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Chesterton, IN real estate

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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 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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Chesterton real estate Market Report.

Information and statistics on the latest trends in the Chesterton real estate market. *

Latest Rolling 3-Month Snapshot

Mar 1, 2026 - May 31, 2026

Median sale price
$376K
+0.2% from Q1 '26
Median list price
$396K
+0.7% from Q1 '26
Active listings
114
+14% from Q1 '26
Homes sold
52
+41% from Q1 '26
New pendings
64
+45% from Q1 '26
New listings
74
+68% from Q1 '26

Quarterly Pricing Trends for Chesterton

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Chesterton Q2 '21 Q2 '22 Q2 '23 Q2 '24 Q2 '25 Q1 '26 Median sale price in Apr 2021 - Jun 2021: $265K Median sale price in Jul 2021 - Sep 2021: $260K Median sale price in Oct 2021 - Dec 2021: $285K Median sale price in Jan 2022 - Mar 2022: $315K Median sale price in Apr 2022 - Jun 2022: $330K Median sale price in Jul 2022 - Sep 2022: $320K Median sale price in Oct 2022 - Dec 2022: $308K Median sale price in Jan 2023 - Mar 2023: $322K Median sale price in Apr 2023 - Jun 2023: $297K Median sale price in Jul 2023 - Sep 2023: $350K Median sale price in Oct 2023 - Dec 2023: $337K Median sale price in Jan 2024 - Mar 2024: $393K Median sale price in Apr 2024 - Jun 2024: $382K Median sale price in Jul 2024 - Sep 2024: $355K Median sale price in Oct 2024 - Dec 2024: $280K Median sale price in Jan 2025 - Mar 2025: $279K Median sale price in Apr 2025 - Jun 2025: $380K Median sale price in Jul 2025 - Sep 2025: $363K Median sale price in Oct 2025 - Dec 2025: $340K Median sale price in Jan 2026 - Mar 2026: $375K Median list price in Apr 2021 - Jun 2021: $255K Median list price in Jul 2021 - Sep 2021: $275K Median list price in Oct 2021 - Dec 2021: $330K Median list price in Jan 2022 - Mar 2022: $376K Median list price in Apr 2022 - Jun 2022: $275K Median list price in Jul 2022 - Sep 2022: $303K Median list price in Oct 2022 - Dec 2022: $325K Median list price in Jan 2023 - Mar 2023: $305K Median list price in Apr 2023 - Jun 2023: $349K Median list price in Jul 2023 - Sep 2023: $347K Median list price in Oct 2023 - Dec 2023: $399K Median list price in Jan 2024 - Mar 2024: $300K Median list price in Apr 2024 - Jun 2024: $368K Median list price in Jul 2024 - Sep 2024: $349K Median list price in Oct 2024 - Dec 2024: $310K Median list price in Jan 2025 - Mar 2025: $430K Median list price in Apr 2025 - Jun 2025: $372K Median list price in Jul 2025 - Sep 2025: $398K Median list price in Oct 2025 - Dec 2025: $345K Median list price in Jan 2026 - Mar 2026: $393K Apr 2021 - Jun 2021 Median sale price $265K Median list price $255K Jul 2021 - Sep 2021 Median sale price $260K Median list price $275K Oct 2021 - Dec 2021 Median sale price $285K Median list price $330K Jan 2022 - Mar 2022 Median sale price $315K Median list price $376K Apr 2022 - Jun 2022 Median sale price $330K Median list price $275K Jul 2022 - Sep 2022 Median sale price $320K Median list price $303K Oct 2022 - Dec 2022 Median sale price $308K Median list price $325K Jan 2023 - Mar 2023 Median sale price $322K Median list price $305K Apr 2023 - Jun 2023 Median sale price $297K Median list price $349K Jul 2023 - Sep 2023 Median sale price $350K Median list price $347K Oct 2023 - Dec 2023 Median sale price $337K Median list price $399K Jan 2024 - Mar 2024 Median sale price $393K Median list price $300K Apr 2024 - Jun 2024 Median sale price $382K Median list price $368K Jul 2024 - Sep 2024 Median sale price $355K Median list price $349K Oct 2024 - Dec 2024 Median sale price $280K Median list price $310K Jan 2025 - Mar 2025 Median sale price $279K Median list price $430K Apr 2025 - Jun 2025 Median sale price $380K Median list price $372K Jul 2025 - Sep 2025 Median sale price $363K Median list price $398K Oct 2025 - Dec 2025 Median sale price $340K Median list price $345K Jan 2026 - Mar 2026 Median sale price $375K Median list price $393K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
18
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).

