Homes for Sale in Chesterton

Browse current home listings in Chesterton, Indiana.

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Chesterton

Chesterton is the kind of town that earns genuine loyalty. Its downtown is walkable and alive, anchored by the beloved European Market and independent businesses that reflect a community that knows what it wants to be. Duneland Schools draw families from across the region. But what defines Chesterton most is its people — residents who are fiercely protective of its small-town identity and deeply skeptical of development that would change what makes it work. That civic instinct has shaped the town for decades, and it shows.

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Chesterton

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Chesterton »
All Residential Listings

This search includes all residential home listings in the town of Chesterton, Indiana.

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66 Matches Found
1145 Harbor Way, Chesterton, IN
Accepting Backup Offers
3BD 4BA 2,329SF
Last Modified: 1:17am, May 8, 2026
Listing Office: RE/MAX Diamond Properties
590 E Oak Hill Road, Chesterton, IN
Accepting Backup Offers
4BD 2BA 1,844SF
Last Modified: 12:00am, May 24, 2026
Listing Office: Coldwell Banker Realty
1248 Dogwood Drive, Chesterton, IN
Active
3BD 2BA 1,419SF
Last Modified: 6:36am, May 18, 2026
Listing Office: Listing Leaders
1395 Waverly Road, Chesterton, IN
Active
3BD 3BA 2,592SF
Last Modified: 10:19pm, June 4, 2026
Listing Office: McColly Real Estate
401 S 15th Street, Chesterton, IN
Active
3BD 2BA 2,115SF
Last Modified: 1:24pm, June 4, 2026
Listing Office: White Hat Realty Group, LLC
769 S Calumet Road, Chesterton, IN
Active
4BD 2BA 2,242SF
Last Modified: 3:06am, June 2, 2026
Listing Office: Century 21 Circle
656 S 4th Street, Chesterton, IN
Active
3BD 2BA 1,542SF
Last Modified: 4:19pm, April 19, 2026
Listing Office: Coldwell Banker Realty
225 Jefferson Avenue, Chesterton, IN
Active
3BD 2BA 1,600SF
Last Modified: 7:02pm, April 29, 2026
Listing Office: CHERYL Real Estate Services, L
702 Admiral Drive, Chesterton, IN
Active
3BD 2BA 1,310SF
Last Modified: 10:39pm, June 2, 2026
Listing Office: Century 21 Circle
1412 Essex Drive, Chesterton, IN
Active
4BD 2BA 1,788SF
Last Modified: 3:03am, June 4, 2026
Listing Office: Listing Leaders
332 Carey Lane, Chesterton, IN
Active
3BD 2BA 1,520SF
Last Modified: 3:56pm, May 25, 2026
Listing Office: McColly Real Estate
1749 Green Meadow Lane, Chesterton, IN
Active
3BD 2BA 1,528SF
Last Modified: 3:27pm, May 29, 2026
Listing Office: McColly Real Estate
214 Woodlawn Avenue, Chesterton, IN
Active
3BD 2BA 2,046SF
Last Modified: 7:42pm, May 27, 2026
Listing Office: Keller Williams Realty - LAF
426 S 11th Street, Chesterton, IN
Active
3BD 2BA 2,152SF
Last Modified: 10:18pm, June 3, 2026
Listing Office: Coldwell Banker Realty
1290 Old Porter Road, Chesterton, IN
Active
3BD 2BA 1,716SF
Last Modified: 4:49pm, May 27, 2026
Listing Office: McColly Real Estate
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This information is not verified for authenticity or accuracy and is not guaranteed and may not reflect all real estate activity in the market. Copyright 2024 Triangle MLS, Inc. All rights reserved. Information Not Guaranteed and Must Be Confirmed by End User. Site contains live data.
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BONNIE HAWKSWORTH
REALTOR®
@properties
219-309-7638
bonniehawksworth@atproperties.com

Thinking about buying or selling in Long Beach?

"Homes in Long Beach don’t trade like typical neighborhoods. Timing, buyer expectations, and preparation matter — especially in a community this tightly held."  — Bonnie

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Bonnie Hawksworth

REALTOR®
219-309-7638
bonniehawksworth@atproperties.com

All information provided on this website is believed to be reliable but is not guaranteed and should be independently verified. Nothing on this site constitutes legal, financial, or tax advice—visitors should consult the appropriate professionals for guidance specific to their situation. Bonnie Hawksworth, the Dunelife Team, @properties | Christie's International Real Estate and their affiliates, and website owner make no representations or warranties, express or implied, regarding the accuracy, completeness, or suitability of any content for any purpose and shall not be liable for any loss arising from reliance on the information provided. This website and its owners comply with all Fair Housing Act and Equal Opportunity provisions. Equal Housing Opportunity. Bonnie Hawksworth, REALTOR® License # RB24000153

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