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+

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604 Delano Road West Windsor VT 05089

West Windsor, VT604 Delano Road

Price$2,070,000

Est. Mortgage: $/month

Pending

MLS Number 4669762

  • Residential Single Family
  • Construction Existing
  • Bathroom 11
  • Bedrooms 6
  • Square Feet 7,352

Country retreat outside of Woodstock perfectly designed for gathering family and friends, with exceptional craftsmanship, open floor plan, stunning panoramic views of Mt. Ascutney and complete privacy. Designed by AIA award winning architect Michael Ertel, the custom 2-story connected stone Cape Farmhouse, c. 1990, offers 7,352 ± sq. ft. of living space with 6 bedrooms. Throughout the house are mural paintings, trompe d'oeil and faux finishes - tortoise shell mantels in the living room, tiger maple paneling in the library, and intricate wood inlay floors using southern pine, maple, walnut and cherry as well as an impressive great hall with fireplaces at each end, big windows facing the view and high ceilings. The AGA stove and fireplace add a coziness to the well-appointed kitchen detailed with painted wood floors with access to a brick porch. The spa has a shower/steam room, exercise room with hand painted murals on the walls, and hot tub with grand views of the mountains. There are 4 bedrooms in the main house, and 2 bedrooms with an additional sleeping alcove in the guest wing. Approached by a private drive through the extensively landscaped 53.21 acres, the property offers the best in private, country living in the heart of the beautiful equestrian countryside.

Listed by T Story Jenks, LandVest, Inc/Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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974 Cemetery Hill Road West Windsor VT 05089

West Windsor, VT974 Cemetery Hill Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4764706

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,884

White Fox Farm's c. 1790 yellow clapboard farmhouse and attached red barn is set just outside the village of Brownsville on a quiet country road where it seems like more horses go by than cars. The 39 acres scale of the farm is manageable with the key Vermont features: a pond, pastures and big views of Mt. Ascutney. The five-bedroom house underwent a major renovation in 2012. The kitchen with its hand hewn beams was enlarged to include a sitting area with views over the field, and outfitted with top-flight appliances for a cook that likes to prepare meals while surrounded by family and friends. Pssst…there is a secret room, believed to be part of the Underground Railway. There are fireplaces in the living room, the two master bedrooms, the birthing room (now used as an office), dining room and paneled family room. The third level is a great place for innovative thoughts (the owner launched a business here) with a two-room study with built in book shelves and a ¾ bath. Throughout the house there is a sense of fine craftsmanship that has stood the test of time in form and function. White Fox Farm is integral to the Green Mountain Horse Association community as the 83-mile marker for the hundred-mile ride.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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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3 Galaxy Hill Road Hartford VT 05059

Hartford, VT3 Galaxy Hill Road, Unit 3

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4730371

  • Residential Single Family
  • Village Quechee
  • Construction Pre-Construction
  • Bathroom 4
  • Bedrooms 4

Dramatic 180 degree views sweep across 2 states, overlooking lake, river, and 2 championship golf courses. The property is located just 15 minutes from 2 interstates making it easily accessible to the culture of the area. The home is architect designed and being sold pre-construction. This will allow you to fine tune the details to fit your own personal needs. Currently designed with 4 bedrooms, there is an unfinished walk-out lower level that can be finished out to be 2 more bedrooms, bath and family room. Come walk the site and picture the excitement of living here.

Listed by Barbara West, Quechee Associates, Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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591 High Pastures Road Pomfret VT 05091

Pomfret, VT591 High Pastures Road

Price$1,990,000

Est. Mortgage: $/month

MLS Number 4665909

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,880

Otis Hill Farm is iconic Vermont! Woods, fields & streams, working barns & fire pond with 3 stall horse barn, pool & pool-house & tennis court. Miles of trails lace woods & fields for walking, riding, cross-country skiing & snowmobiling. Only 2 miles from Woodstock Village, 20 minutes drive from Dartmouth College & 30 minutes from Killington Ski Area. The 200 year-old farmhouse displays the hand-hewed post & beam frame and is sited with expansive windows to view abundant wildlife and an incredible variety of birds The 230+ acres of land has exceptional character with natural meadows, pastures and fields interspersed in forests of northern hardwoods, spruce, hemlock & pine. Active springs supply year round water to brooks running through the property winding down to the Ottauquechee River. Enrolled in Vermont Current Land Use the farm adheres to a Forestry Management Plan to maintain vital, productive & beautiful forests. A two acre apple orchard is sited on plateau above the farmhouse. Abundant gardens with crab apple & cherry trees, raspberries, red & black currents & flowers to enhance your home all summer long. A tranquil close to all area amenities. OFFERED with different land options and prices.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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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296A Town Farm Road Hartland VT 05048

Hartland, VT296A Town Farm Road

Price$1,975,000

Est. Mortgage: $/month

Pending

MLS Number 4764705

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,000

Sky Farm Estate estate consists of 236 acres of well-maintained hay fields, hardwood forests, walking trails, ponds, and a delightful cottage. The property features panoramic mountain views and a wide variety of different vistas that make you feel that you are on top of the world. There is easy passage from Town Farm Hill Road to several private building envelopes with expansive views for your dream home. Convenient access to utilities, high-speed internet, and good water are all close at hand. The estate is enrolled in the State of VT "Current Use" Forestry Plan and supports a wide variety of wildlife. There is a sugar house and over 4,000 tappable sugar maple trees for maple sugar enthusiasts. The .35 acre swimming pond with bathhouse, large open seating deck, rafts, and diving board, awaits your summer recreation activities. The Sky Farm Cottage contains 4 bedrooms and 1.5 baths with open floor concept includes a country kitchen, living room with a wood burning stove and wooden floors throughout. Other features include a stone terrace for outdoor entertaining and a covered front porch that awaits your favorite rocking chair. Sky Farm is just minutes from Woodstock Village for restaurants and shopping. It is near Killington, Suicide Six, and Okemo Mountains for Skiing, GMHA, snowmobiling, hiking, fishing and golf. This breathtakingly beautiful property is an equestrian and sportspersons paradise! Sky Farm is stunning and a rare property with lovely expansive views!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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: 3.49% last updated on Feb 20, 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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694 Goodrich Four Corners Road Norwich VT 05055

