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+

2358 Long Hill Road Woodstock VT 05071

Woodstock, VT2358 Long Hill Road

Price$5,500,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4,165

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 foot Old Baldy Mountain with 360-degree views and a small private cabin at the summit. Landscape design by Shep Butler includes an orchard of 110 productive apple trees with varieties such as Macoun, Empire, Cortland, Spartan and Macintosh.

Listed by T Story Jenks, LandVest, Inc/Woodstock

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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1403 Quechee West Hartford Road Hartford VT 05059

MLS Number 4784050

  • Residential Single Family
  • Village Quechee
  • Construction Existing
  • Bathroom 9
  • Bedrooms 7

Halfway between the storied Village of Woodstock, Vermont and the Ivy League halls of Dartmouth College in nearby Hanover, NH and minutes to every possible recreational amenity in Quechee, Stonehill Farm offers an extraordinary equestrian facility on almost 200 acres of open pastures, mixed northern hardwood forests and miles of interior roads and trails to explore. The main house, with its dramatic stone exterior and soaring two story library, was designed by noted New York architect Alan Wanzenberg whose overall approach is often informed by his deep appreciation for the Arts & Crafts and other related movements. Additionally, Stonehill is strongly influenced by the Tudor style and architectural traditions of the Cotswolds as well as Edwin Lutyens sensibilities. Set high along the top of a south facing ridge, the Vermont countryside unfolds at your feet with commanding views across the Ottaquechee Valley. Copious fenestration on the south walls takes full advantage of the direct southern exposure. Employing old world craftsmanship, this incomparable stone and cedar home features the finest quality materials and decorative finishes throughout. The approximately 9,000 square foot, 15-room residence is an elegant and timeless design in richly textured stone, expansive glass, and mahogany details. The main house offers seven bedrooms, nine baths, a recently remodeled gourmet kitchen, formal living and dining rooms, and a 3,200 bottle wine cellar.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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1095 Eastman Road Sharon VT 05065

Sharon, VT1095 Eastman Road

Price$3,745,000

Est. Mortgage: $/month

MLS Number 4756993

  • Residential Single Family
  • Construction Existing
  • Bathroom 10
  • Bedrooms 8
  • Square Feet 9,587

EASTAWAY ESTATE - The breathtaking Eastaway Estate sits on 128 acres tucked away on a mountainside at the end of a gated private drive. The elegant main residence and guest house are perched at an elevation of 1,400 feet overlooking the Green Mountains, creating the ultimate country escape. The sophisticated contemporary homes offer the highest quality materials including mahogany ceilings and marble floors. The floor-to-ceiling windows and inviting exterior decks and terraces provide full views of the majestic professionally landscaped surroundings. An extensive trail network winds throughout the rolling, wooded property for walking, snowmobiling, cross country skiing and more. The two homes offer over 9,000 square feet of luxurious living space, including 8 bedrooms, 10 bathrooms, 7 fireplaces, 2 wine cellars, a tasting room and garages for 8 cars. There are 2 outdoor spas, 3 ponds, 2 saunas, and a beautiful in-ground pool. Enjoy sunsets from the mountain top gazebo which offers 360 degree views. This is one of the finest estate properties available in Vermont and provides true privacy while still conveniently located within a 25 minute drive to both Hanover, NH and Woodstock, VT. The interior of both homes was professionally designed and the property is being offered fully furnished.

Listed by Zoe Hathorn Washburn, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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4777 Rush Meadow Road West Windsor VT 05089

