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Upper Valley Real Estate $5M & Over

Scroll down to find current luxury homes for sale throughout the Upper Valley. Find a variety of high-end listings in New Hampshire and Vermont, all at $5M or over. Contact us if you are interested in touring one of the listings below or have questions.

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1959 Cox District, Woodstock, VT 05091

Price$9,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4429915

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 6
  • Area Valley
  • Stories 1

A modern architectural masterpiece and important work by award winning and internationally recognized architect Rick Joy, Woodstock Farm presents a dramatic shingle and stone house and barn set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close proximity to Dartmouth College in Hanover, New Hampshire. The high concept contemporary design is executed with the sharpest attention to craft and draws on the vernacular of the rural northeast. The main residence offers a 152-foot elongated gable house with massive end walls of Lake Champlain bedrock and cedar cladding on the roof and side walls. Set at a subtle angle to the barn, the north facade of the main house engages the purity of the setting and looks out onto a large, deep, spring fed swimming pond and the rolling pastureland, hills and mixed northern hardwood forests that comprise the property.

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

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2358 Long Hill Road, Woodstock, VT 05071

Price$6,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 4
  • Area Rural
  • Stories 2

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.

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

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

21 Havelok Hill, Strafford, VT 05072

Price$4,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4511337

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 3
  • Area Mountain, Rural
  • Stories 1.5

Havelok Hill is a world-class and unique property combining luxury and privacy for a discriminating buyer. Located in the equestrian countryside of Strafford, Vermont, the estate consists of 600 acres of rolling terrain including 400 acres of mixed northern woodlands, 200 acres of upland meadows, secluded ponds and eight miles of improved interior roads and riding trails. At the end of a mile-long, immaculately landscaped driveway, the house sits at the height of land, elevation nearly 1900 feet. To the east one sees the lengthy spine of the White Mountains of New Hampshire, while to the west lie the tops of the Green Mountains of Vermont, with continuous views, Killington to the southwest, and past Mt. Mansfield (Stowe) in the north. The views are incomparable. The owners have spared no expense in designing a residence of the highest quality and taste, centered about a magnificent wood-paneled great room measuring 30 by 50 feet, with a 24-foot vaulted ceiling and a massive fieldstone fireplace. The property also includes a four-bedroom guest or caretaker's cottage--built in the 1860s and renovated in 1989--and a barn with three stalls and equipment storage space. Historic Woodstock, Vermont, and Hanover, New Hampshire--home of Dartmouth College--are both only 40 minutes away. At an equal distance is the world-renowned Dartmouth-Hitchcock Medical Center in Lebanon, New Hampshire.

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

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

387 Benedict Road, Woodstock, VT 05071

Price$4,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4609989

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 8
  • Stories 2
  • New Construction Existing

"SUNNYSIDE" is one of the most perfectly designed and constructed brick Georgian Revival residences in New England - located on a prestigious South Woodstock hilltop on 82.5 acres, with beautiful panoramic views of the surrounding hills and offering absolute privacy. Construction was completed in 2002, with unparalleled attention to detail. And the property has been meticulously manicured and maintained. The 7,000 square foot main residence combines a formal elegance with a beautiful Vermont hilltop setting. The residence features four fireplaces, expansive living and dining rooms, a butternut paneled library, den, continuous flow swimming pool, three-story elevator and a large, beautifully appointed gourmet kitchen with adjoining pantry. The master bedroom with fireplace features two dressing rooms and two bathrooms. Three other guest bedrooms are elegantly appointed with en suite baths. Nearby is a guest house with it's own dining and living rooms, and two bedrooms. The property also includes a walk-in 3-bay garage attached to the main residence, and a nearby 4-bay detached garage for your other motorized toys. The pastoral setting, woodlands with over one mile of carriage-width trails, and beautifully landscaped and manicured land component affords this property a distinctive pedigree. Located near the Village of Woodstock in an area of other substantial properties.

Listed by John Snyder and David Donegan of Snyder Donegan REG

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1055 Sayer, Barnard, VT 05031

Price$4,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4609102

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Stories 2
  • New Construction Existing

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance from Woodstock and Hanover, New Hampshire. Circa 1998 6800 square foot main residence with three-car attached garage and spectacular post and beam six-stall barn. 396 acres of managed pasture and forest with 13 miles of riding trails, one of which terminates at a hilltop picnic area with a magnificent 360 view a short half-mile ride from the barn. A 2400 square foot caretaker residence with an attached two-car garage and a beautiful seven-stall post and beam barn occupies a hilltop across the road from the main residence. Two ponds complete this perfect setting. The main 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 main residence with complete butler's apartment wing. A walkout basement level finished into a large media room and corporate size office/conference room with wet bar and full bath.

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

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

336 Stone Bridge Way, Woodstock, VT 05091

Price$3,975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4513290

  • Multifamily Multi-Family
  • Units 2
  • Acreage 22.5
  • Square Feet 9024

Magnificent South Woodstock family compound! The estate is composed of a main residence, substantial guest home and 22.5 acres with long views. The Adirondack style main residence is constructed to the highest standard, by one of Woodstock's premier builders. A well conceived floor plan presents both generously sized common gathering areas as well as quieter private spaces. Family members, of multiple generations, are comfortably accommodated. Large bedroom suites, on 2 levels, can provide adult guests with privacy. All the expected amenities! On the lower level is the truly extraordinary private bar/entertainment area, a large 40x12 exercise room, a hot tub room, with shower, and a workshop, with space for all the motorized toys! The detached 9 room, 3 bedroom guest house is private and substantial. A beloved family compound! well sited, on 20 acres of land, at the end of a private lane, with long views of distant mountains.

