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.
Property located across from the Red Fox Inn (see directions)
Home design
Property on Winhall Hollow Road in Winhall, VT
Utilities
Electric service available at the street
No public water listed
No public sewer listed
No internet service listed
Sale and tax history for Winhall Hollow Rd
Sale History
Tax History
Date
Event
Price
PrimeMLS #5079556
Mar 16, 2026
Listed
$825,000
PrimeMLS #4796882
Dec 9, 2020
Sold
$140,000
Dec 7, 2020
Pending
—
Oct 5, 2020
Contingent
—
May 28, 2020
Price Changed
$150,000
Mar 7, 2020
Listed
$175,000
+12
This special 4+/_ acre parcel is located in Winhall, Vermont. An amazing country setting with views of fields and barns. Cook Brook is across the street adding charm to the neighborhood. This is a gently sloping lot boardered by old stone walls. The swale abutting Winhall Hollow and South Rd could be an ideal spot for a pond. Ideally located to ski Stratton Mt (5 miles), Bromley or Magic Mt. This parcel has a Winhall Town permit for a 4 bedroom home. Owner/broker
PrimeMLS #4619661
Oct 26, 2018
Sold
$187,500
Oct 6, 2018
Contingent
—
Feb 28, 2018
Price Changed
$229,000
Feb 27, 2018
Relisted
—
Feb 22, 2018
Delisted
—
Feb 28, 2017
Listed
$259,000
This 24.9 acre site is composed of two abutting lots, #98 (12.5 A) and #1.11 (12.4A) with over 800 feet of road frontage on Winhall Hollow Road. The Winhall Hollow neighborhood has some of the nicer homes on larger parcels in the greater Stratton area. Current owner has had the septic system designed and permitted for a 5 bedroom home. A rough driveway has been installed, and from which as your walk into the lot the stunning view of Stratton Mountain opens up and becomes evident. The building site is well away from the road way and from which you do not see any other homes.
PrimeMLS #3002514
Aug 30, 2001
Sold
$235,000
Mar 19, 2001
Listed
$235,000
PrimeMLS #3006503
May 4, 2001
Sold
$125,000
Feb 15, 2001
Listed
$129,000
PrimeMLS #3077369
May 11, 2000
Sold
$105,000
Mar 12, 1999
Listed
$125,000
PrimeMLS #3077376
Nov 10, 1999
Sold
$102,500
Mar 15, 1999
Listed
$115,000
Year
Property tax
Land + Additions
Assessment*
2016
$16,692 (+0.6%)
$947,300
2015
$16,592
$947,300
2013
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
260 Acres
Year renovated
—
Finished Sq. Ft.
0
Unfinished Sq. Ft.
0
Total Sq. Ft.
0
Year built
—
Style
Vacant Land
County
Bennington County
APN
34210610246
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Mar 16, 2026.
Historical weather
Winhall, VT • 05340
Average low and high temperatures (°F)
22
11
26
12
42
25
53
34
59
44
72
55
77
61
73
55
68
51
57
40
42
30
29
16
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
96/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 4% for direct sun exposure in Winhall. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.5 hrs
6.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for Winhall Hollow Rd
$731,682
$93K under list price of $825K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $485K to $960K.