The Hollow Road

Active

$825,000

3,380,255 Lot Size77.60 Acres

The Hollow Rd, Winhall, VT 05340

Est: $5,210/moGet pre-approved

LandProperty Type

77.60 acresLot Size

Description

Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on Winhall Hollow Road, the property sits across from the Red Fox Inn & Tavern and is only a short drive to...Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on Winhall Hollow Road, the property sits across from the Red Fox Inn & Tavern and is only a short drive to the Stratton Mountain access road, placing Stratton, Bromley, and Magic Mountain all within easy reach. The current owners originally purchased the property with subdivision potential in mind. While no formal subdivision approvals have been pursued, the property is located within Winhall’s Rural Residential/Agricultural zoning district, which may allow for subdivision subject to all required state and local permitting. Buyers interested in development should perform their own due diligence with the Town of Winhall and the State of Vermont regarding zoning, wastewater permitting, wetlands considerations, and any Act 250 requirements. A few basic soil test pits have been completed, but the land remains otherwise undeveloped. Whether you envision building a private Vermont retreat, exploring potential residential development, or simply enjoying the land for recreation, hunting, or long-term investment, this property offers a beautiful natural setting in one of Southern Vermont’s most desirable four-season locations.

205 days on Market

Listed by: Trent Stephens • Wohler Realty Group

Last updated: 03/17/2026 07:25 PM • Source: New England Real Estate Network, MLS#: 5079556

Location

Listing Courtesy of Wohler Realty Group

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$5,210 per month

30 year fixed, 7.03% Interest

Principal and Interest

$4,404

Property Taxes

$806

HOA Dues

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Property Information for The Hollow Road

Property Details

Taxes: $9,672 / year
MLS Type: Land
County: Bennington County
Zoning: RRA

Building Information

Lot Size: 77.60 AC

Summary

Location and General Information

City: Winhall
County: VT-Bennington

Directions: From Stratton Access Rd at 7-Eleven, go 0.2 mi on Route 30. Turn right onto Winhall Hollow Rd, continue 1.3 mi. Property on right across from Red Fox Inn.
Latitude: 43.156722125460625
Longitude: -72.892653340206763
Road Frontage: TBD
State: VT
Street Designation: Road
Zip Code: 05340

Taxes and HOA Information

SPAN Number: 77124510995
Tax Year: 2025

Taxes TBD: No

Property

Lot Information

Lot Features: Near Skiing, Rural, Mountain View, Wooded
Lot Size Acres: 77.6

Lot Size Square Feet: 3380256.0

Property and Assessments

Current Use: No
Property Class: Land

Easements: Unknown
Flood Zone: Land Only
Resort: No
Surveyed: No

Utilities

Electric: At Street
Sewer: None

Water Source: None
Utilities: None
Internet: None

Property History for The Hollow Road

Date	Event & Source	Price	Appreciation
Mar 16, 2026	Listed (Active) New England Real Estate Network #5079556	$825,000	—
Oct 26, 2018	Sold New England Real Estate Network #4619661	$187,500	—
Feb 22, 2017	Price Change New England Real Estate Network #4619661	$259,000	—
Feb 22, 2017	Listed (Active) New England Real Estate Network #4619661	$229,000	—
Jul 25, 2008	Listed (Active) New England Real Estate Network #3058105	$395,000	—
Jul 9, 2005	Listed (Active) New England Real Estate Network #3021075	$1,750,000	—

Date	Event & Source	Price
03/16/2026	Listed (Active) New England Real Estate Network #5079556	$825,000
10/26/2018	Sold New England Real Estate Network #4619661	$187,500
02/22/2017	Price Change New England Real Estate Network #4619661	$259,000
02/22/2017	Listed (Active) New England Real Estate Network #4619661	$229,000
07/25/2008	Listed (Active) New England Real Estate Network #3058105	$395,000
07/09/2005	Listed (Active) New England Real Estate Network #3021075	$1,750,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Schools near The Hollow Road


Rating	School	Type	Grades	Distance
NR	Mountain School At Winhall	Private - Nearby school	K to 8	0.5 mi


Rating	School	Distance
NR	Mountain School At Winhall PrivateK to 8 Nearby school	0.5 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about The Hollow Road, Winhall, VT 05340

The Hollow Road is a 77.60 ac of land for sale in Winhall, VT 05340. This property was listed for sale on March 16, 2026 by Wohler Realty Group, it's currently listed at $825,000. It has been on the market for a total of 205 days and was last sold on October 26, 2018. Nearby schools include Mountain School At Winhall. The Hollow Road is a 0-bed, 0-bath 77.60 ac of land on a 3,380,255 sq. ft. / 77.60 acres lot.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Wohler Realty Group

Copyright 2026 PrimeMLS, 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 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 10/07/2026 06:04 PM