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!

28-32 The Green Street Woodstock VT 05091

Woodstock, VT28-32 The Green Street

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4798172

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 10
  • Bedrooms 9

3 attached residences, on picturesque Woodstock Village Green! 2 elegantly proportioned brick townhouses, with an attached circa 1830 traditional clapboard home! The gracious interiors, of the brick townhouses, feature attractive antique detailing, high ceilings, multiple fireplaces. The western townhouse, 30 The Green, is fully renovated by quality craftsmen. Ground level is an open floor plan featuring stylish kitchen, dining area, living room with fireplace, and a half bath. A 2nd floor is dedicated to a large primary bedroom, with ensuite bath and walk-in closet! A 3rd floor has 2 comfortable guest bedrooms and full bath. The eastern townhouse, 28 The Green, presents antique detailing, exposed beams, wood flooring, 9 foot ceilings, 3 fireplaces and opportunity to renovate a traditional 3 level home, to suit one's taste. The traditional clapboard #32 The Green has a tastefully renovated contemporary interior with 3 bedrooms, 3 baths, and a finished lower level. Off street parking and a detached 2 car garage are useful amenities. These Woodstock Village landmark properties present a unique opportunity! The 3 bedroom residence at #30 is turn key and luxuriously appointed, for immediate residency. The antique residence at #28 is a very rare opportunity to renovate a traditional Woodstock Village Green residence to indulge new owner's preferences. The clapboard home at #32 is stylishly contemporary and comfortable! All 3 present level walking to Woodstock Village amenities!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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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
  • Bathroom 5
  • Bedrooms 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: 3.24% last updated on May 21, 2020
* 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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591 High Pastures Road Pomfret VT 05091

Pomfret, VT591 High Pastures Road

Price$1,990,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4665909

  • 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. Only 2 miles from Woodstock Village, 20 minutes drive from Dartmouth College & 30 minutes from Killington Ski Area. The 200 year-old farmhouse displays the hand-hewed post & beam frame and is sited with expansive windows to view abundant wildlife and an incredible variety of birds The 230+ acres of land has exceptional character with natural meadows, pastures and fields interspersed in forests of northern hardwoods, spruce, hemlock & pine. Active springs supply year round water to brooks running through the property winding down to the Ottauquechee River. Enrolled in Vermont Current Land Use the farm adheres to a Forestry Management Plan to maintain vital, productive & beautiful forests. A two acre apple orchard is sited on plateau above the farmhouse. Abundant gardens with crab apple & cherry trees, raspberries, red & black currents & flowers to enhance your home all summer long. A tranquil close to all area amenities. OFFERED with different land options and prices.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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2352 Curtis Hollow Road Woodstock VT 05091

Woodstock, VT2352 Curtis Hollow Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

MLS Number 4806321

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 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: 3.24% last updated on May 21, 2020
* 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$1,775,000

Est. Mortgage: $/month

MLS Number 4791217

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

Thistle Hill Retreat - tucked into the Pomfret Hills is the best combination Vermont views and setting along with direct access to the Appalachian Trail system. Property is a delight in all seasons - exciting visuals for the horticulturalist throughout the warmer months, follow the seasonal wildlife changes, and plenty for the outdoor enthusiast. Wonderful for entertaining with generous spaces, gorgeous sight lines, and a spiritually grounding environment. This is an experience worth sharing with friends and family. Main house constructed during WWII with onsite concrete work commissioned by John Taylor Arms. He chose concrete to avoid losing his artwork to fire a second time. The home was substantially renovated and reimagined in 1998 by owner/artist to modernize and return to John Taylor Arms' original proportions. Please see the virtual tour for an intimate view of the property. Less than 20 minutes to Woodstock and White River Junction less than 15 minutes to Quechee.

Listed by Derek Cosentino, BHG Masiello Group/Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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249 Densmore Hill Road Hartland VT 05048

Hartland, VT249 Densmore Hill Road

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: 3.24% last updated on May 21, 2020
* 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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20 Gray Road Hartland VT 05048

Hartland, VT20 Gray Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 4805827

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,536

The best view of Woodstock and the National Park is in Hartland at a cabin called Sun Hill. Built in 2019 on 122+/- acres with 3 bedrooms and 2 baths, the “have to have it” quality of this special property is exceptional. First, the view is mesmerizing and dynamic as changing sunlight, hues and shadows travel across the hilltops and valleys below to the ridges and peaks beyond. Sunrise and sunsets are extraordinary. Second, the home is charming and comfortable, well-built, easy to maintain and takes full advantage of the view and being outside. The first floor has 9 ½ foot ceilings with 8-foot tall double-hung windows and 2 sliding glass doors, one to the timber-framed porch and 5-person hot tub, the other to the patio made of Vermont slate. All of the kitchen cabinets, bathroom vanities and post & beam frames were custom made by local artisans using cherry, oak and pine sourced from the property. Third, the home is completely private surrounded by nature yet located only 3 miles from the Woodstock village green on the east side of town saving time to get to I89 and I91. It also has high speed Internet and cell reception plus a second 4-bedroom septic permit. The last feature is a wonderful old barn and 20-acre field on the west boundary. Perfect for storing equipment, you can hike down to it using one of several trails or drive. Not in view of the cabin, what was farmed here long ago could be farmed again.

Listed by Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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97 & 99 Darling Road Woodstock VT 05071

Woodstock, VT97 & 99 Darling Road

Price$1,575,000

Est. Mortgage: $/month

Pending

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: 3.24% last updated on May 21, 2020
* 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$1,500,000

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: 3.24% last updated on May 21, 2020
* 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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236 Old Farm Road Pomfret VT 05053

Pomfret, VT236 Old Farm Road

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: 3.24% last updated on May 21, 2020
* 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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1862 Lakota Road Barnard VT 05031

Barnard, VT1862 Lakota Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4773880

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 6
  • Square Feet 3,572

A 1930's getaway 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. 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: 3.24% last updated on May 21, 2020
* 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 2020 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 May 28, 2020.