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Windsor County

Browse all available real estate in Windsor County, Vermont. 

Find Homes for Sale in Windsor County VT

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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • Square Feet 5,412

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

$
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%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4913355

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Square Feet 8,225
  • Bathroom 8

SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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255 Round Top Road Plymouth VT 05056

MLS Number 4721059

  • Commercial
  • Square Feet 8,000
  • Year Built 2006
  • Acreage 800

Plymouth Notch......is located in Vermont's "snow belt" along the spine of Green Mountains peaks and offers a unique opportunity to own and operate an existing ski area or create your own private year round recreational estate. Plymouth Notch consists of two mountains, presently with 150 skiable acres and 28 trails all located on Bear Mountain. Salt Ash Mountain adds an additional 300 acres of skiing capacity to the project. The sale includes 800 total acres, an 8,000 sq ft Lodge with a fully equipped kitchen & bar area, double chairlift, snowmaking pond capable of 100% coverage, additional outbuildings, maintenance garage and equipment necessary to maintain the ski area and grounds. In addition, an Act 250 permit has been granted for residential development. The Master Plan allowing for 66 units around the base area with further development located on the mountain. Plymouth Notch is easily accessible located on a major Vermont ski artery near equal distances of Okemo Mtn., Killington and the village of Woodstock. Inquire for your private tour and further details.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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249 Bragg Hill Norwich VT 05055

Norwich, VT249 Bragg Hill

Price$6,000,000

Est. Mortgage: $/month

MLS Number 4883128

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 9,621

Huge views, big land, near everything: Hard to imagine that a nearly 200 acre hilltop estate is within walking distance of the village of Norwich. With the scale, sweeping views to the White Mountains, complete privacy and presence of one of the great Vermont country properties, Highlander is just over a mile to Dan & Whit's and the green. The home and barns are built on the site of an old hilltop farm with massive sugar maples, stone walls, hayfields, managed woodlands, and ponds for swimming and wildlife. The home is elegant and comfortable with an indoor/outdoor flow. Relax and take in the views on the patios and porches or supper in the summer room, which opens out to the pool. At the heart of the house is the capacious, recently renovated, kitchen. Extensive perennial gardens unfold throughout the summer, & an edible landscape yields apples, pears, peaches & berries. An active, outdoorsy family shaped the character of Highlander. Many sets were played on the tennis court and active equestrians grew from ponies to top-flight competitors in the roomy 6 stall stable and on the trails. Kids learned hard work bringing in the hay. The swimming pond converts to pond hockey in the winter, & the other 3 ponds host diverse wildlife all year round. The family hosted an annual cider pressing, skied on the trails & raced on sleds down the long meadows. 2 bedroom apartment over 4 bay equipment barn. Easy access to AT trail.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

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

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: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 15
  • Square Feet 10,206

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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298 Holiday Farm Road Bridgewater VT 05035

Bridgewater, VT298 Holiday Farm Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4929847

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,757

The legacy property of OQ Farm (formerly known as the Holiday Farm) has been adapted several times throughout its historical past, most recently as a 481-acre short-term hospitality and retreat destination with an arts and spiritual focus. Featuring 8 different dwelling structures, OQ Farm offers a diverse range of accommodation options, from 1800s historic, a luxurious lodge retreat center, to sleek and modern eco-cottages, converted maple sugar shack, a studio cabin and caretaker's cabin, all taking advantage of unique views of the river valley and mountain range beyond. Boasting 1,200+ feet of river frontage along the North Branch and Ottauquechee Rivers, which flows into the Connecticut River; OQ Farm is situated equidistant between the Appalachian Trail and ski slopes of Killington and the quaint town of Woodstock - renowned as one of America's most beautiful towns. Several fenced pastures and barns provide for agricultural use beyond the sheep, alpacas, poultry and horses present currently. An extensive network of mountain biking, hiking and snowshoeing trails, and a large bonfire pit offer endless outdoor recreation and gathering opportunities.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4925674

  • Residential Single Family
  • Bathroom 7
  • Square Feet 6,040
  • Construction Existing
  • Bedrooms 6

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SHOWINGS WILL START SUNDAY AUGUST 21.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$3,250,000

Est. Mortgage: $/month

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Square Feet 5,306
  • Bathroom 5

4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America's most beautiful villages.

