11,415

Chesterton, IN Homes

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  • /50

    $399,500

    • 3 Beds
    • 3 Baths
    • 2,332 Sq Ft

    1776 Indian Boundary Rd, Chesterton, IN 46304

    Bring your offer!!! Calling all buyers, contractors, and investors who see potential where others see projects. Some pictures are AI generated. See what the potential is when changing out the paint, carpet, laundry room flooring and stainless appliances. This 3-bed, 3-bath ranch home on a 0.77 acre lot in Chesterton is a rare chance to build instant equity in one of Northwest Indiana's most

    Agent Photo

    Lisa Gaff

    White Hat Realty Group, LLC

    1776 Indian Boundary Rd, Chesterton, IN 46304
  • /50

    Starting at $1,497 Per Month

    • 1 - 3 Beds

    2113 Kelle Dr, Chesterton, IN 46304

    Inside beautiful Coffee Creek is a luxury community like no other. We are ideally situated and near all shopping, dining, and between I-80/90 Toll Rd and I-94. Appointed with numerous luxurious details, ease of living, privacy, and style.

    Eagle Crossing Luxury Apartment Homes

    2113 Kelle Dr, Chesterton, IN 46304
  • /24

    $162,000

    Sold Aug 10, 2026

    2105 Tupelo Ln, Chesterton, IN 46304

    • 3 Beds
    • 2 Baths
    • 1,447 Sq Ft
    • Built 1979

    Last Sold Summary

    • 5% Below List Price
    • $112/SF
    • 55 Days On Market

    Current Estimated Value $169,805

    Last Listing Agent Karen Maynard McColly Real Estate

    2105 Tupelo Ln, Chesterton, IN 46304
    • /42

      Est $326,188

      Not Listed For Sale

      1434 N Veden Rd, Chesterton, IN 46304

      • 4 Beds
      • 2 Baths
      • 1,804 Sq Ft
      • Built 1956
      1434 N Veden Rd, Chesterton, IN 46304

      Last Sold Summary

      • 294 Days On Market

      Last Listing Agent Mary Beth Meyers McColly Real Estate

  • /13

    $58,000

    • Land
    • 11,761 Sq Ft
    • $214,815 per Acre

    25 Karner Blue Ct, Chesterton, IN 46034

    Phase 3 is now open and ready for building. Lot 70 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

    Agent Photo

    Paul Boyter

    McColly Real Estate

    25 Karner Blue Ct, Chesterton, IN 46034
  • /31

    Starting at $1,100 Per Month

    • 1 - 2 Beds

    111 W Taylor St, Chesterton, IN 46304

    Heat, water, garbage, sewer and cooking gas included with rent. Deer Run is conveniently located within the beautiful town of Chesterton, but is surrounded by woods. Residents enjoy the peace and quiet of nature, while still having the convenience of nearby shopping. Many residents take advantage of the quick access to I 94 and the South Shore Rail line to Chicago.This community features

    Deer Run Apartments

    111 W Taylor St, Chesterton, IN 46304
  • /9

    $282,000

    Sold Jul 15, 2026

    403 Sand Creek Dr N, Chesterton, IN 46304

    • 2 Beds
    • 3 Baths
    • 1,810 Sq Ft
    • Built 1991

    Last Sold Summary

    • 1% Above List Price
    • $156/SF
    • 1 Day On Market

    Last Listing Agent Regina Dotto eXp Realty, LLC

    403 Sand Creek Dr N, Chesterton, IN 46304
    • /35

      Est $386,288

      Not Listed For Sale

      205 S 20th St, Chesterton, IN 46304

      • 3 Beds
      • 2.5 Baths
      • 3,360 Sq Ft
      • Built 1997
      205 S 20th St, Chesterton, IN 46304

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Jen Luce Realty Executives Premier

  • /2

    $54,000

    • Land
    • 8,276 Sq Ft
    • $284,211 per Acre

    43 Karner Blue Ct, Chesterton, IN 46304

    Phase 3 is now open and ready for building. Lot 88 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

    Agent Photo

    Paul Boyter

    McColly Real Estate

    43 Karner Blue Ct, Chesterton, IN 46304
  • /9

    $1,350

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • Townhouse for Rent

    351 Woodlawn Ave, Chesterton, IN 46304

    2 Bedroom, 1.5 Bath, back yard and patio, front porch. $1350 plus deposit.

    351 Woodlawn Ave, Chesterton, IN 46304
  • /52

    $460,000

    Sold Oct 10, 2025

    544 Windridge Dr, Chesterton, IN 46304

    • 4 Beds
    • 2.5 Baths
    • 2,261 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $203/SF
    • 85 Days On Market

