4292 Pleasant Hollow Rd, Jackson, WI 53037

Listed by Wendy Wendorf • Homestead Realty, Inc. Bought with LPT Realty.

Off market apr 2026 for $615K

$600,044

•

2,650

sq ft

4292 Pleasant Hollow Rd, Jackson, WI 53037

About this home

Public Remarks: First time to market, this custom-built homeis located perfectly in the Jackson country side it showcases quality craftsmanship and care throughout. Set in a peaceful, private country setting surrounded by nature, this spacious home offers the perfect blend of tranquility and convenience--located in a desirable neighborhood just minutes from highways and town amenities. Well maintained over the years, it provides a solid foundation for your personal updates and vision. Enjoy beautiful views, generous living space, and a setting that truly feels like home. A rare opportunity to bring your ideas and make this special property your own.

Single-familyProperty Type

1981Year Built

1.4 acresLot Size

$226Est. Price/Sq.Ft.

2 car garageParking

Listed by Wendy Wendorf • Homestead Realty, Inc

Bought with Marian Stupar • LPT Realty

Redfin checked: 2 minutes ago

•Source:MetroMLS as distributed by WIREX #1954602

Redfin Estimate

$600,044

$15K since sold in April 2026$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.7% higher than the average sale price ($537K) of 6 comparable homes.

SOLD AUG 21, 2026
$610,000
A
3 beds2.5 baths2,667 sq ft
2729 Pleasant Valley Rd, Jackson, WI 53037
SOLD JUL 20, 2026
$520,000
B
4 beds2.5 baths2,855 sq ft
5099 Valley Trl, West Bend, WI 53095
SOLD AUG 28, 2026
$505,000
C
4 beds2.5 baths2,669 sq ft
W203N17272 Francis Dr, Jackson, WI 53037
SOLD MAY 4, 2026
$482,000
D
4 beds2.5 baths2,297 sq ft
W199N17111 Ridgeway Dr, Jackson, WI 53037
SOLD SEP 11, 2026
$582,000
E
3 beds2.5 baths2,200 sq ft
3395 Overlook Ct, West Bend, WI 53095
SOLD MAY 4, 2026
$525,000
F
4 beds2.5 baths2,583 sq ft
2076 Patrick Ct, West Bend, WI 53095

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Earn from this home

Sell

$75,517

Est. take-home

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Rent

$2,228/mo

Redfin rental estimate

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Market trends in 53037, WI

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

101.2%

0.3% MoM

Median sale price

$420K

$29K MoM

Avg. days on market

57d

3 days MoM

Recently sold homes

9 MoM

New listings for sale

OPEN SUN, 12PM TO 1:30PM
$439,900
3 beds3 baths2,900 sq ft
N161W18878 Heather Lynn Cir, Jackson, WI 53037
Kim Stover • Coldwell Banker Realty
$288,000
2 beds2 baths1,236 sq ft
N161W18927 Heather Lynn Cir, Jackson, WI 53037
Stacy Miller • Greystone Asset, LLC
$655,000
3 beds3 baths2,887 sq ft
N161W21804 Daisy Dr, Jackson, WI 53037
Teresa Tighe • First Weber Inc- West Bend
$299,900
2 beds2 baths1,828 sq ft
N161W19088 Oakland Dr, Jackson, WI 53037
Angela Kallay • Century 21 Benefit Realty
$479,000
3 beds3 baths2,700 sq ft
N162W20293 Butternut Ln, Jackson, WI 53037
Sherry Reiter • Leitner Properties
See all

Provided by Redfin

Sale history for 4292 Pleasant Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,123 (+13.1%)

$53,500 + $333,200

$386,700

2024

$3,646 (+23.1%)

$53,500 + $333,200

$386,700

2023

$2,962 (−8.8%)

$53,500 + $333,200

$386,700

2022

$3,249 (−6.0%)

$53,500 + $333,200

$386,700

2021

$3,458 (−10.6%)

$48,500 + $243,000

$291,500

2020

$3,867 (+7.4%)

$48,000 + $243,000

$291,000

2019

$3,602 (+1.9%)

$48,000 + $243,000

$291,000

2018

$3,533 (−2.0%)

$48,000 + $243,000

$291,000

2017

$3,604 (−4.4%)

$48,000 + $243,000

$291,000

2016

$3,769 (+6.0%)

$48,000 + $243,000

$291,000

2014

$3,554 (−9.9%)

$48,000 + $243,000

$291,000

2013

$3,944

$48,000 + $243,000

$291,000

Tax history for 4292 Pleasant Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,123 (+13.1%)

$53,500 + $333,200

$386,700

2024

$3,646 (+23.1%)

$53,500 + $333,200

$386,700

2023

$2,962 (−8.8%)

$53,500 + $333,200

$386,700

2022

$3,249 (−6.0%)

$53,500 + $333,200

$386,700

2021

$3,458 (−10.6%)

$48,500 + $243,000

$291,500

2020

$3,867 (+7.4%)

$48,000 + $243,000

$291,000

2019

$3,602 (+1.9%)

$48,000 + $243,000

$291,000

2018

$3,533 (−2.0%)

$48,000 + $243,000

$291,000

2017

$3,604 (−4.4%)

$48,000 + $243,000

$291,000

2016

$3,769 (+6.0%)

$48,000 + $243,000

$291,000

2014

$3,554 (−9.9%)

$48,000 + $243,000

$291,000

2013

$3,944

$48,000 + $243,000

$291,000

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

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

1.35 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Washington County

APN

T7 013601100A

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 23, 2026.

