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Featured Agents in Winnetka, IL

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PRIME AGENT
Sheila Doyle profile picture
Baird & Warner

Sheila Doyle

Completed Profile
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22years of experience
35sales in the last 12 months
600transactions all-time
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PRIME AGENT
Virginia Trux profile picture
@properties

Virginia Trux

6 reviews
View Profile
37years of experience
31sales in the last 12 months
400transactions all-time
Prime Agent Badge
PRIME AGENT
Patrick Dalessandro profile picture
Coachlight Realty And Property Mgmt. Inc.

Patrick Dalessandro

Completed Profile
View Profile
53years of experience
34sales in the last 12 months
2,000transactions all-time

Compare 15 top-performing real estate agents in Winnetka, IL

Ar Home Realty

Mark Anthony

2 reviews
Open 9:00 AM - 9:00 PM
Usually responds in 5 minutes
Prime Agent Badge
PRIME AGENT
5 years of experience
19 sales in last 12 months
Serves Winnetka

About

I help homeowners sell with confidence by removing the stress of choosing an agent—especially if you don’t already have one you trust. My listings use 30-day agreements, not long-term contracts. If it’s a fit, we continue. If not, you’re free to move on. No upfront fees, no penalties, and no long-term lock-ins. Every home receives full-service marketing and hands-on representation from day one: professional photography, IMMERSIVE 3D & VIRTUAL REALITY TOURS, laser-measured floor plans, weekly performance analytics, and full management from listing through closing. VIRTUAL REALITY is a 24/7 open house, letting buyers explore anytime without constant foot traffic—so you keep privacy while buyers arrive better informed. I personally handle every listing—no assistants, no hand-offs—so communication stays clear and the process stays simple. This approach is designed to reduce anxiety and give homeowners clarity and flexibility, without 6- or 12-month traps.

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Achievements

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Top Sales Producer 2025
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Top Listing Broker 2025
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Top Negotiator 2025

Top Agent for 2021 and 2022

Bachelor's Degree
Business Management

REALTOR®, CRES, CLP, Real Estate Negotiation Expert

Business Highlights

VA loans, Distressed Properties, Luxury Properties, First Time Buyers
I'm also a licensed mortgage broker, which gives my buyers a seamless experience—working with one trusted professional to handle both the loan and the home purchase.
As a former full-time professional photographer for Homes.com, I provide all my sellers with full marketing at no extra cost—including aerial drone photography, 3D virtual reality tours, and weekly analytics reports that show exactly how many buyers are viewing your home online.
Certified Real Estate Negotiator

Black Label Realty

Nicholas Kravat

Completed Profile
Open 24 hours
Usually responds in 30 minutes
Prime Agent Badge
PRIME AGENT
5 years of experience
17 sales in last 12 months
52 transactions all-time
Serves Winnetka

About

When he isn’t immersed in the Real Estate world, Nicholas enjoys spending quality time with his loved ones, cooking, and traveling the world. From Mexico to Russia, Nicholas loves to emerge himself in and learn customs of different cultures worldwide.Nicholas has an extensive understanding of home construction and renovations as he has spent over 12 years working with several major home renovation/construction companies. Additionally, Nicholas has a degree in Criminal Justice Sciences from Illinois State University. Having structured several successful transactions from Do-It-Yourself clients to entire house flips for developers and contractors, Nicholas has taken his love for the art of deal-making to Keller Williams ONE Chicago and the Home Hunters Chicago Team. Whether you are a first-time homebuyer or a seasoned real estate investor, Nicholas will help you make an informed, educated decision that will produce an optimal outcome for your selling, buying, or investment needs.

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Achievements

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Top Chicago Agent 2025
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Top Negotiator 2025
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Top Luxury Buyer's Agent 2025

Top Agent Network 2023

Bachelor's Degree, Illinois State University
Criminal Justice, Psychology, Political Science, 2006 - 2010

REALTOR®

Business Highlights

Distressed Properties, New Homes, Luxury Properties, Relocation
Relocation Expert: Check out my reviews on Zillow here: https://www.zillow.com/profile/nickkravat
First-Time Home Buyers, Luxury Listings, and Investors can Create a FREE Home Search here: https://zenlist.com/a/nick.kravat
Create a Home Search here: https://zenlist.com/a/nick.kravat or call 815-671-2003 for FREE Access

At Properties

Thomas Downing

9 years of experience
25 sales in last 12 months
300 transactions all-time
Serves Winnetka

About

Thomas Downing, Vice President of Brokerage Services and Designated Managing Broker for @properties' Winnetka office, the top-producing real estate office on the North Shore. The Winnetka office has more than 180 licensed brokers generating over $1 billion in annual closed sales volume. Tom began selling real estate in 2013 after a career in business management consulting, where he specialized in counseling and coaching businesses towards increased profits, and supported Fortune 500 companies like AT&T, Disney, and Pan Am. He joined @properties as an agent in 2015 and built a successful team, leveraging his passion for developing agents to their highest potential. A North Shore native, Tom can often be found at one of Chicagoland's many great restaurants. He has traveled to many places throughout the world and is an avid triathlete, having competed in the Chicago Triathlon and the Ironman Triathlon.

