156 Winhall Hollow Road

Closed 10/3/18Virtual Tour
Closed 10/3/18Virtual Tour
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Sold
Last Sold Price
$495,000
2 beds1,517 sqft$326/sqft
156 Winhall Hollow Rd, Winhall, VT 05340
Single FamilyProperty Type
38.7 acresLot Size
1987Year Built
$326/sq ftPrice per sq ft
4 carsParking Spaces

Description

Equine perfection... 40 acres... pastoral setting wrapped in mountain views... pond... 125 X 70 Indoor Riding Arena with Permaflex (USEF recommended) footing... primary barn offers 13 matted box stalls each with easy hay drop, tack, office, wash stall, attached indoor...14 individual 3 -rail fenced paddocks... outdoor exercise paddock... the second barn offers 6 box-stalls... multiple outbuildings for bedding, equipment and tractor cover... 1000 bail storage options... Main Residence is a one bedroom...Equine perfection... 40 acres... pastoral setting wrapped in mountain views... pond... 125 X 70 Indoor Riding Arena with Permaflex (USEF recommended) footing... primary barn offers 13 matted box stalls each with easy hay drop, tack, office, wash stall, attached indoor...14 individual 3 -rail fenced paddocks... outdoor exercise paddock... the second barn offers 6 box-stalls... multiple outbuildings for bedding, equipment and tractor cover... 1000 bail storage options... Main Residence is a one bedroom Cottage converted from a barn (with existing foot print expansion) offers finished 1500 sf of open one level living and attached garage plus workshop or studio space. Truly a fine property that is ideal for the passionate horse lover... The property is registered in Vermont Current Use... a glorious building site is evident!

    Sold By Josiah Allen Real Estate, Inc.

    • Listed by: Laura Beckwith • Josiah Allen Real Estate, Inc.
    Listing closed: 10/03/2018 12:00 AM • Source: New England Real Estate Network, MLS#: 4643142

    Recent comparable sales

    Median sold price

    $485,000

    Avg days on market

    66

    Sale-to-list ratio

    93.8%

    Winhall, VT

    9 comparable properties found

    $485,000 | 3 Strattonwald Road, Winhall, VT 05340
    1/34
    1

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    3 Strattonwald Road, Winhall, VT 05340

    $426,000 | 46-48 Lower Taylor Hill Road, Winhall, VT 05340
    1/20
    2

    $426,000

    Sold 01/16/26

    2
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    1,798
    Square Feet
    1.9
    Acres

    46-48 Lower Taylor Hill Road, Winhall, VT 05340

    $445,000 | 163 Highway 30, Winhall, VT 05340
    1/23
    3

    $445,000

    Sold 09/16/25

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    1,590
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    0.93
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    163 Highway 30, Winhall, VT 05340

    $615,000 | 29 Burnt Hill Road, Winhall, VT 05340
    1/38
    4

    $615,000

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    Bedrooms
    1,500
    Square Feet
    1.09
    Acres

    29 Burnt Hill Road, Winhall, VT 05340

    $430,000 | 13 Lower Taylor Hill Road, Winhall, VT 05340
    1/25
    5

    $430,000

    Sold 03/26/25

    3
    Bedrooms
    1,716
    Square Feet
    0.56
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    13 Lower Taylor Hill Road, Winhall, VT 05340

    $560,000 | 35 Glendon Hills Road, Winhall, VT 05340
    1/33
    6

    $560,000

    Sold 09/26/25

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    1,400
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    1
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    35 Glendon Hills Road, Winhall, VT 05340

    $580,000 | 39 Todd Hill Road, Winhall, VT 05340
    1/34
    7

    $580,000

    Sold 10/26/24

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    1,484
    Square Feet
    1.3
    Acres

    39 Todd Hill Road, Winhall, VT 05340

    $370,000 | 8 Strattonwald Road, Winhall, VT 05340
    1/22
    8

    $370,000

    Sold 02/28/25

    3
    Bedrooms
    1,392
    Square Feet
    0.59
    Acres

    8 Strattonwald Road, Winhall, VT 05340

    $565,000 | 4 Pearl Buck Drive, Winhall, VT 05340
    1/35
    9

    $565,000

    Sold 06/18/26

    3
    Bedrooms
    1,455
    Square Feet
    2.01
    Acres

    4 Pearl Buck Drive, Winhall, VT 05340

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    $3,406 per month

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    Principal and Interest

    $2,516

    Property Taxes

    $890

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    Property Information for 156 Winhall Hollow Road