    Current Estimated Value $462,475

    Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

    544 Windridge Dr, Chesterton, IN 46304
    • /49

      Est $926,598

      Not Listed For Sale

      1020 N 400 E, Chesterton, IN 46304

      • 4 Beds
      • 3.5 Baths
      • 3,860 Sq Ft
      • Built 2005
      1020 N 400 E, Chesterton, IN 46304

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Roxanne Gottleber RE/MAX Lifestyles

  • /2

    $529,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,162 Sq Ft

    1036 Preserve Ln, Chesterton, IN 46304

    Discover the perfect blend of thoughtful design, modern comfort, and peaceful surroundings in this new construction home. Offering over 2,100 square feet in The Preserve, this premium homesite is uniquely positioned with protected wetlands bordering one side and extending behind the backyard, creating exceptional privacy and picturesque year-round views. The open-concept floor plan seamlessly

    Agent Photo

    Paul Boyter

    McColly Real Estate

    1036 Preserve Ln, Chesterton, IN 46304
  • /12

    $1,575

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Townhouse for Rent

    192 Rail Rd, Chesterton, IN 46304

    TWO BEDROOM TOWNHOUSE WITH DETACHED ONE CAR GARAGEThis unique and spacious townhome features stainless steel appliances and granite countertops. A private entry with a welcoming front porch.All the comforts you expect with central heat/air, ceiling fans in the living room and master bedroom ensuring a cool and comfortable year round atmosphere. The open living space downstairs has a

    192 Rail Rd, Chesterton, IN 46304
  • /53

    $1,000,000

    Sold Feb 27, 2026

    1458 Spyglass Cir, Chesterton, IN 46304

    • 6 Beds
    • 5.5 Baths
    • 7,047 Sq Ft
    • Built 2000

    Last Sold Summary

    • 9% Below List Price
    • $142/SF
    • 8 Days On Market

    Current Estimated Value $1,066,397

    Last Listing Agent Stefanie Neal BHHS Indiana Realty

    1458 Spyglass Cir, Chesterton, IN 46304
    • /19

      Est $341,010

      Not Listed For Sale

      1058 Mission Hills Ct, Chesterton, IN 46304

      • 3 Beds
      • 2.5 Baths
      • 2,059 Sq Ft
      • Built 1995
      1058 Mission Hills Ct, Chesterton, IN 46304

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Jeanne Sommer Century 21 Alliance Group

  • /5

    $389,000

    • Land
    • 1.44 Acres
    • $270,139 per Acre

    1022 N Old State Rd 49, Chesterton, IN 46304

    This 1.44 acre lot is located close to the Indiana Toll Road, I-94, the South Shore train station, The Indiana Dunes State Park, and the Indiana Dunes National Park. Across Highway 49 you will find Culver's, AJ's Pizza, Popeye's, Dunkin Donuts, Hilton Garden Inn, Bob Evans, and multiple medical and office buildings.

    Agent Photo

    Paul Boyter

    McColly Real Estate

    1022 N Old State Rd 49, Chesterton, IN 46304
  • /13

    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft
    • House for Rent

    1101 Jefferson Ave Unit 6, Chesterton, IN 46304

    Move-in ready 2-bedroom, 1-bath apartment available now at Porter Ridge Apartments in Chesterton. This spacious unit features a private balcony, perfect for enjoying the outdoors. Rent includes water, sewer, and trash, plus a storage locker conveniently located in the laundry room with coin-operated washer/dryer access. Rent: 1,300/month Security Deposit: 1,300 Pets welcome with 25/month fee

    Jordan Williams VIA Realty

    1101 Jefferson Ave Unit 6, Chesterton, IN 46304
  • /31

    $365,000

    Sold Apr 27, 2026

    3431 Drivers Way, Chesterton, IN 46304

    • 3 Beds
    • 2 Baths
    • 1,717 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Above List Price
    • $213/SF
    • 4 Days On Market

    Current Estimated Value $360,803

    Last Listing Agent Debra Lightfoot McColly Real Estate

    3431 Drivers Way, Chesterton, IN 46304
    • /28

      Est $369,797

      Not Listed For Sale

      1450 Maximilian Dr, Chesterton, IN 46304

      • 4 Beds
      • 3 Baths
      • 2,009 Sq Ft
      • Built 2005
      1450 Maximilian Dr, Chesterton, IN 46304

