Illinois · as of September 2026

The best luxury home agents in Winnetka

12 agents who close Winnetka's high end, ranked by what they sell for, how much of it is on record, and what their clients say afterward.

No. 1
J

Jena Radnay

@properties

4.9 · 38 reviews

Avg sale
$3.1M
Top sale
$4.2M
Closed
750
No. 2
K

Kathryn and Kelly Mangel

@properties

5.0 · 86 reviews

Avg sale
$2.9M
Top sale
$3.5M
Closed
366
No. 3
P

Paige Dooley

Compass

5.0 · 35 reviews

Avg sale
$2.5M
Top sale
$3.8M
Closed
769
No. 4
B

Bonnie Tripton

@properties

5.0 · 34 reviews

Avg sale
$2.2M
Top sale
$3.4M
Closed
287
No. 5
S

Susan Maman

@properties North Shore and Glencoe

5.0 · 66 reviews

Avg sale
$1.8M
Top sale
$2.7M
Closed
386
No. 6
C

CARRIE McCORMICK

CARRIE McCORMICK Chicago Real Estate REALTOR

5.0 · 184 reviews

Avg sale
$1.3M
Top sale
$1.9M
Closed
1,936
No. 7
L

Laura Fitzpatrick

@ Properties North Shore

4.8 · 41 reviews

Avg sale
$1.8M
Top sale
$2.4M
Closed
393
No. 8
C

Carol Hunt

Baird & Warner

5.0 · 31 reviews

Avg sale
$1.8M
Top sale
$6.3M
Closed
367
No. 9
A

Annika Valdiserri

@Properties

5.0 · 43 reviews

Avg sale
$1.7M
Top sale
$3.9M
Closed
403
No. 10
M

Mary Grant

@properties

5.0 · 50 reviews

Avg sale
$1.7M
Top sale
$3.4M
Closed
376
No. 11
H

Howard Meyers

Compass - Winnetka

5.0 · 28 reviews

Avg sale
$1.7M
Top sale
$3.2M
Closed
199
No. 12
L

Leslie Maguire

@properties

5.0 · 48 reviews

Avg sale
$1.7M
Top sale
$3.4M
Closed
128

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