Greater Woodstock Area Luxury Homes Over $2 Million

Greater Woodstock properties over 2 million dollars offer truly unique features, such as historical or architectural significance, vast acreage, unparalleled views, and the ultimate in privacy. Real estate at this price in the Greater Woodstock, Vermont area is often large enough to be a family compound, comfortably accommodating many generations and visits by many friends. Many properties in this price range are perfect for boarding horses.

Though set apart from other properties in amenities and location, these luxury homes are close to the quintessentially Vermont town of Woodstock, craft breweries (Long Trail and Harpoon) and distilleries (Silo and Vermont Spirits), fine dining in Barnard and Quechee and other towns, several golf courses, miles of hiking and mountain biking trails, and three ski mountains. Amenities such as grocery stores and pharmacies are also short drives away.

Greater Woodstock Luxury Real Estate $2M+

Find your perfect Greater Woodstock, VT multi-million dollar home below or contact Bassette Real Estate. One of our experienced brokers or buyer agents will be happy to help you.

1959 Cox District Road Woodstock VT 05091

Woodstock, VT1959 Cox District Road

Price$10,500,000

Est. Mortgage: $/month

MLS Number 4820913

  • 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, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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5000 Route 106 Route Reading VT 05062

Reading, VT5000 Route 106 Route

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4809895

  • 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 Dia Jenks, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4809703

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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 4820914

  • Residential Single Family
  • Construction Existing
  • 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.

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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$2,600,000

Est. Mortgage: $/month

MLS Number 4760962

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

This secure Vermont retreat sits high on a hill on 55 protected acres. Architect designed, a premier builder, and built on the history and character of two fully reconstructed antique post & beam frames. Unquestionably one of the nicest homes in Woodstock. Five (5) bedrooms, four (4) bathrooms, & over 6,000 sq-ft of living space finished to an exacting level of detail. There is beautiful interior space, private guest quarters, four working fireplaces, & high-end master bathroom finishes. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas range, and a large Sub-Zero refrigerator. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors are quintessential Vermont architecture. The grounds have a duck pond, old stone walls, mature maple trees, a four-car garage, & an impressive 4-stall timber frame horse barn. A newer cedar shake roof & re-sided cedar shingle in 2019 complement all the modern conveniences of the 21st century - high speed internet, whole house generator, underground power. Most of the neighbor's holdings include protected land in VT Current Use. Happy Valley Road is on the exclusive easterly side of town with quick access to, and away from, the major metro hubs of Boston & New York City. Did we mention the two snowmobiles & 6-wheeled Polaris Ranger included in the sale? Enjoy snowmobile trails, wandering the estate, biking & sledding on your secure Vermont domain! Check out the house video!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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122 Best Road Hartland VT 05089

Hartland, VT122 Best Road

Price$2,595,000

Est. Mortgage: $/month

MLS Number 4809529

  • Residential Single Family
  • Construction Existing
  • Bathroom 9
  • Bedrooms 9
  • Square Feet 6,921

BEST ROAD- Historically significant farmstead in a spectacular setting renovated into a modern masterpiece. The options are endless- the property can be run as a working farm, sophisticated rustic resort, family compound, event & wedding space, production facility or all of the above. There are 59 acres- a lovely mix of open pasture, orchards, fields & woodlands- with commanding views to the east and northeast. The attention to detail, quality of workmanship, and style are premium from the house to the cabins to the barns. The 5 “cabins” enjoy a successful rental business- although they are more contemporary small homes that are beautifully constructed. The barns and outbuildings can house any variety of animals. Currently there are sheep, goats, chickens, and seasonal horses on the farm. A wonderful 1 mile walking trail meanders through the woods/meadow, and established blueberries and fruit trees can be found throughout the property. Bring your ideas and dreams to this turnkey estate. The farm is perfectly located in a private setting with easy access to Woodstock, Vermont & Hanover, New Hampshire (home of Dartmouth College). Easy interstate access as well for guests or commerce.

Listed by David Donegan, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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$2,580,000

Est. Mortgage: $/month

Active With Contract

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, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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37 Brothers Road Hartland VT 05048

Hartland, VT37 Brothers Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4820108

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

Hartland Highlands is a Vermont refuge like no other. The land, professionally managed over the span of two decades under the meticulous stewardship of the areas most professional forestry management and land enhancement company, offers over 277 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. This true private kingdom offers a myriad of possibilities for a multi-generational legacy estate, a rural place of refuge or retreat or other more creative possibilities. Enjoying a location that is close to Dartmouth College, Woodstock, Vermont and the crossroads of New England where Interstates 89 and 91 meet, Hartland Highlands offers one of the largest, professionally managed and strategically improved parcels of land currently available anywhere in the Upper Connecticut River Valley. Close to the cultural attractions found only in a town with an Ivy League College and minutes from the picturesque and historic village of Woodstock, Vermont, famous for being one of the prettiest small towns in New England, the kingdom size property offers room to roam without ever leaving the land that you own while still being conveniently located to the country cosmopolitan and lifestyle conveniences of cultured civilization. The historic, expanded Cape on the western side of Brothers Road is surrounded by copious perennial gardens, antique stonewalls and grandfather maples

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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390 Handy Road Pomfret VT 05067

Pomfret, VT390 Handy Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4820078

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 5,000

With over 100 acres spread across the Pomfret and West Hartford line, this Saltbox built by renowned craftsman Doug Gest provides the best of both worlds for those seeking honest Vermont charm and the comfort of modern amenities, systems and conveniences. The classic reproduction colonial was constructed in 1998 in a location chosen by the owners for its proximity to everything the Upper Valley. Over 65 acres of countryside border the protected Appalachian Trail corridor and a large barn perfect for a car collection with caretaker's apartment is across the street. With stone walls and patio, over 250 trees, ornamental gardens, water features, espaliers, allees, gazebo, firepit and other outdoor charms too numerous to mention. varied width hand planed wide plank flooring, hand planed doors graced by authentic period hardware, period moldings, raised panels and built ins, Rumford style fireplaces and oversized living spaces that create a feeling of casual, elegant comfort. The heart of the home is the great room which encompasses the kitchen as well as the dining and informal living areas. A large formal dining room and a double living room open to an inviting screened-in porch overlooking the entrance to the formal gardens. A first floor master bedroom suite makes up the south end of the house. A covered breezeway entrance leads you to the post and beam barn that creates a dramatic two and a half story six car garage. Residence located in West Hartford

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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 August 15, 2020.