Property details

Parking

Garage Information
# of Garage Parking Spaces (Total): 2.5
Garage: Opener Included, Attached, 2 Car

Interior

Bedroom Information
Master Bedroom Dimensions: 16 x 14
Master Bedroom Level: Upper
Bedroom 2 Dimensions: 10 x 10
Bedroom 2 Level: Upper
Bedroom 3 Dimensions: 12 x 10
Bedroom 3 Level: Upper
Bedroom 4 Dimension: 12 x 12
Bedroom 4 Level: Upper

Bathroom Information
Bath Description(s): Master Bedroom Bath, Shower Over Tub
# of Baths (1/2): 1
# of Baths (Full): 2

Interior Features
Cable/Satellite Available, High Speed Internet, Walk-In Closet(s), Wet Bar

Room Information
8'+ Ceiling, Block, Full, Partially Finished
Other Room 1 Dimensions: 8 x 16
Other Room 1 Level: Main
Other Room 1 Name: Sun/Four Season Room
Living Room Dimensions: 16 x 20
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 16 x 10
Dining Room Dimensions: 12 x 12
Dining Room Level: Main
Dining Kitchen: Kitchen Island
Den/Office Dimension: 12 x 12
Den/Office Level: Main

Equipment
Appliances: Dishwasher, Garbage Disposal, Dryer, Microwave, Oven, Refrigerator

Exterior

Building Information
Building Type: 2 Story
Estimated Sq. Ft. Range: 2501-3000, 2501+

Exterior
Exterior: Brick, Brick/Stone, Aluminum Trim, Vinyl

Property Information
Single-Family
Information Source Year Built: Owner

Land Information
Acreage: Over 1 Acre to 2 Acres

Lot Information
Outbuildings: Garden Shed
Lot Acreage: 1.4
Lot Description: Wooded
Zoning: Res

Financial

Tax Information
Total Taxes: $4,123.45
Tax Year: 2025

Utilities

Utility Information
Well, Private Septic System
Heating/Cooling: Central Air, Forced Air
Natural Gas

Location

Neighborhood Information
Municipality: JACKSON
Municipality Type: Town

School Information
School District: West Bend
Elementary School: Jackson
Middle School: Badger

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.35 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Washington County
APN: T7 013601100A

Home facts updated by county records on Oct 23, 2026

Other

Listing Information
SaleType: Arms Length
Inclusions: Stove, Refrigerator in basement, Microwave, Dishwasher, Washer, Dryer, Water Softener, Lawn Mower, Snow Blower,, Fertilizer spreader, Lawn Sweeper, Pond Pump & Equipment, Pool Table
Exclusions: Seller's personal property & Kitchen refirgerator

Around this home

Schools

Jackson Elementary School

Public K-4 • Assigned • 1.7mi

6/10

Badger Middle School

Public 7-8 • Assigned • 4.6mi

4/10

East High School

Public 9-12 • Assigned • 4.3mi

6/10

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

7 days above 99° expected this year, 13 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Jackson, WI • 53037

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

97/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Jackson. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.3 hrs

6.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$571,000 – $691,000

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New listings for sale in 53037

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Home values near 4292 Pleasant Hollow Rd

Data from public records.

Address	Redfin Estimate
4362 Pleasant Hollow Road, Jackson, WI 4 Beds \| - Baths \| - Sq. Ft.	$468,310
4419 Honeywood Lane, Jackson, WI 3 Beds \| 2.5 Baths \| 2700 Sq. Ft.	$535,876

Address	Redfin Estimate
4346 Pleasant Hollow Road, Jackson, WI 3 Beds \| 1.5 Baths \| 1470 Sq. Ft.	$493,932
2632 Oak Knoll Drive, Jackson, WI 4 Beds \| 2.5 Baths \| 2339 Sq. Ft.	$520,044

Address	Redfin Estimate
2614 Oak Knoll Drive, Jackson, WI 3 Beds \| 2 Baths \| 2005 Sq. Ft.	$511,627
2604 Oak Knoll Drive, Jackson, WI 4 Beds \| 3 Baths \| 2809 Sq. Ft.	$573,137

Property information provided by MetroMLS as distributed by WIREX when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 53037, WI

Sale history for 4292 Pleasant Hollow Rd

Tax history for 4292 Pleasant 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 53037

Home values near 4292 Pleasant Hollow Rd

More real estate resources