OFF MARKET

Listed by Bob Maisey • Four Seasons Sotheby's Int'l Realty. Bought with TPW Real Estate.

Off Market Nov 2018 for $615K

$1,448,155

Est. refi paymentEst. refi $3,993/mo

•

5,228

sq ft

165 Winhall Hollow Rd, Winhall, VT 05340

About this home

Single-familyProperty Type

1990Year Built

8.89 acresLot Size

$277Est. Price/Sq.Ft.

4 car garageParking

Listed by Bob Maisey • Four Seasons Sotheby's Int'l Realty

Bought with Karin Hardy • TPW Real Estate

Redfin checked: a few seconds ago

•Source:PrimeMLS #4639538

Redfin Estimate

$1,448,155

$833K since sold in November 2018$28K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.4% lower than the average sale price ($1.73M) of 6 comparable homes.

SOLD MAY 1, 2026
$735,000
A
4 beds3 baths2,091 sq ft
5 Wall St, Winhall, VT 05340
SOLD APR 10, 2026
$1,550,000
B
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, Winhall, VT 05340
SOLD JUL 10, 2026
$949,000
C
5 beds3.5 baths4,000 sq ft
178 High Meadow Rd, Winhall, VT 05340
SOLD JUL 27, 2026
$1,287,500
D
4 beds3.5 baths4,153 sq ft
487 Vermont Route 100, South Londonderry, VT 05155
SOLD MAY 22, 2026
$2,850,000
E
4 beds6 baths5,082 sq ft
41 Stark Farm Rd, Winhall, VT 05340
SOLD MAR 31, 2026
$3,025,000
F
6 beds5 baths6,437 sq ft
67 High Meadow Rd, Winhall, VT 05340

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Market trends in 05340, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.4%

+0.2% MoM

Median sale price

$713K

$86K MoM

Avg. days on market

67d

13 days MoM

Recently sold homes

2 MoM

New listings for sale

FOR SALE BY OWNER
$169,000
— beds— baths— sq ft
0 Signal Hill Rd, Winhall, VT 05340
FOR SALE BY OWNER
$169,000
— beds— baths— sq ft
1 Rogues Ridge Rd, Winhall, VT 05340
$695,000
3 beds2 baths2,000 sq ft
57 Pearl Buck Dr, Winhall, VT 05340
COMING SOON
$1,150,000
4 beds5.5 baths3,206 sq ft
11 Spruce High Rd, Winhall, VT 05340
$679,000
3 beds3 baths1,830 sq ft
Cobble Ridge Rd Unit G6, Bondville, VT 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 TODAY, 12PM TO 2PM
$599,000
3 beds2 baths1,890 sq ft
33 Burnt Hill Rd, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 165 Winhall Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,624 (−0.8%)

$448,200 + $203,400

$651,600

2024

$13,735 (+18.4%)

$448,200 + $203,400

$651,600

2023

$11,605 (−15.6%)

$448,200 + $203,400

$651,600

2022

$13,742 (−2.6%)

$448,200 + $203,400

$651,600

2021

$14,114

$448,200 + $203,400

$651,600

2020

$14,127 (+5.3%)

$448,200 + $203,400

$651,600

2019

$13,410 (−15.4%)

$448,200 + $203,400

$651,600

2018

$15,851 (+7.5%)

$448,200 + $203,400

$651,600

2017

$14,744 (+2.7%)

$448,200 + $203,400

$651,600

2016

$14,361 (+4.4%)

$448,200 + $203,400

$651,600

2015

$13,759 (+0.2%)

$448,200 + $203,400

$651,600

2014

$13,727

$448,200 + $203,400

$651,600

2013

$448,200 + $203,400

$651,600

Tax history for 165 Winhall Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,624 (−0.8%)

$448,200 + $203,400

$651,600

2024

$13,735 (+18.4%)

$448,200 + $203,400

$651,600

2023

$11,605 (−15.6%)

$448,200 + $203,400

$651,600

2022

$13,742 (−2.6%)

$448,200 + $203,400

$651,600

2021

$14,114

$448,200 + $203,400

$651,600

2020

$14,127 (+5.3%)

$448,200 + $203,400

$651,600

2019

$13,410 (−15.4%)

$448,200 + $203,400

$651,600

2018

$15,851 (+7.5%)

$448,200 + $203,400

$651,600

2017

$14,744 (+2.7%)

$448,200 + $203,400

$651,600

2016

$14,361 (+4.4%)

$448,200 + $203,400

$651,600

2015

$13,759 (+0.2%)

$448,200 + $203,400

$651,600

2014

$13,727

$448,200 + $203,400

$651,600

2013

$448,200 + $203,400

$651,600

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

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

8.89 Acres

Year renovated

—

Sq. Ft.

