“She sent my offer in and it was accepted without negotiation. Thats an A in my book.”
EXP Realty
- Agent Pronto
- Indiana
- Chesterton
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for February 2026. *
* 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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“Jeff helped my wife and I find a lovely property that met as many of our criteria as possible given our budget”
Century 21 Bradley
“Deborah was fantastic. She's very polite always was on time. Listen to our concerns was very honest and open. Great person to talk to was very concerned about what we need. She was way above and beyond anyone I have ever dealt with I highly recommend her to anyone looking for a home she was phenomenal”
Brokerworks Real Estate Group
“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!”
Key Realty
“Very friendly and approachable person. Very easy to work with. Was really invested in the process and treated us with respect. I don't feel like just another client when working with her.”
Brokerworks Group
“It was a great pleasure working with Kelly as she is very helpful, supportive, and caring. She promised to find me a great home and she did. She is so responsive when I contacted her. Kelly made me feel secure throughout my journey to find a house. I highly appreciate her professionalism.”
Realty Executives Premier
“Jorrdan was great! He went above and beyond for us! I would highly recommend him to anyone buying a home in Northwest Indiana.”
T.J. Boyle Real Estate
“Cari and Geri was great”
RE/MAX Executives
“I am a 55 year old business man that has purchased a number of primary and secondary residences. Of all of the realtors, Nicole was clearly the best. She was knowledgable and super responsive at all hours. In fact, I am not sure if she sleeps. Nicole helped me identify the exact right condo based on a number of requirements and then helped me to move quickly to lock it down. I would definitely work with Nicole again.”
Compass
“Mary Beth Myers was awesome!!!!”
McColly Real Estate
Chesterton real estate Market Report.
Information and statistics on the latest trends in the Chesterton real estate market, updated for February 2026. *
The typical home value in Chesterton is projected to be $349,380 for the month of February. January’s finalized data reported the typical value of a home in the city to be $342,500—up 29.25% over the previous 12 months. For comparison, county-level data pegged home values at $322,000 in Porter County for the most recent reporting period. That number is expected to float around $325,250 in February.
Chesterton had 5 new listings and 13 listings that went under contract in January, decreasing the area’s total available inventory to 39—down 27.78% from the previous month. Inventory is projected to have further decreased in February.
Of those 39 active listings, 35.9% reduced their price in the month of January. The median listing price for homes in Chesterton fell 1.52% from December to January, bringing the current median listing price to $324,900. Based on projected data for February, 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 January 2026, the median time for a listed property to go pending was 114 days, compared to 178 days in January 2025. 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 February.
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Seller’s Market
Buyer’s Market
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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 welcoming small-town vibe with abundant parks and trails, a thriving local scene, and convenient access to shops, schools, and nature.
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.
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 covering the housing market in and around Chesterton. 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. Find your Chesterton Realtor® or real estate agent today.
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