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Gene Brock Realty Executives Premier

  • /12

    $58,000

    • Land
    • 8,276 Sq Ft
    • $305,263 per Acre

    23 Karner Blue Ct, Chesterton, IN 46034

    Phase 3 is now open and ready for building. Lot 71 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

    Agent Photo

    Paul Boyter

    McColly Real Estate

    23 Karner Blue Ct, Chesterton, IN 46034
  • /13

    $1,790

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • Townhouse for Rent

    1116 Penny Ln, Chesterton, IN 46304

    Welcome home to this beautifully renovated 3-bedroom, 1.5-bath duplex in Chesterton! Enjoy a modern kitchen with stainless steel appliances, brand-new cabinets, butcher block countertops, and cozy built-in booth seating. New LVP flooring runs throughout, and the updated bathroom features fresh tile finishes.Relax on the front deck, take advantage of in-unit washer/dryer, a heated garage, and

    1116 Penny Ln, Chesterton, IN 46304
  • /32

    $435,000

    Sold May 27, 2026

    4221 Burlwood Dr, Chesterton, IN 46304

    • 3 Beds
    • 3 Baths
    • 3,384 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $129/SF
    • 22 Days On Market

    Current Estimated Value $434,494

    Last Listing Agent Jennifer Miga McColly Real Estate

    4221 Burlwood Dr, Chesterton, IN 46304
    • /46

      Est $227,309

      Not Listed For Sale

      605 Jefferson Ave, Chesterton, IN 46304

      • 4 Beds
      • 1.5 Baths
      • 1,850 Sq Ft
      • Built 1969
      605 Jefferson Ave, Chesterton, IN 46304

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Cveta Gass Ned Realty, LLC

  • /15

    $499,900

    • 6 Beds
    • 6 Baths
    • 2,896 Sq Ft

    150 16th St, Chesterton, IN 46304

    This newly completed duplex was finished in 2024. This exceptional investment property features two spacious units--each offering 3 bedrooms, 3 bathrooms, and a convenient one-car garage. Both sides are currently leased, providing immediate rental income. The main level showcases durable LVP flooring, while the primary suite includes a generous walk-in closet. Quality finishes such as 6-panel oak

    Agent Photo

    Paul Boyter

    McColly Real Estate

    150 16th St, Chesterton, IN 46304
  • /4

    $900

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Condo for Rent

    129 S 9th St Unit No. 5, Chesterton, IN 46304

    Now available at 129 S. 9th Street in Chesterton, Indiana — a downstairs apartment offered at $900 per month with a $900 security deposit. The apartment includes a refrigerator, stove with oven and range, and microwave. Water, sewer, and trash are included in the rent. All other utilities and services, including gas and electric, are paid separately by the tenant.The apartment does not

    129 S 9th St Unit No. 5, Chesterton, IN 46304
  • /26

    $264,900

    Sold May 21, 2026

    204 Wagner Rd, Chesterton, IN 46304

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • Built 1977

    Last Sold Summary

    • $210/SF
    • 19 Days On Market

    Current Estimated Value $260,753

    Last Listing Agent John Barlow White Hat Realty Group, LLC

    204 Wagner Rd, Chesterton, IN 46304
    • /4

      Est $346,366

      Not Listed For Sale

      86 Hepburn Way, Chesterton, IN 46304

      • 4 Beds
      • 2.5 Baths
      • 2,014 Sq Ft
      • Built 2025
      86 Hepburn Way, Chesterton, IN 46304

      Last Sold Summary

      • 126 Days On Market

      Last Listing Agent Octavia Valencia Octavia Valencia, Broker

  • /44

    $385,000

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,360 Sq Ft

    455 Woodlawn Ave Unit 457, Chesterton, IN 46304

    Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining

    Agent Photo

    Paul Boyter

    McColly Real Estate

    455 Woodlawn Ave Unit 457, Chesterton, IN 46304
  • /7

    $1,290 Per Month

    • 2 Beds
    • 1.5 Baths
    • Condo for Rent

    117 S 18th St Unit Suite 4, Chesterton, IN 46304

    - Central AC- BasementRental requirements:- Minimum Credit Score: 600- Minimum Income: 3.0 x monthly gross- Security Deposits:1 time rent amount- No evictions or debt from previous landlords in the past 3 yrs- No bankruptcies- No smokers- No felonies- Tenant are responsible for all utilities(water/electric/gas), garbage, and sewer

