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$5,575,000
7 Days On Site

159 Winhall Hollow Road
Winhall, VT 05340

For Sale|Single Family Residence|Active
7
Beds
10
Total Baths
9
Full Baths
1
Partial Bath
9,915
SqFt
$562
/SqFt
2002
Built
County:
Bennington
Listing courtesy of Kim Morgan-Wohler of Wohler Realty Group

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159 Winhall Hollow Road159 Winhall Hollow Road159 Winhall Hollow Road159 Winhall Hollow Road
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Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of permanence here.Thoughtfully positioned for complete privacy, the 7 ensuite Bedroom/9.5 bath home possesses the scale, presence, & quiet grandeur reminiscent of New England's great legacy estates. Its architecture feels substantial yet entirely at home within its surroundings, balancing stately proportions and refined craftsmanship with the warmth and authenticity of a distinguished country property. Expansive lawns, pastoral vistas, mature trees, and distant mountain views create a magnificent natural setting on 42.93 acres, while the home stands as its centerpiece: elegant and enduring.The Main Residence features multiple gathering spaces, three fireplaces, beautiful wood floors, impeccable stonework, fine woodworking and upscale details. It's grand in scale, warm in spirit, and created for gathering. Meticulously crafted stone archways, wood beams and oversized timber mantels frame the hearths. A generous chef’s kitchen with premier appliances and custom design was conceived for those who appreciate the art of cooking and the pleasure of company. An extraordinary barn enhances the property with it's interior grand lodge room framed with reclaimed barn beams, a 2 story stone hearth, ideal for entertaining and apres ski fun, guest quarters with kitchen and 3 bay garage.This represents Vermont country living at its most distinguished a rare convergence of masterful craftsmanship, remarkable acreage, architectural character, and an incomparable natural setting. It's a home for generations to gather. Just 5 minutes to the Stratton Mountain Access Road,20 min to Manchester

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Listing Snapshot
Price 
$5,575,000
Days On Site 
7 Days
Bedrooms 
7
Inside Area (SqFt) 
9,915 sqft
Total Baths 
10
Full Baths 
9
Partial Baths 
1
Lot Size 
42.93 Acres
Year Built 
2002
MLS® Number 
5104104
Status 
Active
Property Tax 
$58,851
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
3 days agoListing updated with changes from the MLS®
7 days agoStatus changed to Active
7 days agoPrice changed to $5,575,000
a week agoListing first seen on site
General Features
Acres 
42.93
Garage 
Yes
Garage Spaces 
5
Number Of Stories 
3
Parking 
Gravel
Parking Spaces 
5
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Above 
9915
SqFt Total 
13012
Style 
FreestandingMulti-LevelNew EnglanderTri-Level
Utilities 
Cable Available
Water Source 
Well
Zoning 
Rural
Interior Features
Basement 
ConcreteFinishedFullUnfinishedStorage Space
Cooling 
Central Air
Electric 
Underground
Heating 
BaseboardHot WaterPropane
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Exterior Features
Construction Details 
Wood Siding
Lot Features 
LevelWoodedOpen LotLandscapedOtherSecludedPrivate
Roof 
Shingle
View 
Mountain(s)
Waterview 
Mountain(s)
Community Features
School District 
Choice
Schools
School District
Choice
Elementary School
Choice
Middle School
Choice
High School
Choice
Listing courtesy of Kim Morgan-Wohler 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 display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Last checked: 2026-08-14 10:48 PM UTC
Neighborhood & Commute
Source: Walkscore
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