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
  • 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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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$1,785,000

Est. Mortgage: $/month

MLS Number 4820067

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 2
  • 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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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41 Pleasant Street Woodstock VT 05091

Woodstock, VT41 Pleasant Street

Price$1,700,000

Est. Mortgage: $/month

MLS Number 4809479

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 9
  • Bathroom 11

"Why not the best?" An exquisite home built with magnificent taste. The wallpaper (Bradbury & Bradbury) in one bedroom, was $10,000.00. When one walks through this amazing property, one stands in awe. Every bedroom has a full bathroom. A perfect place for family and friends, complete with your own bar. Original woodwork, including pocket doors. Custom carpeting. Original stain glass windows. All current and previous owners maintained and improved property. Private living quarters on right side of house.This is a Rockefeller town, once voted "Most beautiful small town." 20 minutes to Killington and Dartmouth. Sidewalks to small stores and restaurants. Mt Peg and Mt Tom trails bordering village. Theater and Health Club including golf course in town.Beautiful historical property priced to sell. Most furnishings included. Move in ready!!! Can be permitted as private residential property with zoning permit. Being sold to use as residential but currently commercial.

Listed by Dorothea Mongulla, High End Realty

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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216 Galaxy Hill Road Pomfret VT 05067

Pomfret, VT216 Galaxy Hill Road

Price$1,650,000

Est. Mortgage: $/month

MLS Number 4831543

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6,427

Named for the active brooks that run through the hills of Pomfret and converge on this property, Three Brooks Farm offers over 133 acres of Vermont countryside on Galaxy Hill Road, a location well known and loved by those lucky enough to call this special hilltop neighborhood home. Positioned just off this quiet country road in a setting well-chosen for its combination of privacy and convenience, the house orients just west of south and takes in a sweeping views of the valley as it unfolds across a pasture and then woodlands below and out across multiple layers of several ridges beyond to the Green Mountains. The built environment includes a main residence that was designed by Samuel Van Dam Architects AIA in 1986. The house has been sited for privacy and to take advantage of the spectacular southwesterly views of distant mountains. Based on open concept living, the floor plan provides pleasing open rooms oriented toward the view with large windows and sliders which open to the stone terrace and deck. The front entry brings one into a large great room that includes the kitchen, dining area and living room with an open hearth wood-burning fireplace. The master bedroom suite is on the first floor and three additional bedrooms can be found upstairs. An oversized two car garage with shop and storage space as well as unfinished potential on the second floor complete the house.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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2039 Randall Road Woodstock VT 05091

Woodstock, VT2039 Randall Road

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822404

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

A hidden gem at the magical “end of the road ” this classic 1840s stone Cape was constructed by Scots craftsmen of hewn stone quarried in nearby South Woodstock. Gently rolling meadows and northern hardwoods surround the homestead which is less than four miles from the public gathering space at the Village Green in Woodstock, often called the “prettiest town in America.” The National Register of Historic Places refers to this part of Windsor County as “the stone house belt of Vermont.” There is simply nothing quite like a stone house cool in summers and snug in harsh winter storms. The well-chosen farm site spreads out across 34 acres of southerly oriented landscape shaped by generations to provide sustenance and shelter. A deep, spring-fed pond serves as a refreshing swimming spot in the summer and perfect skating rink in the winter. The property includes an assemblage of outbuildings that appear like they were placed by a master painter within a frame. Under the current three-decade plus stewardship of a well-known local architect and his family, a purity of form has been retained during periodic renovations providing 21st Century comforts and updated mechanical systems, while honoring the history and embracing the quintessential Vermont vernacular of the house and setting.

Listed by Richard Higgerson and Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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 4819286

  • 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. 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. Be sure to check out the video!

