The Hollow Rd

Winhall, VT 05340

$825,000
Price
3,380,255 / 77.60
Lot Size / Acres
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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.
  1. Listed by Trent Stephens • Wohler Realty Group

Property Details for The Hollow Road

Zoning
RRA
LISTING UPDATED: 03/17/2026 07:25 PM

Property Details for The Hollow Road

StatusActive
MLS #5079556
Days on Market8
Taxes$9,672 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeLand
MLS TypeLand
Year Built-
Lot Size77.60 AC
CountyBennington County
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Location

Listing Courtesy of Wohler Realty Group
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Building Information for The Hollow Road

Lot Size77.60 AC

Payment Calculator

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$4,810 per month

30 year fixed, 6.11% Interest

Principal and Interest

$4,004

Property Taxes

$806

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for The Hollow Road

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
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

DateEvent & SourcePriceAppreciation
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—
DateEvent & SourcePrice
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, Compass often displays two records for one sale: the MLS record and the public record.

Schools near The Hollow Road

Rating
School
Type
Grades
Distance
Mountain School At Winhall
Private - K to 8
Rating
School
Distance
Mountain School At Winhall
PrivateK to 8

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 8 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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 03/24/2026 06:28 PM