Upper Valley Luxury Homes Over $2 Million

Upper Valley homes over 2 million dollars offer truly unique features, such as historical or architectural significance, vast acreage, unparalleled views, and the ultimate in privacy. These country estates for sale in the Upper Valley region of Vermont and New Hampshire are often large enough to be family compounds, comfortably accommodating many generations and visits by many friends.

Though set apart from other properties in amenities and location, luxury real estate in this price range is close to the Upper Valley’s cultural hubs of Woodstock, VT, and Hanover, NH, as well as many fine-dining restaurants such as Simon Pearce in Quechee, VT and Pine in Hanover, NH. Renown cultural institutions such as Dartmouth College’s Hopkins Center for the Arts and the AVA Gallery and Art Center are also close by. The unspoiled beauty of the Upper Valley awaits you beyond the doors of your exquisite home.

Explore Upper Valley Homes for Sale $2M+

No matter the type of Upper Valley multi-million-dollar real estate you are looking for, Bassette Real Estate Group’s knowledgeable and experienced brokers and buyer brokers can help you find your perfect luxury home. Contact us today!

249 Bragg Hill Norwich VT 05055

Norwich, VT249 Bragg Hill

Price$8,000,000

Est. Mortgage: $/month

MLS Number 4883128

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

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.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Bathroom 8
  • Square Feet 5,142
  • Construction Existing
  • Bedrooms 6

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Carol Wood and Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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$4,350,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Bathroom 5
  • Bedrooms 7
  • Square Feet 5,306

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: 5.3% last updated on May 12, 2022
* 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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10 Tavern Lane Lyme NH 03768

Lyme, NH10 Tavern Lane

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4896071

  • Residential Single Family
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,508
  • Construction Existing

Ideally sited at the end of a private drive on a southwest facing plateau with views across the Connecticut River Valley and into the Green Mountains of Vermont, Tavern Ledge Farm offers one of our area's finest examples of the craftsman-inspired Adirondack Mountain style. Set on 75 acres, the home is positioned to take maximum advantage of the views and incomparable sunsets. The main house, with oversized windows that allow for an abundance of natural light, features an open floorplan ideal for both entertaining and comfortable relaxation. A dramatic fieldstone, two-sided wood-burning fireplace divides the living and dining areas. A chef's kitchen features high-end appliances and luxury amenities with a large pantry and first-floor laundry behind sliding barn doors. The adjacent family room has a gas burning fireplace and access to the three-season screened porch. The mudroom entry offers built-in storage and entry to the 3-car garage. Upstairs is the main bedroom suite with a gas fireplace, 3 additional bedrooms, an open loft study, and a spacious rec room over the garage. Stone walls, a large stone patio, custom in-ground hot tub, perennial gardens, apple trees and a chicken coop complement the acreage immediately around the home. Additionally, the property features a recently constructed, solar-roofed multi-purpose building with kitchen and bath and a substantial auxiliary garage and storage barn. Located minutes from the center of Lyme and a short drive to Hanover, NH.

Listed by John Chapin and Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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
  • Bathroom 6
  • Square Feet 7,619
  • Construction Existing
  • Bedrooms 6

Weddings, events, retreats; this property can be reimagined as a boutique hotel, retreat center, or stately residence! Located minutes from Woodstock, in quintessential Barnard, the attractive and welcoming “Barnard Inn” has been a fine residence since 1796 and in recent decades a destination restaurant. Currently it is well known for catering many distinguished destination Vermont wedding events! Being commercially sound with all permitting and infrastructure in place, many turnkey opportunities exist! Nestled on 10 acres are manicured perennial gardens, lush meadows and working gardens. Walking paths lead to a secluded romantic wedding site at a pond! Owners have created an extensive and appealing private residence within the main brick building. Enter up stairs to a deck, and you'll walk into a sprawling designer kitchen. Continue on to a large living room, 5 bedrooms, family rooms and private spaces. The main building front entrance leads to 3 historic elegant formal dining rooms and an updated state of the art restaurant kitchen. Down the hall is a tavern, with 2 dining areas and a classic tavern bar. Large windows overlook the garden and fire pit area. A detached barn presents a dramatic turnkey event venue! Newly renovated studio apartment below the event barn is perfect for guests who value private space. It is currently used as a highly popular short-term Fine dining and event hosting is established! Transformation into a private estate residence is a potential use!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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$2,995,000

Est. Mortgage: $/month

MLS Number 4900904

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

Welcome to Camp Ely, an expansive and whimsical estate perched atop a bluff with views of the wide, meandering Connecticut River. From the original bricks of a cape built in 1818 to an exquisitely designed treehouse nestled among an oak tree with its own acorn nook, this estate has been created with purpose, integrity, and charm. Every design element inspires feelings of comfort and belonging while linking to traditional uses of the land. Take part in a farming past and graze animals in the pasture. Have tea with a friend in the perennial gardens. Invite family into your guest house and make dinner from your vegetable garden. Let the bright and spacious studio space inspire your creative juices to flow steady and constant like the river below. This estate is so much more than a collection of buildings. This estate is an idea. It's an idea of what it means to be at home, to feel like you live in a place that represents you. Let this spacious Vermont Country estate - with all its fundamental elements - be the kernel from which your personal story can grow.

