66 Hollow Farm Road
66 Hollow Farm Road photo 2
66 Hollow Farm Road photo 3
66 Hollow Farm Road photo 4
66 Hollow Farm Road photo 5
66 Hollow Farm Road photo 6
66 Hollow Farm Road photo 7
66 Hollow Farm Road photo 8
66 Hollow Farm Road photo 9
66 Hollow Farm Road photo 10
66 Hollow Farm Road photo 11
66 Hollow Farm Road photo 12
66 Hollow Farm Road photo 13
66 Hollow Farm Road photo 14
66 Hollow Farm Road photo 15
66 Hollow Farm Road photo 16
66 Hollow Farm Road photo 17
66 Hollow Farm Road photo 18
66 Hollow Farm Road photo 19
66 Hollow Farm Road photo 20
66 Hollow Farm Road photo 21
66 Hollow Farm Road photo 22
66 Hollow Farm Road photo 23
66 Hollow Farm Road photo 24
66 Hollow Farm Road photo 25
66 Hollow Farm Road photo 26
66 Hollow Farm Road photo 27
66 Hollow Farm Road photo 28
66 Hollow Farm Road photo 29
66 Hollow Farm Road photo 30
66 Hollow Farm Road photo 31
66 Hollow Farm Road photo 32
66 Hollow Farm Road photo 33
66 Hollow Farm Road photo 34
66 Hollow Farm Road photo 35
66 Hollow Farm Road photo 36
66 Hollow Farm Road photo 37
66 Hollow Farm Road photo 38
66 Hollow Farm Road photo 39
66 Hollow Farm Road photo 40
66 Hollow Farm Road photo 41
66 Hollow Farm Road photo 42
66 Hollow Farm Road photo 43
66 Hollow Farm Road photo 44
66 Hollow Farm Road photo 45
66 Hollow Farm Road photo 46
66 Hollow Farm Road photo 47
66 Hollow Farm Road photo 48
66 Hollow Farm Road photo 49
66 Hollow Farm Road photo 50
66 Hollow Farm Road photo 51
66 Hollow Farm Road photo 52
66 Hollow Farm Road photo 53
66 Hollow Farm Road photo 54
66 Hollow Farm Road photo 55
66 Hollow Farm Road photo 56
66 Hollow Farm Road photo 57
66 Hollow Farm Road photo 58
58 photos

$2,650,000

66 Hollow Farm Road
Woodstock, VT 05091
Listed by David Donegan · Snyder Donegan Real Estate Group
Bedrooms
5
Bathrooms
2.1
Living area
N/A
Year built
1988

About this home

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.

Property details

MLS #
5091062
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
79
On market date
N/A
Stories
N/A
Garage spaces
1
Lot size
105.1 acres
Loading map…

Mortgage calculator

Estimate only — actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$16,109/mo
$530,000 down
$2,120,000 loan
Principal & interest$13,750
Property tax (est.)$2,208
Home insurance (est.)$150

Similar homes you might like

Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 08/13/26.