Sold
Last Sold Price
6 beds2,924 sqft$239/sqft
123 Upper Taylor Hill Rd, Winhall, VT 05340
Single FamilyProperty Type
10.97 acresLot Size
1930Year Built
$239/sq ftPrice per sq ft
2 carsParking Spaces

Description

A piece of Vermont's history within minutes of Stratton Mountain. In the early 1930's Helen and Scott Nearing left the city to embrace the natural environment and rural community of Vermont. Committed to living off the land and pursuing their individual passions, they built Good Life Farm, a compound of five stone structures with its main house as a centerpiece. From this property they ran their maple sugar candy and syrup business and wrote their world famous book documenting their life in Vermont,...A piece of Vermont's history within minutes of Stratton Mountain. In the early 1930's Helen and Scott Nearing left the city to embrace the natural environment and rural community of Vermont. Committed to living off the land and pursuing their individual passions, they built Good Life Farm, a compound of five stone structures with its main house as a centerpiece. From this property they ran their maple sugar candy and syrup business and wrote their world famous book documenting their life in Vermont, Living the Good Life. In the subsequent years, the main house was renovated and expanded to include a cathedral-ceiling master bedroom and more. Offering sweeping mountain views, distinctive local stonework, striking gardens, and swift access to skiing, tennis, and golf, the property continues to offer the keys to the good life. Several stone cabins and barn on nearly 11 acres with possibility of extra building lots. South facing structures allow for good sun through the day along with spectacular views of the iconic Stratton Resort!

    Sold By Four Seasons Sotheby's Int'l Realty

    • Listed by: Bob Maisey • Four Seasons Sotheby's Int'l Realty
    Listing closed: 03/31/2021 12:00 AM • Source: New England Real Estate Network, MLS#: 4842595

    Recent comparable sales

    Median sold price

    $951,014

    Avg days on market

    117

    Sale-to-list ratio

    97.2%

    Winhall, VT

    9 comparable properties found

    $3,025,000 | 67 High Meadow Road, Winhall, VT 05340
    1/58
    1

    $3,025,000

    Sold 03/31/26

    6
    Bedrooms
    6,437
    Square Feet
    1.35
    Acres
    $950,000 | 24 North Branch Road, Winhall, VT 05340
    1/56
    2

    $950,000

    Sold 07/06/26

    5
    Bedrooms
    2,321
    Square Feet
    0.66
    Acres
    $810,000 | 15 Benson Fuller Drive, Winhall, VT 05340
    1/22
    3

    $810,000

    Sold 11/15/24

    5
    Bedrooms
    3,062
    Square Feet
    1.1
    Acres
    $975,000 | 83 Benson Fuller Drive, Winhall, VT 05340
    1/51
    4

    $975,000

    Sold 11/14/25

    5
    Bedrooms
    4,729
    Square Feet
    1.7
    Acres
    $870,000 | 24 Sugarbush Drive, Winhall, VT 05340
    1/36
    5

    $870,000

    Sold 05/13/26

    5
    Bedrooms
    2,897
    Square Feet
    1.26
    Acres
    $2,600,000 | 25 Mountain Haunts Road, Winhall, VT 05340
    1/56
    6

    $2,600,000

    Sold 05/01/26

    6
    Bedrooms
    6,650
    Square Feet
    40.80
    Acres
    $1,603,000 | 143 Stratton Mountain Road, Winhall, VT 05340
    1/44
    7

    $1,603,000

    Sold 01/28/26

    5
    Bedrooms
    3,688
    Square Feet
    2.1
    Acres
    $720,000 | 58 Todd Hill Road, Winhall, VT 05340
    1/37
    8

    $720,000

    Sold 10/21/25

    4
    Bedrooms
    2,389
    Square Feet
    1
    Acres
    $951,014 | 14 Mountain Haunts Road, Winhall, VT 05340
    1/34
    9

    $951,014

    Sold 10/24/25

    5
    Bedrooms
    3,238
    Square Feet
    1.2
    Acres

    Location

    Add your commute

    Payment Calculator

    $4,442 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $3,558

    Property Taxes

    $884

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

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    Property Information for 123 Upper Taylor Hill Road

