Upper Valley Vacation Homes

Vacation Home in the Upper ValleyScroll down to discover the latest vacation homes for sale in the Upper Valley of Vermont and New Hampshire. Look through hundreds of listings to find your new home. To receive updates on this listing or your other favorite homes, you can sign up for our website.

Vacation homes in the Upper Valley region of New Hampshire and Vermont offer an ideal escape from everyday life. These homes are typically situated on sprawling green acres, providing ample outdoor space for activities like fishing, boating, skiing and hiking. Inside, vacation homes feature open floor plans, upgraded fixtures, energy efficient heating/cooling systems and top-of-the-line appliances. Homes often come with modern amenities such as spacious decks for outdoor living or large barns perfect for hobbies or livestock. With plenty of room to entertain family and friends both indoors and outdoors, these homes provide a cozy getaway that can be enjoyed all year round.

Upper Valley Vacation Homes for Sale

Contact Martha Diebold Real Estate if you are interested in touring one of the currently listed Upper Valley homes below or any other property.

1050 Goose Pond Road Canaan NH 03741

Canaan, NH1050 Goose Pond Road

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4968546

  • Residential Single Family
  • Bedrooms 1
  • Construction Existing
  • Square Feet 576
  • Bathroom 1

The Upper Valley's best kept secret, Goose Pond. This cute cottage peers through the trees to the waters edge will be your favorite getaway. A simple design with tons of potential. Use this property as rental income, a ADU while you build your forever home, or an easy vacation spot, this lot has a ton of potential. The waterfront lot is leased from the state every year for a minimal fee. Enjoy watching the sunset from your dock at Goose Pond.

Listed by Colby Clarkson of Roger Clarkson Realtor

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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40 Troon Drive Grantham NH 03753

Grantham, NH40 Troon Drive

Price$385,000

Est. Mortgage: $/month

Pending

MLS Number 4968508

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,588
  • Bathroom 3

Inquire immediately and lock this home up now with no risk! Discover the perfect blend of comfort and nature in this stunning single-family residence nestled in the picturesque Eastman Community. Surrounded by lush greenery and a tranquil wooded lot, this home is an idyllic retreat. You will have a full slate of options in your new home! Noteworthy residence or vacation home. Your primary bedroom on the first or second floor. Option of a guest suite or teenager chill space in the walk-out basement. Fresh air on the deck, the covered patio or at the fire pit. Home office in the loft or the lower level. The options are plentiful! Step inside and be greeted by the warm ambiance and efficient layout that seamlessly connects the inside with the outside on multiple levels to enhance relaxation or your plans to entertain family and friends. The 2-car garage provides parking and storage options for all of your recreation gear. Be sure to ask about the wonderful recreational feature just steps away from your new backdoor! Experience year-round recreation opportunities, from hiking, golf, swimming, boating and skiing on site, to exploring nearby lakes and cultural events. Schedule your showing today and move in for the fall foliage season! The Sellers are planning to move closer to family and have prioritized a seamless sales experience over getting every last penny. Showings start with the public unveiling on Saturday September 9th from 10:30 - 2:30, by appointment only!

Listed by Steven St. Pierre of KW Coastal and Lakes & Mountains Realty/Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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2127 E Woodstock Road Woodstock VT 05091

Woodstock, VT2127 E Woodstock Road

Price$479,000

Est. Mortgage: $/month

Pending

MLS Number 4967184

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Square Feet 1,757
  • Bathroom 2

Discover the essence of Vermont living in this exquisite 2-bedroom, 2-bath home, with spacious bonus room w/bath; from its rustic charm to modern elegance, this property seamlessly combines natural beauty with contemporary comfort. Seeking a vacation retreat with STR income? This is it! Renovated kitchen with hard marble countertops and gleaming, energy-efficient appliances. The living room boasts wood floors & exposed beams, including classic Vermont charm with built in shelves. The bedrooms on the first level are designed for comfort and convenience, offering walk-in closets & direct access to the deck creating a seamless flow between the indoor & outdoor living with views overlooking the Ottauquechee River. The lower level offers a bonus room w/adjoining bath & rec room - complete with walkout to amble level yard offering space for various recreational activities, making it an ideal spot for both relaxation and entertainment. The home is thoughtfully designed with energy-efficient improvements. These upgrades not only contribute to eco-friendliness but cost savings. Only 5 minutes away from downtown Woodstock, under 10 minutes to Quechee Gorge, you'll enjoy convenience without sacrificing tranquility. Embrace all seasons - 30 minutes to Killington Resort & minutes to Saskadena Six Ski Area. Whether it's snowy winter days or warm summer nights, this home is your gateway to the best Vermont has to offer. Home Warranty Included.

