3744 S Cherokee Way, Milwaukee, WI 53221

Listed by Wendy Bolduc • Shorewest Realtors - South Metro. Bought with HomeWire Realty.

Off market nov 2015 for $520K

$793,590

Est. refi paymentEst. refi $3,480/mo

•

5,104

sq ft

3744 S Cherokee Way, Milwaukee, WI 53221

About this home

Public Remarks: Exceptional executive home in Cherokee Point SD. Exquisite tray ceilings w/ stunning crown molding, coupled w/ arched doorways, add style & grace to this open floorplan. Sophisticated gourmet KIT w/ granite & SS you would expect along w/ glorious counter space, pantry & stunning cabinetry. Owners suite w/ FP, spa-like BA w/ shower, whirlpool & double sinks. Gorgeous transom windows. Laundry room w/ B-I lockers, sink & cabinetry. LL w/ wet bar, billiard room, add'l FR, space for home gym, office, playroom & more!

Single-familyProperty Type

2006Year Built

8,276 sq ftLot Size

$155Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Wendy Bolduc • Shorewest Realtors - South Metro

Bought with Emma Allen-Green • HomeWire Realty

Redfin checked: 2 minutes ago

•Source:MetroMLS as distributed by WIREX #1416527

Redfin Estimate

$793,590

$273K since sold in November 2015$58K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 91.5% higher than the average sale price ($414K) of 6 comparable homes.

SOLD AUG 6, 2026
$442,000
A
3 beds3 baths2,818 sq ft
3822 S Centennial Cir, Milwaukee, WI 53221
BOUGHT WITH REDFIN JUL 6, 2026
$535,000
B
3 beds3 baths3,602 sq ft
3818 S Centennial Cir, Milwaukee, WI 53221
SOLD SEP 28, 2026
$381,250
C
3 beds2 baths1,929 sq ft
4329 S 49th St, Greenfield, WI 53220
SOLD MAY 22, 2026
$463,000
D
3 beds2.5 baths2,365 sq ft
4226 W Willow Way, Milwaukee, WI 53221
SOLD AUG 11, 2026
$335,000
E
3 beds3 baths1,575 sq ft
3578 S 48th St, Greenfield, WI 53220
SOLD JUL 6, 2026
$330,000
F
3 beds2 baths1,446 sq ft
3737 S 48th St, Milwaukee, WI 53220

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Earn from this home

Sell

$430,953

Est. take-home

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Refinance

Est. cash available

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Rent

$3,804/mo

Redfin rental estimate

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Market trends in 53221, WI

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.6%

0.9% MoM

Median sale price

$291K

$11K MoM

Avg. days on market

38d

1 days MoM

Recently sold homes

107

5 MoM

New listings for sale

OPEN NOV 16, 4PM TO 6PM
$314,900
3 beds1 bath1,849 sq ft
5252 S Tuckaway Dr, Greenfield, WI 53221
Jackson Villarreal • Villa Realty
NEW 12 HRS AGO
$349,900
4 beds2.5 baths2,177 sq ft
4917 S 28th St, Greenfield, WI 53221
Carrie Lemke • NextKey Realty Group, LLC
$375,000
5 beds2 baths1,608 sq ft
3707 S 15th Pl, Milwaukee, WI 53221
Paulette Kowalski • Shorewest Realtors - South Metro
3D WALKTHROUGH
$274,900
3 beds1.5 baths1,250 sq ft
1624 W Whitaker Ave Unit (AKA - 1626), Milwaukee, WI 53221
Hartland Realty Group* • Arkenstone Real Estate Experts
$349,900
3 beds1 bath1,406 sq ft
1426 W Barnard Ave, Milwaukee, WI 53221
Paulette Kowalski • Shorewest Realtors - South Metro
$389,900
3 beds1.5 baths2,055 sq ft
2504 W Bridge St, Milwaukee, WI 53221
Hoffmann Team* • REMAX Lakeside-Central
$339,999
2 beds1.5 baths1,665 sq ft
5040 S 18th St, Milwaukee, WI 53221
Jose Pimienta • Empowerment Realty Group LLC
$200,000
2 beds1.5 baths1,000 sq ft
4039 W College Ave, Milwaukee, WI 53221
Joshua Spano • Keller Williams Realty-Milwaukee Southwest
$173,000
2 beds1.5 baths944 sq ft
6334 S 20th St, Milwaukee, WI 53221
Jeffry Anderson • Fathom Realty, LLC
$349,000
3 beds1.5 baths1,936 sq ft
1711 W Clayton Crest Ave, Milwaukee, WI 53221
Ina Acuca • A Way Home Real Estate Agency
See all

