Illinois • 54 Top Realtors • 2026 Rankings

Best Real Estate Agents in Winnetka, Illinois

1,320
Transactions
$1.5B
Volume
54
Top Agents
@properties Christie's International Real Estate
Top Brokerage

Discover Winnetka's premier real estate agents on the North Shore of Chicago, where lakefront properties and prestigious estates command some of Illinois's highest values. Our directory features top-performing agents who have collectively closed over 1,320 transactions totaling $1.5 billion in sales, with @properties Christie's International Real Estate leading the market in this affluent, architecturally distinguished community.

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Winnetka Real Estate Agents Ranked by Sales Volume

Finding the right agent is just the beginning.

Jena Radnay

Real Estate Agent

@properties Christie's International Real Estate

$133.91M
49 transactions
Individuals by Volume

Laura Fitzpatrick

Real Estate Agent

@properties Christie's International Real Estate

$45.05M
46 transactions
Individuals by Volume

Mary Grant

Real Estate Agent

@properties Christie's International Real Estate

$40.25M
26 transactions
Individuals by Volume

Susan Maman

Real Estate Agent

@properties Christie's International Real Estate

$38.72M
25 transactions
Individuals by Volume

Katie Hackett

Real Estate Agent

@properties Christie's International Real Estate

$33.35M
24 transactions
Individuals by Volume

Brandie Siavelis

Real Estate Agent

@properties Christie's International Real Estate

$31.52M
7 transactions
Individuals by Volume

Sara Brahm

Real Estate Agent

@properties Christie's International Real Estate

$30.08M
19 transactions
Individuals by Volume

Annika Valdiserri

Real Estate Agent

@properties Christie's International Real Estate

$27.50M
29 transactions
Individuals by Volume

Karen Arenson

Real Estate Agent

Engel & Völkers Chicago North Shore

$27.23M
41 transactions
Individuals by Volume

Courtney Cook

Real Estate Agent

@properties Christie's International Real Estate

$22.81M
17 transactions
Individuals by Volume

Elise Rinaldi

Real Estate Agent

@properties Christie's International Real Estate

$18.62M
12 transactions
Individuals by Volume

Lyn Flannery

Real Estate Agent

@properties Christie's International Real Estate

$18.03M
20 transactions
Individuals by Volume

Shelley Shelly

Real Estate Agent

@properties Christie's International Real Estate

$17.55M
13 transactions
Individuals by Volume

Aly Tesar

Real Estate Agent

@properties Christie's International Real Estate

$16.70M
18 transactions
Individuals by Volume

Jamie Roth

Real Estate Agent

Engel & Völkers Chicago North Shore

$16.56M
18 transactions
Individuals by Volume

Chris Veech

Real Estate Agent

@properties Christie's International Real Estate

$15.79M
16 transactions
Individuals by Volume

Julie Cassin

Real Estate Agent

@properties Christie's International Real Estate

$15.78M
14 transactions
Individuals by Volume

Victoria Stein

Real Estate Agent

Compass

$15.49M
23 transactions
Individuals by Volume

Lisa Finks

Real Estate Agent

Compass

$15.23M
19 transactions
Individuals by Volume

Kate Huff

Real Estate Agent

@properties Christie's International Real Estate

$15.05M
14 transactions
Individuals by Volume

Mike Lefevere

Real Estate Agent

Compass

$14.87M
15 transactions
Individuals by Volume

Keki Cannon

Real Estate Agent

@properties Christie's International Real Estate

$14.33M
16 transactions
Individuals by Volume

Carol Hunt

Real Estate Agent

Baird & Warner

$14.10M
13 transactions
Individuals by Volume

Elizabeth Smith

Real Estate Agent

@properties Christie's International Real Estate

$13.73M
10 transactions
Individuals by Volume

Bonnie Tripton

Real Estate Agent

@properties Christie's International Real Estate

$13.00M
9 transactions
Individuals by Volume

Carrie Tarzon

Real Estate Agent

@properties Christie's International Real Estate

$12.42M
17 transactions
Individuals by Volume

Lori Nieman

Real Estate Agent

@properties Christie's International Real Estate

$12.29M
8 transactions
Individuals by Volume

Monica Sofranko

Real Estate Agent

@properties Christie's International Real Estate

$12.24M
7 transactions
Individuals by Volume

Haley Levine

Real Estate Agent

Compass

$12.09M
19 transactions
Individuals by Volume

Houda Chedid

Real Estate Agent

Compass

$11.62M
8 transactions
Individuals by Volume

Grace Flatt

