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Single Family Homes for Sale

Scroll down to browse single family homes for sale in the Woodstock region of Vermont. Contact us if you have any questions or if you would like to schedule a time to visit a home. Create an account to save your favorite homes and to receive email notifications when similar listings become available. 

6677 Route 4 Route Mendon VT 05051

Price$6,950,000

Est. Mortgage: $/month

MLS Number 4728237

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 8,071

Mendonhall is an enduring tribute to a shared vision of the owners, architect & craftsmen who allied themselves in a remarkable creative endeavor. The elegant residence is constructed of stone, steel & rare woods with careful attention to every detail. Joined like fine furniture; the timeless materials are intended to withstand the rigors of Vermont's climate far into the future. The home is sited to secure views from every room. The perspective is dominated by Pico Moutnain, where New England Alpine ski was pioneered. The horizon to the east is defined by Deer's Leap crested by the combined paths of the Appalachian & Long Trail's. The estate is comprised of 200 acres of private land bordering the Green Mt. National Forest & graced by 200 acres of majestic hardwoods, fruit trees, flowering shrubs & perennials. Two spring-fed ponds, one with a waterfall & the other a picnic island accessed by an arched bridge wash the scene with soft sounds of moving water. Designed by Robert Carl Williams Associates AIA reminiscent of the Craftsman Style, influenced by the Japanese period of Frank Lloyd Wright. The structure is subtly integrated into striking natural surrounding providing a seamless transition between inside & outside environments. Spacious gathering rooms, secluded personal spaces & a dedicated spa level are unified around a hand-crafted 4 story mahogany staircase illuminated through its core by an exquisite Murano chandelier. A serene celebration of excellence.

Listed by Laird C. Bradley of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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2358 Long Hill Road Woodstock VT 05071

Price$5,500,000

Est. Mortgage: $/month

MLS Number 4475560

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4,165

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 foot Old Baldy Mountain with 360-degree views and a small private cabin at the summit. Landscape design by Shep Butler includes an orchard of 110 productive apple trees with varieties such as Macoun, Empire, Cortland, Spartan and Macintosh.

Listed by T Story Jenks of LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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5000 Route 106 Reading VT 05062

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4738758

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 7,982

The right dose of Vermont living: high meadows, mountain views, in the heart of horse country near Woodstock, end of the road, and complete privacy. Warner Hill Farm's beginnings as a late 1700's sheep farm have been transformed into a comfortable, but distinguished property that has been on the cover of House Beautiful and featured in Architectural Digest. Today, this well-stewarded property, with its own helipad, is sited on 120 acres and is one of the most exceptional properties in Vermont taking inspiration from Old World elements including a gracious courtyard, Dutch gables, and formal gardens. A gated one-mile drive wends up through the trees to open on to a verdant landscape of rolling meadows and ponds. To the west there are expansive views of the mountains and lavish sunsets. The home has a gourmet kitchen, five bedrooms, 6.5 bathrooms and spacious living spaces. Connected by a breezeway is a guest room ensuite. Behind the house is a stone patio next to a deep, clear pond fed by a cascading waterfall. A gym, office and home theater can be found across the courtyard. A 4-stall horse barn, is attached to a party barn with a massive stone fire place and cathedral ceilings. Down an allée of maple trees is the pool. Also, on premise is a caretaker's house/guest house with 3 bedrooms and stunning views. There is an extensive network of trails for walking, cross-country skiing or riding, and connects to GMHA trails. Close to Killington and Okemo for skiing.

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

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%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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21 Havelok Hill Road Strafford VT 05072

Price$3,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4749419

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 4,896

"HAVELOK HILL" is privately situated in the midst of +/- 600 acres just 25 minutes to Dartmouth/Hanover, and 35 mins to Woodstock, in lovely Strafford, Vermont. The land component is the most extraordinary parcel our firm has ever offered for sale, including absolutely stunning long range mountain views from the main residence that includes the White Mountains of New Hampshire to the east, and to the west, the Green Mountains of Vermont including direct views (from the patio area) of Mt. Ascutney, Okemo, Killington, Pico, Camels Hump and Mt. Mansfield (Stowe) among others. The property has five secluded ponds, approximately 200 acres of upland meadows, and eight miles of improved interior roads and riding trails for every conceivable type of outdoor activity - all on your own private compound. The main residence is situated at the height of land, perfectly oriented towards the views. The present owners spared no expense in designing a residence of the highest quality and taste, centered around a magnificent 1,500 square foot wood-paneled great room ("the concert hall") with a 24-foot vaulted ceilings, 8-foot custom-built mahogany french doors to the patio/view, and a massive fieldstone fireplace. The property also includes a four-bedroom guest or caretaker's cottage - nearby but out of view of the main residence.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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1095 Eastman Road Sharon VT 05065

