Upper Valley Real Estate $2M-$5M

Upper Valley Luxury Homes for SaleScroll down to find current luxury homes for sale throughout the Upper Valley. Find a variety of high-end listings in New Hampshire and Vermont. Contact Martha Diebold Real Estate or give us a call at 603.795.4816 if you are interested in touring one of the listings below or have questions.

Upper Valley Luxury Homes for Sale from $2M to $5M 

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253 Main Street Norwich VT 05055

Norwich, VT253 Main Street

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4995497

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,357

Welcome to 253 Main Street, where the past meets the present in perfect harmony in the heart of Norwich, VT. Steeped in history and charm, this iconic brick Federal residence is a testament to timeless elegance and modern comfort. First of the three brick houses on Main St, the oldest part of the house was originally built in 1780, and it serves today as the rear wing; the distinguished brick facade was crafted in 1821. With 11 total rooms, 4 bedrooms and 4.5 baths, the house offers ample space for comfortable living. Meticulously renovated by its current owner, the property seamlessly blends historic charm with carefully curated modern amenities, including a chef's kitchen, updated bathrooms, a luxurious primary ensuite bath, AC, and smart-home features. Embracing sustainability, the home features an owned solar power system with a battery backup. Step outside to enjoy the landscaped gardens, serene blue stone patio and fire pit, or admire the classic front stone wall - a perfect balance of tradition and contemporary living. Located in Norwich, a town known for its rich heritage, vibrant community, and top-rated schools, this property offers a lifestyle of unparalleled charm and convenience. Explore the delights of the Upper Valley, from scenic landscapes to bustling local establishments like Dan and Whit's General Store, where you'll find everything you need and more. Don't miss your chance to be the next steward of this piece of history combined with modern luxury.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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68 Stevens Street Enfield NH 03748

Enfield, NH68 Stevens Street

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4995020

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,809

Perched gracefully on the shores of Mascoma Lake, this exquisite and unique property offers a serene 3.26-acre private oasis with a sweeping 280 feet of direct waterfront. This meticulously updated home invites relaxation and enjoyment, whether gathering around a cozy fire at the water's edge or soaking in spectacular sunsets from the roof deck overlooking the lake. The house itself is a testament to superior craftsmanship and architectural thoughtfulness, featuring gorgeous oak flooring that adds warmth and elegance throughout. The kitchen is a chef's dream, equipped with high-end Wolf appliances and granite countertops that meld functionality with luxury. Outdoor living is elevated to an art form here, with amenities that include a charming greenhouse, an invigorating outdoor shower, and a relaxing hot tub, all designed to enhance your connection with nature. The handcrafted wood and wrought iron staircase is a centerpiece and an art piece, exemplifying the bespoke detail evident in every corner of the home. Perfect for hosting and entertaining, the house includes three bedrooms and three bathrooms. The primary suite is a retreat within a retreat, with its beautifully tiled floors in the calming colors of the ocean and a large, walk-in tiled shower that promises a spa-like experience. The first-floor suite allows for comfortable living at every stage of life. This property was recently fully transformed with love and care, designed for life's finest moments.

Listed by Lori Shipulski and Tracy Nangeroni of BHHS Verani Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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$3,500,000

Est. Mortgage: $/month

MLS Number 4994787

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,184

Hartland Highlands is a singular Vermont agrarian paradise. The property's 277 pastoral acres, improved on over two decades of meticulous stewardship and management, feature rolling meadows, mixed northern hardwood forests, four ponds, three brooks, and miles of interior roads and trails. Conveniently located between Hanover, NH, and Woodstock, VT, this is one of the largest parcels of land currently available in the Upper Connecticut River Valley. The historic, expanded cape on the western side of Brothers Road is bounded by perennial gardens, antique stonewalls, heritage maples, and sweeping lawns. Built circa 1850, the house retains its original pine floors and exposed hand-hewn beams and enjoys an elevated, sunny position above the pastures. Views from the property extend to Smarts Mountain in the north and dramatic vistas of Mount Ascutney to the south. The heart of the home is an inviting, open eat-in kitchen that flows into the living and dining rooms. There is a spacious formal living room with a wood burning fireplace as well as a three-season glass and screened-in porch, and first-floor laundry and half-bathroom. Upstairs is a large primary suite with attached bath and two additional bedrooms served by a bath off the wide hallway and landing. Across Brothers Road to the east lies a significant barn complex offering a variety of purposes. This idyllic refuge offers a myriad of possibilities as the potential exists for the development of additional house sites.