Real Estate Agent

@properties Christie's International Real Estate

$10.98M
16 transactions
Individuals by Volume

Lynn Romanek Holstein

Real Estate Agent

Baird & Warner

$10.66M
10 transactions
Individuals by Volume

Lori Neuschel

Real Estate Agent

@properties Christie's International Real Estate

$10.63M
11 transactions
Individuals by Volume

Bridget Orsic

Real Estate Agent

@properties Christie's International Real Estate

$10.54M
8 transactions
Individuals by Volume

Chris Smith

Real Estate Agent

Baird & Warner

$10.49M
19 transactions
Individuals by Volume

Mawicke Group

Real Estate Agent

@properties Christie's International Real Estate

$50.97M
29 transactions
Small Teams by Volume

The Dave + Amy Chung Team

Real Estate Agent

Compass

$49.06M
35 transactions
Small Teams by Volume

Capitanini Team

Real Estate Agent

Compass

$42.63M
38 transactions
Small Teams by Volume

Christie Ascione Property Group

Real Estate Agent

@properties Christie's International Real Estate

$36.89M
31 transactions
Small Teams by Volume

Meg + Katie Group

Real Estate Agent

Compass

$34.39M
24 transactions
Small Teams by Volume

Dinny Dwyer

Real Estate Agent

Compass

$27.98M
28 transactions
Small Teams by Volume

Kathryn and Kelly Mangel

Real Estate Agent

@properties Christie's International Real Estate

$27.96M
24 transactions
Small Teams by Volume

The Flanagan Group

Real Estate Agent

@properties Christie's International Real Estate

$23.61M
17 transactions
Small Teams by Volume

Patti + Julie Team

Real Estate Agent

Compass

$22.00M
13 transactions
Small Teams by Volume

Coco & April Group

Real Estate Agent

Compass

$20.73M
15 transactions
Small Teams by Volume

The Meyers Group

Real Estate Agent

Compass

$20.67M
21 transactions
Small Teams by Volume

Team Kaage

Real Estate Agent

Compass

$18.45M
15 transactions
Small Teams by Volume

The Pepoon Team

Real Estate Agent

Compass

$14.88M
21 transactions
Small Teams by Volume

The Paige Dooley Team

Real Estate Agent

Compass

$142.17M
80 transactions
Medium Teams by Volume

The Joanne Hudson Group

Real Estate Agent

Compass

$50.78M
42 transactions
Medium Teams by Volume

REV Group

Real Estate Agent

@properties Christie's International Real Estate

$37.25M
124 transactions
Medium Teams by Volume

Bradbury Miller & Burgoon

Real Estate Agent

Compass

$26.31M
19 transactions
Medium Teams by Volume

Mabadi Group

Real Estate Agent

Compass

$24.14M
27 transactions
Medium Teams by Volume

MacPherson Group

Real Estate Agent

@properties Christie's International Real Estate

$55.51M
81 transactions
Large Teams by Volume

Frequently Asked Questions

Who are the best real estate agents in Winnetka, Illinois?

The best real estate agents in Winnetka include Jena Radnay of @properties Christie's International Real Estate (49 transactions), Laura Fitzpatrick of @properties Christie's International Real Estate (46 transactions), Mary Grant of @properties Christie's International Real Estate (26 transactions), among others. Our directory tracks 54 top-performing agents ranked by verified sales volume and transaction history.

How do I find a good realtor near me in Winnetka?

To find a top realtor in Winnetka, compare their sales volume, transaction history, and client reviews. Our directory tracks 54 agents in Winnetka—filter by specialty, review verified contact info, and reach out directly. Look for agents who specialize in your specific needs, whether buying, selling, or investing.

How can IonDocs help real estate agents in Winnetka?

IonDocs analyzes property disclosure packages for homes in Winnetka, Illinois in 60 seconds—work that typically takes agents 4–6 hours. Our AI catches costly surprises like pending HOA special assessments, permit issues, and structural discrepancies so Winnetka agents can close more deals and spend less time on paperwork.

What are property disclosure packages and why do they matter?

Property disclosure packages are documents that sellers must provide to buyers in Illinois, revealing the property's condition, history, and any known issues. These packages often contain critical information about structural problems, pest damage, HOA finances, and legal issues. Missing a single detail can cost buyers tens of thousands of dollars—or kill a deal entirely.

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Agent in Winnetka?

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