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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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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 10
  • Square Feet 11,470

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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85 Pallottas Hill Road Ludlow VT 05149

Ludlow, VT85 Pallottas Hill Road

Price$9,995,995

Est. Mortgage: $/month

MLS Number 4955858

  • Land
  • Acreage 127
  • Zoning Mixed

127 Acres of Meadows, Forest, Trail Networks and Panoramic Views at the foot of Okemo Mountain, 2 minutes to downtown Ludlow and the Okemo ski lifts. This sprawling acreage can become single family homes, condominiums, town houses, a hotel or any combination thereof. Engineering work has identified the potential subdivision of the property. This developers dream is truly a blank canvas. Meticulously maintained, the property offers direct access to the VAST trail system. Enjoy cross country skiing, hiking and a multitude of other outdoor activities on the expansive trail network. Inspirational views in every direction including Okemo Mountain, Mount Ascutney and the Green Mountains to New Hampshire and beyond. It stands as one of the last undeveloped large parcels in Ludlow. A playground for the ultimate outdoor lover, this must see property awaits your creative vision to be transformed into the latest in luxury mountain living. The pristine four bedroom farm house can be subdivided off and sold or be used as a guest house. Endless possibilities!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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85 Pallottas Hill Road Ludlow VT 05149

Ludlow, VT85 Pallottas Hill Road

Price$9,995,595

Est. Mortgage: $/month

MLS Number 4955863

  • Residential Single Family
  • Village Ludlow
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2

Welcome home to this breathtaking 127-acre estate nestled at the foot of Okemo Mountain, just two minutes from downtown Ludlow. This extraordinary property encompasses sprawling meadows, enchanting forests, a network of scenic trails & panoramic views that will leave you in awe. Meticulously maintained, this generational farm sets the standard for perfection. The centerpiece of this remarkable estate is a beautifully renovated 4-bedroom, farmhouse. As you step onto the expansive stone patio, you'll be greeted by inspiring views in every direction, making it an ideal space for outdoor entertaining. Enter the oversized mudroom complete with laundry and custom storage designed to accommodate an abundance of gear. Inside the antique farmhouse, you'll find natural wood accents throughout, exposed natural beams, and tin ceiling, adding to its timeless charm and character. This well-appointed home can serve as your primary residence, a guest house, or sold to make way for your dream home on the surrounding acreage. The possibilities are endless. This exceptional parcel of land is one of the last remaining undeveloped properties in the area. It represents the ultimate playground for outdoor enthusiasts, unmatched in its offerings and natural beauty. Words alone cannot convey the possibilities and the sheer beauty of this unique parcel-this is a property that must be seen in person to fully appreciate its magnificence.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4943673

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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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: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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62 Moon Shadow Drive Ludlow VT 05149

Ludlow, VT62 Moon Shadow Drive

Price$4,889,000

Est. Mortgage: $/month

MLS Number 4941971

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 10,059

This unique mountain home is a one of a kind; an icon of slope side living on Okemo since it was constructed on the Moon Shadow ski trail in 2003. With its seven wood burning fireplaces and extensive stonework both inside and out, this home is as comfortable as it is extraordinary. The overall impressive design delivers on unparalleled , genuine log construction with its wide chinking and broad hewn timbers. Walking through this home is an exploration of grand spaces as well as intimate and luxurious niches such as the great room with soaring timber ceilings and the elevated soaking tub in the primary bath with its magnificent view. There are three private ensuites, including guest quarters with its own private entrance and great room as well as an king-sized bedroom, of course, with another fireplace. This home is a perfect allocation of space and light and every inch has been thoughtfully considered. The contrast of rustic and refinement is perfectly represented in the Gourmet kitchen with its wood burning stone fireplace and high-end appliances. There is no shortage of fun to be had with the oversized hot tub on the stone patio overlooking the ski trail, the open and airy loft with billiard table and the generous game room. Time is precious, why not spend it here?

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • 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: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1484 Bowman Road Barnard VT 05031

Barnard, VT1484 Bowman Road

Price$4,195,000

Est. Mortgage: $/month

MLS Number 4949146

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 9
  • Square Feet 10,030

In the heart of Vermont's Green Mountains, on over 30 acres of open pastures, StoneMeadow is an authentically reproduced 2nd period American Stone Cape with clapboard additions created by aficionados of the form and its history. Custom-built and completed in 2010, a secure gated entry and private drive lead to an elevated position from which the approach, the four-stall horse barn, and most of the 33 acres can be observed. The home is sited to take full advantage of southeastern exposure and local views. Executed with a devotion to the highest and most exacting degree of reproduction, the owners looked to the classic 1780s Capes constructed by Scots craftsmen that dot Windsor County; the National Register of Historic Places refers to this part of Windsor County as “the stone house belt of Vermont.” Seamlessly combining a convincing period experience inside and out, with the state-of-the-art systems and amenities that can only be found in 21st-century construction, the owners employed their four decades of housewright experience in the property's creation. From hand-chamfered white pine floors finished with square-head, forged nails, hand-planed surfaces, and hand-struck hardware, to the highest-grade kitchen including French cooktop, warming drawers, and steam oven, Wolf and Sub-Zero appliances, all overlooking the ducks, pond, and waterfall, StoneMeadow is an incomparable home in one of Vermont's most well-loved towns, an ark of safety and the ideal country retreat

Listed by Richard Higgerson of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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298 Holiday Farm Road Bridgewater VT 05035

Bridgewater, VT298 Holiday Farm Road

Price$3,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4929847

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • 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: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4951694

  • Residential Single Family
  • Bathroom 5
  • Square Feet 6,403
  • Bedrooms 4
  • Construction Existing

Designed by AIA award-winning architect Lewis Davis, of the New York firm Davis Brody Bond in 1976, whose work ranged from modernist skyscrapers to the renovation of the Reading Room at the New York Public Library, High Birch's sleek white design is striking in Vermont's green hills. Davis firmly believed in the power of architecture to enrich people's lives, and that ethos is evident in every aspect of this magnificent property. A drive wends its way through rolling meadows with stunning views to provide a sense of sanctuary, only 2.5 miles from Woodstock village. One of the standout features of High Birch is the abundance of natural light that floods in through the tall windows, illuminating the interior and framing breathtaking views of the surrounding mountains. The split-level design creates intimate spaces perfect for reading, reflection, or simply taking in nature. During winter, the entire family can gather around the fireplace, while the stone terrace becomes the perfect venue for outdoor entertaining during summer. Recent renovations by Studio Nexus added a contemporary touch to the kitchen, living room, bathrooms, and offices while still preserving the essence of Lewis Davis' original intent. The kitchen was designed by Deane. The home comes fully furnished, ready for you to move in and make it your own. There is a two car attached garage, storage barn and high speed internet. It is 6 miles to Saskadena and 34 miles to Killington for skiing. SHOWINGS BEGIN MAY 12

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$3,550,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4917788

  • Residential Single Family
  • Bedrooms 10
  • Bathroom 15
  • Construction Existing
  • 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: 6.71% last updated on Jun 8, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 10, 2023 9:09 PM EDT

 
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