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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. 

1959 Cox District Road Woodstock VT 05091

Woodstock, VT1959 Cox District Road

Price$9,750,000

Est. Mortgage: $/month

MLS Number 4792976

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 9,515

Woodstock Farm is a modern architectural masterpiece and landmark work by award winning and internationally recognized architect Rick Joy. Based on a conceptual framework that draws from the simplest archetypical forms, this dramatic stone and shingle house and counterposed barn is set on over 200 acres of Vermont countryside minutes from the picturesque village of Woodstock and in close to ivy league Dartmouth College in Hanover, New Hampshire. Melding effortlessly into the Green Mountains, the property is sensationally experiential in nature and the design is executed with the sharpest attention to craft and detail. Drawing directly from the architectural vernacular of the rural northeast, the tension between the historical and contemporary is conveyed, to paraphrase the architect, through the massive character of the walls, through the qualities of light and dark, through spatial movement and through atmosphere. The four-bedroom main residence offers a 152-foot elongated gable house with massive end walls of quarried Lake Champlain bedrock and cedar cladding on the roof and side walls. Extraordinary, unique and exceptional in every way, Woodstock Farm presents the opportunity for a new owner to acquire an important piece of the history of modern architecture, an incomparable lifestyle, and a work of art.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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6677 Route 4 Route Mendon VT 05051

Mendon, VT6677 Route 4 Route

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

Woodstock, VT2358 Long Hill Road

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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1224 US Route 5 Norwich VT 05055

Norwich, VT1224 US Route 5

Price$4,700,000

Est. Mortgage: $/month

MLS Number 4790292

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 8,100

A dramatic architectural landmark combining a unique and spectacular site, modern aesthetic design principles and innovative technical execution, the 6390 square foot River House in Norwich, Vermont presents a unique opportunity for the next owner to experience life at a singular level. Minutes from the cultural hub of Hanover, New Hampshire, home to the renowned Ivy League Dartmouth College, and two hours to Boston's Back Bay, River House is within an hour's drive of an array of world class recreational, cultural and entertainment attractions. Sited on a peninsula exactly eighty feet above the Connecticut River and boasting a 180-degree vantage point with long range water views both north and south, the house and its outbuilding are constructed entirely of concrete. This raw, versatile material makes up both the exterior and interior surfaces of the home and the dramatic views from the main living spaces are achieved through a flip of the traditional floor plan with the main living quarters on the second floor. Soaring 14 foot high interior spaces in the main living room open directly to the exterior and the stackable glass doors that run both the entire north and south walls blurring the visual boundary between indoors and out.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

Pomfret, VT3429 Cloudland Road

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: 3.24% last updated on May 21, 2020
* 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

Barnard, VT1055 Sayer Road

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

Woodstock, VT1532 Happy Valley Road

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: 3.24% last updated on May 21, 2020
* 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

Barnard, VT3147 Mt. Hunger Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4804027

  • 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: 3.24% last updated on May 21, 2020
* 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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3114 Church Hill Road Woodstock VT 05091

Woodstock, VT3114 Church Hill Road

Price$2,740,000

Est. Mortgage: $/month

MLS Number 4800371

  • Residential Single Family
  • Construction New Construction
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 9,320

Between the storied Village of Woodstock, Vermont and the country cosmopolitan hamlet of equestrian-oriented South Woodstock a remarkable retreat can be found. The spectacular post and beam residence and barn/guest house are the result of a collaboration between two partners uniquely qualified and united in the passion to create something extraordinary. The architect designed main house is sited to take maximum advantage of the homes south elevation and provides a view of the barn, fenced pasture and paddock area. Employing old world craftsmanship, C.G. Nichols Builders brought over 35 years of custom residential construction experience to create a dramatic statement in wood, glass and stone. The connected open flow of the first floor plan is centered around the kitchen and its remarkable four season solar surround. The home features the finest quality materials and highest quality and most current construction standards. With approximately 6800 square feet, the 9-room main house offers four bedrooms, four and a half baths, open-concept kitchen, living and dining area, mudroom, entry and expansive first floor master bedroom suite and the main house is surrounded by bluestone terraces, dry laid stone walls, lush lawns and gardens. The detached barn and guest house provide everything one needs for the equestrian lifestyle and the nearby Green Mountain Horse Association is a short 2.5 mile hack away. Delayed showings until 4/15/20.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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2574 Garvin Hill Road Woodstock VT 05091

Woodstock, VT2574 Garvin Hill Road

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4804667

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 6,545

"GARVIN HILL GETAWAY"- Newer custom built residence (that easily sleeps 15+) on 50 acres of farm pasture fields and woods with a fabulous long-range mountain view - just minutes from Woodstock village. Designed for family gatherings and entertaining friends, the residence also lives beautifully on one level. Wonderful open floor plan with high ceilings and large-proportioned rooms. The 1,200 sf great room / gathering area combines kitchen, dining and living room areas with stone fireplace that opens to an expansive wrap-around deck with its own indoor-outdoor entertaining space - with indoor and outdoor spaces all sharing the long-range mountain view over the pasture fields. A spacious first level master bedroom suite provides for 1-level living. Excellent mechanicals. Subject to current use conservation program. An oversized 3-car garage - for all your motorized toys bikes, skis, kayaks and other outdoor gear - walks into a mud-laundry room and into the house. Minimal gardens and landscaping make for a low-maintenance, super-fun gathering house on 50 acres with big views, just minutes and easy access on public roads from Woodstock village.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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

Killington, VT40 Mountainside Drive

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4781455

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

Average Gross Revenue $190,200 between 2013 & 2018 makes this home a dual purpose property for any investor or family. 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. OWNER FINANCING AVAILABLE.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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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100 Fairbanks Road Grafton VT 05146

Grafton, VT100 Fairbanks Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 4700648

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 5,872

Nestled discreetly in the hills of historic Grafton with panoramic long-range southerly views, Pine Hill Farm is a unique, totally private country estate. The understated elegance, and organic elements of this home invoke a tranquility that transcends throughout. The walk-in field- stone fireplace commands the great room within a massive antique hand-hewn chestnut barn. tIt is ideal for entertaining with an exceptional chef's kitchen complete with La Canche range with dual fuel ovens, a magnificent custom antique refrigerator, and beautiful local red slate counters. The patinaed copper and black walnut bar with integrated audio system is perfect for entertaining your guests. Enjoy the luxurious grand master suite, with fireplace, copper soaking tub, wet and dry sauna and private deck with a large wood hot tub. The attached four-season greenhouse and potting room off the kitchen will give you a head start on the planting season or fresh greens year round. Beautifully landscaped with copious gardens and mature plantings to offer an ever-changing palate throughout the seasons. Comprised of 69 forested acres as an award-winning Tree Farm, Pine Hill Farm features a separate guest house, heated swimming pool, barn with fenced pasture, equipment barn, a swimming pond and an extensive trail network. 5 minutes from Grafton Village. Close proximity to Stratton and Okemo resorts and beautiful Grafton and Grafton Ponds. Escape the city's hectic life to your own very secluded private est

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.24% last updated on May 21, 2020
* 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 2020 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 May 26, 2020.