West Windsor, VT4777 Rush Meadow Road

Price$3,650,000

Est. Mortgage: $/month

MLS Number 4726033

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 5,899

Sheep Run Farm in West Windsor, is named for the stone walled lanes where Ira Taylor, a prosperous mid-19th century farmer, herded sheep from the barn to the upper meadows. Today, a newly reimagined 2017 4-bedroom plus loft (6-bedroom septic), 6.5 bath farmhouse fits seamlessly into the classic Vermont scenery, just 3 miles to the South Woodstock store, and 8 miles to Woodstock Village. Classic on the outside, hip on the inside, the farmhouse's 1st floor has an open floor plan, with large windows and high ceilings, abundant light and views from every window. Connected buildings include a 2-bay garage, carriage house party barn, wood room and yoga studio. A huge glass door of the three-season carriage barn opens to the stone terrace, while a massive stone fireplace and soaring ceilings make this a remarkable gathering spot for family and friends, and the second floor boasts a comfortable guest suite. EC fiber provides high speed access for this smart-home to control; lights, climate, video, security, and property access via apps from anywhere in the world. The property encompasses all the right elements; the exceptionally beautiful 21+ acres, including views of rolling meadows, Rush Meadow Valley and Mount Ascutney; endless stone walls; apple trees; a cascading brook and two ponds.

Listed by Christopher Lang and Dia Jenks, LandVest, Inc/Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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3429 Cloudland Road Pomfret VT 05067

Pomfret, VT3429 Cloudland Road

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4779987

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5,134

"SLEEPY HOLLOW FARM" - One of the most iconic properties in Vermont - Sleepy Hollow Farm is located on desirable Cloudland Road, just 10 minutes from Woodstock village. The incredibly picturesque, pastoral land component comprises 115 acres of fields, gardens, woods, trails, and two ponds. The property is conserved both in the Vermont Current Use program and by the Vermont Land Trust. Next to the large second pond is a small cabin complete with bunk beds and a wood stove - perfect when you want to go “off-grid” and camp out on your own property. The original farmhouse c. 1790 - has been updated and expanded and now connects via a radiant-heated brick passageway to a newer, fabulous barn complete with 6 horse stalls, tack room, and a large finished wood-paneled recreation room upstairs. Two other large barns with workshops and garages and for storage- are nearby. The property comes with an array of motorized vehicles and equipment including a tractor, UTV and ATVs w wheels and tracks, two dirt bike motorcycles and a diesel-powered snowcat groomer. The property also includes a separate historic 1-room schoolhouse up on Cloudland Road, that was converted into a 1 bedroom apartment perfect for guests, kids or caretakers, with some of the best views in the area - and looks down over the Sleepy Hollow Farm itself.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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37 Brothers Road Hartland VT 05048

Hartland, VT37 Brothers Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4629754

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,800

Offering some of the most beautifully managed and meticulously maintained acreage available in Windsor County, Hartland Highlands offers over 279 acres of high, rolling meadows, mixed northern hardwoods forests, four ponds, three brooks, miles of interior roads and trails and multiple developable future house sites in addition to the mid-19th century Cape and barn complex currently in place. Views from the property extend from Smarts Mountain in Lyme, NH through dramatic near range vistas of Mount Ascutney to the south. Professionally managed by the premier Upper Valley land enhancement company for more than two decades, the quality of the acreage is unsurpassed. The main house is surrounded by copious perennial gardens, antique stonewalls, grandfather maples and sweeping lawns. Multiple barns and outbuildings provide storage space for every conceivable outdoor pursuit. A true legacy property in a location less than 25 minutes from the heart of the Upper Valley, Hanover and Dartmouth College.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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1055 Sayer Road Barnard VT 05031

Barnard, VT1055 Sayer Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4687009

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 8,264

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance to Woodstock, Vermont and Hanover New Hampshire. Circa 1995 6500 sq.ft. residence with attached three-car garage and spectacular three-story, six stall post and beam barn. An additional 2000 sq.ft. in the walk-out basement finished into a media room and large conference/office area with a wet bar and full bath. 252+/- acres of conserved and managed forest and pastures with miles of maintained riding trails. The residence was five years in the building by a local builder renowned for his quality and attention to detail. Furniture-quality woodwork throughout this four-bedroom, six-bath residence with complete butler/guest apartment wing.

