109 Winhall Hollow Rd

Winhall, VT 05340

$1,200,000
Price
—
Beds
950 Sq. Ft.
$1,263 / Sq. Ft.
950
Sq. Ft.
$1,263
per Sq. Ft.
Get preapproved with Rocket Mortgage1

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 home—it 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...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 home—it 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 area—the 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.
  1. Listed by Margaret McMahon • Four Seasons Sotheby's Int'l Realty
  2. Listed by Robin Apps • Four Seasons Sotheby's Int'l Realty

Property Details for 109 Winhall Hollow Road

Zoning
residential
LISTING UPDATED: 04/04/2026 10:10 PM

Property Details for 109 Winhall Hollow Road

StatusActive
MLS #5081867
Days on Market4
Taxes$10,467 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2020
Lot Size23.50 AC / 1,023,660 SF
CountyBennington County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Four Seasons Sotheby's Int'l Realty
Add your commute

Building Information for 109 Winhall Hollow Road

Stories2Year Built2020Building Size-Lot Size23.50 AC / 1,023,660 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$6,915 per month

30 year fixed, 6.46% Interest

Principal and Interest

$6,043

Property Taxes

$872

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 109 Winhall Hollow Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: From Route 30, take a right onto winhall hollow road, follow approximately a mile, property will be on the left.
  • Latitude: 43.153349500002122
  • Longitude: -72.895666089965815
  • Road Frontage: No
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05340
Taxes and HOA Information
  • SPAN Number: 771-245-10773
  • Tax Year: 2026
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Mountain View, Wooded
  • Lot Size Acres: 23.5
  • Total Finished Area: 950.0
  • Above Grade Finished Area: 950.0
  • Above Grade Finished Area Source: Assessor
  • Above Grade Unfinished Area: 0.0
  • AboveGradeUnfinishedAreaSource: Other
  • Below Grade Finished Area: 0.0
  • Below Grade Finished Area Source: Assessor
  • Below Grade Unfinished Area: 0.0
  • BelowGradeUnfinishedAreaSource: Assessor
  • Lot Size Square Feet: 1023660.0
  • Total Area: 950.0
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: Yes
  • Surveyed: Unknown
  • Year Built: 2020
  • School District: Choice
  • High School: Choice
  • Middle/Jr School: Choice
  • Elementary School: Choice
Utilities
  • Electric: Underground
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Cable Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Construction Materials: Wood Frame
  • Roof: Metal
Interior Features
  • Basement: No
  • Rooms: Level 1: Level 1: Mudroom
  • Rooms: Level 2: Level 2: 3/4 Bathroom, Level 2: Kitchen/Living
  • Rooms: Level 3: Level 3: Loft
  • Heating: Radiant Floor
  • Cooling: Mini Split
  • Total Stories: 2.5
  • Rooms Total: 4
  • Bathrooms Full: 0
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 0
  • Bathrooms Total: 1
Room Information
Room 1
  • Room Level: 2
  • Room Type: Bathroom Three Quarter
Room 2
  • Room Level: 1
  • Room Type: Mudroom
Room 3
  • Room Level: 2
  • Room Type: Kitchen/Living
Room 4
  • Room Level: 3
  • Room Type: Loft

Property History for 109 Winhall Hollow Road

DateEvent & SourcePriceAppreciation
Apr 2, 2026

Listed (Active)

New England Real Estate Network #5081867

$1,200,000—
DateEvent & SourcePrice
04/02/2026

Listed (Active)

New England Real Estate Network #5081867

$1,200,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 109 Winhall Hollow Road

Rating
School
Type
Grades
Distance
Mountain School At Winhall
Private - K to 8
Rating
School
Distance
Mountain School At Winhall
PrivateK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 109 Winhall Hollow Road, Winhall, VT 05340

109 Winhall Hollow Road is a single family home for sale in Winhall, VT 05340. This property was listed for sale on April 2, 2026 by Four Seasons Sotheby's Int'l Realty, it's currently listed at $1,200,000. Nearby schools include Mountain School At Winhall. 109 Winhall Hollow Road is a 0-bed, 1-bath, 950 sqft single family home built in 2020.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Four Seasons Sotheby's Int'l Realty

Copyright 2026 PrimeMLS, Inc. 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 04/06/2026 01:29 PM