Provided by Redfin

Sale history for 3744 S Cherokee Way

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Year

Property tax

Land + Additions

Assessment*

2025

$17,595 (+7.1%)

$67,100 + $623,800

$690,900

2024

$16,423 (+6.9%)

$67,100 + $570,300

$637,400

2023

$15,364 (+17.7%)

$77,400 + $484,100

$561,500

2022

$13,056 (−6.8%)

$77,400 + $484,100

$561,500

2021

$14,014 (−10.2%)

$77,400 + $468,000

$545,400

2020

$15,601 (+2.8%)

$77,400 + $468,000

$545,400

2019

$15,172 (+9.0%)

$77,400 + $466,200

$543,600

2018

$13,921 (−0.2%)

$77,300 + $455,400

$532,700

2017

$13,953 (−4.2%)

$77,300 + $455,400

$532,700

2016

$14,559 (+13.2%)

$86,200 + $428,600

$514,800

2014

$12,863 (−2.2%)

$86,200 + $337,500

$423,700

2013

$13,147

$86,200 + $350,200

$436,400

Tax history for 3744 S Cherokee Way

Year

Property tax

Land + Additions

Assessment*

2025

$17,595 (+7.1%)

$67,100 + $623,800

$690,900

2024

$16,423 (+6.9%)

$67,100 + $570,300

$637,400

2023

$15,364 (+17.7%)

$77,400 + $484,100

$561,500

2022

$13,056 (−6.8%)

$77,400 + $484,100

$561,500

2021

$14,014 (−10.2%)

$77,400 + $468,000

$545,400

2020

$15,601 (+2.8%)

$77,400 + $468,000

$545,400

2019

$15,172 (+9.0%)

$77,400 + $466,200

$543,600

2018

$13,921 (−0.2%)

$77,300 + $455,400

$532,700

2017

$13,953 (−4.2%)

$77,300 + $455,400

$532,700

2016

$14,559 (+13.2%)

$86,200 + $428,600

$514,800

2014

$12,863 (−2.2%)

$86,200 + $337,500

$423,700

2013

$13,147

$86,200 + $350,200

$436,400

*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
Permits

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

8,293 Sq. Ft.

Year renovated

—

Sq. Ft.

5,104

Year built

2006

Style

Single Family Residential

County

Milwaukee County

APN

5540161000

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: 15 x 21
Master Bedroom Level: Main
Bedroom 2 Dimensions: 12 x 14
Bedroom 2 Level: Main
Bedroom 3 Dimensions: 12 x 13
Bedroom 3 Level: Lower
Bedroom 4 Dimension: 15 x 18
Bedroom 4 Level: Lower
Bedroom 5 Dimension: 15 x 21
Bedroom 5 Level: Upper

Bathroom Information
Bath Description(s): Shower on Lower, Ceramic Tile, Whirlpool, Master Bedroom Bath, Shower Stall, Vanity
# of Baths (1/2): 1
# of Baths (Full): 4

Interior Features
Great Room, Living Room, Built-in Bookcase, Circuit Breakers, Electric Appliance Hookup, Gas Appliance Hookup, Pantry, Smoke Detector(s)

Room Information
Full, Full Size Windows, Walk Out/Outer Door, Exposed
Other Room 1 Dimensions: 14 x 15
Other Room 1 Level: Main
Other Room 1 Name: Other Room
Living Room Dimensions: 16 x 21
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 22 x 27
Family Room Level: Main
Family Room Length: 15 x 16
Dining Room Dimensions: 12 x 13
Dining Room Level: Main

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

Exterior

Building Information
Building Type: 2 Story
Roofing: Composition/Fiberglass
Estimated Sq. Ft. Range: 3501+, 5001+, 2501+

Exterior
Exterior Features: Deck, Patio
Exterior: Brick, Brick/Stone, Fiber Cement (Partial), Stucco/Slate

Property Information
Single-Family
Information Source Year Built: Assessor/Public Record

Land Information
Acreage: Less Than 1/2

Lot Information
Lot Acreage: 0.19
Lot Description: Sidewalks
Zoning: PD

Subdivision
Subdivision: Cherokee Point

Financial

Tax Information
Total Taxes: $12,863
Tax Year: 2014

Utilities

Utility Information
Municipal Sewer, Municipal Water
Heating/Cooling: Central Air, Forced Air, Multiple Units
Natural Gas

