SOLD DEC 23, 2025

Listed by Trisha Rose • Century 21 Affiliated (Pref: 608-290-5866). Bought with Keller Williams Realty.

Off Market Dec 2025 for $1.3M

$1,498,944

•

5,828

sq ft

5140 N Kennedy Rd, Milton, WI 53563

About this home

Public Remarks: Amazingly beautiful property! This exclusive custom built 31-acre estate is ideally located between Chicago and Madison. Offering spacious living areas, stunning year-round views & an array of upscale amenities. Inside you?ll find a relaxing sauna, a jacuzzi tub & a chef?s kitchen complete w/ double ovens, built-in indoor grill w/ both breakfast & formal dining areas. Outdoors, the meticulously curated arboretum showcases a diverse collection of trees, 2 stocked ponds & direct access to the iconic Ice Age Trail. Equestrian enthusiasts will appreciate the 7-stall horse barn, while summer days are made for the 22x44 in-ground pool, complete w/ a pool house. This estate is more than a home?it's a lifestyle. This retreat offers a rare combination of privacy, luxury & nature.

Single-familyProperty Type

1970Year Built

31 acresLot Size

$257Est. Price/Sq.Ft.

3 car garageParking

Listed by Trisha Rose • Century 21 Affiliated

Listed by Karla Clark • Century 21 Affiliated

Contact: Pref: 608-290-5866

Bought with Living In Madison Real Estate Group • Keller Williams Realty

Redfin checked: 2 minutes ago

•Source:SCWMLS #1999282

Redfin Estimate

$1,498,944

$149K since sold in December 2025$158K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 194.3% higher than the average sale price ($509K) of 6 comparable homes.

SOLD FEB 27, 2026
$760,000
A
4 beds3.5 baths4,568 sq ft
2370 E Sylvan Ln, Milton, WI 53563
SOLD AUG 14, 2026
$529,900
B
4 beds3.5 baths3,873 sq ft
4455 Pheasant Run, Janesville, WI 53546
SOLD JUL 31, 2026
$450,000
C
4 beds2.5 baths2,864 sq ft
2613 E Grandview Dr, Milton, WI 53563
SOLD JUN 12, 2026
$455,900
D
4 beds2.5 baths2,967 sq ft
4828 N Brentwood Dr, Milton, WI 53563
SOLD OCT 24, 2025
$460,000
E
4 beds3.5 baths4,003 sq ft
4587 N Brentwood Dr, Milton, WI 53563
SOLD JUN 26, 2026
$400,000
F
4 beds2.5 baths2,226 sq ft
5126 N Grandeur Dr, Milton, WI 53563

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Earn from this home

Sell

$343,820

Est. take-home

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Rent

$4,034/mo

Redfin rental estimate

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Market trends in 53563, WI

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.6%

0.1% MoM

Median sale price

$427K

$95 MoM

Avg. days on market

56d

16 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 11 HRS AGO
$529,900
4 beds2.5 baths2,018 sq ft
4869 Monarch Dr, Milton, WI 53563
Mary Gilbank • Shorewest, REALTORS
OPEN SAT, 10AM TO 12PM
$445,000
4 beds3 baths3,078 sq ft
4562 Parkwood Dr, Milton, WI 53563
Caitlin Schmidt • Realty Executives Premier
$489,900
4 beds2.5 baths2,211 sq ft
5110 N Waverly Dr, Milton, WI 53563
Kari Reilly • Pat's Realty Inc
$1,300,000
3 beds2.5 baths4,266 sq ft
5143 N Kennedy Rd, Milton, WI 53563
Krista Shortreed • Realty Executives Premier
$885,000
3 beds2.5 baths2,803 sq ft
5921 N Sessler Ct, Milton, WI 53563
Sarah Mclean • Realty Executives Premier
$575,000
3 beds2.5 baths2,841 sq ft
5837 N Valley Dr, Milton, WI 53563
Amy Finn • Kim Colby Homes
$624,900
6 beds3 baths2,797 sq ft
3551 Pickard Dr, Milton, WI 53563
Jerilyn Endrizzi • Coldwell Banker Real Estate Group
$244,900
2 beds2 baths1,140 sq ft
1010 Parkview Dr #2, Milton, WI 53563
Seth Pfaehler • The McGrady Group, LLC
3D WALKTHROUGH
$370,000
5 beds2 baths2,476 sq ft
125 Parkview Dr, Milton, WI 53563
Charles Clark • NextHome My Way
$375,000
3 beds2.5 baths1,521 sq ft
32 E Sunset Dr, Milton, WI 53563
Stacey Schultz • Compass Wisconsin-Lake Geneva
See all

