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Chesterton, IN Homes for Sale — Page 2 | Realty.com
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3 beds
69 listings
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New construction
With a pool

Homes for Sale in Chesterton, IN

Homes for Sale in Chesterton, IN

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24 of 69 Listings
Map

Homes for Sale in Chesterton, IN

24 of 69 Listings

Your local brokerage

SM

Steve Merritt

Realty.com

Lic. #RB21000412

Call Steve
  1. 2246 Pradera Trail — photo1Active

    $599,900

    4 bd · 2 ba · 2,000 sqft

    2246 Pradera Trail, Chesterton, IN

    Madison Young · Brokerworks Group

  2. 1429 Calais Court — photo44Active

    $649,500

    3 bd · 4 ba · 3,780 sqft

    1429 Calais Court, Chesterton, IN

    Lisa Gaff · White Hat Realty Group, LLC

  3. 2342 Westwood Lane — photo26Active

    $354,900

    4 bd · 2 ba · 1,828 sqft

    2342 Westwood Lane, Chesterton, IN

    Melissa Capellari · Coldwell Banker Real Estate Gr

  4. 1147 N 400 E — photo50Active

    $849,000

    4 bd · 4 ba · 4,028 sqft

    1147 N 400 E, Chesterton, IN

    Lesley Sweeney · Encore Sotheby's International

  5. 18 Blue Grass Way — photo56Active

    $679,000

    4 bd · 3 ba · 2,409 sqft

    18 Blue Grass Way, Chesterton, IN

    Madison Young · Brokerworks Group

  6. 1913 David Drive — photo17Active

    $186,500

    2 bd · 2 ba · 1,165 sqft

    1913 David Drive, Chesterton, IN

    Edwin Negron · BluKey Realty

  7. 2420 Pradera Trail — photo2Active

    $519,900

    3 bd · 2 ba · 1,800 sqft

    2420 Pradera Trail, Chesterton, IN

    Madison Young · Brokerworks Group

  8. 2350 Pradera Trail — photo2Active

    $559,900

    4 bd · 3 ba · 1,820 sqft

    2350 Pradera Trail, Chesterton, IN

    Madison Young · Brokerworks Group

  9. 2431 Pradera Trail — photo2Active

    $569,900

    3 bd · 2 ba · 2,000 sqft

    2431 Pradera Trail, Chesterton, IN

    Madison Young · Brokerworks Group

  10. 515 S Park Drive — photo21Active

    $269,900

    2 bd · 1 ba · 1,204 sqft

    515 S Park Drive, Chesterton, IN

    Diane Cline · McColly Real Estate

  11. 1602 Melanie Lane — photo13Active

    $449,900

    3 bd · 3 ba · 1,857 sqft

    1602 Melanie Lane, Chesterton, IN

    Michelle Renninger · Brokerworks Group

  12. 229 E Morgan Avenue — photo79Active

    $875,000

    5 bd · 5 ba · 6,360 sqft

    229 E Morgan Avenue, Chesterton, IN

    Alexis Metcalf · Seramur Properties, LLC

  13. 1600 Melanie Lane — photo13Active

    $449,900

    3 bd · 3 ba · 1,857 sqft

    1600 Melanie Lane, Chesterton, IN

    Michelle Renninger · Brokerworks Group

  14. 1002 Preserve Lane — photo1Active

    $525,500

    3 bd · 2 ba · 1,894 sqft

    1002 Preserve Lane, Chesterton, IN

    Paul Boyter · McColly Real Estate

  15. 1036 Preserve Lane — photo1Active

    $529,900

    3 bd · 3 ba · 2,162 sqft

    1036 Preserve Lane, Chesterton, IN

    Paul Boyter · McColly Real Estate

  16. 1003 Preserve Lane — photo1Active

    $519,900

    3 bd · 2 ba · 1,851 sqft

    1003 Preserve Lane, Chesterton, IN

    Paul Boyter · McColly Real Estate

  17. 961 Monterey Drive — photo58Active

    $529,900

    4 bd · 3 ba · 2,412 sqft

    961 Monterey Drive, Chesterton, IN

    Shelley Seely · Realty Executives Premier

  18. 1591 Hogan Avenue — photo46Active

    $649,900

    4 bd · 4 ba · 2,878 sqft

    1591 Hogan Avenue, Chesterton, IN

    Stefanie Neal · BHHS Indiana Realty

  19. 801 Ashwood Lane — photo3Active

    $575,000

    3 bd · 3 ba · 2,173 sqft

    801 Ashwood Lane, Chesterton, IN

    Tonia Dragon · Better Homes and Gardens Real

  20. 2645 W 1100 N — photo26Active

    $419,900

    3 bd · 2 ba · 1,488 sqft

    2645 W 1100 N, Chesterton, IN

    Debra Lightfoot · McColly Real Estate

  21. 1089 N 200 W — photo52Active

    $529,900

    4 bd · 4 ba · 2,970 sqft

    1089 N 200 W, Chesterton, IN

    Lauren Piazza · Realty Executives Premier

  22. 1035 Kilarney Road — photo38Active

    $869,900

    4 bd · 5 ba · 4,299 sqft

    1035 Kilarney Road, Chesterton, IN

    Stefanie Neal · BHHS Indiana Realty

  23. 397 E 1300 N — photo42Active

    $350,000

    3 bd · 3 ba · 1,941 sqft

    397 E 1300 N, Chesterton, IN

    Shawn Franz · Brokerworks Group

  24. 3624 Fairway Drive — photo47Active

    $359,900

    4 bd · 2 ba · 1,975 sqft

    3624 Fairway Drive, Chesterton, IN

    Geremy Rinker · @properties/Christie's Intl RE

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Explore Chesterton homes

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Listing data & MLS disclosures

Northwest Indiana Association of REALTORS
Based on information submitted to the MLS GRID as of 2026-09-18 12:23:14 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    SM

    Steve Merritt

    Realty.com

    Lic. #RB21000412

    Call Steve

    Chesterton, IN community profile

    Population
    14,405
    Median income
    $86,088
    Housing units
    5,965
    People per sq. mi.
    233.1
    Area
    61.8 sq. mi.

    Source: HJN community data

    Chesterton housing market

    August 2026 · This period is still settling

    Chesterton 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 19 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 20, 2026

    Median sale price
    $327,240$278,159–$489,850 typical range
    Price per sq. ft.
    $167
    Sales
    13
    Paid in cash
    0.0%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $527,700
    Homes for sale
    58
    Median days on market
    11 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -34.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,992 sq. ft.

    Nearby areas

    ZIP codes

    • 46307 (301)
    • 46385 (145)
    • 46360 (132)
    • 46350 (118)
    • 46410 (113)
    • 46342 (104)
    • 46368 (104)
    • 46383 (104)

    Cities

    • Crown Point (285)
    • Gary (254)
    • Valparaiso (249)
    • Michigan City (121)
    • Merrillville (112)
    • La Porte (107)
    • Hobart (105)
    • Portage (102)