Upper Valley Luxury Homes in Vermont

The Upper Valley of Vermont offers some beautiful luxury homes in Woodstock, Hartland, and beyond. Are you looking for a private country estate, equestrian property, historic hilltop farm, or a family retreat with plenty of recreational opportunities and amazing views? Look no further! Bassette Real Estate Group can help you find your dream home in Vermont. Below you’ll find homes for sale in the Upper Valley priced at $1M and higher.

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Luxury Homes $1M to $2M | Luxury Homes $2M+

186 Reading Farms Road Reading VT 05062

Reading, VT186 Reading Farms Road

Price$6,375,000

Est. Mortgage: $/month

MLS Number 4866260

  • Residential Single Family
  • Bathroom 15
  • Bedrooms 17
  • Construction Existing
  • Square Feet 13,010

Upon the first glance of the massive estate you notice the generations of carefully curated and thoughtful planned landscaping, expansive meadows and lawns, stocked fish ponds which catch the reflection of the main house as you drive by. You might even get a glimpse of the Merganser Hooded Ducks who nest each year. Owned for 100 years, the property has graced the cover of House Beautiful and in Architectural digest. The estate compound includes a main house reminiscent of an country manor with 9 bedrooms, 9 bathrooms, extensive living areas, a Library which is in the original cape built 1776 with original floors. Also a theatre, gym and 2 bedrooms with one bath. A carefully situated gazebo catches the evening sunsets through mature pines. Features a entertainment barn complete with kitchenette, 3 bed, 2 bath and pavilion for large groups or events. Also a cottage offering 3 bed,1.5 bath and kitchen. After a stroll on your private trails relax in the heated pool at the end of a mature maple alley. The estate is listed at 120 acres with an additional 115 acres available for a true kingdom of 235+. Many have tried replicating the setting at great expense to capture the estates decades of devotion to the grounds which cannot duplicated. Close to skiing and heart of horse country with access to GMHA trails. Minutes to Historic Woodstock. Presently being used as a Special Events venue as well as the owner''s primary home. Possibility of Owner financing and/or joint ownership.

Listed by Derek Eisenberg, Continental Real Estate Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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249 Bragg Hill Norwich VT 05055

Norwich, VT249 Bragg Hill

Price$5,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4883128

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 9,621

Huge views, big land, near everything: Hard to imagine that a nearly 200 acre hilltop estate is within walking distance of the village of Norwich. With the scale, sweeping views to the White Mountains, complete privacy and presence of one of the great Vermont country properties, Highlander is just over a mile to Dan & Whit's and the green. The home and barns are built on the site of an old hilltop farm with massive sugar maples, stone walls, hayfields, managed woodlands, and ponds for swimming and wildlife. The home is elegant and comfortable with an indoor/outdoor flow. Relax and take in the views on the patios and porches or supper in the summer room, which opens out to the pool. At the heart of the house is the capacious, recently renovated, kitchen. Extensive perennial gardens unfold throughout the summer, & an edible landscape yields apples, pears, peaches & berries. An active, outdoorsy family shaped the character of Highlander. Many sets were played on the tennis court and active equestrians grew from ponies to top-flight competitors in the roomy 6 stall stable and on the trails. Kids learned hard work bringing in the hay. The swimming pond converts to pond hockey in the winter, & the other 3 ponds host diverse wildlife all year round. The family hosted an annual cider pressing, skied on the trails & raced on sleds down the long meadows. 2 bedroom apartment over 4 bay equipment barn. Easy access to AT trail. Showings begin September 25.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$5,200,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5

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

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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336 Stone Bridge Way Woodstock VT 05091

Woodstock, VT336 Stone Bridge Way

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4887084

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,824
  • Construction Existing

Room for all, close to town, very private: Stone Bridge is a capacious and thoughtfully-built 2002 5824sf Craftsman Style home set at the end of a private way, with a two-bedroom guest house on a total of 22.65+/- acres. Stone Bridge Way is off of Densmore Hill Road, well-located between Woodstock and South Woodstock Villages in the heart of horse and gravel cycling country. Lovely views to Killington, the western exposure makes for dramatic sunsets from the wide stone patio. Comfortable in all seasons, the spaces flow from open kitchen to living and dining areas warmed by a fireplace (with a conveniently located bar off the living area). Ground floor primary suite, second-floor master, two bedrooms with shared bath and guest suite. The ground floor offers a sports pub, gym and indoor spa. Plenty of space for toys alongside the garage. The guesthouse is privately sited away from the main house, with two bedrooms, two baths, fireplaced living room, dining room, kitchen and study. The site is elevated and largely open around the houses, with woodlands on the other side of the private drive. Great site quality, location, and amenities make for a well-rounded compound offering.