Listed by John Wetmore of William Raveis Woodstock

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

336 Stone Bridge Way, Woodstock, VT 05091

Price$3,975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4509981

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 6
  • Area Rural
  • Stories 2

Magnificent South Woodstock family compound! The estate is composed of a main residence, substantial guest home and 22.5 acres with long views. The Adirondack style main residence is constructed to the highest standard, by one of Woodstock's premier builders. A well conceived floor plan presents both generously sized common gathering areas as well as quieter private spaces. Family members, of multiple generations, are comfortably accommodated. Large bedroom suites, on 2 levels, can provide adult guests with privacy. All the expected amenities! On the lower level is the truly extraordinary private bar/entertainment area, a large 40x12 exercise room, a hot tub room, with shower, and a workshop, with space for all the motorized toys! The detached 9 room, 3 bedroom guest house is private and substantial. A beloved family compound! well sited, on 20 acres of land, at the end of a private lane, with long views of distant mountains.

Listed by John Wetmore of William Raveis Woodstock

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

630 Morgan Hill Rd, Woodstock, VT 05191

Price$3,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4484291

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 6
  • Stories 3
  • New Construction Existing

Glenmorgan is an iconic early 19th century turn-key estate with a 5-bedroom 1835 Brick Federal residence, 2-bedroom carriage house, antique bank barn, 3 car garage, cottage and 1 acre swimming pond on 75 acres located in a premier area in South Woodstock surrounded by major estates. The elegant residence is warm and inviting in a distinguished Vermont vernacular, with great light and flow. The carriage house is set up beautifully for guests or party space: the great room is centered on a stone fireplace next to a country kitchen, with a 2nd floor bunk room. The classic bank barn 1st level opens to a pastoral view of the pond and gardens, perfect for larger gatherings, studio or working barn. MacKenzie Hall, a tiny charming pondside cottage with a bedroom, sitting room and wood stove is perfect for a summer nap or a peaceful writing. Located in the heart of the GMHA trail network, walking distance to the South Woodstock Store, and 6 miles to Woodstock.

Listed by T Story Jenks of LandVest, Inc/Woodstock

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

164 Hewitt Lane, Woodstock, VT 05091

Price$3,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4607265

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 8
  • Stories 1.5
  • New Construction Existing

A sophisticated country family retreat, Havenwood combines close-to-the-village location with end of the road privacy on 119.6+/- acres. Impeccably renovated and intelligently planned, the main house feels intimate yet expands to fit a crowd. The central open kitchen/family area is centered around a big fireplace with ample separation for a quiet study. Other gathering spaces include a beautiful screen porch and multiple outdoor terraces to enjoy the gorgeous landscape. The lower level has a fun game room as perfect recreation space that opens on to a stone terrace, and a sophisticated temperature controlled wine room. The gracious master suite is on the ground level, with 4 additional bedrooms on the second floor. The guest house-barn has a sophisticated rustic feel with finished Chestnut paneling and includes a private office space, gym and one-bedroom guest quarters, light meal prep kitchen, and lovely views from the porch. There is a lot to do outside: batting cage, basketball ½ court, in-ground trampoline, hilltop camp site, trails that goes for miles, and a swimming pond.

Listed by T Story Jenks of LandVest, Inc/Woodstock

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

535 Peace Mountain Way, Woodstock, VT 05091

Price$3,275,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4602562

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 6
  • Stories 3
  • New Construction Existing

The Peace Mountain Ranch (the “Ranch”) is a private estate with breathtaking views of the Ottauquechee River Valley. Custom built in 2008, the Ranch is a spectacular Arts & Crafts shingle style home situated on 183 acres with scenic trails for hiking, snowmobiling, mountain biking and cross country skiing for year round recreation. The Peace Mountain Ranch is designed for gracious living and offers total peace and tranquility. The property is located at the end of a paved private road engineered for New England's rugged weather. Spacious gathering rooms open out to a wide veranda surrounding 3 sides of the home with a beautiful stone fireplace and grilling area for 3 season use. The property includes five river stone fireplaces as well as a wood-fired pizza oven in the kitchen to enjoy in winter evenings. The property was designed for an active family and extended family and includes a climate controlled hardwood basketball court, rock climbing wall with spectacular views and an expansive storage area for outdoor recreation equipment. The property is convenient to the Killington Ski area, Dartmouth College and is located four miles from the Woodstock Village. The Peace Mountain Ranch is an exceptional property and is ideal for a residence, corporate retreat or family compound with multiple building sites served by underground utilities.

Listed by Laird Bradley of Williamson Group Sotheby`s Intl. Realty

On the Green
P.O. Box 1
Lyme NH, 03768
Office: 603-795-4816

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.17% last updated on 2017-02-09

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 2017 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.