Listed by Betty McEnaney, TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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38 Tinkham Hill Road Hartland VT 05048

Hartland, VT38 Tinkham Hill Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4828294

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 6,700

Mountain top 16+ acre estate, views for 12 miles in three directions and 9 minutes to Woodstock Village. 3 bedrooms, 3.5 baths in the main house, 2 bedrooms 2.5 baths in the carriage house. Less than 2 hrs to Boston and 4 hrs to NYC. Located 2 miles off I-91 and 45 minutes from the MASS border, there's no reason to spend the day in the car. 25 minutes to Killington Mountain and just over an hour to Stratton, Okemo and others. Main house was built in 2017 with all the modern conveniences such as central air, radiant heat, stainless appliances and granite counter tops. It is connected to the Carriage House by a heated subterranean passageway. Garages consist of 2/2 car heated garages in the main house, and one heated garage in the carriage house. Also a new huge 65'x 26' garage with 15' door attached to the carriage house. There is heated four stall barn for the horses with two more upper levels for hay or storage. Barn also has a heat bathroom and tack room. Three decks in the main house, one screened breakfast room to the east and south, one under cover to the south and one large open deck to the south and west. The carriage house has two balconies facing south and west, as well as a deck to the east. The mountain has lightening fast fiber optic internet, and 5 bars of cell reception, as you can several cell towers atop Mt. Auscutney. Business is a breeze from the comfort of your home. The home is being offered fully furnished and absolutely turn key.

Listed by Jason Saphire, www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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22 Prospect Street Woodstock VT 05091

Woodstock, VT22 Prospect Street

Price$1,399,900

Est. Mortgage: $/month

MLS Number 4820298

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

This is a rare opportunity to own over four acres within the town of Woodstock. This immaculately updated expanded Cape puts you walking distance to schools, shops, restaurants, golf, and hiking. At home, sit back and relax while you enjoy quintessential Vermont views of Mount Tom and your own landscaped pond from the wrap-around deck or star-gaze from the perfectly situated spa. The cook's kitchen has granite/soapstone countertops, stainless steel appliances, a breakfast nook, and a sitting area with a mount for a television and a propane stove. The dining room has beautiful built-ins and pastoral views. The living room has vaulted ceilings and a wood-burning fireplace. The first-floor master bedroom suite has mountain views, a large dressing room, an office, and a spa-quality bathroom with amenities including a bubbler-tub and multi-nozzled shower. Upstairs there is an ensuite bedroom and two family rooms, one is a TV room and the other is a game room. On the walk-out basement level, there are two ensuite bedrooms, a full kitchen, pantry, and two offices, and a sauna. The lovely landscaped grounds are surrounded by woodlands affording privacy not often found in town.

Listed by Jennifer Falvey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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675 College Hill Road Woodstock VT 05091

Woodstock, VT675 College Hill Road

Price$1,385,000

Est. Mortgage: $/month

MLS Number 4833519

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

This newly constructed, Ambrose design/build home is privately situated on 20+ acres just a short walk to the Woodstock Village Green and includes a separate 3.5-bedroom, 1.5-bath, 1,500-square foot farmhouse/guest house (currently rented for $1,700/mo) plus an historic barn, 4-bay shed-garage and swimming pond. The beautifully crafted main residence, built in 2016, features an open floor plan main living level with high ceilings and large windows which flood the kitchen/living/dining area with natural light. The main level also enjoys a generous pantry, mudroom with adjoining laundry, bedroom and 1/2 bath (to which a shower could easily be added). Upstairs is the master bedroom featuring a walk-in closet and full bath with a clawfoot tub, shower and double vanity, and two additional bedrooms and full bath. The finished lower level offers a wonderful rec/hangout room and another full bath. The house also features rooftop solar panels and is certified for excellence in energy-efficient design and construction through Efficiency Vermont. Well-maintained and beautifully landscaped grounds with a mix of lawn, gardens, a swimming pond, and woods, all of which can be enjoyed from the comfort of the covered wraparound porch. Newer, state-approved 7-bedroom septic, and a total of 4,200 sf between both homes. This is a prime opportunity for a private spot within walking distance of all of the many amenities Woodstock Village life has to offer.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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$1,300,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4821248

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

A perfect Vermont retreat! Privately located, in an area known for substantial rural homes and the beloved Green Mountain Horse Association equestrian trail network. This impeccably maintained Vermont Cape residence shows an obvious pride of ownership. The land component is extraordinary even by Vermont's high standard of pastoral beauty. Dramatic long range mountain views to the west display stunning sunsets! A pleasing mixture of large open fields, apple trees and stands of maple trees, are accented by by graceful old stone walls. A large multipurpose barn is classic in appearance and benefits from being contemporary in its construction. Off a quiet country road the entrance to the property curves up a graceful driveway through beautiful grounds and immediately provides a sense of entering a peaceful and safe retreat.

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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 October 24, 2020.