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!

353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 10
  • Square Feet 11,470

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang, LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 8,921

High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • Square Feet 6,799

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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290 Hanover Center Road Hanover NH 03755

Hanover, NH290 Hanover Center Road

Price$6,875,000

Est. Mortgage: $/month

MLS Number 4917483

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 11,881

Greystone is one of the region's finest examples of American Shingle Style architecture and one of only a handful of truly world-class homes in Hanover, New Hampshire. Conveniently located within 15 minutes of Dartmouth College and only six miles to downtown Hanover, the property takes full advantage of the privacy and panoramic southerly views afforded by the finely landscaped 13-acre parcel. Established gardens, extensive stonework, and beautiful outdoor spaces distinguish the design. Employing natural wood finishes, generous porches, and asymmetrical structural features to integrate with the natural surroundings, it takes advantage of light, views, and breezes. The multiple levels of the home feature a dramatic central stairwell that culminates in a rooftop observation deck. The five bedrooms, four full and two half baths as well as a perfectly executed guest suite and bunk room combine with both formal and informal gathering spaces that include a magnificent great room, handsomely appointed home offices, a home theater, family rooms, and a workshop. The roughly 12,000+/- square feet of interiors executed at the highest level of fit and finish always feels as inviting and as intimate as the Inglenook that connects the dining area to the main foyer. A covered breezeway attaches the main house to an oversize, three-car studio/garage with a finished heated second floor with a barrel-vaulted ceiling, a full bath, and currently, a large in-home gym.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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
  • Square Feet 5,142
  • Bedrooms 6
  • Construction Existing
  • Bathroom 8

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: 6.42% last updated on Mar 23, 2023
* 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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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 15
  • Square Feet 10,206

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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298 Holiday Farm Road Bridgewater VT 05035

Bridgewater, VT298 Holiday Farm Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4929847

  • Residential Single Family
  • Square Feet 3,757
  • Bathroom 4
  • Construction Existing
  • Bedrooms 5

The legacy property of OQ Farm (formerly known as the Holiday Farm) has been adapted several times throughout its historical past, most recently as a 481-acre short-term hospitality and retreat destination with an arts and spiritual focus. Featuring 8 different dwelling structures, OQ Farm offers a diverse range of accommodation options, from 1800s historic, a luxurious lodge retreat center, to sleek and modern eco-cottages, converted maple sugar shack, a studio cabin and caretaker's cabin, all taking advantage of unique views of the river valley and mountain range beyond. Boasting 1,200+ feet of river frontage along the North Branch and Ottauquechee Rivers, which flows into the Connecticut River; OQ Farm is situated equidistant between the Appalachian Trail and ski slopes of Killington and the quaint town of Woodstock - renowned as one of America's most beautiful towns. Several fenced pastures and barns provide for agricultural use beyond the sheep, alpacas, poultry and horses present currently. An extensive network of mountain biking, hiking and snowshoeing trails, and a large bonfire pit offer endless outdoor recreation and gathering opportunities.

Listed by Rachel Arsenault and Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4925674

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,040

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. See property specific website.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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25 Rope Ferry Road Hanover NH 03755

Hanover, NH25 Rope Ferry Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4941966

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5,625

Like a time-honored book, this beloved 1900s home meets every purpose and fancy - a classic among the preeminent properties of Rope Ferry Road. All eleven rooms have a distinctive quality, inviting both formal and informal living. The dining room, kitchen, and patio provide space for entertaining. The breakfast nook, central living room, and porch serve as places for resting. The 3-bay garage, office, and studio offer privacy for working. Set a grand table and entertain guests for dinner or kick back and engage friends to a barbeque under the covered porch. With ample tree coverage and notable privacy despite being centered in the heart of the neighborhood, this outdoor porch and patio are the hub of the home, expanding the liveable space into the outdoors during the spring, summer, and fall. The primary bedroom on the second floor is a retreat unto itself, with natural light, a central fireplace, and spacious closet. Flanking both ends of the house are rooms that can be transformed into potential guest suites, a studio, or office space. A jaunt into the Pine Park Trail system is accessible from the front door, with miles of trails for use. The mudroom wood stove will dry your shoes and warm your toes after a cold winter outing. Located in the heart of Hanover, enjoy an easy walk to the Dartmouth campus and downtown for dining and fun. Replete with versatility, utility, and charm this wonderfully traditional home meets modern day needs. Live, work, rest, play, and entertain!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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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60 Goodwin Road Enfield NH 03748

Enfield, NH60 Goodwin Road

Price$3,349,000

Est. Mortgage: $/month

MLS Number 4937980

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 6,882
  • Bathroom 6

Located on the coveted eastern shore of pristine 1100 acre Mascoma Lake - this stunning Contemporary invites glistening water and big sky views into warm welcoming living spaces. Custom designed and built new in 2001 by Old Hampshire Designs, the main level features living, dining and relaxing spaces that easily transition to outdoor decks, terraces and a sweeping waterfront lawn. First floor primary suite with spa bath and private office. Large bedroom, second office and home gym up. The lower level features a family room with fireplace, pub, home theater, wine cellar and two en-suite bedrooms. Step outside to a waterfront porch that runs the length of the house providing options for entertaining or curling up with a good book. Relax in the outdoor hot tub after a day on the water or the slopes. Attached four car garage. This property includes a second waterfront lot currently featuring a large heated barn/workshop and garden shed. Options available for building a guest house or even selling separately. This magical location is 10 short minutes to the Hanover Village and Dartmouth College or DHMC Medical Center. Minutes to local skiing at Whaleback. Several world-class ski options within an hour including Stowe and Killington. Enjoy a robust waterfront lifestyle in every season!

Listed by Pamela Perkins, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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
  • Construction Existing
  • Square Feet 7,619
  • Bedrooms 6
  • Bathroom 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: 6.42% last updated on Mar 23, 2023
* 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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5 Gates Road Hanover NH 03750

Hanover, NH5 Gates Road

Price$3,199,900

Est. Mortgage: $/month

MLS Number 4942656

  • Residential Single Family
  • Village Etna
  • Bedrooms 8
  • Square Feet 14,073
  • Construction Existing

Designed and constructed with the highest standards, no attention to detail spared, commercial mechanicals and electrical set the tone for this stunning opportunity. The kitchen is adorned with Wolf Range and warming drawers, two Sub-Zero refrigerators, floor to ceiling cabinetry, and a hand laid mosaic marble floor. The open concept kitchen/dining creates an entertaining space for large gatherings with access to the outdoor decks. Two bedrooms with mountain views serve as a private enclave for the owners suite and complete with outdoor space. The lower level presents opportunities for an indoor pool, hot tub, spa, fitness facility, and an unrivaled entertainment experience in this one-of-a-kind home. This once imagined dream is ripe for the next owner to create a multi-generational compound. Please join us on SUNDAY, MARCH 5TH from 10-1 for a PUBLIC OPEN HOUSE!

Listed by Marco Day and Lochrane Gary, BHHS Verani Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 23, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 April 1, 2023 3:08 AM EDT