Listed by Ruth Sudduth and T Story Jenks, LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4884374

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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5518 Vermont Route 12 Barnard VT 05031

Barnard, VT5518 Vermont Route 12

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4882340

  • Residential Single Family
  • Square Feet 7,619
  • Bedrooms 6
  • Bathroom 6
  • Construction Existing

A nationally known restaurant well located within the extended Woodstock community! This circa 1796 brick showplace has long been a favorite elegant dining destination, for Vermonters and visitors alike! A presence created by historic buildings complimented by extensive landscaped grounds continually provides a sense of romance and a memorable ambience sought by the most discriminating brides. A property that will satisfy the highest expectations and professional standards! Current chef and family have been on site for over 21 years with acclaim as "Best Vermont Restaurant!" Infrastructure of fine buildings, superior restaurant equipment in place, and an established excellent reputation are awaiting the next entrepreneur! Many well conceived components are thoughtfully combined to create both a practical and a truly stately property. The owners have created an extensive and appealing private residence within the main brick building, with designer kitchen, 5 bedrooms, family rooms and private spaces. Within the brick, the main restaurant includes 3 elegant formal dining rooms. Separately entered is a tavern with 2 dining areas and a classic tavern bar. A detached barn presents a dramatic event space. Within this barn is a highly popular short term guest rental unit. The land component is spectacular! The 10 acres present gardens, long walking paths and private pond! Fine dining and event hosting is established! Transformation into a private estate residence is a potential use!

Listed by John Wetmore, William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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66 Hollow Road Woodstock VT 05091

Woodstock, VT66 Hollow Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4885504

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,350
  • Construction Existing

John Curtis, a veteran of the American Revolution, received a land grant to establish a homestead in the new State of Vermont circa 1780. The fields & pastures carved out of a wilderness sustained his family for 5 generations. Stonewalls & tumbled dams remain as evidence of the industry & effort of early pioneers. The Hollow Farm consists of the striking 6 bedroom/4 bath Homestead House & the 3 Bedroom/2 bath Brook House sited in the middle of the 91-acre property. The new Homestead created in 1988 around the stone fireplace & native timber framed original home. The southwesterly exposure illuminates the spacious gathering rooms & private spaces through the enormous round windows. The interior layout reflects casual country lifestyle with an open floor plan spiraling around the central kitchen complex, which opens out on to a wide, elevated terrace, decks & balcony's on each level. Common rooms & quiet corners are visually connected & access by open stairways. The architectural form expresses the Vermont farmhouse on a grand scale with a cupola & splendid views of the surrounding fields & mountains. The property adjoins Coolidge State Forest at a place where a magical waterfall & sweet swimming hole are formed over exposed bedrock. The maintained road ends a mile or so beyond the old farmstead & continues on with miles of trails leading to South Woodstock, Plymouth & Reading townships. Nearby are Woodstock Village, the ski resorts of Killington & Okemo & public waters.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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541 & 523 Ely Road Thetford VT 05045

Thetford, VT541 & 523 Ely Road

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4858046

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 7,280

A Vermont Country Estate historic and inspiring and placed upon a hill overlooking the Connecticut River. A large main house, a quaint guest home, a unique treehouse, a clay tennis court, an outdoor living room, and a sprawling barn set the landscape for this quintessential estate. With expansive rooms and gathering spaces, a traditional & contemporary melded design, and opulent lighting are present throughout this Vermont home. The guest home is a charming two-room schoolhouse with two bedrooms placed above. An acorn treehouse situated and perched between an oak and a maple tree adorns the center of the property while overlooking the pastures and southern views of the Connecticut River. This Vermont riverfront retreat prominently displays outdoor gathering spaces, opulent views, and resides in an idyllic setting within the surrounding landscape. Within 20 minutes of Dartmouth College and an easy destination spot from Boston and New York, this property is primed for its successors coming from near or far.