Chesterton’s rolling three-month snapshot through May 2026 shows a lean but active market, with about 114 homes listed and 74 new listings entering the pipeline. Pending sales held near that pace at 64, while 52 homes closed, and with just 2.6 months of supply, conditions still tilt toward sellers even as active listings are down compared with a year ago.

Pricing has adjusted modestly in this environment, as the typical home value around $375,775 is slightly lower than a year earlier while the median list price is up by more than 5 percent year over year. Homes are being priced with some ambition, yet the average sale-to-list ratio near 99 percent and a smaller share of properties selling above asking indicate that buyers have a bit more room to negotiate than in prior years.

Time on market has changed sharply, with the median days on market dropping to about a month, a big shift from the much longer marketing times seen earlier in the year. Over half of listings go off the market within two weeks, underscoring that well-priced, well-presented homes can still move quickly despite the cooler year-over-year sales count. Whether you are a buyer trying to time your offer or a seller aiming to price correctly from day one, Agent Pronto can connect you with a Chesterton agent who understands these trends and can guide your next move.



Learn more about what Chesterton has to offer.

Chesterton offers residents a welcoming, family-friendly community with abundant parks and trails, strong local services, good schools, and a lively downtown that together create a connected, high-quality everyday life.

Chesterton offers a practical balance of small-town scale with strong regional access, sitting close to Lake Michigan and major routes into Chicago and South Bend. Daily life centers on an active downtown, established neighborhoods, and easy connections to nearby Portage and Valparaiso.

Residents appreciate the commuter options, including the South Shore Line station that connects to Chicago, and quick access to I‑94 and the Indiana Toll Road. Outdoor time is a real part of life here, with the Indiana Dunes National Park and Indiana Dunes State Park offering beaches, trails, and year‑round programs just minutes away. Local parks such as Coffee Creek Watershed Preserve add walking paths and open space close to residential areas.

Chesterton’s schools, including Chesterton High School, are part of the Duneland School Corporation, a key consideration for many buyers. The Westchester Public Library and seasonal events at Thomas Centennial Park contribute to a steady community rhythm rather than only tourist traffic.

Navigating housing options from in‑town bungalows to newer subdivisions near Liberty Township can feel complex without local insight. Agent Pronto connects you with a Chesterton real estate agent who understands the area’s commutes, schools, and amenities, helping both buyers and sellers move forward with less stress.

Find your Chesterton real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“Finding a home/property can be a stressful journey, but having Debra Hull by our side was a game-changer. What truly stood out was how much Debra cared about our family's well-being and finding us the right property. Debra always took the time to listen to our needs (even when we were just having sidebar conversation), addressed every concern with patience, incredibly attentive to the little details we wanted in a home/property and responded to our texts and calls almost instantly, no matter the time. We never felt pressured; instead, she treated us with such care and compassion that it felt like we were working with a trusted friend. If you want a realtor who goes above and beyond, look no further!”

Marcella Lindo · Gary, IN

Photo of Debra Hull
Brokerworks Real Estate Group
“Thank you Tracy for helping. Tracy actually made sure to teach how the market works and kept at every single step of this process. She was detailed and organized throughout the whole time and answered all the questions that came along. If you want a stress-free experience, go with her!!!!”

Juan · Hobart, IN

Photo of Tracy Wondaal
EXP Realty
“We met Jeff at an Open House. He started helping us since then. He referred us to a mortgage broker and it really paid off. Jeff was really patient showing us numerous houses and options. He was also very knowledgeable of the area. My family appreciated working with him. I would recommend him to family and friends. He was great to work with.”

Leonel Preza Bonilla · Fort Wayne, IN

Photo of Jeffery Holtsclaw
Century 21 Bradley
“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!”

Lori K. · La Porte, IN

Photo of Team Hammonds
Key Realty
“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.”

Atta Alla F. · Dyer, IN

Photo of Kelly O'Neill
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.”

Melissa G. · Cedar Lake, IN

Photo of Jorrdan Orr
McColly Real Estate
“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.”

Richard B. · South Bend, IN

Photo of Barry Skalski
Michiana Realty
“Cari and Geri was great”

William H · Merrillville, IN

Photo of Geri Norfleet
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.”

James Johnston · Chicago, IL

Photo of Nicole Milford
Compass
“Mary Beth Myers was awesome!!!!”

Tanya & Joel Z. · Michigan City, IN

Photo of Mary Beth Meyers
McColly Real Estate

Frequently Asked Questions

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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