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.
Active under contract
Listed by: Snyder Donegan Real Estate Group • David Donegan
Price cut: $250K (8/13)
$2,650,000
66 Hollow Farm Road, Woodstock, VT 05091
5beds
4,843sqft
Single Family Residence
Built in 1988
105.1 Acres Lot
$2,373,000 Zestimate®
$547/sqft
$-- HOA
What's special
Generous dining space nearbyUpdated main houseOpen-concept main levelMature landscapingLarge level lawnsAbundant natural light
- 122 days
- 1,203
- 101
Zillow last checked:
Listing updated:
Listed by:
David Donegan,
Snyder Donegan Real Estate Group Cell:603-443-0044
Source: PrimeMLS,MLS#: 5091062
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 2
- 3/4 bathrooms: 1
- 1/2 bathrooms: 1
Heating
- Oil, Baseboard
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer, Wine Cooler
- Laundry: 1st Floor Laundry
Features
- Dining Area, In-Law/ADU, In-Law Suite, Kitchen Island, Kitchen/Family, Kitchen/Living, Living/Dining, Primary BR w/ BA, Natural Light, Indoor Storage, Vaulted Ceiling(s)
- Flooring: Tile, Wood
- Windows: Skylight(s)
- Basement: Concrete Floor,Storage Space,Interior Entry
Interior area
- Total structure area: 5,299
- Total interior livable area: 4,843 sqft
- Finished area above ground: 4,843
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Gravel, Driveway, Garage
- Garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: 3.5
- Stories: 3.5
- Exterior features: Deck, Garden, Natural Shade, Shed
- Has view: Yes
- Waterfront features: Wetlands
- Frontage length: Road frontage: 1499
Lot
- Size: 105.1 Acres
- Features: Country Setting, Horse/Animal Farm, Field/Pasture, Landscaped, Level, Recreational, Sloped, Trail/Near Trail, Views, Walking Trails, Wooded, Adjoins St/Nat'l Forest, Near Country Club, Near Golf Course, Near Paths, Near Shopping, Near Skiing, Near Snowmobile Trails, Near School(s)
Details
- Additional structures: Guest House, Outbuilding
- Parcel number: 78625011592
- Zoning description: Residential
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: New Englander
- Property subtype: Single Family Residence
Materials
- Post and Beam, Wood Frame, Clapboard Exterior
- Foundation: Concrete
- Roof: Metal,Standing Seam
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Sewer, Septic Tank
- Utilities for property: Other
Community & HOA
Location
- Region: Woodstock
Financial & listing details
- Price per square foot: $547/sqft
- Tax assessed value: $1,217,200
- Annual tax amount: $32,646
- Date on market: 5/27/2026
Estimated market value
$2,373,000
$2.25M - $2.49M
$6,264/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/13/2026 | Price change | $2,650,000-8.6%$547/sqft |
Source: | ||
| 7/14/2026 | Price change | $2,900,000-6.5%$599/sqft |
Source: | ||
| 5/27/2026 | Listed for sale | $3,100,000+23.6%$640/sqft |
Source: | ||
| 4/29/2022 | Sold | $2,508,000-12%$518/sqft |
Source: | ||
| 12/13/2021 | Price change | $2,850,000-10.9%$588/sqft |
Source: | ||
| 10/4/2021 | Listed for sale | $3,200,000$661/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $34,847 | $1,217,200 |
| 2024 | -- | $1,217,200 |
| 2023 | -- | $1,217,200 |
| 2022 | -- | $1,217,200 |
| 2021 | -- | $1,217,200 |
| 2020 | -- | $1,217,200 |
| 2019 | -- | $1,217,200 |
| 2018 | -- | $1,217,200 |
| 2017 | -- | $1,217,200 |
| 2016 | -- | $1,217,200 +13248% |
| 2015 | -- | $9,119 +0.1% |
| 2014 | -- | $9,111 +0% |
| 2013 | -- | $9,109 0% |
| 2012 | -- | $9,112 +0% |
| 2011 | -- | $9,110 +0% |
| 2010 | -- | $9,108 0% |
| 2009 | -- | $9,109 -0.1% |
| 2008 | -- | $9,120 -0.1% |
| 2007 | -- | $9,129 +0.1% |
| 2006 | -- | $9,118 +25.5% |
| 2003 | $13,654 | $7,263 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 05091
Nearby schools
Schools provided by the listing agent
- Elementary: Woodstock Elementary School
- Middle: Woodstock Union Middle Sch
- High: Woodstock Senior UHSD #4
- District: Windsor Central
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.




