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Find the perfect real estate agent for veterans and active U.S. military members
We analyze top real estate agents in Chesterton and across the country to find you the best veteran and military-friendly local agents, for free.
Compare the top real estate agents in Chesterton
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.
“Mary Beth Myers was awesome!!!!”
“Wendy is a wonderful agent and person. She did everything the way we wanted it and the house had an offer on day 2 or 3. Would highly recommend her if you are looking for a great agent!”
“Josh Latham was knowledgeable, helpful, patient, kind, and very pleasant to work with. Promptly answered my questions returned emails, text and phone calls. I am planning to sell my house soon and Josh will be my go-to guy.”
“Our agent was very helpful. He kept us informed every step of the way. I never thought the house would sell during the quarantine, but our agent, Barry, was able to sell our house anyway. Made things go very smooth, easy and fast. Was a great experience.”
“My initial contact with Mr. Gall went very well and over the next week, we looked at a number of properties within the specifications I had provided. The last morning just as I was about to go back to Vermont, he saw a home just listed by an estate. We signed a contract within a few hours.”
“Justin was most helpful dealing with an uncooperative property manager. He got the property sold quickly. I was very happy with his performance.”
“Chad was a great agent and we have referred him to others who are selling. Thank you Agent Pronto for connecting him with us.”
“Instant match of agent and a great fit for us! Giselle was very professional and helpful in guiding us every step of the way. She's prompt with responses and incredibly patient with us with our questions, concerns, and requests. Even after the deal has closed, she still took the time to follow up with us to make sure we are properly settled in.”
“Cindy and Michael Stockhaus are, by far, the best realtors I've dealt with. Aside from their professionalism, their communication, their availability, their patience, and their overall knowledge, they are people with heart. This wasn't an easy sale, for any of us, but they maintained professionalism and absolutely seemed to care about me and what I was going through in this process of selling my dad's home. Thank you for the recommendation!”
“I was pleasantly surprised and impressed with how professional Lisa was and how quickly the property sold. We had a closing within a month of listing.”
Chesterton real estate Market Report.
Information and statistics on the latest trends in the Chesterton real estate market, updated for June 2025. *
The typical home value in Chesterton is projected to be $415,030 for the month of May. April’s finalized data reported the typical value of a home in the city to be $387,500—up 13.97% over the previous 12 months. For comparison, county-level data pegged home values at $329,900 in Porter County for the most recent reporting period. That number is expected to float around $337,350 in May.
Chesterton had 18 new listings and 17 listings that went under contract in April, decreasing the area’s total available inventory to 40—down 9.09% from the previous month. Inventory is projected to have further decreased in May.
Of those 40 active listings, 27.5% reduced their price in the month of April. The median listing price for homes in Chesterton fell 19.56% from March to April, bringing the current median listing price to $369,950. Based on projected data for May, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In April 2025, the median time for a listed property to go pending was 93 days, compared to 150 days in April 2024. In recent months the median number of days from listed to pending appears to be decreasing. 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 Chesterton has to offer.
Chesterton offers residents a charming blend of small-town hospitality and community-rich experiences, making it an inviting place to live.
Chesterton impresses with its perfect blend of small-town character and easy access to top Midwestern destinations. Located just minutes from the southern shore of Lake Michigan, residents enjoy proximity to the expansive trails and sandy beaches of Indiana Dunes National Park, making outdoor adventure and scenic relaxation part of daily life. Only a short drive from Valparaiso and an easy commute to Porter County, the town uniquely balances serene residential neighborhoods with vibrant connections to neighboring communities.
Education thrives in Chesterton, supported by the acclaimed Duneland School Corporation, where academic excellence and innovative programs draw families focused on student success. The new Chesterton High School features state-of-the-art facilities and a robust selection of extracurriculars, while the Chesterton Montessori School offers families alternative learning experiences from preschool through elementary years.
Local life brims with cultural and social opportunities. Downtown Chesterton is alive with unique boutiques, local eateries, the bustling European Market, and year-round community events. Parks like Coffee Creek Watershed Preserve provide peaceful green spaces and host public gatherings that foster a warm, welcoming atmosphere.
Whether you’re seeking a family-friendly environment, outdoor recreation, or easy connections to regional hubs, Chesterton provides a remarkable setting to call home. If you’re considering a move, or looking to make a change within Chesterton, Agent Pronto can match you with a top real estate agent to expertly guide you whether you’re buying or selling.
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 Chesterton 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 Chesterton. 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 Chesterton 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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