66 Hollow Farm Road, Woodstock, VT, 05091

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$3,100,000
New Listing

66 Hollow Farm Road
Woodstock, VT 05091

For Sale|Single Family Residence|Active
5
Beds
6
Total Baths
2
Full Baths
4
Partial Baths
4,843
SqFt
$640
/SqFt
1988
Built
County:
Windsor
Listing courtesy of David Donegan of Snyder Donegan Real Estate Group Cell: 603-443-0044
Call Now: 603-392-7145
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603-392-7145
66 Hollow Farm Road66 Hollow Farm Road66 Hollow Farm Road66 Hollow Farm Road
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CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef’s kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

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Listing Snapshot
Price 
$3,100,000
Days On Site 
0 Days
Bedrooms 
5
Inside Area (SqFt) 
4,843 sqft
Total Baths 
6
Full Baths 
2
Partial Baths 
4
Lot Size 
105.1 Acres
Year Built 
1988
MLS® Number 
5091062
Status 
Active
Property Tax 
$32,646
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
7 hours agoListing updated with changes from the MLS®
9 hours agoListing first seen on site
General Features
Acres 
105.1
Garage 
Yes
Garage Spaces 
1
Number Of Stories 
3
Parking 
Gravel
Parking Spaces 
1
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Above 
4843
SqFt Total 
5299
Style 
New Englander
Water Source 
WellPrivate
Zoning 
Residential
Interior Features
Appliances 
DishwasherDryerRefrigeratorWasher
Basement 
Concrete
Flooring 
Tile
Heating 
Baseboard
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Exterior Features
Lot Features 
LevelSlopedWetlandsWooded
Roof 
Metal
View 
Water
Waterfront Features 
Stream
Waterview 
Water
Community Features
School District 
Windsor Central
Schools
School District
Windsor Central
Elementary School
Woodstock Elementary School
Middle School
Woodstock Union Middle Sch
High School
Woodstock Senior UHSD #4
Listing courtesy of David Donegan of Snyder Donegan Real Estate Group Cell: 603-443-0044



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Last checked: 2026-05-27 08:43 PM UTC
Neighborhood & Commute
Source: Walkscore
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