Location

Neighborhood Information
Municipality: MILWAUKEE
Municipality Type: City

School Information
School District: Milwaukee

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,104
Stories: 1.0
Lot Size: 8,293 square feet
Style: Single Family Residential
Year Built: 2006
Year Renovated: —
County: Milwaukee County
APN: 5540161000

Home facts updated by county records on Oct 23, 2026

Around this home

Schools

K - 12
Preschool & daycare

Jeremiah Curtin Leadership Academy

Public PreK-8 • Assigned • 0.7mi

4/10

Audubon Technology and Communication High

Public 9-12 • Assigned • 0.5mi

4/10

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 98° expected this year, 13 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Milwaukee, WI • 53221

Average low and high temperatures (°F)

28°

13°

36°

20°

50°

31°

58°

39°

66°

46°

79°

60°

84°

67°

80°

63°

75°

57°

64°

49°

50°

37°

35°

22°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10.1 hours in June and 3.3 hours in December, placing it below the U.S. average for solar exposure.

10.1 hrs

3.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$754,000 – $913,000

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Hoffmann Team* • REMAX Lakeside-Central

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Home values near 3744 S Cherokee Way

Data from public records.

Address	Redfin Estimate
3764 S Cherokee Way, Milwaukee, WI 4 Beds \| 2.5 Baths \| 2313 Sq. Ft.	$484,335
3637 S Cherokee Way, Milwaukee, WI 4 Beds \| 2.5 Baths \| 2431 Sq. Ft.	$584,004
3710 S Cherokee Way, Milwaukee, WI 3 Beds \| 3.5 Baths \| 3493 Sq. Ft.	$505,182
3727 S Cherokee Way, Milwaukee, WI 4 Beds \| 3 Baths \| 3292 Sq. Ft.	$728,212
4027 W Stonebridge Court, Milwaukee, WI 3 Beds \| 2.5 Baths \| 2586 Sq. Ft.	$489,931
4034 W Stonebridge Court, Milwaukee, WI 4 Beds \| 2.5 Baths \| 2096 Sq. Ft.	$433,960
3770 S Centennial Circle, Milwaukee, WI 3 Beds \| 2 Baths \| 2305 Sq. Ft.	$482,647

Address	Redfin Estimate
3733 S Cherokee Way, Milwaukee, WI 5 Beds \| 6.5 Baths \| 4405 Sq. Ft.	$736,330
3700 S Cherokee Way, Milwaukee, WI 3 Beds \| 3.5 Baths \| 2256 Sq. Ft.	$467,122
3751 S Cherokee Way, Milwaukee, WI 4 Beds \| 3.5 Baths \| 2708 Sq. Ft.	$545,514
4014 W Stonebridge Court, Milwaukee, WI 5 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$578,216
4033 W Stonebridge Court, Milwaukee, WI 4 Beds \| 2.5 Baths \| 3156 Sq. Ft.	$583,644
3776 S Centennial Circle, Milwaukee, WI 3 Beds \| 2.5 Baths \| 1807 Sq. Ft.	$418,944
4001 W Stonebridge Court, Milwaukee, WI 4 Beds \| 2.5 Baths \| 3057 Sq. Ft.	$570,758

Address	Redfin Estimate
3718 S Cherokee Way, Milwaukee, WI 3 Beds \| 3 Baths \| 3464 Sq. Ft.	$502,958
3726 S Cherokee Way, Milwaukee, WI 3 Beds \| 2.5 Baths \| 2138 Sq. Ft.	$442,226
3745 S Cherokee Way, Milwaukee, WI 4 Beds \| 2.5 Baths \| 2875 Sq. Ft.	$538,043
4007 W Stonebridge Court, Milwaukee, WI 4 Beds \| 2.5 Baths \| 2743 Sq. Ft.	$539,245
4022 W Stonebridge Court, Milwaukee, WI 5 Beds \| 3.5 Baths \| 3790 Sq. Ft.	$589,378
4015 W Stonebridge Court, Milwaukee, WI 3 Beds \| 2.5 Baths \| 2158 Sq. Ft.	$443,397
4040 W Stonebridge Court, Milwaukee, WI 4 Beds \| 2.5 Baths \| 3749 Sq. Ft.	$529,575

Property information provided by MetroMLS as distributed by WIREX when last listed in 2015. 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 53221, WI

Sale history for 3744 S Cherokee Way

Tax history for 3744 S Cherokee Way

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 53221

Home values near 3744 S Cherokee Way

More real estate resources