    117 S 18th St Unit Suite 4, Chesterton, IN 46304
  • /2

    $220,000

    Sold May 07, 2026

    1939 Chamborde Ln, Chesterton, IN 46304

    • Land
    • 1.08 Acres
    • $203,704 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Stefanie Neal BHHS Indiana Realty

    1939 Chamborde Ln, Chesterton, IN 46304
    • /35

      Est $731,148

      Not Listed For Sale

      1300 Brassie Ave, Chesterton, IN 46304

      • 4 Beds
      • 2.5 Baths
      • 3,880 Sq Ft
      • Built 2016
      1300 Brassie Ave, Chesterton, IN 46304

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Joshua Vida Paradigm Realty Solutions, LLC

  • /2

    $58,000

    • Land
    • 9,147 Sq Ft
    • $276,190 per Acre

    37 Karner Blue Ct, Chesterton, IN 46304

    Phase 3 is now open and ready for building. Lot 91 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is You Neighbor.

    Agent Photo

    Paul Boyter

    McColly Real Estate

    37 Karner Blue Ct, Chesterton, IN 46304
  • /17

    $2,900 Per Month

    • 5 Beds
    • 3 Baths
    • 2,412 Sq Ft
    • House for Rent

    267 Arbor Dr, Chesterton, IN 46304

    Spacious 5 bed, 3 bath bi-level on just over a 1/2 acre lot, just minutes from the beach, shopping and food. Recently renovated with a modern feel. Tenant responsible for lawn care and utilities. Spacious 5 bed, 3 bath bi-level on just over a 1/2 acre lot, just minutes from the beach, shopping and food. Recently renovated with a modern feel. Tenant responsible for lawn care and utilities.

    267 Arbor Dr, Chesterton, IN 46304
  • /39

    $511,000

    Sold Jan 21, 2026

    4131 Abercrombie Dr, Chesterton, IN 46304

    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft
    • Built 2007

    Last Sold Summary

    • $135/SF
    • 7 Days On Market

    Current Estimated Value $508,549

    Last Listing Agent Claudia Miller Forrest Century 21 Circle

    4131 Abercrombie Dr, Chesterton, IN 46304
    • /25

      Est $253,500

      Not Listed For Sale

      945 S 5th St Unit 101, Chesterton, IN 46304

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1925
      945 S 5th St Unit 101, Chesterton, IN 46304

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Patty Raffin McColly Real Estate

  • /39

    $314,900

    • 4 Beds
    • 2.5 Baths
    • 2,396 Sq Ft

    419 S 9th St, Chesterton, IN 46304

    Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The

    Agent Photo

    Crystal Soliday

    @properties/Christie's Intl RE

    419 S 9th St, Chesterton, IN 46304
  • /7

    $1,275 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1202 Park Ave, Chesterton, IN 46304

    Spacious and Charming 2 bedroom/1 bath Duplex now Available for Rent. Located in a Quiet and Desirable Neighborhood of Chesterton. Duplex features Vaulted Ceilings, Unique Kitchen Flooring and Cabinets, Charming Woodwork and Convenient Upfront Parking. Minutes away from Shopping, Restaurants and Chesterton schools.***Showings will be available by Appointment Only after 2pm***~Monthly Rent is

    1202 Park Ave, Chesterton, IN 46304
  • /25

    $250,000

    Sold Jul 24, 2026

    2136 Texas St, Chesterton, IN 46304

    • 3 Beds
    • 2 Baths
    • 1,207 Sq Ft
    • Built 1998

    Last Sold Summary

    • $207/SF
    • 1 Day On Market

    Current Estimated Value $249,893

    Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

    2136 Texas St, Chesterton, IN 46304
    • /25

      Est $414,306

      Not Listed For Sale

      2432 Legend Cir, Chesterton, IN 46304

      • 4 Beds
      • 2 Baths
      • 2,169 Sq Ft
      • Built 2012
      2432 Legend Cir, Chesterton, IN 46304

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Dianne Cline McColly Real Estate

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$359,900
Median Single Family Sale Price
$380,500
Median Townhouse Sale Price
$439,500
Median 2 Bedroom Sale Price
$243,500
Average Price Per Sq Ft
$188
Number of Homes for Sale
11,415
Last 12 months Home Sales
381
Months of Supply
2.40
Median List Price
$389,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
6%
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