159 Winhall Hollow Road Winhall, VT $ 5,575,000
159 Winhall Hollow Road
$ 5,575,000
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159 Winhall Hollow Road

Winhall, VT, 05340
$ 5,575,000
Bedrooms7 Baths9.1 Sq 9,915

Monthly Estimate*

$ 35,201

Listed by Kim Morgan-Wohler, Wohler Realty Group, 802-297-7600, kimwohler@wohlerrealtygroup.com
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Single Family Home for sale in Winhall, VT

for $5,575,000 with 7 bedrooms and 9 full baths, 1 half bath. This 9,915 square foot home was built in 2002 on a lot size of 42.93.

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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Single Family Active

Price

$ 5,575,000

Bedrooms

7

Full Bath

9

Half Bath

1

Property Type

Single Family

Taxes

$ 0

Style

Freestanding,Multi-Level,New Englander,Tri-Level

Lot Size

42.93

Year Built

2002

Town/City

Winhall

County/Region

Bennington

MLS | Web ID

5104104

Features
Interior
Basement Description Concrete Concrete Floor Full Storage Space Unfinished
Basement Yes
Beds 7
Total Rooms 18
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General
Road Frontage Yes
Sewer 1000 Gallon Septic
Heating Propane Baseboard Hot Water
Cooling Central AC
Utilities Cable Telephone at Site
Roof Asphalt Shingle
Garage Yes
Flood Zone No
Zoning Rural
3/4 Baths 0
Full Baths 9
Half Baths 1
Bathrooms 10
Year Built 2002
Electric Underground
Style Freestanding Multi-Level New Englander Tri-Level
Stories Count 3
Type Single Family
Property Condition Existing
Tax Year 2025
Status Detail 0
Covenants Unknown
Construction Materials Wood Frame Wood Exterior
Directions Route 30 in Winhall to Winhall Hollow Road. No Drive-ins without broker appointment. Property is occupied.
High School Choice
City Winhall
School District Choice
Seasonal No
Elementary School Choice
Middle School Choice
DOM 4
Price Per Sq Ft Total AG 562.28
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Exterior
Lot Features Country Setting Field/Pasture Landscaped Level Mountain View Open Other Secluded View Walking Trails Wooded Mountain Near Skiing Private
Driveway Gravel
Lot Size Area 42.93
Water Source Drilled Well
Garage Capacity 5
Foundation Concrete
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* Excluded Features
List By
Kim Morgan-Wohler

Listing Agent

Wohler Realty Group

Broker

(802) 297-7600

Phone

kimwohler@wohlerrealtygroup.com

Email

Affordability Calculator

$35,201
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Monthly Principal & Interest
$35,201
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1784809 Elementary School
449202 Middle School
Choice High School High School
Pricing History
DatePricePrice ChangeDescription
8/8/2026$5,575,000 Listed Price

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159 Winhall Hollow Road, Winhall, VT, 05340 is a Single Family Home for sale at $5,575,000 with 9,915 sqft and a lot size of 42.93. 159 Winhall Hollow Road has 7 bedrooms, 9.1 baths, and was built in 2002. The property's zip code is 05340 which is in Winhall, VT