    Property Details
    • Taxes: $10,678 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Parking: Driveway, On-Site
    • Water Body Type: Pond
    • Waterfront Property: Yes
    • Zoning: Rural Residential
    Building Information
    • Stories: 1
    • Year Built: 1987
    • Lot Size: 38.70 AC / 1,685,772 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: RT 30 to Winhall Hollow Rd... to 156
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05340
    Taxes and HOA Information
    • SPAN Number: 77124512205
    • Tax - Gross Amount: $10,678.38
    • Tax Year: 2017
    • Taxes TBD: No
    School Information
    • School - High: Choice
    • School - Elementary: Choice
    • School - Middle/Jr: Choice
    Parking
    • Garage: Yes
    • Garage Capacity: 4.00
    • Driveway: Gravel
    Property
    Lot Information
    • Lot - Sqft: 1685772.0
    • Lot Size Acres: 38.7
    • Road Frontage Length: 2249.0
    • Square Feet Apx Finished Above Grade: 1517.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 1517.0
    • Square Feet Apx Total Finished: 1517.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete, Slab w/ Frost Wall
    • PreConstruction: No
    • Resort: No
    • Surveyed: Yes
    • Year Built: 1987
    Utilities
    • Electric: Other
    • Sewer: Septic
    Interior and Exterior Features
    Exterior Features
    • Features - Exterior: Barn, Fence - Full, Outbuilding, Shed, Storage
    • Roads: Paved, Public
    • Roof: Metal, Shingle - Other
    Interior Features
    • Appliances: Dishwasher, Microwave, Range - Electric, Refrigerator
    • Basement: No
    • Baths - Total: 1
    • Baths - Full: 1
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 5
    • Rooms: Level 1: Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Master Bedroom, Level 1: Office/Study
    • Bedrooms - Total: 2
    • Features - Interior: Kitchen/Dining, Living/Dining, Storage - Indoor, Laundry - 1st Floor
    • Flooring: Carpet, Ceramic Tile
    • Heat Fuel: Oil, Pellet
    • Heating: Hot Water, Radiator, Stove - Pellet
    • Cooling: None
    • Total Stories: 1
    Room Information
    Room 1
    • Room Dimensions: 14' x 10'
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 14' x 11'
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 28' x 25'
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 9' x 7'
    • Room Level: 1
    • Room Type: Office/Study
    Room 5
    • Room Dimensions: 14' x 19'
    • Room Level: 1
    • Room Type: Master Bedroom

    Property History for 156 Winhall Hollow Road

    DateEvent & SourcePriceAppreciation
    Oct 4, 2018

    Sold (Public Record)

    Public Record #632812042

    		$495,000—
    Oct 3, 2018

    Sold

    New England Real Estate Network #4643142

    		$495,000—
    Sep 25, 2018

    Pending

    New England Real Estate Network #4643142

    		—
    DateEvent & SourcePrice
    10/04/2018

    Sold (Public Record)

    Public Record #632812042

    $495,000
    10/03/2018

    Sold

    New England Real Estate Network #4643142

    $495,000
    09/25/2018

    Pending

    New England Real Estate Network #4643142

    —

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

    Public Records for 156 Winhall Hollow Road

    Taxable ValueLand$773,600Additions$296,100Total$1,069,700
    Tax Record2021$23,575 ($1,965 / month)
    Home Facts
    Baths1Total Finished SqFt902 SqFtAbove Grade Finished SqFt902 SqFtStories1Lot Size5,832,248 SqFtStyleMiscellaneous CommercialCountyBENNINGTONAPN(245)01387

    Schools near 156 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.

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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 156 Winhall Hollow Road, Winhall, VT 05340
    $495,000
    2
    1,517
    1,685,772
    The Hollow Road, Unit 3, Winhall, VT 05340
    $190,000
    –
    –
    –
    578,041
    181 Winhall Hollow Road, Bondville, VT 05340
    –
    –
    –
    –
    52,272
    19 Lightfoot Camp Road, Bondville, VT 05340
    –
    –
    –
    –
    28,314
    124 Old Town Road, Winhall, VT 05340
    $1,000,000
    4
    4,969
    570,636
    146 Winhall Hollow Road, Winhall, VT 05340
    $100,000
    –
    –
    –
    217,800

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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 Josiah Allen Real Estate, Inc.

    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 09/06/2026 04:14 AM