Listed by Lochrane Gary and Leah McLaughry, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4884402

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 37.8 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award-winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-level bank barn has a wide center aisle, 3 box stalls and heat throughout on the first level; hayloft and office with high-speed internet on the second level; and storage on the third level. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Daily pleasures range from a plum fresh picked eaten at the outdoor table overlooking the perennial garden Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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529 Kerwin Hill Road Norwich VT 05055

Norwich, VT529 Kerwin Hill Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4842921

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,985

At the end of a private road just a few miles' drive north of Ivy League Dartmouth College and one of the most picturesque villages in Vermont, you will find the stillness and privacy of Holiday Hill Farm. Controlling both sides of the road, the property's 54.5 acres of Vermont countryside encompass open meadows, fenced pastures, northern hardwood forests, ancient grandfather stonewalls. The Federal-style farmhouse enjoys views across the valley to New Hampshire's White Mountains and was built by Doug Gest and Co's renowned craftsmen. Providing the best of both worlds for those who are attracted to the charm and vernacular of a historic Vermont hill farmstead along with the comfort of ca. 2007 modern amenities, systems, and conveniences, the interior includes cherry floors, period moldings, two fireplaces with lovely hand-built composed mantels and custom built-in cabinetry. With exacting standards and attention to detail, the resulting 11 room home offers a place for everyone and everything - from the inviting four season porch that even in winter becomes the heart of the house to the Great Room with its open hearth and wood-burning fireplace at one end linked by hand-hewn beams to the gourmet kitchen at the other. A private kingdom located two hours from Boston, four hours from NYC, and three hours from Montreal, recreational, educational, and cultural opportunities abound - from skiing at Killington to world-class medical care at nearby Dartmouth Hitchcock.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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797 North Road Barnard VT 05031

Barnard, VT797 North Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4877325

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,806

Designed and built by the current owners in 2008, the house is in the middle of a 27-acre parcel. The land includes open meadows, a spring-fed pond, fenced paddocks and pastures, and a riding arena. Trails wind through two wooded areas on either side the property. Combining historically inspired details with modern construction techniques and state-of-the-art systems, the owners created a sense of space and volume with a functional and organized floor plan. A dramatic center staircase is the focal point of the entry. Throughout the first floor are 12-foot ceilings. Large windows and elegant room proportions create interiors that are grand yet livable. An open concept kitchen and a formal dining room provide options for entertaining. Off the front hall is a large mudroom, a washer/dryer, sink, open shower for dogs or muddy boots and an automatic dog door. The first-floor bedroom suite includes 2 separate bathrooms. A private screened porch off the bedroom is wired for a hot tub. Thoughtful attention to detail can be found in every room from the custom woodwork, stone and tile choices down to the cabinet knobs in the kitchen. There are 10-foot ceilings throughout the second floor with 3 generously sized bedrooms with large closets (one bedroom is being used as a exercise studio) and a full bathroom. In the center of the second floor is a large room with limitless potential. A mahogany, L-shaped farmers porch runs on the north and east sides of the house.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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234 Hidden Ridge Farm Road Pomfret VT 05067

Pomfret, VT234 Hidden Ridge Farm Road

Price$2,475,000

Est. Mortgage: $/month

MLS Number 4876336

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 6
  • Construction Existing
  • Square Feet 11,200

Room to roam, big views, privacy, space for everyone: This exceptional Vermont recreational retreat on 75.8+/- private acres has sweeping vistas from Killington to New Hampshire. The 8-bedroom, 6-bath residence is set up to provide suites for privacy, as well as comfortable gathering spaces opening to the views of meadows on to layered hills and distant mountains. Extensive recreational amenities include an in-ground heated pool, clay tennis court, sledding hill and, of course, the beautiful countryside to explore. Horses and their people will appreciate the 85 x 150 heated and sprinklered indoor arena complex with a 5-stall stable, viewing area with kitchen and office, ample hay storage, 2-bedroom apartment, 80 x 100 outdoor arena, 6-stall field barn and post & rail fenced pastures. Located within 15 minutes of Woodstock on a quiet country road. Bring your friends and your horses, or just soak up the quiet.

Listed by T Story Jenks and Ruth Sudduth, LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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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 October 16, 2021.