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Upper Valley Real Estate $2M-$5M

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 between $2M-$3M. Contact us if you are interested in touring one of the listings below or have questions.

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21 Havelok Hill Road, 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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
  • 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 Real Estate Group

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: 4.03% last updated on 2017-04-27

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
  • 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 degree 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: 4.03% last updated on 2017-04-27

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

20 Rope Ferry, Hanover, NH 03755

Price$3,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4634420

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

Approached down Hanover's most desirable road, this eye-catching executive estate is framed by beloved Occom Pond, mature trees, a circular drive, gardens and greenery. Combining timeless formal and informal living spaces, the house boasts walls of glass overlooking the gardens and light dancing on the water in a perfect pondscape. The home offers luxurious amenities, including hardwood floors, top-of-the-line appliances, hardwire communications, radiant heat, central air conditioning, high-efficiency windows, security system, multiple zones for climate control, and attached Conservatory. Given the desirable location and proximity to the College, the Property benefits from a continuous patrol, essentially a private security detail paid for by the College. Throughout the Rope Ferry Estate a feeling of rejuvenation pervades, from the warm and inviting formal foyer to artfully configured transition spaces whose contours are delimited by their natural uses more than by interior walls. Custom craftsmanship throughout the house make every inch look like a work of art. The warm wood is accentuated by a neutral color scheme executed with an emphasis on natural materials. Formal gardens and walled terraces create a virtual oasis of privacy and comfort at the Rope Ferry Estate. Lofty deciduous and evergreen trees and sculpted formal garden beds brimming with vivid flowers outline the house and the property's expansive perimeter.

Listed by Celina Barton and John Bertolami of Big Green Real Estate

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: 4.03% last updated on 2017-04-27

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

36 Brothers Road, Hartland, VT 05048

Price$3,985,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4629754

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Area Rural
  • Stories 1.5

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, guest house 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 and one bedroom guest house are 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 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: 4.03% last updated on 2017-04-27

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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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
  • 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: 4.03% last updated on 2017-04-27

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
  • 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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
  • 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 Sothebys Intl. 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: 4.03% last updated on 2017-04-27

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.