66 Hollow Farm Rd
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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...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.
- Listed by David Donegan • Snyder Donegan Real Estate Group • Cell: 603-443-0044
Property Details for 66 Hollow Farm Road
Zoning
Residential
LISTING UPDATED: 05/27/2026 01:55 PM
Property Details for 66 Hollow Farm Road
| Status | Active |
|---|---|
| MLS # | 5091062 |
| Days on Market | 7 |
| Taxes | $32,646 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Residential / Single Family |
| Year Built | 1988 |
| Lot Size | 105.10 AC / 4,578,156 SF |
| County | Windsor County |
Location
Listing Courtesy of Snyder Donegan Real Estate Group
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Building Information for 66 Hollow Farm Road
Stories3Year Built1988Building Size-Lot Size105.10 AC / 4,578,156 SF
Payment Calculator
$18,168 per month
30 year fixed, 6.36% Interest
Principal and Interest
$15,448
Property Taxes
$2,721
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 66 Hollow Farm Road
Summary
Location and General Information
- City: Woodstock
- County: VT-Windsor
- Directions: From Woodstock Village take Route 4 West. Enter Bridgewater village and take a left onto Blanchard Road/ Woolen Mill Lane, then go over the bridge. Take a left onto Curtis Hollow Road. Stay on Curtis Hollow for approximately 1.5 miles. Look for "Curtis Hollow Farm" sign, property on left.
- Latitude: 43.568967659159398
- Longitude: -72.619604711639440
- Road Frontage: Yes
- Seasonal: No
- State: VT
- Street Designation: Road
- Zip Code: 05091
Taxes and HOA Information
- SPAN Number: 786-250-11592
- Tax Year: 2026
- Taxes TBD: No
Parking
- Garage: Yes
- Garage Capacity: 1.00
- Driveway: Gravel
Property
Lot Information
- Lot Features: 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 Skiing, Near Snowmobile Trails, Near School(s), Private
- Lot Size Acres: 105.1
- Road Frontage Length: 1499.0
- Total Finished Area: 4843.0
- Above Grade Finished Area: 4843.0
- Above Grade Finished Area Source: Public Records
- Above Grade Unfinished Area: 0.0
- AboveGradeUnfinishedAreaSource: Public Records
- Below Grade Finished Area: 0.0
- Below Grade Finished Area Source: Public Records
- Below Grade Unfinished Area: 456.0
- BelowGradeUnfinishedAreaSource: Estimated
- Lot Size Square Feet: 4578156.0
- Total Area: 5299.0
Property and Assessments
- Current Use: Yes
- Property Class: Residential
- Property Type: Single Family
- Construction Status: Existing
- Flood Zone: Unknown
- PreConstruction: No
- Surveyed: Yes
- Year Built: 1988
- School District: Windsor Central
- High School: Woodstock Senior UHSD #4
- Middle/Jr School: Woodstock Union Middle Sch
- Elementary School: Woodstock Elementary School
Utilities
- Electric: Circuit Breaker(s)
- Sewer: Private, Septic
- Water Source: Drilled Well
- Utilities: Other
- Internet: Fiber Optic Internet
Interior and Exterior Features
Exterior Features
- Color: White
- Construction Materials: Post and Beam, Wood Frame, Clapboard Exterior
- Roof: Metal, Standing Seam
Interior Features
- Appliances: Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer, Wine Cooler
- Basement: Yes
- Basement Access Type: Interior
- Basement Description: Concrete Floor, Storage Space
- Rooms: Level 1: Level 1: Bedroom, Level 1: Dining Room, Level 1: Eat-in Kitchen, Level 1: Family Room, Level 1: Laundry Room, Level 1: Living Room
- Rooms: Level 2: Level 2: Bedroom, Level 2: Library, Level 2: Primary Bedroom
- Rooms: Level 3: Level 3: Loft
- Flooring: Tile, Wood
- Heating: Oil, Baseboard
- Cooling: None
- Total Stories: 3.5
- Rooms Total: 15
- Bathrooms Full: 2
- Bathrooms Half: 2
- Bathrooms One Quarter: 0
- Bathrooms Three Quarter: 2
- Bedrooms Total: 5
- Bathrooms Total: 6
Room Information
Room 1
- Room Dimensions: 15x14
- Room Level: 1
- Room Type: Eat-in Kitchen
Room 2
- Room Dimensions: 34x19
- Room Level: 1
- Room Type: Living Room
Room 3
- Room Dimensions: 16x14
- Room Level: 1
- Room Type: Dining Room
Room 4
- Room Dimensions: 19x17
- Room Level: 1
- Room Type: Family Room
Room 5
- Room Dimensions: 7x6
- Room Level: 1
- Room Type: Laundry Room
Room 6
- Room Dimensions: 14x13
- Room Level: 1
- Room Type: Bedroom
Room 7
- Room Dimensions: 15x15
- Room Level: 2
- Room Type: Primary Bedroom
Room 8
- Room Dimensions: 14x12
- Room Level: 2
- Room Type: Bedroom
Room 9
- Room Dimensions: 12x11
- Room Level: 2
- Room Type: Bedroom
Room 10
- Room Dimensions: 14x11
- Room Level: 2
- Room Type: Bedroom
Room 11
- Room Dimensions: 11x11
- Room Level: 2
- Room Type: Library
Room 12
- Room Dimensions: 19x11
- Room Level: 3
- Room Type: Loft
Property History for 66 Hollow Farm Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 27, 2026 | Listed (Active) New England Real Estate Network #5091062 | $3,100,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/27/2026 | Listed (Active) New England Real Estate Network #5091062 | $3,100,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 66 Hollow Farm Road
Taxable ValueLand$536,500Additions$680,700Total$1,217,200
Tax Record2022$30,045 ($2,504 / month)
Home Facts
Lot Size3,968,752 SqFtStyleMulti-Family Dwelling (2-4)CountyWINDSORAPN(250) 10.02.05
Schools near 66 Hollow Farm Road
This home is within Windsor Central Unified Union School District.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 6 | |||
| Public - | 7 to 12 |
Rating | School | Distance |
|---|---|---|
Woodstock Elementary School PublicPK to 6 | ||
Woodstock Senior Uhsd #4 Public7 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of Snyder Donegan Real Estate Group
Copyright 2026 PrimeMLS, Inc. 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 06/04/2026 08:30 AM
