- Agent Pronto
- Illinois
- Winnetka
- Veterans
Find the perfect real estate agent for veterans and active U.S. military members
We analyze top real estate agents in Winnetka and across the country to find you the best veteran and military-friendly local agents, for free.
Compare the top 25 real estate agents in Winnetka
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for June 2025. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
The easiest way to find the best VA-specialist real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“James called me within the hour and was available to meet with me in just a few days. He put the listing up and it sold in 10 days. Very happy with the result!”
“Mike Frank provided excellent service and was a pleasure to work with.”
“It was great! We were put in touch with the best real estate agent around!”
“Thank you, Agent Pronto, for recommending Karl. He was an amazing agent and just got the job done! I would recommend your service and Karl to any future home sellers or buyers!!!”
“Dena was absolutely incredible. I could not be happier.”
“It's been great working with Bobbi - she is very responsive (never once missed a phone call or text), always on point but never pushy, be it her advice on pricing changes or negotiating an offer or following up on repairs. She arranged multiple open houses, brought in a steady stream of potential buyers, helped us a lot thru the whole process, made it easy for us even after we moved out of state and got our home sold just before the winter hit. Loved working with her and would definitely recommend her. ”
“Excellent! Very pleased with the process and the agent I chose to work with. It was expedient and simple, which worked perfectly for me as I'm located in another state away from the property I sold!!”
“Cheri Gibson was the best I have ever dealt with. She was professional at all times. She answered all our questions. She is very knowledgeable. I would highly recommend her to anyone looking to sell/buy. The house was listed and sold in one day.”
“Jodi got the job done!”
“I found a great agent! We were able to sell the property within three days after it was listed. It was a pleasure working with Diana Matichyn and her team. I would highly recommend her.”
Winnetka real estate Market Report.
Information and statistics on the latest trends in the Winnetka real estate market, updated for June 2025. *
The typical home value in Winnetka is projected to be $1,727,500 for the month of May. April’s finalized data reported the typical value of a home in the city to be $1,687,500—down 8.78% over the previous 12 months. For comparison, county-level data pegged home values at $360,000 in Cook County for the most recent reporting period. That number is expected to float around $362,500 in May.
Winnetka had 19 new listings and 15 listings that went under contract in April, increasing the area’s total available inventory to 32—up 10.34% from the previous month. Inventory is projected to have further increased in May.
Of those 32 active listings, 12.5% reduced their price in the month of April. The median listing price for homes in Winnetka grew 10.03% from March to April, bringing the current median listing price to $2,195,000. Based on projected data for May, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In April 2025, the median time for a listed property to go pending was 23 days, compared to 6 days in April 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this May.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Winnetka has to offer.
Winnetka offers its residents a charming blend of scenic beauty, vibrant community life, and excellent amenities that make it a wonderful place to call home.
Winnetka captivates residents and newcomers with its tree-lined streets, striking lakefront vistas, and a genuine sense of community. This North Shore gem stands out for its harmonious blend of architectural grandeur, from historic Tudor homes to sleek contemporary builds. With stretches of sand along Winnetka’s public beaches and miles of walking and biking trails, outdoor enthusiasts and families alike relish year-round activities. The local Winnetka Community House pulses at the heart of civic life, offering everything from fitness classes to art fairs.
Education shines here; the Winnetka Public Schools District 36 is celebrated for its innovative approach and engaged faculty, and nearby New Trier High School consistently earns accolades for academic excellence and extracurricular achievement. Walkable shopping villages invite browsing, where locally owned boutiques mingle with cozy cafés and the storied Winnetka-Northfield Public Library District fosters a love of literature and learning.
Bordering communities such as Wilmette and Glencoe contribute to the area's cosmopolitan ambiance, and convenient rail access to Chicago places world-class dining, museums, and business hubs just a short ride away. Whether you’re searching for a dream home or seeking the best offer for your property, Agent Pronto connects buyers and sellers with experienced real estate agents who understand every facet of this exceptional village.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
Take the guesswork out of finding an agent.
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winnetka to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Data analysis with a human touch.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winnetka. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Resources for buyers and sellers.
Tips and market insights to make your Winnetka real estate journey a success.
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents.
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