Price$3,745,000

Est. Mortgage: $/month

MLS Number 4756993

  • Residential Single Family
  • Construction Existing
  • Bathroom 10
  • Bedrooms 8
  • Square Feet 9,587

EASTAWAY ESTATE - The breathtaking Eastaway Estate sits on 128 acres tucked away on a mountainside at the end of a gated private drive. The elegant main residence and guest house are perched at an elevation of 1,400 feet overlooking the Green Mountains, creating the ultimate country escape. The sophisticated contemporary homes offer the highest quality materials including mahogany ceilings and marble floors. The floor-to-ceiling windows and inviting exterior decks and terraces provide full views of the majestic professionally landscaped surroundings. An extensive trail network winds throughout the rolling, wooded property for walking, snowmobiling, cross country skiing and more. The two homes offer over 9,000 square feet of luxurious living space, including 8 bedrooms, 10 bathrooms, 7 fireplaces, 2 wine cellars, a tasting room and garages for 8 cars. There are 2 outdoor spas, 3 ponds, 2 saunas, and a beautiful in-ground pool. Enjoy sunsets from the mountain top gazebo which offers 360 degree views. This is one of the finest estate properties available in Vermont and provides true privacy while still conveniently located within a 25 minute drive to both Hanover, NH and Woodstock, VT. The interior of both homes was professionally designed and the property is being offered fully furnished.

Listed by Zoe Hathorn Washburn of Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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4777 Rush Meadow Road West Windsor VT 05089

Price$3,650,000

Est. Mortgage: $/month

MLS Number 4726033

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 5,899

Sheep Run Farm in West Windsor, is named for the stone walled lanes where Ira Taylor, a prosperous mid-19th century farmer, herded sheep from the barn to the upper meadows. Today, a newly reimagined 2017 4-bedroom plus loft (6-bedroom septic), 6.5 bath farmhouse fits seamlessly into the classic Vermont scenery, just 3 miles to the South Woodstock store, and 8 miles to Woodstock Village. Classic on the outside, hip on the inside, the farmhouse's 1st floor has an open floor plan, with large windows and high ceilings, abundant light and views from every window. Connected buildings include a 2-bay garage, carriage house party barn, wood room and yoga studio. A huge glass door of the three-season carriage barn opens to the stone terrace, while a massive stone fireplace and soaring ceilings make this a remarkable gathering spot for family and friends, and the second floor boasts a comfortable guest suite. EC fiber provides high speed access for this smart-home to control; lights, climate, video, security, and property access via apps from anywhere in the world. The property encompasses all the right elements; the exceptionally beautiful 21+ acres, including views of rolling meadows, Rush Meadow Valley and Mount Ascutney; endless stone walls; apple trees; a cascading brook and two ponds.

Listed by Christopher Lang and Dia Jenks of LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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3429 Cloudland Road Pomfret VT 05067

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4779987

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5,134

"SLEEPY HOLLOW FARM" - One of the most iconic properties in Vermont - Sleepy Hollow Farm is located on desirable Cloudland Road, just 10 minutes from Woodstock village. The incredibly picturesque, pastoral land component comprises 115 acres of fields, gardens, woods, trails, and two ponds. The property is conserved both in the Vermont Current Use program and by the Vermont Land Trust. Next to the large second pond is a small cabin complete with bunk beds and a wood stove - perfect when you want to go “off-grid” and camp out on your own property. The original farmhouse c. 1790 - has been updated and expanded and now connects via a radiant-heated brick passageway to a newer, fabulous barn complete with 6 horse stalls, tack room, and a large finished wood-paneled recreation room upstairs. Two other large barns with workshops and garages and for storage- are nearby. The property comes with an array of motorized vehicles and equipment including a tractor, UTV and ATVs w wheels and tracks, two dirt bike motorcycles and a diesel-powered snowcat groomer. The property also includes a separate historic 1-room schoolhouse up on Cloudland Road, that was converted into a 1 bedroom apartment perfect for guests, kids or caretakers, with some of the best views in the area - and looks down over the Sleepy Hollow Farm itself.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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 Mountainside Drive Killington VT 05751

Price$3,100,000

Est. Mortgage: $/month

MLS Number 4781455

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 10,022

Simply majestic views of Killington peak and Snowden peak are waiting for you at 40 Mountainside Drive, one of Killington Resorts premiere ski home communities. A gated paved driveway leads you to this grand residence, as you step into the foyer you are greeted with ample natural light and mountain views. Just off the main living room you will find the kitchen with massive island and plenty of space for everyone to gather or head into the sitting room off of the kitchen for a quieter atmosphere. Also located on the main level of the house is the master bedroom with ensuite bath and stately walk in closet. There are no shortage of views here either, the master bath has direct views of Killington resort. On the lower level this home is its own micro resort, complete with game room, sauna, gym, bar and exquisite slate hot tub room. At the end of a long day of skiing or riding retire to one of 6 bedrooms, three on the upper level. All of the details of this house are done to the upmost standards, from multiple types of wood to unique stone work to the finished garage this home has it all. Detached from the main three car garage is another oversize garage with storage above. A incomparable property in many ways.

