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  • Listed by: Snyder Donegan Real Estate Group • David Donegan • 802-457-2600
    Bought with: LandVest, Inc/Woodstock
    $2,460,000

    66 Hollow Farm Road, Woodstock, VT 05091

    5beds
    4,843sqft
    Single Family Residence
    Built in 1988
    105.1 Acres Lot
    $2,460,600 Zestimate®
    $508/sqft
    $6,243 Estimated rent

    Home value

    $2,460,600

    $2.26M - $2.68M

    $6,243/mo

    Zestimate® history
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    What's special

    Generous dining space nearbyUpdated main houseOpen-concept main levelMature landscapingLarge level lawnsAbundant natural light
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    David Donegan,

    Snyder Donegan Real Estate Group Cell:603-443-0044

    Bought with:

    T Story Jenks

    LandVest, Inc/Woodstock

    Source: PrimeMLS,MLS#: 5091062MLS Logo

    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: $508/sqft
    • Tax assessed value: $1,217,200
    • Annual tax amount: $32,646
    • Date on market: 5/27/2026

    Price history

    DateEventPrice
    10/30/2026Sold$2,460,000-7.2%$508/sqft
    Source: PrimeMLS #5091062 Report a problem
    8/13/2026Price change$2,650,000-8.6%$547/sqft
    Source: PrimeMLS #5091062 Report a problem
    7/14/2026Price change$2,900,000-6.5%$599/sqft
    Source: PrimeMLS #5091062 Report a problem
    5/27/2026Listed for sale$3,100,000+23.6%$640/sqft
    Source: PrimeMLS #5091062 Report a problem
    4/29/2022Sold$2,508,000-12%$518/sqft
    Source: PrimeMLS #4885504 Report a problem
    12/13/2021Price change$2,850,000-10.9%$588/sqft
    Source: PrimeMLS #4885504 Report a problem
    10/4/2021Listed for sale$3,200,000$661/sqft
    Source: PrimeMLS #4885504 Report a problem

    Public tax history

    YearProperty taxesTax 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

    Neighborhood: 05091

    Nearby schools

    GreatSchools rating
    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.

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    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $2,460,600
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    +$49,212
    With Zillow Showcase(estimated)

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