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.

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.

5250 West Woodstock Road Woodstock VT 05091

Woodstock, VT5250 West Woodstock Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4918791

  • Residential Single Family
  • Square Feet 4,502
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing

The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes' drive of the Killington and Okemo ski resorts, respectively. Known locally as the Robinson Farm, after the family that build the handsome home and legendary barn shortly after the turn of the 20th Century. The property has been converted by the present owners into a gracious and authentic rural farm environment for vacations, weddings, and other events large and small. The historic 1905 Farmhouse Inn offers accommodation in the 7 Guest Rooms, all with private baths and gracious gathering rooms on the first floor. A 2-bedroom Innkeeper's quarters provides private living space. The Red Barn was constructed in the style of a 'bank barn' with grade level entry points to the different levels of the barn where they served a variety of agricultural purposes. The massive timber frame is exposed on all levels with the upper two having been adapted for the event venue hosting up to 150 guests. The White Barn accommodates 50 guests for smaller ceremonies and other events with a wide deck providing a place of seasonal outdoor dining. 13 acres of open land and convenient location offer the potential to create a farm-to-table restaurant, direct-to-consumer shop selling local and regional goods or an immersive Agri-tourism guest experience. Less hospitality-oriented uses as a gentleman's farm or niche farm producing or marketing local goods are great options as well.

Listed by Rachel Arsenault and Laird Bradley of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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88 Davenport Lane Hartford VT 05059

Hartford, VT88 Davenport Lane

Price$659,000

Est. Mortgage: $/month

MLS Number 4917130

  • Residential Single Family
  • Village Quechee
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Bright, sunny, four bedroom four bath Contemporary Quechee Lakes house built in 2006. Enjoy the brand new oak hardwood floors on the second level, with cherry floors on the first floor. This house is easily accessible and very easy to maintain. Primary bedroom with en suite bath on the first floor, so it can easily accommodate one floor living if needed. Upstairs you will find another bedroom with en suite bath, as well as two other bedrooms serviced by a second full bath. Enjoy the sitting area or use it as an office or hangout. On the main level, the propane gas fireplace is lovely to enjoy in all seasons! Main level complimented by wraparound deck. Embrace all the space for gathering and visits from family and friends! The basement has plenty of storage to either fully finish off, or for storage and extra toys. Off of the basement you can step out onto a screened in porch and still soak in the views and fresh air. Plenty of space to spread out, and a great layout for a primary home owner, or a second home to vacation in!

Listed by Audrey Micca of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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1157 West Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4916726

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,760
  • Construction Existing

Gorgeous fully restored farmhouse with modern amenities and original charm! This sunny and pristine four-bedroom home is conveniently situated in west Woodstock village - just a short drive from Killington, Hanover, and DHMC and within the desirable Windsor Central School District. Comprehensively and meticulously renovated in 2017 from roof to basement, this property boasts all new electrical and plumbing, high-quality polyethylene foam insulation, a new standing seam roof and all new appliances, fixtures, and flooring throughout. Turn-key, convenient, and low maintenance, this home is ideal for primary homebuyers, vacation enthusiasts, and investment shoppers alike. From the soapstone countertops and the exposed beams to the spacious deck and easy-keeping yard, you'll find something to enjoy in every season. Offering flexible upstairs spaces and expansion opportunities, the layout gracefully accommodates both intimate gatherings and larger crowds. With luxe farmhouse design influences and an unbeatably convenient location, this property is a rarity in the Woodstock marketplace! Showings begin 6/28/2022. No showings shall be held 7/1/2022-7/4/2022.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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2864 Camp Brook Road Bethel VT 05032

Bethel, VT2864 Camp Brook Road

Price$275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4916567

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,500
  • Bathroom 1
  • Bedrooms 3

Exceptionally well-maintained 3BR home on 3.6 acres, offering privacy, a sunny southern exposure and winter views. The house includes a large kitchen with newer appliances, open to a comfortable living area with handsome yellow pine floors, natural wood trim and plenty of sunlight. A full walkout basement with 1-car garage provides ample storage space for all your tools and toys. This home would be great for year round living or for a private vacation getaway.

Listed by Seth Barbiero of Bean Group / Vermont

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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7 Sylvan Walk Grantham NH 03753

Grantham, NH7 Sylvan Walk

Price$1,700,000

Est. Mortgage: $/month

MLS Number 4916417

  • Residential Single Family
  • Village Eastman
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Waterfront Home in Eastman!! This impressive 4-bedroom, 3.5-bath contemporary home is a beautifully designed masterpiece! Enter into this Post and Beam home and immediately be captivated by the floor-to-ceiling window display, 2-story double-sided stone fireplace and a gorgeous view of the sparkling lake. Explore many richly detailed rooms with soaring ceilings - each designed for views of the lake. The wide yellow pine floors and warm wood beam accents enhance the setting of this contemporary home. With 3 levels of living space, it boasts a 1st floor primary suite, a hot tub on the deck, an expansive 3-season porch, a lower level walkout, guest quarters, a steam room and large bathrooms throughout. Plenty of space to entertain as well as relax and unwind with family and friends. Nestled back from the road with wooded privacy, this is an ideal location for a vacation home or primary residence in the Dartmouth/Lake Sunapee region. The four-season community of Eastman offers lake activities, championship golf, groomed cross-country ski trails, walking trails, tennis, an indoor pool and exercise facility and more!