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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739 Westerdale Road Woodstock VT 05091

Woodstock, VT739 Westerdale Road

Price$2,695,000

Est. Mortgage: $/month

MLS Number 4993252

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,017

Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mountain views and 10+ acres of privacy. The present owners have completed over $1 million in documented renovations in the past three years, including a fabulous new gourmet kitchen, powder bath, new bamboo flooring throughout the open floorplan kitchen-dining-living area. They added a wood burning fireplace in the living room behind which was added a new, spacious screened porch that overlooks and listens to the sounds of the babbling brook below. The primary bedroom suite (with ensuite office) on the first floor received a bathroom renovation and a stack laundry washer and dryer. The lower level was renovated into a large recreation hangout room with bar, stone fireplace with a propane wood stove, pool table area, TV area, a full bath, a new full laundry area and a workout room, and added A/C throughout. In addition to the attached 3-car garage, they built a brand-new detached barn-garage with commercial overhead doors and room for ALL your motorized vehicles, toys, outdoor gear, workshop tools (or any other purpose you have in mind). 1st-rate mechanicals: Viesmann propane boiler system, automatic backup generator, radiant/radiator/mini-split heat and A/C on all levels and all bedrooms. Both the attached 3-bay garage and the detached barn-garage are insulated and heated. SEE FULL PROPERTY WEBSITE.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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327 Fletcher Schoolhouse Road Woodstock VT 05071

MLS Number 4993127

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,939

ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations of the main house, an additional 825 feet were added on for the kitchen and an extension to the upstairs bedroom suite. Vernacular character: Hand-plastered walls reflect the Vermont light, hand-planed boards, hand-hewed beams and a dining room mural by the Hudson River painter, Kevin Paulsen. Comfortable living, beautifully done. Attached to the farmhouse are two parking bays and a bank barn. On the lower level of the post and beam barn is a large gym or studio space. A picnic area on the top of the knoll has views of the rounded hills and the Kedron Valley-- a landscape that has not changed much over the last 200 years. New geothermal system, solar array and a hook-up for an electric car. The main dwelling has whole house A/C. EC fiber high speed internet. 0.2 miles from Kedron Valley Inn/Ransom Tavern and South Woodstock Country Store and less than a mile from GMHA, the oldest horse club in the country. 26m from Killington and 40m from Okemo. 2h 19m from Boston. Showings begin May 10th.

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

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$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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2 & 4 River Road Hanover NH 03755

Hanover, NH2 & 4 River Road

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4992579

  • Land
  • Acreage 12.3
  • Utilities None
  • PricePerSqFt 203252.03
  • Water View

Amazing opportunity to build your dream home on the Connecticut River. 12.3 acres, comprised of three lots, that stretch along the river bank. The property includes a charming island that is home to many birds, you'll often see a pair of eagles that love to watch the river from their perch high above the water. Rolling fields, with two high points and a path leading to a beach with easy access for boating, swimming or paddle boarding. On the southern crest two Adirondack chairs provide the perfect spot to watch the river and work out which river view you want to wake up to. Imagine the possibilities!

Listed by Rowan Carroll of Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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496 Shaker Boulevard Enfield NH 03748

Enfield, NH496 Shaker Boulevard

Price$2,195,000

Est. Mortgage: $/month

MLS Number 4992409

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 2
  • Square Feet 2,060

The Lake House on Mascoma - Situated on one of the best parcels Mascoma Lake has to offer, this stunning 6 bedroom, 2 bathroom home offers the ultimate lake living experience. It has been fully renovated, with updated heating and air conditioning systems, electrical, plumbing, roof, windows, stunning stone hearth with a propane fireplace and more, yet it retains the comfortable, easy-going feel of a classic lake house. Beautiful landscaping frames over 110' of lake frontage, a private sandy beach, boat launch, large lawn, and views for miles - this property is a dream for lake-living enthusiasts. 20 minutes from Dartmouth College, Dartmouth Health, Colby-Sawyer College, Kimball Union Academy and Cardigan Mountain School. Less than 2 hours to Boston. Delayed showings start Saturday 4/27/24.

Listed by Zoe Hathorn Washburn of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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 4986511

  • 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. Excellent equestrian / horse potential with historic 5-stall barn and fencing for pastures/paddocks already in place. 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 FULL PROPERTY WEBSITE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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17 Wheeler House Drive Orford NH 03777

Orford, NH17 Wheeler House Drive

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4986387

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 6,074

ROGERS HOUSE- One of the seven iconic Ridge Houses that sit prominently facing west in Orford Village, this home has undergone two years of meticulous renovation and restoration under the eye of premium builders G.R. Porter & Sons. The result is a grand, sophisticated home with new systems and endless style and grace. There is ample space for gatherings with family and friends and other private areas throughout the interiors. The kitchen faces east for morning light and is anchored by a premium Aga stove with a custom copper hood, all of which opens to a cozy sitting room with raised fireplace and built-ins. A gorgeous butler's pantry nearby highlights original craftsmanship and woodwork, while the front of the house features formal living and dining rooms and a separate custom library office rounds out the floor. Updated fixtures perfectly complement the period details to seamlessly blend original charm with modern amenities. Three staircases provide access to the second floor with a split landing grand staircase that's a masterpiece of design and engineering. There are seven spacious bedrooms with new bathroom and en suite options to host guests. Additionally, the carriage house offers a lovely and private two-bedroom dwelling. The exteriors are well-landscaped with beautiful, mature trees, shrubs, and an idyllic gazebo anchoring the height of the back lawn. Truly a historic gem, the quality of finish and attention to detail of Rogers House is without parallel.

Listed by David Donegan of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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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10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$2,395,000

Est. Mortgage: $/month

MLS Number 4985985

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,214

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* 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 2024 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 May 20, 2024 1:37 AM EDT