Listed by Isabella Luhrs of BHG Masiello Keene

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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70 Troon Drive Grantham NH 03753

Grantham, NH70 Troon Drive

Price$499,000

Est. Mortgage: $/month

Pending

MLS Number 4966648

  • Residential Single Family
  • Square Feet 2,526
  • Bathroom 3
  • Construction Existing
  • Bedrooms 4

Privately located near the end of the road, yet super convenient to the main Entrance to Eastman and within walking distance to the golf course and the lake is a quick 10 min walk. The Eastman Brook runs along the back of the property. This home has been beautifully updated with great kitchen with granite counters and stainless appliances. The cathedral living room is wonderfully spacious and features a wood burning fireplace. The enclosed porch/sunroom is just a great space to enjoy a cup of coffee while listening to the babbling brook and there is a spacious deck as well. The primary bedroom suite is incredibly spacious with a beautiful update bath and two walk-in closets. There is another bath and first floor bedroom. The lower level opens to the family/rec room with a wood stove to enjoy those cold winter nights. There are two more bedrooms along with a full bath and a full walk-out to the deck and patio. There is a private back yard area as well. Come enjoy all that Eastman has to offer! Great as a full time home or vacation getaway. Offers due by 5p Monday, 8/28/23.

Listed by Linda Rosenthall of Rosenthall Realty Group LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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167 Church Street Bethel VT 05032

Bethel, VT167 Church Street

Price$445,000

Est. Mortgage: $/month

Pending

MLS Number 4964711

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 5
  • Square Feet 3,260

167 Church Street is two beautiful homes in one, providing many possibilities for full-time home owners, renters or vacationers. It's conveniently located in the Village of Bethel, walking distance from the famous Babes Bar, Cockadoodle Pizza, hiking trails, excellent bike routes, 30 minutes from Pico and Killington ski areas, Dartmouth, and 6 miles from Vermont Law School, S. Royalton, as well as Randolph. Both main house and carriage house have been renovated and restored beyond their former glory. A row of arborvitae trees creates private front garden and the back garden is a quiet space overlooking the river. The main kitchen features reclaimed soapstone counters and a wide-planked birch floor built from a massive tree cut from the property. Morning sun warms the side glassed in porch and sunset lights up the front glassed in porch. The main house has a spacious living room, formal dining, as well as a cozy den with wood stove. All bedrooms are spacious with ample closet space and light. Impressive, best describes the renovations and care taken in the quality improvements throughout this Victorian village home. The "carriage house" is now a spacious two bedroom rental unit.

Listed by Dean Goulet of Dunrovin Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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443 Alden Partridge Road Hartford VT 05059

MLS Number 4964404

  • Condo
  • Bedrooms 3
  • New Contruction Existing
  • Square Feet 1,806
  • Complex The Ridge

Enjoy cool breezes and cool views high above the Ottauquechee River Valley in this spacious condo at The Ridge in Quechee, featuring 3 bedrooms, 3 bathrooms plus an exercise/bonus room. Being offered partially furnished: living room & dining room furniture stay as well as 1 queen bed and 3 dressers. The unit is differentiated by its updated kitchen and a rare finished-out storage room below the unit. The Ridge is an exclusive community of just 28 condominium units, built on a granite ridge high above the Lakeland golf course and Lake Pinneo, with its own private swimming pool. In contrast to most other areas within Quechee Lakes, The Ridge requires a minimum of 1 month for vacation rentals, contributing to its stable and neighborly atmosphere. Ridge owners automatically become members of The Quechee Club, with its outstanding four-season amenities (golf, skiing, racquet sports, fitness, dining, etc).

