Woodstock, VT | 66 Hollow Farm Road

Christie's International Real Estate
$2,650,000
MLS#: 5091062
4,843
Sq Ft
105.1
Acres
4
Baths
5
Bedrooms
General Property Information
Property Status
Active Under Contract
Price
$2, 650, 000
Property Type
Single Family
County
VT-Windsor
Agency / Brokerage
David Donegan
Snyder Donegan Real Estate Group
List Date
5/26/2026 8:00 PM
Acres
105.1
Year Built
1988
Bedrooms
5
Total Baths
4
Sq. Ft. (Total)
4,843
Tax Year
2026
Taxes
$32,646

Virtual Tour

Description

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.

Map

Interior Features
# Of Stories
3.5
Sq. Ft. (Total)
4,843
Sq. Ft. (Above Ground)
4,843
Sq. Ft. (Below Ground)
0
Sq. Ft. Unfinished
456
Rooms
15
Bedrooms
5
Baths
4
Interior Desc
Dining Area, In-Law/ADU, In-Law Suite, Kitchen Island, Kitchen/Family, Kitchen/Living, Living/Dining, Primary BR w/ BA, Natural Light, Skylight, Indoor Storage, Vaulted Ceiling, 1st Floor Laundry
Appliances Included
Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer, Wine Cooler
Flooring
Tile, Wood
Heating
Oil, Baseboard
Basement Desc
Concrete Floor, Storage Space

Town Market Snapshot

Source: Data provided by PrimeMLS, graph generated by Pall Spera Company

Exterior Features
Style of Residence
New Englander
House Color
White
Time Share
No
Exterior Details
Deck, Garden Space, Guest House, Natural Shade, Outbuilding, Shed
Land Desc.
Country Setting, Horse/Animal Farm, Field/Pasture, Landscaped, Level, Recreational, Sloping, Trail/Near Trail, View, Walking Trails, Wetlands, Wooded, Adjoins St/Nat'l Forest, Near Country Club, Near Golf Course, Near Paths, Near Shopping, Near Skiing, Near Snowmobile Trails, Near School(s), Private
Suitable Land Usage
Farm, Field/Pasture, Horse/Animal Farm, Maple Sugar, Orchards, Recreation, Residential, Woodland
Roof Desc.
Metal, Standing Seam
Driveway Desc.
Gravel
Foundation Desc.
Concrete
Sewer Desc.
Private, Septic
Garage / Parking
Yes
Garage Spaces
1
Road Frontage
1,499
Zoning
Residential
Elementary School
Woodstock Elementary School
Middle School
Woodstock Union Middle Sch
High School
Woodstock Senior UHSD #4

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