165 Winhall Hollow Rd

5,228 Sq. Ft.
$118 / Sq. Ft.
5,228
Sq. Ft.
$118
per Sq. Ft.

Description

Remarkable views of Stratton Mountain from this spacious five bedroom home on Winhall Hollow Road. Close to Recreation, schools shopping and Ski resort in your back yard. Setting is stunning in the tucked away location. Custom amenities through out house. The home is a pleasure to see and happy to show.Remarkable views of Stratton Mountain from this spacious five bedroom home on Winhall Hollow Road. Close to Recreation, schools shopping and Ski resort in your back yard. Setting is stunning in the tucked away location. Custom amenities through out house. The home is a pleasure to see and happy to show.
  1. Listed by Bob Maisey • Four Seasons Sotheby's Int'l Realty

Sold By TPW Real Estate

Property Details for 165 Winhall Hollow Road

Parking
Driveway, Garage
Zoning
Residential
LISTING CLOSED: 11/16/2018 12:00 AM

Property Details for 165 Winhall Hollow Road

StatusClosed
MLS #4639538
Days on Market481
Taxes$13,727 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1990
Lot Size8.89 AC / 387,248 SF
CountyBennington County

Location

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Building Information for 165 Winhall Hollow Road

Stories2Year Built1990Building Size-Lot Size8.89 AC / 387,248 SF

Payment Calculator

$4,270 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,126

Property Taxes

$1,144

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 165 Winhall Hollow Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: Winhall Hollow Road to 165 West of Red Fox Inn
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip: 05340
Taxes and HOA Information
  • SPAN Number: 77124511325
  • Tax - Gross Amount: $13,726.60
  • Tax Year: 2016
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 4.00
  • Driveway: Circular, Gravel
Property
Lot Information
  • Lot - Sqft: 387248.0
  • Lot Size Acres: 8.89
  • Road Frontage Length: 221.0
  • Square Feet Apx Finished Above Grade: 4628.0
  • Square Feet Apx Finished AG Source: Public Records
  • Square Feet Apx Finished Below Grade: 600.0
  • Square Feet Apx Finished BG Source: Public Records
  • Square Feet Apx Total: 7256.0
  • Square Feet Apx Total Finished: 5228.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished AG Source: Public Records
  • Square Feet Apx Unfinished Below Grade: 2028.0
  • Square Feet Apx Unfinished BG Source: Public Records
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: Unknown
  • Foundation: Concrete
  • PreConstruction: No
  • Resort: No
  • Surveyed: Yes
  • Year Built: 1990
Utilities
  • Electric: 200 Amp
  • Sewer: Septic
  • Utilities: Cable, DSL
Interior and Exterior Features
Exterior Features
  • Color: Yellow
  • Features - Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Laundry
  • Features - Exterior: Deck, Garden Space, Patio
  • Roads: Paved
  • Roof: Shingle - Asphalt
Interior Features
  • Appliances: Cooktop - Gas, Dishwasher, Dryer, Microwave, Oven - Wall, Range - Gas, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Partially Finished
  • Baths - Total: 5
  • Baths - Full: 3
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 1
  • Rooms - Total: 9
  • Rooms: Level 1: Level 1: Dining Room, Level 1: Foyer, Level 1: Kitchen, Level 1: Living Room, Level 1: Master Bedroom
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Bonus Room
  • Rooms: Level B: Level B: Office/Study
  • Bedrooms - Total: 5
  • Features - Interior: Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Screens/Equip, Fireplace - Wood, Master BR w/ BA, Natural Woodwork, Vaulted Ceiling, Walk-in Closet, Laundry - 1st Floor
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heat Fuel: Gas - LP/Bottle, Wood
  • Heating: Baseboard, Wood Boiler
  • Cooling: None
  • Total Stories: 2.5
Room Information
Room 1
  • Room Dimensions: 11x9
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 10x12
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 24x20
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Dimensions: 10x8
  • Room Level: 1
  • Room Type: Foyer
Room 5
  • Room Dimensions: 12x12
  • Room Level: 1
  • Room Type: Dining Room
Room 6
  • Room Dimensions: 15x15
  • Room Level: 1
  • Room Type: Master Bedroom
Room 7
  • Room Dimensions: 14x12
  • Room Level: Basement
  • Room Type: Office/Study
Room 8
  • Room Dimensions: 12x12
  • Room Level: 2
  • Room Type: Bedroom
Room 9
  • Room Dimensions: 10x10
  • Room Level: 2
  • Room Type: Bedroom
Room 10
  • Room Dimensions: 14x14
  • Room Level: 2
  • Room Type: Bedroom
Room 11
  • Room Dimensions: 12x12
  • Room Level: 2
  • Room Type: Bedroom
Room 12
  • Room Dimensions: 19x15
  • Room Level: 2
  • Room Type: Bonus Room

Property History for 165 Winhall Hollow Road

DateEvent & SourcePriceAppreciation
Nov 28, 2018

Sold (Public Record)

Public Record #635439858

$616,100—
Nov 16, 2018

Sold

New England Real Estate Network #4639538

$615,000—
Nov 16, 2018

Pending

New England Real Estate Network #4639538

—
DateEvent & SourcePrice
11/28/2018

Sold (Public Record)

Public Record #635439858

$616,100
11/16/2018

Sold

New England Real Estate Network #4639538

$615,000
11/16/2018

Pending

New England Real Estate Network #4639538

—

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

Public Records for 165 Winhall Hollow Road

Taxable ValueLand$448,200Additions$203,400Total$651,600
Tax Record2024$18,245 ($1,520 / month)
Home Facts
Beds5Baths3.5Total Finished SqFt4,628 SqFtAbove Grade Finished SqFt4,628 SqFtUnfinished Basement SqFt2,628 SqFtStories2Lot Size387,248 SqFtStyleSingle Family ResidenceYear Built1990CountyBENNINGTONAPN(245)01619Fireplace TypeHas Fireplace

Schools near 165 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.

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 01:49 PM