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Patrick Cooper
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66 Hollow Farm Road, Woodstock, VT 05091

$3,100,000
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Active
BEDS5 BATHS4 full 2 partial SQUARE FEET4,843 MLS#5091062
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWindsor Central

Listing Courtesy of: Snyder Donegan Real Estate Group
Agency Contact: Cell: 603-443-0044
Associate Name: David Donegan
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Property 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.

66 Hollow Farm Road | MLS# 5091062

This single family home located at 66 Hollow Farm Road, Woodstock, VT 05091 is currently listed for sale with an asking price of $3,100,000. This property was built in 1988 and has 5 bedrooms and 4 full and 2 partial baths with 4843 sq. ft. Hollow Farm Road is located within the Windsor Central school district. Search Woodstock real estate on patrickcooper.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Concrete Floor, Storage Space
Cooling: None
Garage: 1
Heating: Oil, Baseboard
Home Style: New Englander
Lot Size: 105.10 Acres
Roof Type: Metal, Standing Seam
Stories: 3.5
Taxes: $32,646
Year Built: 1988

Amenities

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
Deck
Garden Space
Guest House
Natural Shade
Outbuilding
Shed

Feature Descriptions

Appliances: Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer, Wine Cooler
Baths 1/2: 2
Baths 3/4: 2
Baths Full: 2
Color: White
Construction: Post and Beam, Wood Frame, Clapboard Exterior
Construction Status: Existing
Days on Site: 14
Driveway: Gravel
Electric: Circuit Breaker(s)
Equipment: Wood Stove
Exterior: Post and Beam, Wood Frame, Clapboard Exterior
Flood Zone: Unknown
Flooring: Tile, Wood
Foundation: Concrete
Lot: Country Setting, Horse/Animal Farm, Field/Pasture, Landscaped, Level, Recreational, Sloping, Stream, Trail/Near Trail, View, Walking Trails, Water View, Wetlands, Wooded, Adjoins St/Nat'l Forest, Near Country Club, Near Golf Course, Near Paths, Near Shopping, Near Skiin
Number of Rooms: 15
Parking: Driveway, Garage
Road Frontage: 1499
Roads: Public
Sewer: Private, Septic
Sq. Ft. Above Grade Finished: 4843
Sq. Ft. Total Finished: 4843
Total Stories: 3.5
Water: Drilled Well
Zoning: Residential

Room Sizes

Eat-in Kitchen: 15x14 Level - 1
Living Room: 34x19 Level - 1
Dining Room: 16x14 Level - 1
Family Room: 19x17 Level - 1
Laundry Room: 7x6 Level - 1
Bedroom: 14x13 Level - 1
Primary Bedroom: 15x15 Level - 2
Bedroom: 14x12 Level - 2
Bedroom: 12x11 Level - 2
Bedroom: 14x11 Level - 2
Library: 11x11 Level - 2
Loft: 19x11 Level - 3

Local Schools

High School: Woodstock Senior UHSD #4
Middle School: Woodstock Union Middle Sch
Elementary School: Woodstock Elementary School
School District: Windsor Central

Listed By / Shown By

Listed By

Agency Name: Snyder Donegan Real Estate Group
Agency Contact: Cell: 603-443-0044
Agent Name: David Donegan

Shown By

Agent Name: Patrick Cooper
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 10,523.92 per month $6,899.26 Principal & Interest $2,720.50 Property Tax $904.17 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 06/10/2026. The listing information on this page last changed on 06/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 06/10/2026 12:00:34 AM EST) or MLSPIN MLS (last updated Tue 06/09/2026 11:38:25 PM EST) or Prime MLS (last updated Tue 06/09/2026 11:33:35 PM EST) or MREIS (last updated Tue 06/09/2026 11:55:12 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 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 2026-06-09 23:33:35

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