Listed by Richard Higgerson and Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5518 Vermont Route 12 Barnard VT 05031

Barnard, VT5518 Vermont Route 12

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4882340

  • Residential Single Family
  • Square Feet 7,619
  • Bedrooms 6
  • Construction Existing
  • Bathroom 6

Weddings, events, retreats; this property can be reimagined as a boutique hotel, retreat center, or stately residence! Located minutes from Woodstock, in quintessential Barnard, the attractive and welcoming “Barnard Inn” has been a fine residence since 1796 and in recent decades a destination restaurant. Currently it is well known for catering many distinguished destination Vermont wedding events! Being commercially sound with all permitting and infrastructure in place, many turnkey opportunities exist! Nestled on 10 acres are manicured perennial gardens, lush meadows and working gardens. Walking paths lead to a secluded romantic wedding site at a pond! Owners have created an extensive and appealing private residence within the main brick building. Enter up stairs to a deck, and you'll walk into a sprawling designer kitchen. Continue on to a large living room, 5 bedrooms, family rooms and private spaces. The main building front entrance leads to 3 historic elegant formal dining rooms and an updated state of the art restaurant kitchen. Down the hall is a tavern, with 2 dining areas and a classic tavern bar. Large windows overlook the garden and fire pit area. A detached barn presents a dramatic turnkey event venue! Newly renovated studio apartment below the event barn is perfect for guests who value private space. It is currently used as a highly popular short-term Fine dining and event hosting is established! Transformation into a private estate residence is a potential use!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5518 Vermont Route 12 Barnard VT 05031

MLS Number 4882232

  • Commercial
  • Square Feet 8,363
  • Year Built 1796
  • Acreage 10

Weddings, events, retreats; this property can be reimagined as a boutique hotel, retreat center, or stately residence! Located minutes from Woodstock, in quintessential Barnard, the attractive and welcoming “Barnard Inn” has been a fine residence since 1796 and in recent decades a destination restaurant. Currently it is well known for catering many distinguished destination Vermont wedding events! Being commercially sound with all permitting and infrastructure in place, many turnkey opportunities exist! Nestled on 10 acres are manicured perennial gardens, lush meadows and working gardens. Walking paths lead to a secluded romantic wedding site at a pond! Owners have created an extensive and appealing private residence within the main brick building. Enter up stairs to a deck, and you'll walk into a sprawling designer kitchen. Continue on to a large living room, 5 bedrooms, family rooms and private spaces. The main building front entrance leads to 3 historic elegant formal dining rooms and an updated state of the art restaurant kitchen. Down the hall is a tavern, with 2 dining areas and a classic tavern bar. Large windows overlook the garden and fire pit area. A detached barn presents a dramatic turnkey event venue! Newly renovated studio apartment below the event barn is perfect for guests who value private space. It is currently used as a highly popular short-term Fine dining and event hosting is established! Transformation into a private estate residence is a potential use!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

210 Bear Hill Road Plymouth VT 05056

Plymouth, VT210 Bear Hill Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number 4907489

  • Residential Single Family
  • Square Feet 8,309
  • Bathroom 8
  • Bedrooms 3
  • Construction Existing

Magnificent "Bear Hug Den" is the ultimate private escape. First time offered on market. This exquisite multi-level contemporary mountain estate is located minutes to Killington, Okemo/Jackson Gore and Woodstock. This post and beam masterpiece was created by architect Robert Carl Williams and was constructed by Moore Construction. Perhaps one of the finest estates in the heart of the Green Mountains. You must tour this gem to appreciate its fine beauty and great attention to every detail. The interior of the residence has elegant finishes throughout. The spacious open concept main level is ideal for entertaining with loads of glass to savor the mountain views, vaulted ceilings, three fireplaces with extensive floor to ceiling stonework, and a professional chef's kitchen to fall in love with. The home has 6 en-suite bedrooms and sleeps 22 comfortably. Amenities to enjoy is a state of the art fitness center, steam room, sauna, recreation room, an outdoor stone custom built hot tub that seats 10+, and large outdoor firepit with beautiful Adirondack style chairs. The home has radiant floors on every level, central AC, whole house Kohler generator, Sonos sound system inside and out, security system. This magnificent estate is being sold professionally furnished and totally turnkey. The property has sweet 180 degree mountain views and is located slopeside to Plymouth Notch Ski Area. VAST snowmobile trails, endless hiking/ mountain biking & pristine lakes are minutes away!

Listed by Alexandra Lemesciuc and Marni Rieger of KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 2, 2022 10:09 PM EDT.

 
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