Provided by Redfin

Sale history for 5140 N Kennedy Rd

Year

Property tax

Land + Additions

Assessment*

2025

$15,988 (+14.1%)

$305,900 + $1,042,700

$1,348,600

2024

$14,018 (+3.2%)

$141,700 + $708,700

$850,400

2023

$13,587 (+2.1%)

$141,700 + $708,700

$850,400

2022

$13,302 (+2.0%)

$141,700 + $708,700

$850,400

2021

$13,044 (−4.1%)

$141,700 + $708,700

$850,400

2020

$13,599 (+11.0%)

$141,700 + $521,300

$663,000

2019

$12,254 (+13.4%)

$141,700 + $521,300

$663,000

2018

$10,807

$141,700 + $521,300

$663,000

2017

$10,810 (−4.0%)

$141,700 + $521,300

$663,000

2016

$11,257 (+6.7%)

$141,700 + $463,700

$605,400

2014

$10,554

$141,700 + $463,700

$605,400

Tax history for 5140 N Kennedy Rd

Year

Property tax

Land + Additions

Assessment*

2025

$15,988 (+14.1%)

$305,900 + $1,042,700

$1,348,600

2024

$14,018 (+3.2%)

$141,700 + $708,700

$850,400

2023

$13,587 (+2.1%)

$141,700 + $708,700

$850,400

2022

$13,302 (+2.0%)

$141,700 + $708,700

$850,400

2021

$13,044 (−4.1%)

$141,700 + $708,700

$850,400

2020

$13,599 (+11.0%)

$141,700 + $521,300

$663,000

2019

$12,254 (+13.4%)

$141,700 + $521,300

$663,000

2018

$10,807

$141,700 + $521,300

$663,000

2017

$10,810 (−4.0%)

$141,700 + $521,300

$663,000

2016

$11,257 (+6.7%)

$141,700 + $463,700

$605,400

2014

$10,554

$141,700 + $463,700

$605,400

*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

—

Stories

—

Lot width

—

Lot depth

—

Lot size

31 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Rock County

APN

014 0150031

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 26, 2026.

Rural Residential District

The purpose of the R-R District is to provide a means of obtaining the residential goals and objectives of the Development Plan. The R-R District is to provide a quiet, pleasant and relatively spacious living area protected from traffic hazards and the intrusion of incompatible land uses. The intent of the R-R District is to provide for rural residential development at slightly higher population densities, on soils that are compatible for on-site sewage disposal systems.

Permitted uses

Include but are not limited to:

Community / recreation center
Religious facility
Housing-Single unit
Public service
Park & open space

Property details

Parking

Garage Information
# of Garage Parking Spaces (Total): 3
Garage: 3 Car, Attached, Heated, Opener Included

Interior

Bedroom Information
Master Bedroom Dimensions: 22 x 14
Master Bedroom Level: Upper
Bedroom 2 Dimensions: 20 x 14
Bedroom 2 Level: Upper
Bedroom 3 Dimensions: 31 x 14
Bedroom 3 Level: Upper
Bedroom 4 Dimension: 12 x 12
Bedroom 4 Level: Upper

Bathroom Information
Bath Description(s): Whirlpool, Steam Shower, Master Bedroom Bath (Full), Master Bedroom Bath, Walk-In Shower in Master Bathroom, Tub/No Shower in Master Bathroom
# of Baths (1/2): 1
# of Baths (Full): 4

Interior Features
Walk-In Closet(s), Water Softener, Security System, Sauna, Wet Bar, Cable/Satellite Available, Walk-Thru Bedroom

Room Information
Full, Finished, Sump Pump, Poured Concrete
Other Room 1 Dimensions: 20 x 22
Other Room 1 Level: Main
Other Room 1 Name: Mud Room
Other Room 2 Name: Screened Porch
Living Room Dimensions: 15 x 28
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 15 x 15
Family Room Level: Main
Family Room Length: 27 x 13
Dining Room Dimensions: 22 x 17
Dining Room Level: Main
Dining Kitchen: Breakfast Bar, Pantry, Kitchen Island

Equipment
Appliances: Range/Oven, Refrigerator, Dishwasher, Microwave, Garbage Disposal, Washer, Dryer

