123 Upper Taylor Hill Road

Closed 3/31/21
Closed 3/31/21
Gallery Image 1
Sold
Last Sold Price
$700,000
6 beds2,924 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!
  • 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

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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

67 High Meadow Road, Winhall, VT 05340

$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

24 North Branch Road, Winhall, VT 05340

$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

15 Benson Fuller Drive, Winhall, VT 05340

$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

83 Benson Fuller Drive, Winhall, VT 05340

$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

24 Sugarbush Drive, Winhall, VT 05340

$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

25 Mountain Haunts Road, Winhall, VT 05340

$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

143 Stratton Mountain Road, Winhall, VT 05340

$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

58 Todd Hill Road, Winhall, VT 05340

$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

14 Mountain Haunts Road, Winhall, VT 05340

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Property Information for 123 Upper Taylor Hill Road

Property Details
  • Taxes: $10,604 / year
  • MLS Type: Residential / Single Family
  • County: Bennington County
  • 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
Stratton Mountain School
Private - 7 to 12
Mountain School At Winhall
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
125 Upper Taylor Hill Road, Bondville, VT 05340
–
4
4.5
2,594
72,745
127 Upper Taylor Hill Road, Winhall, VT 05340
$487,500
3
1,540
44,866
6 Sap Bucket Road, Bondville, VT 05340
–
4
2.5
960
43,560
4 Sap Bucket Road, Winhall, VT 05340
$675,000
4
4,100
49,658
4 Forest Haunts Road, Bondville, VT 05340
–
4
3
1,650
749,668

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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 09/29/2026 04:56 AM