# 66 Hollow Farm Road, Woodstock, VT 05091

> **TL;DR:** 5bd/6ba single family, $3,100,000 ($640/sqft), built 1988, 4,843 sqft. Est. $13,433/mo. Listed 28 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $3,100,000 |
| Price/sqft | $640 |
| Bedrooms | 5 |
| Bathrooms | 2 full, 2 half |
| Square Feet | 4,843 |
| Year Built | 1988 |
| Lot Size | 4,578,156 sqft (105.10 acres) |
| Stories | 4 |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 28 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $13,433 |
| **Total** | **$13,433** |

## Nearby Schools

- **Elementary:** Woodstock Elementary School
- **Middle:** Woodstock Union Middle Sch
- **High:** Woodstock Senior UHSD #4

## Property Highlights

- Built in 1988
- 105.10 acre lot
- 4 stories

## Description

### Agent 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.

## Location

- **Address:** 66 Hollow Farm Road, Woodstock, VT 05091
- **County:** VT-Windsor
- **Coordinates:** 43.56896766, -72.61960471
- **Google Maps:** https://www.google.com/maps?q=43.56896766,-72.61960471

## Virtual Tour & Media

- **Video Tour:** https://my.matterport.com/show/?m=fEZK5meYqt6

## Listing Agent

- **Name:** David Donegan
- **Brokerage:** Snyder Donegan Real Estate Group
- **Phone:** (802) 457-2600
- **Email:** partners@snyderdonegan.com

## Primary Photo

![66 Hollow Farm Road - Primary Photo](http://lh.rdcpix.com/0ffc94feb41b9ddcd68b1f7958b1553fl-f4106671653r.jpg)

*58 total photos available on [listing page](https://www.propertysimple.com/listing/66-hollow-farm-road-woodstock-vt-05091-5091062)*

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**MLS#:** 5091062 | **Updated:** 2026-06-25
**Source:** listhub

*Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/66-hollow-farm-road-woodstock-vt-05091-5091062)

---

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