$1,200,000
 $6,442 est/mo Sourced by Back At You

109 Winhall Hollow Road,Winhall, VT 05340

Winhall, VT 05340

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Description

Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a homeit is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling that masterfully blends industrial strength with warm, natural aesthetics. Its bold, dark-bronze standing seam metal exterior provides a sleek, low-maintenance finish that stands out against the lush Vermont landscape. The upper-level living space features a massive wall of glass that opens onto a spacious deck, offering a one-of-a-kind vantage point to enjoy your morning coffee while scouting the ski conditions across the valley. Complementing the living quarters, the ground floor offers high-clearance multi-functional space, perfect for a professional-grade workshop, gear room, or housing a full fleet of UTVs and mountain bikes. Beyond the residence, the land has been transformed into a premier recreational paradise. You can navigate professionally designed and carved mountain bike trails that wind through the expansive 23.5-acre forest. Below the main house, a vast, rolling meadow leads to a custom stone firepit areathe ultimate destination for après-bike gatherings under the stars. Located just minutes from Stratton Mountain Resort, this estate offers a rare combination of architectural sophistication and private access to the best of the Vermont outdoors.This property is also primed for future expansion and the creation of a grander mountain estate. The septic system was specifically built to accommodate a new five-bedroom house, and comprehensive plans are available for viewing for the proposed home. Representing the very best of the Vermont lifestyle, this offering provides both a turnkey adventure hub and a ready-to-build canvas for your dream residence.

Details

MLS #5081867
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
Status(10) Active - Active
Year2020
Days On Site143
Listing Provided ByFour Seasons Sotheby's Int'l Realty | Margaret McMahon

Features

Bath(s) 1 Total
Garage1
Story(s)2
Zoningresidential
Acreage23.50

Interior

Rooms Total4
CoolingMini Split
HeatingRadiant Floor

Exterior

RoofMetal
Construction MaterialsWood Frame
Foundation DetailsConcrete
Lot FeaturesMountain View, Wooded

Parking

Garage Yes / NoYes

Utilities

UtilitiesCable Available
ElectricUnderground
SewerSeptic Tank

Taxes

Tax Annual Amount10467.38
Tax Year2026

Area Information

StateVT
CountyBennington
CityWinhall
Zip Code05340
AreaVT Bennington
School DistrictChoice
Elementary SchoolChoice
High SchoolChoice
Listing VS Median (in 05340)
Price:
$1,200,000
low | high
Med:
$0
On site:
143
low | high
Med:
Sourced by Back At You

Market Activity 05340

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Learn More About This Property

StateVT
CountyBennington
CityWinhall
Zip Code05340
AreaVT Bennington
School DistrictChoice
Elementary SchoolChoice
High SchoolChoice
Listing VS Median (in 05340)
Price:
$1,200,000
low | high
Med:
$0
On site:
143
low | high
Med:
Sourced by Back At You
Nearby Listings (Within 1/2 mile)
Price: $900K - $1.5M
sqft: 0 - 0
Nearby Listings Property ImageNearby Listings Details
Winhall Hollow Road Property Photo 1
$825,000
Winhall Hollow Road
Winhall, VT 05340
159 Winhall Hollow Road Property Photo 1
$5,575,000
159 Winhall Hollow Road
Winhall, VT 05340
11 Stratton View Road Property Photo 1
$675,000
11 Stratton View Road
Winhall, VT 05340
Listing Updated: July 28, 2026 at 1:16:05 PM PDT