Google satellite image for 69 Upper Taylor Hill Rd, Winhall, VT 05340

Off Market Oct 2025 for $2.2M

$2,837,478

Est. refi paymentEst. refi $14,262/mo

•

4.5 ba

•

6,471

sq ft

69 Upper Taylor Hill Rd, Winhall, VT 05340

About this home

69 Upper Taylor Hill Rd is a 6,471 square foot house on a 11.55 acre lot with 4 bedrooms and 4.5 bathrooms. - it last sold on October 06, 2025 for $2,250,000. Based on Redfin's Winhall data, we estimate the home's value is $2,837,478.

Single-familyProperty Type

2009Year Built

11.55 acresLot Size

$438Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,837,478

$587K since sold in October 2025$173K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 77.9% higher than the average sale price ($1.59M) of 6 comparable homes.

SOLD AUG 31, 2026
$1,100,000
A
3 beds4 baths2,745 sq ft
65 Lower Taylor Hill Rd, Winhall, VT 05340
SOLD MAY 22, 2026
$2,850,000
B
4 beds6 baths5,082 sq ft
41 Stark Farm Rd, Winhall, VT 05340
SOLD FEB 12, 2026
$2,150,000
C
4 beds4.5 baths5,000 sq ft
16 Hunters Rdg, Winhall, VT 05340
SOLD MAY 22, 2026
$1,600,113
D
4 beds3.5 baths2,813 sq ft
264 French Hollow Rd, Winhall, VT 05340
SOLD AUG 17, 2026
$580,000
E
4 beds3 baths3,700 sq ft
53 Country Ln, West Wardsboro, VT 05360
SOLD JUL 27, 2026
$1,287,500
F
4 beds3.5 baths4,153 sq ft
487 Vermont Route 100, South Londonderry, VT 05155

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Earn from this home

Refinance

Est. cash available

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Rent

$4,463/mo

Redfin rental estimate

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Market trends in 05340, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.2%

+0.7% MoM

Median sale price

$799K

$64K MoM

Avg. days on market

80d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

3D & VIDEO TOUR
$1,050,000
4 beds4 baths2,380 sq ft
20 W Branch Rd, Winhall, VT 05340
3D WALKTHROUGH
$749,000
3 beds2 baths976 sq ft
7 Woodrock Rd, Winhall, VT 05340
$1,325,000
4 beds3.5 baths3,400 sq ft
11 Round Tree Rd, Winhall, VT 05340
OPEN SAT, 12PM TO 2PM
$599,000
3 beds2 baths1,890 sq ft
33 Burnt Hill Rd, Winhall, VT 05340
$345,000
2 beds2 baths960 sq ft
19 Winhall Condo Rd #4, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 69 Upper Taylor Hill Rd

Year

Property tax

Land + Additions

Assessment*

2025

$38,278 (−0.8%)

$588,400 + $1,242,300

$1,830,700

2024

$38,589 (+18.4%)

$588,400 + $1,242,300

$1,830,700

2023

$32,605 (−15.6%)

$588,400 + $1,242,300

$1,830,700

2022

$38,609 (+5.3%)

$588,400 + $1,242,300

$1,830,700

2021

$36,655

$588,400 + $1,103,900

$1,692,300

2020

$36,691 (+5.3%)

$588,400 + $1,103,900

$1,692,300

2019

$34,828 (+6.0%)

$588,400 + $1,103,900

$1,692,300

2018

$32,844 (−0.7%)

$588,400 + $1,103,900

$1,692,300

2017

$33,061 (−4.3%)

$588,400 + $1,103,900

$1,692,300

2016

$34,531 (+2.3%)

$588,400 + $1,103,900

$1,692,300

2015

$33,742 (+3.4%)

$588,400 + $1,103,900

$1,692,300

2014

$32,636

$588,400 + $1,103,900

$1,692,300

2013

$588,400 + $1,103,900

$1,692,300

Tax history for 69 Upper Taylor Hill Rd

Year

Property tax

Land + Additions

Assessment*

2025

$38,278 (−0.8%)

$588,400 + $1,242,300

$1,830,700

2024

$38,589 (+18.4%)

$588,400 + $1,242,300

$1,830,700

2023

$32,605 (−15.6%)

$588,400 + $1,242,300

$1,830,700

2022

$38,609 (+5.3%)

$588,400 + $1,242,300

$1,830,700

2021

$36,655

$588,400 + $1,103,900

$1,692,300

2020

$36,691 (+5.3%)

