159 Winhall Hollow Road,Winhall, VT 05340
Winhall, VT 05340
Description
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
Details
| MLS # | 5104104 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | (10) Active - Active |
| Year | 2002 |
| Days On Site | 17 |
| Listing Provided By | Wohler Realty Group | Kim Morgan-Wohler |
Features
| Bed(s) | 7 |
|---|---|
| Bath(s) | 10 Total |
| Garage | 5 |
| Basement | Y |
| Story(s) | 3 |
| Zoning | Rural |
| Acreage | 42.93 |
Interior
| Rooms Total | 18 |
|---|---|
| Cooling | Central Air |
| Heating | Propane, Baseboard, Hot Water |
Exterior
| Roof | Asphalt Shingle |
|---|---|
| Construction Materials | Wood Frame, Wood |
| Foundation Details | Concrete |
| Lot Features | Country Setting, Pasture, Landscaped, Level, Mountain View, Open Lot, Other, Secluded, Views, Walking Trails, Wooded, Mountain, Near Skiing, Private |
Parking
| Garage Yes / No | Yes |
|---|
Utilities
| Utilities | Cable, Phone Connected |
|---|---|
| Electric | Underground |
| Sewer | 1000 Gallon, Septic Tank |
Taxes
| Tax Annual Amount | 58851 |
|---|---|
| Tax Year | 2025 |
Area Information
| State | VT |
|---|---|
| County | Bennington |
| City | Winhall |
| Zip Code | 05340 |
| Area | VT Bennington |
| School District | Choice |
| Elementary School | Choice |
| High School | Choice |
| Listing VS Median (in 05340) | |
Price: $5,575,000 low | high Med: $0 On site: 17 low | high Med: | |
Market Activity 05340
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Copyright 2026 PrimeMLS. 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.
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Learn More About This Property
| State | VT |
|---|---|
| County | Bennington |
| City | Winhall |
| Zip Code | 05340 |
| Area | VT Bennington |
| School District | Choice |
| Elementary School | Choice |
| High School | Choice |
| Listing VS Median (in 05340) | |
Price: $5,575,000 low | high Med: $0 On site: 17 low | high Med: | |
Copyright 2026 PrimeMLS. 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.
