“I appreciated the helpfelness and work he provided. I was sometimes disappointed in his lack of responsiveness to phone calls and texts. Overall it was a good experience.”

We analyze top real estate agents in Chesterton and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 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.
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Information and statistics on the latest trends in the Chesterton real estate market, updated for August 2025. *
The typical home value in Chesterton is projected to be $353,750 for the month of July. June’s finalized data reported the typical value of a home in the city to be $365,000—up 5.08% over the previous 12 months. For comparison, county-level data pegged home values at $354,900 in Porter County for the most recent reporting period. That number is expected to float around $357,860 in July.
Chesterton had 23 new listings and 24 listings that went under contract in June, increasing the area’s total available inventory to 54—up 3.85% from the previous month. Inventory is projected to have further increased in July.
Of those 54 active listings, 27.78% reduced their price in the month of June. The median listing price for homes in Chesterton grew 2.74% from May to June, bringing the current median listing price to $374,900. Based on projected data for July, 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 June 2025, the median time for a listed property to go pending was 21 days, compared to -2 days in June 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 July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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!
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.
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!
Tips and market insights to make your Chesterton real estate journey a success.
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.
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.
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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