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Single family home for sale at 66 Hollow Farm Rd, Woodstock, VT 05091 | MLS# 5091062 | Listing updated on 2026-09-16
Photo 1 of Single family home for sale at 66 Hollow Farm Rd, Woodstock, VT 05091 | MLS# 5091062 | Listing updated on 2026-09-16
Photo 2 of Single family home for sale at 66 Hollow Farm Rd, Woodstock, VT 05091 | MLS# 5091062 | Listing updated on 2026-09-16
Photo 3 of Single family home for sale at 66 Hollow Farm Rd, Woodstock, VT 05091 | MLS# 5091062 | Listing updated on 2026-09-16
Photo 4 of Single family home for sale at 66 Hollow Farm Rd, Woodstock, VT 05091 | MLS# 5091062 | Listing updated on 2026-09-16
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Listed by: David Donegan | Snyder Donegan Real Estate Group (802) 457-2600

$2,650,000

Monthly Est:$13,190

  • Beds Icon5 Beds
  • Beds Icon
    4 Baths
  • Beds Icon4,843sqft

66 Hollow Farm Rd, Woodstock, VT 05091

$13,190/moEst:

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  • Single Family Residence

  • Built in 1988

  • $-- HOA

  • 105.1 acres lot

  • $547/sq.ft

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.

  • Houzeo last checked: 6 hours ago
  • Listing updated: September 16, 2026 at 2:06 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5091062 NEREN/Prime MLS-NH

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Windsor County

  • City

    Woodstock

  • Neighborhood

    --

  • Year Built

    1988

  • HOA Fees

    -

  • Finished Area

    4,843 sqft

  • Lot Size

    105.1 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5091062

  • MLS Status

    (31) Under Contract - Active Under Contract

  • Days on Market

    135

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 4

Interior

  • Sewer

    Private, Septic Tank

  • Interior Features

    Dining Area, In Law/adu, 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

  • Appliances

    Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer, Wine Cooler

  • Exterior Features

    Deck, Garden, Guest House, Natural Shade, Outbuilding, Shed

  • Flooring

    Tile, Wood

  • Cooling

    None

  • Heating

    Oil, Baseboard

Construction

  • Year Built

    Year Built: 1988

  • Home type

    Single Family Residence

  • Property Condition

    Existing

  • Foundation Details

    Concrete

  • Architectural Style

    New Englander

  • Roof

    Metal, Standing Seam

  • Construction Materials

    Post And Beam, Wood Frame, Clapboard

Utilities & Energy

  • Water Source

    Drilled Well

  • Utilities

    Other

  • Basement

    Concrete Floor, Storage Space

  • Parking Features

    Driveway, Garage

  • Electric

    Circuit Breakers

Other Features

  • Lot Features

    Country 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

Price History

DateEventPrice

08/12/2026

Source: mls_logoNEREN/Prime MLS-NH #5091062

Contingent (Active Under Contract)

$2,650,000 -8.62%

$547/sqft

07/13/2026

Source: mls_logoNEREN/Prime MLS-NH #5091062

Listed for Sale

$2,900,000

$599/sqft

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Based on information from PrimeMLS Inc. through Oct 09, 2026, 02:32PM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Oct 09, 2026, 02:32PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group