Exterior

Building Information
Building Type: 2 Story
Estimated Sq. Ft. Range: 5001+
Finished Below Grade Sq. Ft.: 680
Finished Above Grade Sq. Ft.: 5,148

Exterior
Exterior Features: Porch (Screened), Patio, Pool (Inground)
Exterior: Brick

Property Information
Single-Family
Improvement Value: $708,700
Information Source Year Built: Owner

Property Features
Body of Water: Two Stocked Ponds
Water Features: Pond

Land Information
Farm Features: Barn(s), Outbuilding(s)

Lot Information
Lot Acreage: 31
Lot Description: Wooded, Horse Allowed
Zoning: Rural Res

Financial

Assessment Information
Land Assessment Value: $141,700
Total Assessment: $850,400

Tax Information
Total Taxes: $14,018
Tax Year: 2024

Utilities

Utility Information
Well, Private Septic System
Heating/Cooling: Forced Air, Central Air, Zoned Heating, Multiple Units
Lp Gas

Location

HOA Information
HOA Payment Freq: Unknown
Yearly HOA Fee: $0

Neighborhood Information
Municipality: HARMONY
Municipality Type: Town

School Information
School District: Milton
Elementary School: Harmony
Middle School: Milton
High School: Milton

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 31 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Rock County
APN: 014 0150031

Home facts updated by county records on Aug 26, 2026

Other

Listing Information
SaleType: Arms Length
Inclusions: Stove, Refrigerator, 2 washers, 2 dryers, 2 water softeners, ionizer, window treatments, greenhouse, dog house, dog pen, pool cleaner, pool house mini refrigerator, pool pump pool filter
Exclusions: Seller's personal property, commercial refrigerator and freezer in garage

Around this home

Schools

Harmony Elementary School

Public PreK-3 • Assigned • 2.3mi

9/10

Milton Middle School

Public 7-8 • Assigned • 3.5mi

4/10

Milton High School

Public 9-12 • Assigned • 3.0mi

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

2/10 Heat Factor

7 days above 101° expected this year, 14 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, 3 days in 30 years

Provided by First Street

Historical weather

Milton, WI • 53563

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 9.9 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

9.9 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.42M – $1.72M

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Nearby similar homes

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Sarah Mclean • Realty Executives Premier

New listings for sale in 53563

NEW 11 HRS AGO

$529,900

4 beds2.5 baths2,018 sq ft

4869 Monarch Dr, Milton, WI 53563

Mary Gilbank • Shorewest, REALTORS

OPEN SAT, 10AM TO 12PM

$445,000

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Caitlin Schmidt • Realty Executives Premier

$489,900

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Kari Reilly • Pat's Realty Inc

$1,300,000

3 beds2.5 baths4,266 sq ft

5143 N Kennedy Rd, Milton, WI 53563

Krista Shortreed • Realty Executives Premier

$885,000

3 beds2.5 baths2,803 sq ft

5921 N Sessler Ct, Milton, WI 53563

Sarah Mclean • Realty Executives Premier

$575,000

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5837 N Valley Dr, Milton, WI 53563

Amy Finn • Kim Colby Homes

$624,900

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Jerilyn Endrizzi • Coldwell Banker Real Estate Group

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Seth Pfaehler • The McGrady Group, LLC

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$370,000

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Charles Clark • NextHome My Way

Home values near 5140 N Kennedy Rd

Data from public records.

Address	Redfin Estimate
5143 N Kennedy Road, Milton, WI 3 Beds \| 2.5 Baths \| 4266 Sq. Ft.	$1,297,973
4921 N Brentwood Drive, Milton, WI 3 Beds \| 2.5 Baths \| 3211 Sq. Ft.	$544,425

Address	Redfin Estimate
5029 N Kennedy Road, Milton, WI 4 Beds \| 3.5 Baths \| 3408 Sq. Ft.	$624,393
5031 N Grandview Drive, Milton, WI 4 Beds \| 2.5 Baths \| 2563 Sq. Ft.	$591,716

Address	Redfin Estimate
5308 N Kennedy Road, Milton, WI 3 Beds \| 2.5 Baths \| 3193 Sq. Ft.	$485,415
5121 N Grandview Drive, Milton, WI 4 Beds \| 4.5 Baths \| 5823 Sq. Ft.	$791,901

Property information provided by SCWMLS when last listed in 2025. This data may not match . Learn more.

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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 53563, WI

Sale history for 5140 N Kennedy Rd

Tax history for 5140 N Kennedy Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 53563

Home values near 5140 N Kennedy Rd

More real estate resources