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.

Whatever type of luxury 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 luxury home. Contact us today!

974 Cemetery Hill Road West Windsor VT 05089

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4764706

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

White Fox Farm's c. 1850 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: 3.56% 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 Horton Hill Road Hartland VT 05048

Price$1,950,000

Est. Mortgage: $/month

MLS Number 4747287

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

The Hartwell House Estate beautifully fuses modern state of the art construction techniques with antique character and charm. The hilltop location on 32 acres assures complete privacy and offers sweeping panoramic views over the Connecticut River valley while being less than 20 minutes from both Woodstock and Hanover. The 7000 square foot residence features 4 bedrooms and 3.5 baths, exposed hand hewn beams of two 200 year old barn frames, a great room with field stone fireplace and waterfall rising to the cathedral ceiling, gourmet kitchen with large fireplace, mahogany paneled library, a wrought iron spiral staircase climbing to the cupola look-out room, mahogany floors with radiant heat, a finished walk-out basement with wine cellar, and an attached heated 4 car garage. A solar heated in-ground pool, stone patio, two ponds, two barns and a putting green complement the mature landscaping. A 10kW grid tied solar array and battery bank reduce utility costs and provide battery back-up. Built by the late highly respected builder Dana Ennis as his personal residence, this property is a showcase of craftsmanship, design, and materials.

Listed by Seth Warren, Seth Warren Real Estate

$
$
%
$/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

651 North Road Barnard VT 05031

Price$1,850,000

Est. Mortgage: $/month

MLS Number 4763049

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 4,856

FINCH HILL - A magnificent european-inspired estate with lovely south facing views overlooking the picturesque village of Barnard, VT - just 15 mins to Woodstock. Nestled on 60 +/- gentle acres with spectacular open meadows, fern groves, beautiful perennial gardens, apple trees, stonewalls and a spring fed pond. 2nd home site identified with stunning southwesterly views. Enjoy complete privacy and tranquility on this perfectly manicured estate. Built in 2003, this meticulous residence is comprised of gracious sun-lit rooms, beautiful antique elm flooring, two elegant wood burning fireplaces, kitchen fit for a chef with 2 walk-in pantries. Enjoy entertaining: open floor concept with handsome french doors onto a lovely stone terrace from family room or the bar room that incorporates an antique soapstone sink. Exquisite craftsmanship throughout the dwelling: 11 foot ceilings, custom iron balusters, handsome mahogany doors and cobblestone parking area. Underground fiber optic internet.

Listed by John Snyder, 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

7 Laber Road Bridgewater VT 05035

Price$1,699,000

Est. Mortgage: $/month

MLS Number 4775026

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • 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 Tucker Adirondack Lange, KW Vermont

$
$
%
$/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

249 Densmore Hill Road Hartland VT 05048

Price$1,600,000

Est. Mortgage: $/month

MLS Number 4767801

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 2,959

This superbly maintained Vermont Cape residence captures stunning sunsets from a vantage point overlooking westerly river valleys to the peaks of Killington and Shrewsbury. The home is offered fully equipped and furnished for gracious country living. A large multipurpose barn, run-in and fenced pasture reflects the traditional use in 'horse country' with GMHA (Green Mountain Horse Association) trails providing access throughout the surrounding area. A mix of open fields, apple trees and northern hardwoods is defined by old stone walls. A spring fed pond is a year round source of water for a variety of wildlife thriving in the sparsely populated community. Ideal situation for those seeking the peace and quiet of rural New England.