$588,400 + $1,103,900

$1,692,300

2019

$34,828 (+6.0%)

$588,400 + $1,103,900

$1,692,300

2018

$32,844 (−0.7%)

$588,400 + $1,103,900

$1,692,300

2017

$33,061 (−4.3%)

$588,400 + $1,103,900

$1,692,300

2016

$34,531 (+2.3%)

$588,400 + $1,103,900

$1,692,300

2015

$33,742 (+3.4%)

$588,400 + $1,103,900

$1,692,300

2014

$32,636

$588,400 + $1,103,900

$1,692,300

2013

$588,400 + $1,103,900

$1,692,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Zoning

Residential District

The Residential District is established as areas primarily intended for single-family dwellings.

Permitted uses

Include but are not limited to:

Agriculture
Housing-Single unit
Cemetery

Property details

Interior

Basement Information
Basement Sq. Ft: 2,881
Basement Finish: Finished
Basement Type: Partial

Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Room Information
# of Rooms: 9

Exterior

Exterior Information
Physical Condition: Excellent
Building Style Type: Contemporary
Exterior Wall: Wood Siding/Shingle

Property Information
Living Sq. Ft: 6,471
Building Sq. Ft: 6,956
Legal Description: E/S UPPER TAYLOR HILL ROAD LOT D

Lot Information
# of Buildings: 1
Land Sq. Ft: 503,118
Legal Lot Number: D
Municipality Name: WINHALL
Acres: 11.55
County Use Description: RESIDENTIAL-2

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 6,471
Stories: —
Lot Size: 11.55 acres
Style: Single Family Residential
Year Built: 2009
Year Renovated: —
County: Bennington County
APN: 77124512238

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Mountain School At Winhall

Private K-8 • 1.3mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

8 days above 85° expected this year, 19 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winhall, VT • 05340

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.2 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

8.2 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.70M – $3.26M

Sell confidently with a local market expert in Winhall. 3 minutes to get started.

Nearby similar homes

$1,475,000

2 beds2 baths1,601 sq ft

691 Black Bear Rd, Jamaica, VT 05343

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

$549,000

4 beds2.5 baths2,359 sq ft

116 Teacher Rd, Jamaica, VT 05343

VIDEO TOUR

$1,200,000

Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

VIDEO TOUR

$795,000

4 beds3.5 baths4,104 sq ft

25 Benson Fuller Rd, Winhall, VT 05340

$595,000

4 beds2 baths1,430 sq ft

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New listings for sale in 05340

3D & VIDEO TOUR

$1,050,000

4 beds4 baths2,380 sq ft

20 W Branch Rd, Winhall, VT 05340

3D WALKTHROUGH

$749,000

3 beds2 baths976 sq ft

7 Woodrock Rd, Winhall, VT 05340

$1,325,000

4 beds3.5 baths3,400 sq ft

11 Round Tree Rd, Winhall, VT 05340

OPEN SAT, 12PM TO 2PMVIDEO TOUR

$599,000

3 beds2 baths1,890 sq ft

33 Burnt Hill Rd, Winhall, VT 05340

$345,000

2 beds2 baths960 sq ft

19 Winhall Condo Rd #4, Winhall, VT 05340

Home values near 69 Upper Taylor Hill Rd

Data from public records.

Address	Redfin Estimate
67 Upper Taylor Hill Rd, Jamaica, VT 3 Beds \| 4 Baths \| 2644 Sq. Ft.	$918,416
69 Upper Taylor Hill Rd, Winhall, VT 8 Beds \| 8.5 Baths \| 7562 Sq. Ft.	$3,465,020

Address	Redfin Estimate
57 Upper Taylor Hill Rd, Winhall, VT 5 Beds \| 5.5 Baths \| 6479 Sq. Ft.	$1,910,059
69 Upper Taylor Hill Rd Apt D, Winhall, VT 8 Beds \| 8.5 Baths \| 6471 Sq. Ft.	$2,799,506

Address	Redfin Estimate
67 Upper Taylor Hill Rd, Winhall, VT 4 Beds \| 3 Baths \| 3552 Sq. Ft.	$924,303
119 Benson Fuller Dr, Winhall, VT 2 Beds \| 1 Baths \| 1596 Sq. Ft.	$449,098

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05340, VT

Sale history for 69 Upper Taylor Hill Rd

Tax history for 69 Upper Taylor Hill Rd

Zoning

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05340

Home values near 69 Upper Taylor Hill Rd

More real estate resources