Upper Valley Homes with a Guest House

Upper Valley Home with a Guest HouseBrowse homes for sale with a guest house in the Upper Valley area. Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. Register to save your favorite listings and get email notifications when similar properties become available.

Houses for Sale with Guest House in NH & VT

Homes for sale in the Upper Valley region of Vermont and New Hampshire featuring guest houses offer added versatility for accommodating visitors or creating additional living space. With separate quarters, these properties provide privacy and flexibility for hosting guests or utilizing the space for personal needs such as a home office or studio. 

1490 Beaver Meadow Road Norwich VT 05055

Norwich, VT1490 Beaver Meadow Road

Price$1,450,000

Est. Mortgage: $/month

Pending

MLS Number 4987219

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4,196

Extremely high quality home in private location on 5.6+/- ac in Norwich. Exquisitely renovated with an open floor plan, the fabulous kitchen with Thermador appliances, granite counters and attractive lighting is designed to allow you to entertain groups of all sizes. An outstanding master suite features luxurious ensuite baths and an adjoining room for relaxation, exercise or office. The lower level, with private entrances to each of its comfortable bedrooms, has abundant natural light, a very pretty sitting room and a wine cellar. A total of three screened porches -- one on each level; beautiful cherry millwork; gorgeous landscaping. Add to that an adorable guest house or rental with 1100 sq ft of space on one level, with one bedroom, one bath, sweet kitchen with cherry cabinets, radiant heated flooring and remarkable light. Garage space for 4 cars. A truly great one!

Listed by Jane Darrach of Martha E. Diebold/Hanover

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$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

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$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

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$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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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30 Fairground Road Springfield VT 05156

Springfield, VT30 Fairground Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4975706

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,400

Surrounded by Ascutney Mountain to the north, Monadnock Mountain to the east and Stratton Mountain to the south in beautiful Windsor County Vermont is an amazing property named the Estate of North Mowing. Winding through the granite pillar entrance you will find expansive views of hay fields and the Connecticut River Valley. Steeped in history you will find approximately nine buildings including the updated main house. This property has been used as a family compound and an event destination for weddings and other venues. The stone walls and stairs that lead you through the gardens originally designed by Ellen Biddle Shipman, designer of the Saint-Gaudens National Historic site. Pausing at the top of the stairs of the garden and looking around, the views are just breathtaking. Inside the main home you will find five generous bedrooms with five full baths. Kitchen nicely updated looks north to spectacular views of Mount Ascutney. Tranquility is the main theme here with a stone patio and reflection pool for entertaining. Across the courtyard is a small barn that has a fireplace and gathering space, also a larger barn for equipment, snowmobiles and cars. Across the walkway are a few other buildings, one that is a great one bedroom guest house and another that was once a mapping room is now a workout room. There are trails on property for hiking, ATV or snowmobiling. 230 plus acres and more options on this beautiful retreat that is only hours drive from both NY and MA.

Listed by Bob Maisey of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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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72 Frenchs Road Woodstock VT 05091

Woodstock, VT72 Frenchs Road

Price$1,895,000

Est. Mortgage: $/month

MLS Number 4968402

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4

Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the stately living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a large center room with an elegant fireplace. In addition to the main house, there is a detached garage with a 2 bedroom apartment and a 2 bedroom cottage which includes a living room with fireplace, dining room, kitchen and bath. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away.

Listed by Dan Noble of Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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 Croydon Brook Road Newport NH 03773

Newport, NH2 Croydon Brook Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4965445

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 7,465

Set on over 100 acres of protective field and forest land is one of New Hampshire's most elegant and historic estates remodeled in the late 1800's by Austin Corbin, a dynamic self-made millionaire who was known as the "Father of the Banking Industry" and founder of the nearby 25,000 acre Corbin Park hunting preserve and Blue Mountain Forest. Offering views of Mt. Sunapee and distant hills, flanked by the Sugar River and accessed by a covered bridge, the hilltop residence offers exquisite living space including a 51 foot great room gallery with gilded ceiling, exotic walnut and mahogany detailing and massive fireplace hearth, ornate mahogany bar with curved gilded paper ceiling, elegant paneled reception hall with fireplace and sitting room, modern kitchen with wet-bar pantry, large master suite with delightful sleeping porch, recently installed elevator, central air conditioning and three-car attached garage. Property also includes four bedroom guest house, to be sold subject to life tenancy agreement to caretaker. Several additional outbuildings include gentlemen's library, heated workshop and a wonderful 40 x 45 barn/guest house with vehicle storage. Showings by appointment only-Proof of funds required. A magnificent personal domain!

Listed by Andrew Peterson and George Quackenbos of Four Seasons Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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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36 Pony Hill Lane Lyme NH 03768-3706

Lyme, NH36 Pony Hill Lane

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4944611

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,392

A "woods' house" high in the hills of Lyme, surrounded by trees and meadow, in the area known as "Hardscrabble", this custom-built post and beam structure (Outback Post and Beam) would be a great home for a small family, artist, writer, or anyone seeking a beautiful, peaceful spot surrounded by nature. Trout Brook runs across the land, and there are views East and West of surrounding hills. The interior is open, with a tall window-wall facing the woods, much custom carpentry, and offers a relaxed lifestyle. Some finish work remains to be done. Property also includes a detached studio/guest cabin, small 1-car garage/barn, work shed, concrete slab intended for a shop-barn which was never built (24'x50' + 20'x20'), porch, patio and deck. A 3rd floor loft area could be used for sleeping quarters or quiet spot. Water currently supplied by long-serving dug well, but a drilled well is available. This property is a gem, and, needs to be seen to be appreciated. NOTES: 1. A purchase would be contingent on resolution of an ongoing boundary line dispute. 2. This property has been enrolled in Current Use, but the recently completed survey shows less acreage than necessary to be eligible for CU, so that status will need to be addressed. 2. The property is accessed by an "old road", which also provides a non-exclusive ROW access (the only) to the property behind, but not stated in sellers' deed--this will be addressed prior to closing.

Listed by William Johnson of Big Green Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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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5518 Vt Route 12 Barnard VT 05031

Barnard, VT5518 Vt Route 12

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4882340

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 7,619

An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events at Dartmouth College are well under an hour away! The spacious 1st floor consists of a state-of-the-art commercial kitchen, to please any gourmet chef, elegant formal dining rooms and for casual entertaining a tavern complete with bar. Upstairs you'll find a designer kitchen with ample cooking, eating & lounging spaces, 5 bedrooms & cozy reading nooks. A beautifully framed detached barn presents, on a lower level, a newly renovated yoga studio and guest suite with radiant floor heat! A large great room is above, for entertaining or studio space. These compelling structures are nestled on a well maintained 10 acres which include expansive lawns, gardens, and lush meadow paths leading to a secluded pond with a gazebo. Nearby the pond additional property value is provided by existence of a site for an additional 2 bedroom residence, with certified septic. A significant residence complimented by an extraordinary detached auxiliary building, with well conceived grounds! An opportunity to create a home base that could be long enjoyed by every generation of the family! Genuine Vermont appeal!

Listed by John Wetmore of William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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 April 24, 2024 7:24 AM EDT