95 Winhall Hollow Rd

6,721 Sq. Ft.
$335 / Sq. Ft.
6,721
Sq. Ft.
$335
per Sq. Ft.

Description

Nestled on 23 acres of secluded natural beauty with breathtaking mountain vistas, this custom-crafted estate offers a blend of comfort and leisure. Equestrian enthusiasts will appreciate the horse facilities, including a three-stall barn and a fenced paddock. The barn's versatility allows it to serve as a party space or extra storage as needed. A spacious three-car attached garage complements the property, while a charming stone patio and perennial gardens create an outdoor oasis where relaxation...Nestled on 23 acres of secluded natural beauty with breathtaking mountain vistas, this custom-crafted estate offers a blend of comfort and leisure. Equestrian enthusiasts will appreciate the horse facilities, including a three-stall barn and a fenced paddock. The barn's versatility allows it to serve as a party space or extra storage as needed. A spacious three-car attached garage complements the property, while a charming stone patio and perennial gardens create an outdoor oasis where relaxation and functionality harmonize. Step indoors, and you'll find a home filled with exquisite features. The kitchen is a culinary masterpiece, the great room boasts a stone fireplace, and the billiard room invites friendly competition. The residence features high ceilings throughout and boasts seven ensuite bedrooms, ensuring maximum comfort and privacy for residents and guests alike. The inviting three-season porch hints at opportunities for entertaining in this private retreat. Conveniently located near Stratton, Bromley, and Magic resorts, this property is a dream for winter sports enthusiasts. It embodies a tranquil mountain lifestyle, seamlessly blending natural beauty with the comforts of upscale living.
  1. Listed by Kevin Moran • Four Seasons Sotheby's Int'l Realty

Sold By Four Seasons Sotheby's Int'l Realty

Property Details for 95 Winhall Hollow Road

Zoning
Residential
LISTING CLOSED: 11/03/2023 12:00 AM

Property Details for 95 Winhall Hollow Road

StatusClosed
MLS #4968392
Days on Market18
Taxes$37,341 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built2001
Lot Size23.00 AC / 1,001,880 SF
CountyBennington County

Location

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Building Information for 95 Winhall Hollow Road