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Achievements

Agent Choice Awards, 2016, Top Producer 2017

Bachelor's Degree, Trinity University
BS

e-PRO, GRI, REALTOR®, ABR

Business Highlights

Buyer Representative, Concierge Services, Condominiums, First Time Buyers

Berkshirehathaway Homeservices Chicago

Martha May

Completed Profile
62 reviews
Open 24 hours
Usually responds in 10 minutes
Prime Agent Badge
PRIME AGENT
40 years of experience
25 sales in last 12 months
775 transactions all-time
Serves Winnetka

About

EXPERIENCE MATTERS! My success story started in 1986, (40 amazing years in 2026!) and I still am madly in love with what I do! Year after year, an award-winning agent with Berkshire Hathaway HomeServices Chicago, I have marked many of those years as #1 Individual Agent in the Glenview office! I am a member of the esteemed BHHS Hall of Fame, President's Circle, & The National Gold Chairman's Circle! One of the reasons I am among the most successful & respected Realtors in the North Shore area is that I take my business & my clients to heart. Communication is high on my list! I will give you 200% in everything I do to make your move or purchase as effortless as possible! My artistic background will serve you beautifully as I use creativity & imagination to achieve your goal. This "artistic approach" is the foundation of each relationship I develop with every client I serve . My knowledge & commitment to my profession sets me apart. Let me turn your transaction into a work of art!

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Achievements

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Top Buyer's Agent 2025
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Top Listing Agent 2025
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Top Negotiator 2025

Leading Edge Award-2023, Honor Society-2024, National Gold Chairman's Circle Award 2014, 2015, 2017; President's Circle Award 2016, 2018, 2019, 2020, 2021, 2022; BHHS KoenigRubloff Hall of Fame Inductee 2015; Crain's Chicago Most Influential Real Estate Broker 2018

Bachelor's Degree, University of Iowa
Bachelor of Fine Arts

GRI, CRS, ASP, SFR

Martha May's Video

Re/max Premier Luxury Collection

Marc Perlove Eric Shoemaker

Completed Profile
3 reviews
Open 10:00 AM - 4:00 PM
Usually responds in 5 minutes
Prime Agent Badge
PRIME AGENT
40 years of experience
6 sales in last 12 months
500 transactions all-time
Serves Winnetka

About

I have been a real estate broker in the Chicagoland area for 35 years. I specialize in residential real estate, specifically multi family residences, single family homes, townhouses, and condos. Anywhere from downtown Chicago out to the suburbs is where you may find me working.

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Achievements

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Top Listing Agent 2025
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Top Listing Broker 2025
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Top Negotiator 2025

remax hall of fame remax platinum

Bachelor's Degree

REALTOR®

Business Highlights

1031 Tax Exchange, Buyer Representative, Condominiums, Distressed Properties
I specialize in residential real estate, specifically multi family residences, single family homes, townhouses, and condos.

We've introduced over 4,940,482 buyers and sellers to top local real estate agents in the past 15 years

  • R V

    "The service was great and the recommendation of the realtor was fantastic. The realtor was fair and honest he gave me a very reasonable selling price and follow the listing all the way through. The house sold within the first week."
    Rita V. from Tennessee / Sold a home using RealEstateAgents.com
  • A C

    "I used the website to identify potential agents in the new city I was moving too. I ultimately went with one of the recommended agents and had a very smooth home buying process."
    Alexis C. from Iowa / Bought a home using RealEstateAgents.com
  • R J

    "My realtor was very professional in every aspect of the sale. My house sold within a week. She called or texted me through out the whole process."
    Ruth J. from Ohio / Sold a home using RealEstateAgents.com
  • S M

    "We found an excellent Realtor, who guided us through the sale and did an excellent job along the way."
    Steve M. from Florida / Sold a home using RealEstateAgents.com
  • J B

    "Very professional, we had a great experience."
    Jon B. from Wisconsin / Bought a home using RealEstateAgents.com
  • S K

    "The agent you recommended was fantastic. He stayed in touch throughout the process. He kept us informed every step of the way. The sale was quick and couldn't have gone smoother. Would definitely recommend to anyone else and will definitely use in the future if needed."
    Stanley K. from Indiana / Sold a home using RealEstateAgents.com
  • J L

    "Great realtors. My home sold in five days!"
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    Bonnie W. from Indiana / Sold a home using RealEstateAgents.com
  • J S

    "Had issues with the title company, which agents handled."
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  • J H

    "We had a very unique situation... My sister and I live in different states and the house belonged to our deceased Mother... Service was great could not have been any better..."
    Joe H. from Texas / Sold a home using RealEstateAgents.com

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Winnetka Housing Market Report

Market Action Index

We are extensively tracking the housing market in Winnetka, IL. Here are the strongest factors contributing to this score:

Fewer sellers are listing their homes compared to last year
Houses are selling quickly compared to the amount on the market
93
seller's market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$2.39M

Per Square Foot

$517

Days on Market

101

Total Listings

27

Median List Price

Thu, May 7, 2026

Median List Price
1 Year

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