MLS Number 4793079

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 6,356

A new house with an old soul: Frog Holler c1800 farmhouse was moved from Enfield, N.H., renovated and expanded. The location is near Hanover and Norwich village, but totally private: 71.5 acres on a hilltop with great views, surrounded by woods and fields at the end of a long driveway. The house is a total surprise: a great mix of period patina, 21st century practicality, and whimsy. Its heart is a large country kitchen and family area opening on to a stone terrace with gardens to the south, and a living room with huge fireplace to the west. A private guest suite, elegant dining room, office and awesome mudroom round out the first floor. Above are four bedrooms including the capacious master suite. Two more whimsical bedrooms are in the attic. It's not obvious from the outside or the inside that there is ample finished space on the lower level: the indestructible, rubber-floored soccer/ping-pong room, gym, workshop, media room and storage area. Attached to the house is a 3-bay garage with more storage space. Surrounding the house are beautiful but unfussy perennial gardens (designed for maximum impact and minimal maintenance), a wildflower meadow, apple, birch, oak and maple trees, and lovely views. The 2+/- miles of trails on the property were designed by John Morton.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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477 Thistle Hill Road Pomfret VT 05053

Pomfret, VT477 Thistle Hill Road

Price$1,775,000

Est. Mortgage: $/month

MLS Number 4791217

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

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

Listed by Derek Cosentino, BHG Masiello Group/Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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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7 Laber Road Bridgewater VT 05035

Bridgewater, VT7 Laber Road

Price$1,699,000

Est. Mortgage: $/month

MLS Number 4788709

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 4,906

Looking for a grand yet refined Vermont home? Look no further than Stonewall Manor! Situated on close to 30 acres in Bridgewater, you'll be pleasantly surprised by the space provided in this home. Arts & Crafts style allows home to grow as you enter, looking quaint & not massive, from the front elevation. 2 elevator shafts & stair chair offers wheelchair accessibility & can accommodate all needs. 2-car garage comfortably fits 3 cars & features man cave, complete with a living area, wood stove, bath & laundry room! Stonewall Manor features 5 living rooms, 7 bathrooms, 3 full kitchens (all complete w/ granite counter tops & Bosch appliances), 3 laundry centers, & secret passages between rooms. Additional option to rent out the two private 2-bedroom apartments! Stonewall Manor was designed to fully integrate w/ surrounding land & take advantage of all the property has to offer. Front of home is stunning in the morning light, while the back is beautiful in the afternoon with the way the sun hits & reflects off the house. 4th story cupola features historic 225 yr old bar end from the original Bridgewater Boarding house, & oversees glorious surrounding views of mountains, w/ peaks over 4,000 ft- including trail map view of Killington! Stunning great room features three story windows that allow for sunlight to pour in & heat the whole house during the colder VT winter months. Exceptional property w/ so much to offer- you need to see it to truly believe all of its features!

Listed by Tucker Adirondack Lange, KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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249 Densmore Hill Road Hartland VT 05048

Hartland, VT249 Densmore Hill Road

Price$1,600,000

Est. Mortgage: $/month

MLS Number 4767801

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

This superbly maintained Vermont Cape residence captures stunning sunsets from a vantage point overlooking westerly river valleys to the peaks of Killington and Shrewsbury. The home is offered fully equipped and furnished for gracious country living. A large multipurpose barn, run-in and fenced pasture reflects the traditional use in 'horse country' with GMHA (Green Mountain Horse Association) trails providing access throughout the surrounding area. A mix of open fields, apple trees and northern hardwoods is defined by old stone walls. A spring fed pond is a year round source of water for a variety of wildlife thriving in the sparsely populated community. Ideal situation for those seeking the peace and quiet of rural New England.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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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1285 Union Village Road Norwich VT 05055

Norwich, VT1285 Union Village Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 4789110

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,618

Exceptional, elegant, beautifully restored and energy efficient, this 4 bedroom, 4 bathroom home is picture perfect. With privacy ensured (you own land on both sides of the road), the 117+/-ac include trails, 2 ponds, pastures, woods, 2 barns and views to the White Mountains of NH. A super new kitchen adjoins the fireplaced living room, providing a wonderful area for the family to gather and chat. Fabulous wood floors gleam in every room. A separate family room makes a good TV watching space, or quiet retreat, and there is also an office and a more formal dining room. The 2nd floor has 4 bedrooms and 2 bathrooms and the 3rd floor would make a superb home office, but is currently guest space. Just a 15 minute drive from downtown Norwich.

Listed by Jane Darrach, Martha E. Diebold/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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97 & 99 Darling Road Woodstock VT 05071

Woodstock, VT97 & 99 Darling Road

Price$1,575,000

Est. Mortgage: $/month

MLS Number 4767586

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,749

High Riding's 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson's (NYC Mayor Fiorello LaGuardia's “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible. The “Studio” at 97 Darling Road, a 2,384 square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio. The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a swimming pond. There are over 800 sugar maples- tapped for maple syrup, apple trees, well maintained pastures, forest, private riding and hiking trails and a 3-stall stable.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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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 February 26, 2020.