Listed by Laird Bradley, 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

591 High Pastures Road Pomfret VT 05091

Price$1,595,000

Est. Mortgage: $/month

MLS Number 4772297

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,880

Otis Hill Farm is iconic Vermont! Woods, fields & streams, working barns & fire pond with 3 stall horse barn, pool & pool-house & tennis court. Miles of trails lace woods & fields for walking, riding, cross-country skiing & snowmobiling. Near Woodstock, 20 minutes from Hanover, NH, 30 minutes & 2 hours from Boston. The 200 year-old farmhouse reveals historic craftsmanship with ”hand-hewn" beams joined by mortise & tenon. Abundant wildlife Whitetail deer, turkeys, fox, hawks, owls & a variety of song birds. The land consists of an estimated 165+/- TBD diverse acres of northern hardwoods, spruce, hemlock & pine, open fields, active springs & long frontage on the Ottauquechee River. Enrolled in Vermont Current Land Use the farm adheres to a Forestry Management Plan to maintain vital, productive & beautiful forests. An ancient apple orchard is sited on plateau above the farmhouse. Perennial gardens, crab apple & cherry trees, raspberries, red & black currents & flowers are enjoyed all summer long. Close to everything & still a tranquil refuge in a frantic world. A perfect place to nurture lives & grow memories.

Listed by Laird Bradley, 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

97 & 99 Darling Road Woodstock VT 05071

Price$1,575,000

Est. Mortgage: $/month

MLS Number 4767586

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,749

High Riding's 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson's (NYC Mayor Fiorello LaGuardia's “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible. The “Studio” at 97 Darling Road, a 2,384 square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio. The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a swimming pond. There are over 800 sugar maples- tapped for maple syrup, apple trees, well maintained pastures, forest, private riding and hiking trails and a 3-stall stable.

Listed by T Story Jenks and Dia Jenks, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1702 North Puckerbrush Road Reading VT 05062

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4759535

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 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 for even more protection. 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...the 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.

Listed by Betty McEnaney, TPW Real Estate

$
$
%
$/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

236 Old Farm Road Pomfret VT 05053

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4755026

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 6,000

SEAVER HILL FARM - Quietly and discreetly, Seaver Hill Farm is located in one of the most desirable and spectacular settings in central Vermont. There are commanding views to the east into New Hampshire from the 1,200 ft altitude. The property has 10.5 mostly open acres, some of which are in the land trust and also surrounded by over 100 acres of conservation lands which are in perpetuity for generations to come. The house is newer construction and has been meticulously updated in recent years. The spaces are comfortable and bright, most well sited to take in the persistent views. The gathering spaces both inside and out are numerous and perfect for entertaining or large gatherings. The main section of the house has 4 bedrooms on the upper level including a large master suite with large picture windows to the view. There is an amazing guest suite on the north side of the house with its own living space, new bath and loft. The basement is finished and houses a theater room, incredible bar and indoor games area. Notwithstanding the secluded and remote feeling at the property, Seaver Hill Farm is only 5 miles from Interstates 89 & 91. It is also minutes from Quechee, and includes a membership to the renowned Quechee Club. Woodstock, Vermont and Hanover, New Hampshire (home to Dartmouth College) are only a short ride away.

Listed by David Donegan, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1862 Lakota Road Barnard VT 05031

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4773880

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 7
  • Square Feet 3,572

A 1930's rustic camp tuned up for the 21st century with a whimsical, yet sure-footed, sense of style. Redtop has been in the family since the early 20th century, and was built at the same time as the abutting Lakota Club, the private fishing club. The property is located off a quiet dirt road, surrounded by 59.4 acres of meadows and woodlands, with lovely far views of valleys and mountains. Summer living is centered on the wide covered porch, where breezes flow up the valley and make for relaxing reading, dozing and conversation. Winter is all about the huge stone fireplace in the living room and sledding on the long hill off the side of the house. Consistent with its camp character, the house is manageable in scale but sleeps a crowd, with two bedrooms on the ground floor and another 5 on the second floor, with 4 total baths. The current owner's full-on renovation has drawn repeat vacation rentals, covering the annual operating costs while giving her plenty of time to enjoy the property as a second home. It is a hit with visitors because it is fun and hip while still very Vermont (furnishings are included). The acreage offers potential for a family compound or investment value.

Listed by T Story Jenks and Dia Jenks, 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.

Save 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, 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

779 PETERKIN HILL Road Woodstock VT 05091

Price$1,475,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4655908

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,370

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: 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 18, 2019.