Upper Valley Vermont Homes with Virtual Tours

Scroll down to browse all homes in the Upper Valley of Vermont that feature virtual tours. Select the "Virtual Tour" button below a listing to view the tour. Please note that some listings may have virtual tours coming soon! 

Upper Valley VT Homes for Sale with Virtual Tours

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View all Upper Valley VT listings by town here.

2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 8,921

High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4923048

  • Residential Single Family
  • Bedrooms 5
  • Square Feet 6,799
  • Construction Existing
  • Bathroom 6

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Bathroom 8
  • Construction Existing
  • Square Feet 5,142
  • Bedrooms 6

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$3,425,000

Est. Mortgage: $/month

MLS Number 4951694

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,403

Designed in 1976 by AIA award-winning architect Lewis Davis, of the New York firm Davis Brody Bond, whose work ranged from modernist skyscrapers to the renovation of the Reading Room at the New York Public Library, High Birch's sleek white design is striking amid Vermont's green hills. Davis believed in the power of architecture to enrich life, and that ethos is evident in every aspect of this property. The drive winds through rolling meadows to elevated views: a serene sanctuary, only 2.5 miles from Woodstock village. The curving design captures the abundance of natural light flooding through the tall windows, illuminating the interior and framing the green of mountains and meadows. The multi-level design sets up intimate spaces for gathering and retreating: reading, reflection, or taking in nature. In winter, everyone can gather around the fireplace. In summer, the stone terrace is the venue for outdoor entertaining. Recent renovations by Studio Nexus brought the kitchen (a Deane design), living room, bathrooms, and offices into the 21st century, while honoring Lewis Davis' intent. The interior designer, Eric Roseff, added his sense of whimsy and delight. Raycroft Meyer Landscape Architects' designs for the outdoor spaces: perennials, a vegetable garden, and berries, complement the home's aesthetic. A pond near the house is a favorite spot for kids and dogs to swim. There is a two car attached garage, storage barn, and high speed internet. Fully furnished, move in ready.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4966761

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 6,443

Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding Vermont countryside. The two bedroom guest cottage has its own garage and entrance off of Ebbin Lockwood Way. The 6,048 s/f main house and 1,584 s/f guest cottage were designed by architect, Michael Weinberger. The property was recently renovated: main house was upgraded and many new system improvements. From the stone terrace, there are views of a cascading waterfall flowing into a small Koi pond and perennial gardens. On the Northeast side, an outside sitting area takes in views of a long, rolling meadow with a pond and a glimpse of the local hills. The main house includes a detached garage with additional storage space. Less than 1/2 mile from South Woodstock Country Store and Kedron Valley Inn/Ransom Tavern and one mile from Green Mountain Horse Association. 25 min. from Mt. Ascutney mountain biking trails, 38 min. from Killington and 2:23 hrs. from Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$2,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4932341

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,456

This extraordinary 115 acre property, located in the towns of Woodstock & Hartland, offers the perfect mosaic of qualities that buyers are looking for. The acreage is unencumbered and presents the perfect opportunity for a family estate, future development or equestrian opportunities with grass covered hillsides, trail systems and the GMHA just 3 miles away. The diverse topography of the property with trails throughout has an easily accessible summit offering a unique homesite location with spectacular unobstructed panoramic long range views that can be captured from sunrise to sunset. For the winter sports enthusiast, you have it all right here. The extensive trail systems can be combined for snowmobiles, nordic or alpine skiing. The level of stewardship is evident from the maintenance of the extensive trail systems, existing structures and grounds to the main pond that is deep and well stocked. The structures include a very comfortable two story cottage with long vista views, a large barn/garage, two stall horse barn with run-in and a split rail fenced area. There is also a three sided oversize pole barn currently being used for equipment storage located at the end of one of the trails. The property is accessed off a municipal road via (3) gated entry points. A gazebo at the summit takes in nearly 360 degree long range views providing the idyllic setting for a substantial residence. The properties captivating views and trailed woodlands stand ready to implant your vision.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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5518 Vermont Route 12 Barnard VT 05031

Barnard, VT5518 Vermont Route 12

Price$2,875,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$2,444,000

Est. Mortgage: $/month

MLS Number 4945641

  • 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.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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1817 Taplin Hill Road Corinth VT 05089

Corinth, VT1817 Taplin Hill Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4968498

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 1,658

Located along the rolling hills of Vermont's picturesque countryside sits the Taplin Hill Farm. This unique property offers over 177 acres of open and wooded pastures, manicured lawns, an old sugar bush, a Christmas tree plot and breathtaking long range views. Drive to the cottage built in 2022 overlooking the swimming pond. This is Contemporary open concept living with one bedroom and one bath. As you travel up the scenic gravel drive you come to the overlook landing. Here you can sit by the wood burning fire pit, watch the Highlander cows graze and listen to the horses gallop by. Continue to the off-grid barn/home built in 2018. The barn's second floor features cathedral ceilings, a brightly lit kitchen, dining and living area with a wood burning stove. Also, on the second level is a beautiful bedroom with ensuite bath and office all with large windows to maximize the views. The lower level offers a second office space, laundry/utility room and an unfinished storage area. Outside, there are two outbuildings, a chicken coop and acres of fenced in pastures. Up the road another quarter mile sits a private one room off-grid cabin with a kitchenette, and three quarter bath, built in 2016. Here you can sit on the front deck, relax, listen to nature and on a clear day see the top of Mount Washington. The property has high speed internet, is located less than three hours from Boston, and only 15 minutes to I-91. This remarkable property must be seen to be truly appreciated.

Listed by Annette Hartley-White and Laurie Kirkpatrick of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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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2018 Church Hill Road Woodstock VT 05091

Woodstock, VT2018 Church Hill Road

Price$2,275,000

Est. Mortgage: $/month

MLS Number 4969169

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,610

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the spring-fed swimming pond. Designed for gracious country living the eat-in kitchen and generous great room are accented by a fieldstone fireplace and vaulted ceilings. The primary bedroom suite and two guest bedrooms are located on the main living level with a walk-out level offering an additional bedroom with media and exercise areas. A 'bonus room' used as a studio is available for many alternative pursuits. Fifty acres of private woodland and open meadows is laced with trails enabling access to nature year round. A small stable is a resource to take advantage of South Woodstock's network of horse trials and miles of gravel roads. A private retreat within minutes of Woodstock's Village Green or the South Woodstock and the Green Mountain Horse Association. The best of all possible worlds.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 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 December 2, 2023 7:23 PM EST