Listed by Chris Crowe of Quechee Lakes Real Estate Center

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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299 Moose Run Groton VT 05046

Groton, VT299 Moose Run

Price$495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4963787

  • Residential Single Family
  • Square Feet 1,957
  • Bathroom 2
  • Bedrooms 2
  • Construction Existing

Looking for your own private oasis with breathtaking mountain views? Look no further than this charming 2 bedroom, 2 bathroom home with a 2 car attached garage located on approximately 50 acres of pristine land. Recently remodeled bathrooms boast handcrafted beams, while the interior features an open-concept design with natural wood floors in the upstairs bedroom and plenty of natural light throughout. The impressive farmer's porch is the perfect place to watch sunsets, and the large pole bard offers ample storage for all your needs. This property has only had one owner and has been lovingly maintained since it was built in 2003. Located just 25 minutes from Barre and 21 minutes from Woodsville, this home offers the perfect balance of privacy and seclusion while still being close enough to all the amenities of town. Whether you're looking for a full-time residence or a vacation home, this property is the perfect place to call your own. Don't miss your chance to own this incredible property - schedule a showing today! **Delayed showings until Open House on Saturday 8/5/23 from 10a - 11:30a** Please no drivebys - home is on private road.

Listed by Samantha Catterall of KW Coastal and Lakes & Mountains Realty/Laconia

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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2409 South Road Woodstock VT 05091

Woodstock, VT2409 South Road

Price$1,125,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4961738

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Bathroom 3
  • Square Feet 3,218

This splendid 1920 Vermont Farmhouse with Post and Beam Great Room and detached barn with a 1-bedroom guest apartment is sited beautifully on 2.74 acres that are detailed with a pond and frontage on the Kedron Brook . The main level design of the original farmhouse has been intelligently updated with the addition of a spacious open concept kitchen with vaulted ceilings and exposed beams that is accented with a cozy breakfast nook and the original walk-in pantry that flow into the fabulous Post and Beam Great Room which opens onto a deck with a lovely view of the pond. There is a separate dining room with a gas fireplace for more intimate dining. A primary ensuite bedroom. living room/study, half bath and mudroom entry complete the main level design. The second level offers 3 additional bedrooms, a full bath and office. The delightful 1 bedroom/1 bath guest apartment with separate laundry overlooks the pond and brook. A wonderful opportunity for a fabulous family vacation compound or a primary residence with rental income producing apartment. Private but convenient location within minutes of the four-season recreation, arts, theatre, and dining that make Woodstock, Vermont living so desirable! Showings begin on Wednesday July 19.

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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588 Kendall Road Woodstock VT 05091

Woodstock, VT588 Kendall Road

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4956721

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 2,904
  • Bedrooms 5

While relaxing on the gracious front porch of this classic New England home the mesmerizing sound of the nearby cascading brook can transport your cares away! Located in equestrian oriented South Woodstock, this home presents generous interior space to entertain the friends and family who will surely come to enjoy all that Woodstock offers. The principal rooms feel large and welcoming. Yet, throughout the house private areas are easily found. As is typical in traditional New England homes, there are well placed windows and beautiful wood flooring. Upon entering the home this striking flooring is immediately displayed, in a practical entry room, which opens to a bright recently remodeled tastefully updated kitchen. Adjacent to the kitchen is a pantry and a 3/4 bath. A large double living room provides comfortable gathering spaces, with a fireplace in 1 room and windows viewing out to a large front porch in the other. A primary bedroom, with adjacent dressing room completes the 1st floor. On the 2nd floor are 4 well placed bedrooms, all with beautiful wood floors. Adjacent to a full bath is a den/sitting room. Well separated, at the opposite end from the bedrooms, is an office area with space for 3 workstations. Conveniently, this workspace has interior stairs leading directly down to the kitchen. Both the desirable South Woodstock location and the spacious interior floor plan make this home equally suited to be a convenient year round residence or a wonderful vacation retreat!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 2023 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 September 28, 2023 10:40 AM EDT