Views
Address
159 Winhall Hollow Road, Winhall, VT
Price
$ 5,575,000
Property Attributes
- MLS#5104104
- TypeSingle Family
- Listing Status Active
- CountyBENNINGTON
- CityWinhall
- AreaBennington
- Zip05340
- StyleFreestanding,Multi-Level,New Englander,Tri-Level
- Year Built2002
- Price$ 5,575,000
- Bedrooms7
- Full Bathrooms9
- Half Bathrooms1
- Sqr Footage9915
- Lot Size42.93 Acres
Data Source:
PrimeMLS
Property 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
| Elementary School | Middle School | High School |
|---|---|---|
| Choice Elementary School | Choice Middle School | Choice High School |
| Price History | |
|---|---|
| 8/8/2026 | Listed $5,575,000 |
General Features
| 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 |
| 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 |
| Documents Available | Deed,Property Disclosure,Tax Map,Town Approvals |
| Property Condition | Existing |
| Tax Year | 2025 |
| Fuel Company | Suburban |
| 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 |
| Property Class | Residential |
| School District | Choice |
| Seasonal | No |
| Elementary School | Choice |
| Middle School | Choice |
| DOM | 42 |
| Price Per Sq Ft Total AG | 562.28 |
| Last Updated | 08/11/2026 16:18:11 |
Interior Features
| Basement Description | Concrete,Concrete Floor,Full,Storage Space,Unfinished |
|---|---|
| Basement | Yes |
| Beds | 7 |
| Total Rooms | 18 |
| Internet | Cable Internet |
| Total Finished Area | 9915 |
| Basement Access Type | Interior |
Exterior Features
| 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 |
| Road Frontage Length | 2034 |
| Road Frontage Type | Public Maintained Road |
| Surveyed | Yes |
| Lot Size Square Feet | 1870031 |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 05340
Statistics provided by Inside Real Estate
Price
Year Built
Visits
Massachusetts MLS Property Info Network (MLSPIN) - The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and
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. Data last updated September 21, 2026 7:39 AM UTC
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