Stories2Year Built2001Building Size-Lot Size23.00 AC / 1,001,880 SF

Payment Calculator

$14,548 per month

30 year fixed, 6.55% Interest

Principal and Interest

$11,436

Property Taxes

$3,112

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 95 Winhall Hollow Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: Route 30 to Winhall Hollow Road. No Drive by's
  • Latitude: 43.151903925839527
  • Longitude: -72.891733423278808
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05340
Taxes and HOA Information
  • SPAN Number: 771-245-10702
  • Tax - Gross Amount: $37,341.05
  • Tax Year: 2023
  • Taxes TBD: No
School Information
  • School - High: Choice
  • School - District: Winhall School District
  • School - Elementary: Choice
  • School - Middle/Jr: Choice
Parking
  • Garage: Yes
  • Garage Capacity: 3.00
  • Driveway: Circular, Gravel
Virtual Tour
Property
Lot Information
  • Common Land Acres: 0.0
  • Lot - Sqft: 1001880.0
  • Lot Size Acres: 23.0
  • Road Frontage Length: 700.0
  • Square Feet Apx Finished Above Grade: 5641.0
  • Square Feet Apx Finished AG Source: Public Records
  • Square Feet Apx Finished Below Grade: 1080.0
  • Square Feet Apx Finished BG Source: Public Records
  • Square Feet Apx Total: 7321.0
  • Square Feet Apx Total Finished: 6721.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished AG Source: Public Records
  • Square Feet Apx Unfinished Below Grade: 600.0
  • Square Feet Apx Unfinished BG Source: Other
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • Foundation: Concrete
  • PreConstruction: No
  • Resort: No
  • Suitable Use: Farm - Horse/Animal, Mixed Use, Recreation, Residential
  • Surveyed: Yes
  • Year Built: 2001
Utilities
  • Electric Company: GMP
  • Fuel Company: Haskins
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Utilities: Gas - LP/Bottle
Interior and Exterior Features
Exterior Features
  • Color: White
  • Features - Exterior: Barn, Fence - Full, Fence - Partial, Outbuilding, Patio, Porch - Covered, Porch - Screened, Stable(s)
  • Roads: Public
  • Roof: Shingle
Interior Features
  • Appliances: Cooktop - Down-Draft, Dishwasher, Disposal, Dryer, Microwave, Oven - Double, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Other, Partially Finished, Stairs - Interior
  • Baths - Total: 10
  • Baths - Full: 4
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 5
  • Rooms - Total: 17
  • Rooms: Level 1: Level 1: Dining Room, Level 1: Kitchen - Eat-in, Level 1: Laundry Room, Level 1: Living Room, Level 1: Primary Bedroom, Level 1: Mudroom, Level 1: Other, Level 1: Rec Room, Level 1: Sunroom
  • Rooms: Level B: Level B: Other, Level B: Playroom
  • Bedrooms - Total: 7
  • Equipment: Humidifier, Satellite Dish, Security System, Smoke Detector
  • Features - Interior: Bar, Blinds, Cedar Closet, Ceiling Fan, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 1, Primary BR w/ BA, Sauna, Walk-in Closet, Walk-in Pantry, Wet Bar
  • Flooring: Carpet, Tile
  • Heat Fuel: Gas - LP/Bottle
  • Heating: Baseboard, Hot Water, Multi Zone
  • Cooling: Multi Zone
  • Total Stories: 2
Room Information
Room 1
  • Room Dimensions: 9x8
  • Room Level: 1
  • Room Type: Mudroom
Room 2
  • Room Dimensions: 5x7
  • Room Level: 1
  • Room Type: Laundry Room
Room 3
  • Room Dimensions: 16x24
  • Room Level: 1
  • Room Type: Kitchen - Eat-in
Room 4
  • Room Dimensions: 16x20
  • Room Level: 1
  • Room Type: Dining Room
Room 5
  • Room Dimensions: 14x15
  • Room Level: 1
  • Room Type: Sunroom
Room 6
  • Room Dimensions: 23x27
  • Room Level: 1
  • Room Type: Living Room
Room 7
  • Room Dimensions: 18x21
  • Room Level: 1
  • Room Type: Rec Room
Room 8
  • Room Dimensions: 17x20
  • Room Level: 1
  • Room Type: Primary Bedroom
Room 9
  • Room Dimensions: 14x16
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 10
  • Room Dimensions: 16x16
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 11
  • Room Dimensions: 12x14
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 12
  • Room Dimensions: 14x14
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 13
  • Room Dimensions: 11x15
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 14
  • Room Dimensions: 15x15
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 15
  • Room Dimensions: 15x20
  • Room Level: Basement
  • Room Type: Playroom
Room 16
  • Room Dimensions: 10x20
  • Room Level: Basement
  • Room Type: Other
Room 17
  • Room Dimensions: 6x11
  • Room Level: 1
  • Room Type: Other
Rental
Rent Information
  • Rented: No

Property History for 95 Winhall Hollow Road

DateEvent & SourcePriceAppreciation
Nov 3, 2023

Sold (Public Record)

Public Record #1526040083

$2,250,000

+46.1% / yr

Nov 3, 2023

Sold

New England Real Estate Network #4968392

$2,250,000—
Sep 28, 2023

Pending

New England Real Estate Network #4968392

—
DateEvent & SourcePrice
11/03/2023

Sold (Public Record)

Public Record #1526040083

$2,250,000

+46.1% / yr

11/03/2023

Sold

New England Real Estate Network #4968392

$2,250,000
09/28/2023

Pending

New England Real Estate Network #4968392

—

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

Public Records for 95 Winhall Hollow Road

Taxable ValueLand$508,800Additions$1,197,500Total$1,706,300
Tax Record2024$47,776 ($3,981 / month)
Home Facts
Beds7Baths7.5Total Finished SqFt5,437 SqFtAbove Grade Finished SqFt5,437 SqFtUnfinished Basement SqFt1,720 SqFtLot Size1,024,096 SqFtStyleSingle Family ResidenceYear Built2001CountyBENNINGTONAPN(245)99058Fireplace TypeHas Fireplace

Schools near 95 Winhall Hollow Road

Rating
School
Type
Grades
Distance
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.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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 07/23/2026 07:14 AM