Listed by Carol Shepherd of C.G. Shepherd Realty,LLC

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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1064 Route 25A Orford NH 03777

Orford, NH1064 Route 25A

Price$279,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4916416

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,512
  • Bedrooms 3
  • Bathroom 1

Situated amongst clear rolling hills, yet tucked within private wooded acres is 1064 Route 25A in Orford, otherwise known as 1064 Governor Meldrim Thomson Scenic Highway. This 1992 cape boasts an open concept floor plan with a bedroom on the first floor, the full bathroom, and a wood stove. Upstairs find two additional bedrooms, one with a large attached flex space, perfect for a home office or oversized closet. Outside you can relax by your beautiful fire pit, or appreciate the mature landscape of the front yard. The front yard's view is open to the walking trails in the back of the property where the current owner currently enjoys games of disk golf or leisurely walks through the wooded trails. The exterior also features two large outbuildings, and a custom-built firewood shelf that's easily accessible during the chilly New Hampshire winters. Live where people dream to vacation, this property really is a retreat! Private showings begin immediately!

Listed by Amanda Carlson of Bean Group / Portsmouth

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 Boulder Trail Enfield NH 03748

Enfield, NH17 Boulder Trail

Price$499,000

Est. Mortgage: $/month

MLS Number 4914679

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,128

201 FT SHARED WATERFRONT on pristine Crystal Lake! Enjoy 1.32 acres, boat slip available, picnic area, canoe/kayak/paddleboard rack and swim raft. Jump in your golf cart and zip down to the waterfront and have a great day on the lake boating, kayaking, swimming, taking in the sun and watching the spectacular sunsets! It's like a vacation every day! The 3 bedroom, 3 bathroom property with oversized 2-bay garage, sits on 1.3 private, wooded acres. Gather in the spacious eat-in kitchen or enjoy the separate dining area. The large windows allow for the natural sunlight to fill the entire home making it light, bright, and airy. Upstairs you will find 2 bedrooms, a full bathroom with double vanity, a bonus room, and the primary bedroom with a 3/4 bathroom with a large walk-in closet. Don't miss this rare opportunity to part of Crystal Lake Estates. Conveniently located 20 mins to the Upper Valley, 1 hr to Concord, 2 hrs Boston.

Listed by Tracy Nangeroni of Harbor Light Realty

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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436 Bradley Hill Road Benton NH 03785

Benton, NH436 Bradley Hill Road

Price$329,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4912116

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 1,440
  • Bedrooms 2

You'll fall in love with this vintage custom designed log home located in Benton NH. a town surrounded by thousands of acres of National Forest and a view of the Kinsman Range & Mt. Lafayette make this a unique find. Some of the town amenities are: The Black Mountain Trails, Tunnel Stream Trails, Blueberry Mountain Trails to hike or just leisurely explore. Long Pond for kayaking & canoeing and to enjoy the wildlife in peaceful and tranquil setting. Also, within 30 minutes to Loon Mt. & Cannon Mt. ski slopes. The 2BR1.5BA home has been a vacation home for the present owners for thirty years and all the custom details have remained. Hardwood floors, custom stone chimney with hearth, sleeping loft with built ins, finished family room with built in bar and custom log window sills . New roof on the house and garage in late 2021, chimney repointed and capped late 2021, new hot water tank, new deck, new retaining wall and steps. The property is comprised of 5 lots which are merged into one and are not in current use. A new survey completed in May 2022 shows 13.93+/-AC. The town of Benton has 11.5+/- AC on the tax card. The town planning board is in the process of correcting the town map to reflect the 13.93AC.This is a great opportunity to escape to the mountains. The home comes furnished except for personal items! Delayed showings begin Monday, May 30th.

Listed by Charles Crannell of Badger Peabody & Smith Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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1 Border Lane Woodstock VT 05091

Woodstock, VT1 Border Lane

Price$599,000

Est. Mortgage: $/month

MLS Number 4912025

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Square Feet 1,368
  • Bedrooms 3

A highly desirable Woodstock location! Conveniently situated only a few minutes from the Woodstock Village Green, in a lush pastoral setting, is a bright 3 bedroom home. The land component of the property is truly high quality, with ample lawn area for entertaining or recreation, pleasant meadow views and a sunny exposure. All the convenience of single level living is provided in this home of a manageable size! A well conceived floor plan features a large living room/dining area with a fireplace and a dramatic bow window, a kitchen with an area for breakfast dining, a well designed sunroom, 3 bedrooms with wood flooring and 1.5 baths. The sunny back patio presents a private sitting area with tranquil views of a large meadow. The interior of the home feels comfortable and well built. The land is idyllic! Neighboring homes are substantial. All of these attributes combine to offer a property that is equally appealing as a manageable vacation home or a comfortable year round residence!

Listed by John Wetmore of William Raveis Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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187 Hartland Hill Road Hartland VT 05091

Hartland, VT187 Hartland Hill Road

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4911601

  • Residential Single Family
  • Square Feet 3,191
  • Bathroom 3
  • Construction Existing
  • Bedrooms 3

Privately situated on a knoll overlooking verdant lawns, gardens and pasture with a long-range westerly view, just minutes to the Woodstock Village Green, this bright, open concept contemporary cape home features a floor plan ideal for entertaining, and daily living. The spacious kitchen with custom maple and cherry built-ins opens to the Dining Room and steps out to a 3-season screened porch. Living room is anchored by a sweeping stone fireplace, oversized windows and doors to maximize the lovely view. First floor primary BR and laundry. Lots of potential for a home office. Plenty of room for expansion with a spacious bonus room, and spotless basement. The efficient, 3-stall 36'x24' barn with heated tack room and auto-waterer is surrounded by established, fenced pasture and a round pen. Ride out onto dirt roads and beautiful trails. Central AC, full power generator. Close to skiing and GMHA. Ideal as primary residence, or vacation home. Property available for showings beginning Tuesday, May 31.

Listed by Danny Kogut and Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 2022 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. 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 July 7, 2022.