66 Hollow Farm Road, Woodstock, VT, 05091 | $2,900,000

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.

Features

  • Rooms: 15
  • Bedrooms: 5
  • Baths: 2 full / 1 three-quarter / 1 half
  • Style: New Englander
  • Year Built: 1988
  • Garage: 1-car Garage
  • Heating: Oil,Baseboard
  • Cooling: None
  • Basement: Concrete Floor,Storage Space
  • Approx Sq. Feet: 4,843
  • Acreage: 105.1
  • Est. Taxes: $32,646
  • Lot Desc: 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
  • Elem. School: Woodstock Elementary School
  • Middle School: Woodstock Union Middle Sch
  • High School: Woodstock Senior UHSD #4
  • School District: Windsor Central
  • MLS#: 5091062
  • Website: https://www.raveis.com
    /eprop/5091062/66hollowfarmroad_woodstock_vt?source=qrflyer
©2026 New England Real Estate Network, 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 PrimMLS. 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 7/27/2026

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66 Hollow Farm Road, Woodstock, VT, 05091

$2,900,000

Isabel Villagomez

Sales Associate

William Raveis Real Estate

Phone: 203.570.8611

Isabel.Villagomez@raveis.com

Joseph Mollica

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.952.8600

Joseph.Mollica@raveis.com

NMLS Mortgage Loan Originator ID 130058

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,320,000 $2,320,000 $2,320,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.250% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.165% 6.361% 6.183%
Monthly Tax Payment $2,721 $2,721 $2,721
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $13,173 $14,285 $19,577
Total Monthly Payment $16,018 $17,130 $22,422

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.