Listed by Leah McLaughry and Evan Pierce, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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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4281 Rush Meadow Road West Windsor VT 05089

West Windsor, VT4281 Rush Meadow Road

Price$2,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4895074

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 4,281

“RUSH MEADOW” is the most perfect example of a “Modern Vermont Farmhouse” that we have ever listed for sale. Over the past 3 years, the current owner (a designer and co-founder of Farmhouse Pottery) completely gutted and transformed a 1,700 sf Vermont farmhouse (c. 1800), adding two new-construction additions that nearly tripled the finished area of this spectacular residence. The 3 downstairs rooms of the original farmhouse were opened end-to-end into a stunning oversized gourmet kitchen and dining room with wood-burning fireplace. A large glass-and-steel sliding door opens the kitchen to the spectacular 26x32 great room with vaulted ceiling, oversized black-metal frame farmhouse windows. Wide-plank radiant-heated oak floors and white plaster walls in new addition areas. An oversized main level primary BR suite with ensuite bath and walk-in closet. Downstairs a radiant-heated concrete floor rec/mudroom is perfect as a separate hangout/game/TV room. All new mechanicals, insulation, windows, roof, and automatic backup generator. The original upstairs farmhouse bedrooms and baths were also renovated, while retaining the original 1800s farmhouse charm and character. The land component includes two ponds, open pastures, a stream and a wonderful horse-barn with stalls and hayloft is also used for winter car storage. The property is part of the GMHA horse trail network. 16 mins to Woodstock and 6 mins to South Woodstock. See property website for virtual walkthrough.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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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40 Wolfeboro Road Hanover NH 03755

Hanover, NH40 Wolfeboro Road

Price$2,750,000

Est. Mortgage: $/month

Pending

MLS Number 4901282

  • Residential Single Family
  • Construction Existing
  • Square Feet 7,205
  • Bedrooms 6
  • Bathroom 6

This stunning Hanover home sits high on a hill surrounded by conservation land, on the most scenic road in Hanover. With 180 degree views to Ascutney, Okemo and Killington, you will rarely get such an exquisite private setting on 9 acres, just 8 miles to town. The main house, which has been totally renovated, is complimented by spacious sun-filled rooms with oversized windows. One will enjoy the open concept on the first floor which combines the large kitchen, dining room and living room, with an elegant fireplace. All complimented by large windows facing the dramatic views! On the second floor, the home boasts 4-5 bedrooms, 2 sharing a new full bath, the master with a full ensuite bath and office and the 4th and 5th bedroom, each with their own new ensuite bath. Bedrooms?, offices?, au pair space?, it will all work. The walk-out basement has a large rec room, office and plenty of storage. Hi-speed internet service-20 megabits download speed, 1.5 megabits upload speed. The final coup de gras is the fabulous new guest suite with long range views situated over the 4-car garage. Located on a dead-end road, with only 2 other residences, this unique offering awaits its new owner.

Listed by Linde McNamara, LindeMac Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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$2,700,000

Est. Mortgage: $/month

Pending

MLS Number 4888494

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

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 driveway on 10.15+/- 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). Main level primary suite, second-floor primary, plus two bedrooms with shared bath and guest suite. The lower level offers a sports pub, gym and indoor spa. Plenty of space for toys alongside the garage. The site is elevated and largely open around the houses, with woodlands on the other side of the private drive. Site quality, location, and amenities make for a great offering. This listing is also offered with a guest house. See MLS# for more details.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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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109 Eastman Hill Road Lebanon NH 03766

Lebanon, NH109 Eastman Hill Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4903915

  • Residential Single Family
  • Bathroom 5
  • Bedrooms 3
  • Construction Existing
  • Square Feet 6,876

Top of the world, panoramic views of endless mountains. Not one detail spared in this 3 bedroom 5 bath home. Gleaming Mahogany and tiger-wood floors along with custom tile and epoxy, gourmet kitchen with a massive kitchen island for everyone to gather together, open floor plan with views from every room. Living room features cathedral ceilings, with a beautiful 2 story stone fireplace. Primary suite with luxurious master bath, gas fireplace and private balcony to enjoy the amazing views, and his and her closets. Large family room in the lower level, with a wet bar that leads out to a stone patio. Beautiful pond with lots of wildlife. Private location with over 26 acres and only 15 minutes to Dartmouth.

Listed by Jessica Dolan and Anthony Dolan, Dolan Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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$2,250,000

Est. Mortgage: $/month

MLS Number 4876336

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5
  • 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 6-bedroom, 5-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 Dia Jenks, LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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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244 Happy Valley Road Woodstock VT 05091

Woodstock, VT244 Happy Valley Road

Price$2,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4896882

  • Residential Single Family
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 3,456
  • Construction Existing

This very charming home is located in the historic hamlet of Taftsville. The tree lined driveway leads to a custom designed house built in 2002 by a top local design/ builder team using top quality materials. The lovely open grounds include meadows , fruit trees , fenced paddock, as well as a very large pond . Also there are 5 miles of trails for riding , walking , snowshoeing. The gardens include lovely spaces for entertaining. The finished lower area is complete with bathroom . A great space for family activities. The home is light filled with pastoral views from every window.Price includes all furnishings as well as tractor ,riding mower and many other high end pieces of equipment . This is as "turn key" as it gets right dow to the Waterford wine glasses !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 2022 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 17, 2022.