    Property Details
    • Taxes: $10,604 / year
    • MLS Type: Residential / Single Family
    • Parking: Off Street, Covered
    • Water View: No
    • Zoning: Res
    Building Information
    • Stories: 1
    • Year Built: 1930
    • Lot Size: 10.97 AC / 477,853 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: Upper Taylor Hill Road to 123 on left
    • Latitude: 43.120176869586011
    • Longitude: -72.881448017196661
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Map: 12
    • Zip: 05340
    Taxes and HOA Information
    • SPAN Number: 771-245-11402
    • Tax - Gross Amount: $10,604.18
    • Tax Year: 2020
    • Taxes TBD: No
    School Information
    • School - High: Choice
    • School - District: Choice
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Crushed Stone, Gravel
    Property
    Lot Information
    • Block: 4
    • Lot: 28
    • Lot - Sqft: 477853.0
    • Lot Size Acres: 10.97
    • Road Frontage Length: 900.0
    • Square Feet Apx Finished Above Grade: 2924.0
    • 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: 3924.0
    • Square Feet Apx Total Finished: 2924.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 1000.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Easements: Unknown
    • Flood Zone: Unknown
    • Foundation: Slab - Concrete, Stone
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 1930
    Utilities
    • Electric: 100 Amp
    • Sewer: Septic
    • Utilities: Cable, DSL - Available, Internet - Cable
    Interior and Exterior Features
    Exterior Features
    • Features - Exterior: Balcony, Barn, Garden Space, Outbuilding, Storage
    • Roads: Paved, Public
    • Roof: Metal
    Interior Features
    • Appliances: Cooktop - Gas, Dishwasher, Range - Electric, Refrigerator, Washer, Stove - Wood Cook
    • Basement: No
    • Baths - Total: 6
    • Baths - Full: 2
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 4
    • Rooms - Total: 9
    • Bedrooms - Total: 6
    • Equipment: Smoke Detector, Stove-Wood
    • Features - Interior: Fireplace - Screens/Equip, Fireplace - Wood, In-Law/Accessory Dwelling, Kitchen/Dining, Master BR w/ BA, Natural Light, Natural Woodwork, Laundry - 1st Floor
    • Flooring: Slate/Stone, Wood
    • Heat Fuel: Gas - LP/Bottle, Oil, Other, Wood
    • Heating: Baseboard, Hot Water, Stove - Gas, Stove - Wood, Mini Split
    • Cooling: None
    • Total Stories: 1.75

    Property History for 123 Upper Taylor Hill Road

    DateEvent & SourcePriceAppreciation
    Mar 31, 2021

    Sold (Public Record)

    Public Record #1457151223

    $725,000

    +8.5% / yr

    Mar 31, 2021

    Sold

    New England Real Estate Network #4842595

    $700,000
    Feb 17, 2021

    Pending

    New England Real Estate Network #4842595

    DateEvent & SourcePrice
    03/31/2021

    Sold (Public Record)

    Public Record #1457151223

    $725,000

    +8.5% / yr

    03/31/2021

    Sold

    New England Real Estate Network #4842595

    $700,000
    02/17/2021

    Pending

    New England Real Estate Network #4842595

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

    Public Records for 123 Upper Taylor Hill Road

    Taxable ValueLand$180,900Additions$408,800Total$589,700
    Tax Record2025$10,833 ($903 / month)
    Home Facts
    Lot Size477,853 SqFtStyleVines and Bush FruitsCountyBENNINGTONAPN(245)01401

    Schools near 123 Upper Taylor Hill Road

    Rating
    School
    Type
    Grades
    Distance
    Private - 7 to 12
    Private - K to 8
    Rating
    School
    Distance
    Stratton Mountain School
    Private7 to 12

    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: 123 Upper Taylor Hill Road, Winhall, VT 05340
    $700,000
    6
    2,924
    477,853
    2,060
    43,560
    4
    3
    1,857
    104,544
    2,594
    72,745
    $285,666
    4
    3.5
    3,284
    44,867
    $117,500
    83,635

    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 09/07/2026 10:27 AM