Listed by Stan Butler, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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1532 Happy Valley Road Woodstock VT 05091

Woodstock, VT1532 Happy Valley Road

Price$2,895,000

Est. Mortgage: $/month

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This contemporary cape with classic Vermont lines is built on the history and character of two fully reconstructed antique post & beam frames. Architect designed, premier builder, and unquestionably one of the nicest homes in Woodstock. It has a newer cedar shake roof and has been completely re-sided with beautiful cedar shingles in 2019. There is beautiful interior space, newly created guest quarters, four working fireplaces, high-end master bathroom finishes, and 55.76 acres of playground. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas stove, a large double door Sub-Zero refrigerator, and even space for a kitchen herb garden. The look and feel is classic Vermont charm with all the modern conveniences of the 21st century. Five (5) bedrooms, four (4) bathrooms, and over 6,000 sq-ft of living space finished to an exacting level of detail. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. The grounds have a duck pond, ancient stone walls, mature maple trees, a four car garage, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Happy Valley Road is on the exclusive easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat.

Listed by John Bassette, Bassette Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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3147 Mt. Hunger Road Barnard VT 05031

Barnard, VT3147 Mt. Hunger Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4755552

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 4,531

"HONEY HILL FARM” - located in desirable Barnard, Vermont, has been in the same family for more than 30 years, with both land and residence meticulously and lovingly maintained throughout the family's stewardship of the property. Situated on 264.4 surveyed acres, the land component is comprised of open pastures and conserved and managed woodlands with miles of trails for walking, x-c skiing and snowshoeing, biking or other outdoor pleasures. The property has beautiful long-range mountain views, a deep swimming pond, perennial gardens, and a lovely mountain brook that courses through the property, plus a wonderful and totally private swimming pool in the center rear of the residence with access from the living room and the kitchen. A nearby barn - a portion of which was once utilized as a caretakers apartment - provides storage for motorized toys and vehicles. The residence itself is a classic Vermont farmhouse design with slate roofs, three fireplaces, covered porches and an attached guest apartment above the attached three-car garage. The living room, which has exceptional woodwork, can easily accommodate large parties for entertaining. Five bedrooms, four baths, and three half-baths in total. House boasts excellent mechanicals, backup generator, security systems, underground wires, and more. High speed internet is available via EC Fiber. 18 mins to Woodstock, 10 mins to I-89, and 30-45 minutes to a private airport and skiing at numerous major Vermont ski resorts.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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$2,499,000

Est. Mortgage: $/month

MLS Number 4731571

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 5,242

Fabulous 11 room home in a super-private location in Norwich. Built by a master builder in 2007 with superb attention to detail and with 54.5+/-ac of open meadows, woods, trails, stone walls and views. Gorgeous outbuilding, presently a barn, could be a guest house or office. Picture perfect lush meadows. The home is spacious without being huge. Fantastic Great Room, beautiful wood floors, 4 bedrooms, 3.5 baths, year round screened porch, delightful patio. Easy access to the vibrant town of Hanover, NH (home of Dartmouth college). A rare opportunity!

Listed by Jane Darrach, Martha E. Diebold/Hanover

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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$2,450,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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6310 Bryant Road Hartland VT 05091

Hartland, VT6310 Bryant Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 4693928

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,900

"HUBBARD FARM” - Fully renovated, classic, historic hilltop farm property on +/- 130 acres with long-range mountain views of Killington, a swimming pond, tennis court, open meadows and a 3-mile private trail network - much of which is enrolled in the Vermont Current Use Program. The recently and beautifully fully renovated residence has hip, contemporary styling, a large gourmet kitchen, two den/family rooms, a private dining room, expansive wrap around porch oriented to take in the view, downstairs recreation room, 5 fireplaces, radiant heat throughout, MBR with bath and steam shower, and other fully renovated bedrooms and baths. Russound speaker sound system throughout the 1st floor & porch. Large breezeway leads to the huge historic post-and-beam barn that presently serves as a garage. Located approximately 7 minutes from the village green in Woodstock, Vermont - with end of road privacy - this property has access only from Woodstock, a South Woodstock mailing address and emergency services, but is legally located in the town of Hartland. Truly a special property and residence with all the features most desirable in a Vermont getaway, relocation or retirement home.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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 2019 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 November 12, 2019.