5,092

Year built

1990

Style

Other

County

Bennington County

APN

77124511325

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 4
Location: Attached
Driveway, Garage

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 3
# of Baths (3/4): 1
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Partially Finished

Other Interior Features
# of Rooms: 9
Level B: Office/Study
Flooring: Carpet, Ceramic Tile, Hardwood
Water Heater: Off Boiler
Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Screens/Equip, Fireplace - Wood, Master Bedroom With Bath, Natural Woodwork, Vaulted Ceiling, Walk-in Closet, Laundry - 1st Floor

Accessibility Information
1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Laundry

Equipment & Appliance Information
Cooktop - Gas, Dishwasher, Dryer, Microwave, Oven - Wall, Range - Gas, Refrigerator, Washer

Room 1 Information
Kitchen
Kitchen
Dimensions: 11x9
Level: 1

Room 2 Information
Dining Room
Dimensions: 10x12
Level: 1

Room 3 Information
Living Room
Dimensions: 24x20
Level: 1

Room 4 Information
Foyer
Dimensions: 10x8
Level: 1

Room 5 Information
Dining Room
Dimensions: 12x12
Level: 1

Room 6 Information
Master Bedroom
Master Bedroom
Dimensions: 15x15
Level: 1

Room 7 Information
Office/Study
Dimensions: 14x12
Level: Basement

Room 8 Information
Bedroom
Dimensions: 12x12
Level: 2

Room 9 Information
Bedroom
Dimensions: 10x10
Level: 2

Room 10 Information
Bedroom
Dimensions: 14x14
Level: 2

Room 11 Information
Bedroom
Dimensions: 12x12
Level: 2

Room 12 Information
Bonus Room
Dimensions: 19x15
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 5228
Approximate Sq. Ft. Total: 7256
Color: Yellow
Deck, Garden Space, Patio
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Clapboard, Wood

Driveway
Circular, Gravel

Lot, Zoning, & Easement Information
Landscaped, Mountain View, Ski Area, View

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1990

Financial

Tax Information
Tax Year: 2016
Gross Amount Tax: 13726.6
SPAN Number: 77124511325

Other Tax Information
Page Deed: 451

Utilities

Heating & Cooling Information
Heat: Baseboard, Wood Boiler
Heat Fuel: Gas - Liquid Propane Bottle, Wood

Sewer Information
Septic

Electric Information
200 Amp

Water Information
Drilled Well

Other Utilities Information
Cable, DSL

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 221
Paved

Other Location Information
Directions: Winhall Hollow Road to 165 West of Red Fox Inn

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 5,092
Stories: 1.5
Lot Size: 8.89 acres
Style: Other
Year Built: 1990
Year Renovated: —
County: Bennington County
APN: 77124511325

Home facts updated by county records on Jul 15, 2026

Other

Water Body Information
Flood Zone: Unknown

Around this home

Schools

Mountain School At Winhall

Private K-8 • 1.1mi

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 87° expected this year, 19 days in 30 years

3/10 Wind Factor

7% 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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$1.38M – $1.67M

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

Nearby similar homes

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VIDEO TOUR

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4 beds3.5 baths4,104 sq ft

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4 beds2 baths1,816 sq ft

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New listings for sale in 05340

FOR SALE BY OWNER

$169,000

— beds— baths— sq ft

0 Signal Hill Rd, Winhall, VT 05340

FOR SALE BY OWNER

$169,000

— beds— baths— sq ft

1 Rogues Ridge Rd, Winhall, VT 05340

$695,000

3 beds2 baths2,000 sq ft

57 Pearl Buck Dr, Winhall, VT 05340

COMING SOON

$1,150,000

4 beds5.5 baths3,206 sq ft

11 Spruce High Rd, Winhall, VT 05340

$679,000

3 beds3 baths1,830 sq ft

Cobble Ridge Rd Unit G6, Bondville, VT 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 TODAY, 12PM TO 2PMVIDEO TOUR

$599,000

3 beds2 baths1,890 sq ft

33 Burnt Hill Rd, Winhall, VT 05340

Home values near 165 Winhall Hollow Rd

Data from public records.

Address	Redfin Estimate
156 Winhall Hollow Rd, Winhall, VT 2 Beds \| 1 Baths \| 1517 Sq. Ft.	$947,158
179 Winhall Hollow Rd, Winhall, VT 3 Beds \| 2 Baths \| 1309 Sq. Ft.	$458,506

Address	Redfin Estimate
159 Winhall Hollow Rd, Winhall, VT 7 Beds \| 9.5 Baths \| 9915 Sq. Ft.	—
18 Alta Rd, Winhall, VT 3 Beds \| 2 Baths \| 2604 Sq. Ft.	$564,614

Address	Redfin Estimate
167 Winhall Hollow Rd, Winhall, VT 3 Beds \| 2.5 Baths \| 2540 Sq. Ft.	$965,812
25 Stoney Hill Rd, Winhall, VT 3 Beds \| 2.5 Baths \| 1849 Sq. Ft.	$681,632

Property information provided by PrimeMLS when last listed in 2017. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05340, VT

Sale history for 165 Winhall Hollow Rd

Tax history for 165 Winhall Hollow Rd

Public record

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 165 Winhall Hollow Rd

More real estate resources