with enough water for a pond. Underground utilities, upscale mechanicals, and even radiant & FHW heat. Exceptional craftsmanship and superior location in West Windsor's horse country give you easy access to GMHA trails, Woodstock, & Ascutney Outdoor Center recreational trails. Purchase now and be in by early June!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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

MLS Number 4754916

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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1702 North Puckerbrush Road Reading VT 05062

Reading, VT1702 North Puckerbrush Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4819286

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 7,374

A magical property located in the hills of Reading surrounded by large country properties in the heart of horse country. State Forest land abuts this property. This home is a perfect retreat for those seeking solitude. The sweeping drive carries you through the woods to the home-site which is centered in an open area totally hidden from the town gravel road. Pleasant view are here now, with dramatic views if you chose to thin the woodland below. Walking the grounds you will find a natural landscape with added fruit trees, a new barn with storage for 2 or 4 cars and a loft, a hidden back field and even an ancient "lime kiln". Inside there are so many quality features that you may have only dreamed about... top of the line kitchen with Sub-Zero freezer and fridge, Wolf range, refrigerator drawers, cookbook library, and a separate prep room known as the "gadget room". There is an office, den, living, dining room on the first floor along with screen porch to the rear. There are two wings to the second floor, giant master suite with abundant storage and a stunning bath along with two guest rooms and a laundry room that will make you want to do your laundry. The other wing would be a perfect in-law suite or nanny's quarters with two sleeping rooms, sitting room, full bath and washer/dryer. The lower level has a large family room, gallery, exercise room and 2 storage areas. This property is second to none with Okemo and Woodstock just miles away. Be sure to check out the video!

Listed by Betty McEnaney, TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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762 Royalton Turnpike Barnard VT 05031

Barnard, VT762 Royalton Turnpike

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4844537

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,842

At the end of a private drive, 'Sonnenberg Haus' is sited on the top of an open rise overlooking a sweeping lawn, raised bed gardens and dramatic long-range westerly views of the center of the Green Mountains. The striking post and beam saltbox, offering an open floor plan and abundant natural light throughout, is privately located in an area of substantial country estates, minutes from downtown Woodstock, Vermont and steps from the five-star, luxury hotel Twin Farms and Barnard's Silver Lake. The four-bedroom, three-bath Colonial inspired home is set at an elevation of just over 1500 feet and nestled at the edge of the wooded portion of the property's 11.72 acres which include an enchanting pond not far from the house. Extensively updated and upgraded over the last two owner's stewardship, the home offers spa-like bathrooms, a new farmer's porch and a completely remodeled second level offering an elegant master suite and two additional bedrooms that share a bath. Originally constructed by Hans Kurash and his son as part of the storied Sonnenberg development, named by the owner and originator after his favorite ski slope in the Swiss Alps, Sonnenberg still exists today in a certain measure and includes Twin Farms, named by Forbes Magazine as the 2020 Hotel of the Year. Across the street you will find Kiss the Cow Farm, an organic, grass-based dairy and Barnard Feast & Field Market. Showings begin 1/22. No showings 1/23.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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39 RIVER Street Woodstock VT 05091

Woodstock, VT39 RIVER Street

Price$1,175,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4814947

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,188

This striking 1903 Colonial Revival home was commissioned by Edward and Marianne Faulkner to house their farm & mill manager and his family. Massively built with timber framing, lathe and plaster on the stone foundation of an 1805 residence it replaced. The winter light flows through the south facing home overlooking the Ottauquechee River. A 1990 addition included a main level family room and master suite on the second with views north and westerly of Mt. Tom and the National Park lands. Spacious fenced back and side yards are landscaped with flowering shrubs and perennial gardens with an outdoor entertainment area featuring charcoal barbecue and Italian wood fired oven. All mechanical systems, plumbing and wiring have been replaced and upgraded, including the installation of two Tesla Power Walls to provide electrical service during extreme weather events. A short walk over the Covered Middle Bridge to all Village amenities and around the corner from Faulkner Park.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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89 Silver Hill Road West Windsor VT 05037

West Windsor, VT89 Silver Hill Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 4837914

  • Residential Single Family
  • Construction New Construction
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,200

NEW CONSTRUCTION IN 2021! Gracious VT country home boasts 4,200+ sqft, 3-4 bedrooms, 2.5 baths, hand-plastered walls, Fiber Optic high-speed internet, a 2-car garage, and a stunning 18 foot beamed cathedral ceiling with a soaring New England stone fireplace in the Family Room. Exceptional craftsmanship and superior location in West Windsor's horse country giving you easy access to Woodstock & Ascutney Outdoor Center recreational trails. There is a fully equipped country kitchen with custom walnut cabinetry, Kitchen Aid appliances, a 48-inch WOLF dual-fuel double oven range, and elegant Equinox VT Soapstone countertops will accommodate generous counter space for your next dinner party. This home has a gracious open flowing floor plan and the large first-floor private master bedroom suite has a spa-like bathroom (all baths have marble countertops). Quality Andersen series windows, pre-stained hemlock siding, a 48-foot mahogany porch, and a private office in wainscoted Alderwood. Oversized Andersen Patio doors extend out to the rear lawn & lovely stonewalled grounds. There is a full basement, abundant attic storage, and the drilled well delivers over 50gpm with enough water for a pond. Underground utilities, upscale mechanicals, and even radiant & FHW heat. An additional 17.3 acres of woods and rolling grassy meadow could turn this into an ideal horse property for a total of 26 acres - available at MLS #4845445. Purchase now and be in by June 2021!

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 2021 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 April 21, 2021.