Listed by Nathan Mastroeni of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4629754

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,800

Offering some of the most beautifully managed and meticulously maintained acreage available in Windsor County, Hartland Highlands offers over 279 acres of high, rolling meadows, mixed northern hardwoods forests, four ponds, three brooks, miles of interior roads and trails and multiple developable future house sites in addition to the mid-19th century Cape, guest house and barn complex currently in place. Views from the property extend from Smarts Mountain in Lyme, NH through dramatic near range vistas of Mount Ascutney to the south. Professionally managed by the premier Upper Valley land enhancement company for more than two decades, the quality of the acreage is unsurpassed. The main house and one bedroom guest house are surrounded by copious perennial gardens, antique stonewalls, grandfather maples and sweeping lawns. Multiple barns and outbuildings provide storage space for every conceivable outdoor pursuit. A true legacy property in a location less than 25 minutes from the heart of the Upper Valley, Hanover and Dartmouth College.

Listed by Richard Higgerson of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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1055 Sayer Road Barnard VT 05031

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4687009

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 8,264

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance to Woodstock, Vermont and Hanover New Hampshire. Circa 1995 6500 sq.ft. residence with attached three-car garage and spectacular three-story, six stall post and beam barn. An additional 2000 sq.ft. in the walk-out basement finished into a media room and large conference/office area with a wet bar and full bath. 252+/- acres of conserved and managed forest and pastures with miles of maintained riding trails. The residence was five years in the building by a local builder renowned for his quality and attention to detail. Furniture-quality woodwork throughout this four-bedroom, six-bath residence with complete butler/guest apartment wing.

Listed by Stan Butler of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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1532 Happy Valley Road Woodstock VT 05091

Price$2,895,000

Est. Mortgage: $/month

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This contemporary cape with classic Vermont lines is built on the history and character of two fully reconstructed antique post & beam frames. Architect designed, premier builder, and unquestionably one of the nicest homes in Woodstock. It has a newer cedar shake roof and has been completely re-sided with beautiful cedar shingles in 2019. There is beautiful interior space, newly created guest quarters, four working fireplaces, high-end master bathroom finishes, and 55.76 acres of playground. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas stove, a large double door Sub-Zero refrigerator, and even space for a kitchen herb garden. The look and feel is classic Vermont charm with all the modern conveniences of the 21st century. Five (5) bedrooms, four (4) bathrooms, and over 6,000 sq-ft of living space finished to an exacting level of detail. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. The grounds have a duck pond, ancient stone walls, mature maple trees, a four car garage, a substantial 4-stall timber frame horse barn with hay storage, and 20 acres of open meadows. Happy Valley Road is on the exclusive easterly side of town with quick access to major metro hubs and downtown Woodstock. Close to trails for biking, hiking, snowmobiling, or horseback riding. This private setting is just gorgeous and the perfect quintessential Vermont retreat.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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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3147 Mt. Hunger Road Barnard VT 05031

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4755552

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 4,531

"HONEY HILL FARM” - located in desirable Barnard, Vermont, has been in the same family for more than 30 years, with both land and residence meticulously and lovingly maintained throughout the family's stewardship of the property. Situated on 264.4 surveyed acres, the land component is comprised of open pastures and conserved and managed woodlands with miles of trails for walking, x-c skiing and snowshoeing, biking or other outdoor pleasures. The property has beautiful long-range mountain views, a deep swimming pond, perennial gardens, and a lovely mountain brook that courses through the property, plus a wonderful and totally private swimming pool in the center rear of the residence with access from the living room and the kitchen. A nearby barn - a portion of which was once utilized as a caretakers apartment - provides storage for motorized toys and vehicles. The residence itself is a classic Vermont farmhouse design with slate roofs, three fireplaces, covered porches and an attached guest apartment above the attached three-car garage. The living room, which has exceptional woodwork, can easily accommodate large parties for entertaining. Five bedrooms, four baths, and three half-baths in total. House boasts excellent mechanicals, backup generator, security systems, underground wires, and more. High speed internet is available via EC Fiber. 18 mins to Woodstock, 10 mins to I-89, and 30-45 minutes to a private airport and skiing at numerous major Vermont ski resorts.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.57% last updated on Oct 10, 2019
* 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 2019 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 October 16, 2019.