Price Reduced Listing
$2,650,000
 $14,226 est/mo Sourced by Back At You

66 Hollow Farm Road,Woodstock, VT 05091

Woodstock, VT 05091

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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 homesteadwith its native timbers and stone fireplacecreates 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 Housea 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.

Details

MLS #5091062
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
Status(10) Active - Active
Year1988
Days On Site85
Listing Provided BySnyder Donegan Real Estate Group | David Donegan

Features

Bed(s)5
Bath(s) 4 Total
Garage1
BasementY
Story(s)3
ZoningResidential
Acreage105.10

Interior

Rooms Total15
CoolingNone
HeatingOil, Baseboard
Interior FeaturesDining Area, In-Law/Accessory Dwelling, In-Law Floorplan, Kitchen Island, Kitchen/Family, Kitchen/Living, Living/Dining, Primary BR w/ BA, Natural Light, Skylight, Indoor Storage, Vaulted Ceiling(s), 1st Floor Laundry
AppliancesDishwasher, Dryer, Exhaust Hood, Electric Range, Refrigerator, Washer, Wine Cooler

Exterior

Exterior FeaturesDeck, Garden, Guest House, Natural Shade, Outbuilding, Shed
RoofMetal, Standing Seam
Construction MaterialsPost and Beam, Wood Frame, Clapboard
Foundation DetailsConcrete
Lot FeaturesCountry Setting, Horse/Animal Farm, Pasture, Landscaped, Level, Recreational, Sloped, Trail/Near Trail, Views, 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

Parking

Garage Yes / NoYes
Parking FeaturesDriveway, Garage

Utilities

UtilitiesOther
ElectricCircuit Breakers
SewerPrivate Sewer, Septic Tank

Taxes

Tax Annual Amount32646
Tax Year2026

Area Information

StateVT
CountyWindsor
CityWoodstock
Zip Code05091
AreaVT Windsor
School DistrictWindsor Central
Elementary SchoolWoodstock Elementary School
High SchoolWoodstockS
Listing VS Median (in 05091)
Price:
$2,650,000
low | high
Med:
$3,397,500
21.792452830189% of Average
On site:
85
low | high
Med:
989
8.594539939333% of Average
Sourced by Back At You

Market Activity 05091

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Learn More About This Property

StateVT
CountyWindsor
CityWoodstock
Zip Code05091
AreaVT Windsor
School DistrictWindsor Central
Elementary SchoolWoodstock Elementary School
High SchoolWoodstockS
Listing VS Median (in 05091)
Price:
$2,650,000
low | high
Med:
$3,397,500
21.792452830189% of Average
On site:
85
low | high
Med:
989
8.594539939333% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $1.987M - $3.312M
sqft: 0 - 0
Nearby Listings Property ImageNearby Listings Details
1326 Curtis Hollow Road Property Photo 1
$799,000
1326 Curtis Hollow Road
Woodstock, VT 05091
Listing Updated: August 17, 2026 at 1:57:54 PM PDT