Chesterton, IN Homes

• 

  

  

  /25

  $239,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  511 S 22nd St, Chesterton, IN 46304

  Live just minutes from the Indiana Dunes, where miles of hiking trails, sandy beaches, and sunset lake views become part of your everyday routine, in this updated 3 bedroom, 1 bath Chesterton home that feels almost like new construction, offering a bright, modern, move in ready interior with comfortable living space for relaxing, working from home, and hosting friends, plus the convenience of

  

  Jeana Consier

  Realty Executives Premier

  (219) 832-8057

  511 S 22nd St, Chesterton, IN 46304
• Explore Chesterton

• 

  

  

  /38

  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Condo for Rent

  2121 Dogwood Ln, Chesterton, IN 46304

  Welcome to 2121 Dogwood Lane in Chesterton -- a beautifully renovated 3-bedroom, 2-bathroom upper-unit condo offering 1,368 square feet of comfortable living space. Enjoy peaceful pond views from your private balcony, no neighbors above, and an open-concept layout with granite countertops, slow-close cabinets, and a large pantry. Major updates include the roof, furnace, water heater, and air

  

  Anthony Sobczak

  VIA Realty

  (219) 837-1297

  2121 Dogwood Ln, 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 $452,969

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  544 Windridge Dr, Chesterton, IN 46304
• 

  

  

  /31

  Est $380,304

  Not Listed For Sale

  886 N 350 E, Chesterton, IN 46304

  • 3 Beds
  • 1.5 Baths
  • 1,778 Sq Ft
  • Built 1963

  886 N 350 E, Chesterton, IN 46304

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /58

  $290,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  214 Woodlawn Ave, Chesterton, IN 46304

  Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning

  

  Aaron Bagsby

  Keller Williams Realty - LAF

  (219) 327-5063

  214 Woodlawn Ave, 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

  (855) 701-8745

  

  2113 Kelle Dr, 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 $1,038,536

  Last Listing Agent Stefanie Neal BHHS Indiana Realty

  1458 Spyglass Cir, Chesterton, IN 46304
• 

  

  /27

  Est $346,161

  Not Listed For Sale

  1599 Colonial Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1999

  1599 Colonial Dr, Chesterton, IN 46304

  Last Sold Summary

  • 4 Days On Market
• 

  

  /46

  $599,000

  • 4 Beds
  • 3 Baths
  • 3,066 Sq Ft

  1650 Hogan Ave, Chesterton, IN 46304

  Located on a picturesque pond in the desirable Sand Creek community, this stunning 4-bedroom, 3-bath home seamlessly blends luxury, comfort, and modern updates. The home features LED lighting throughout, hardwood floors, crown molding, and a stone fireplace just five years old. The main floor and upper level both include convenient laundry areas, while the huge primary suite offers a tray

  

  Paul Boyter

  McColly Real Estate

  (219) 342-2742

  1650 Hogan Ave, Chesterton, IN 46304
• 

  

  /31

  Starting at $940 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

  (855) 506-0713

  111 W Taylor St, Chesterton, IN 46304
• 

  

  /15

  $367,991

  Sold Sep 10, 2025

  70 Fairmont Dr, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $183/SF
  • 20 Days On Market

  Current Estimated Value $354,938

  Century Complete St. Andrews

  70 Fairmont Dr, Chesterton, IN 46304
• 

  

  /19

  Est $454,494

  Not Listed For Sale

  476 Eagle Nest Dr, Chesterton, IN 46304

  • 4 Beds
  • 4 Baths
  • 3,803 Sq Ft
  • Built 2001

  476 Eagle Nest Dr, Chesterton, IN 46304

  Last Sold Summary

  • 33 Days On Market
• 

  

  /53

  $313,900

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1412 Essex Dr, Chesterton, IN 46304

  Freshly updated Split-level located just outside Chicago & minutes from Lake Michigan. Set in the desirable Porter Cove community you'll instantly love this open concept home complete with brand new carpet, just painted, & updated bathrooms making it turn-key. 3 bedroom & 2 baths on upper level with main level offering living room, dining/flex room, & large eat-in kitchen leading out to the

  

  Nick Scalise

  Listing Leaders

  (219) 800-2451

  1412 Essex Dr, Chesterton, IN 46304
• 

  

  /20

  Starting at $992 Per Month

  • 1 - 3 Beds

  1623 Westchester Ave, Chesterton, IN 46304

  Quiet location and minutes to South Shore Train, State Place Apartments feature a central location just west of the 49 Bypass, and close to Lake Michigan, shopping and bike trails. Move-in today and see what real hospitality feels like!

  State Place Apartment Homes

  (219) 841-5986

  

  1623 Westchester Ave, 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 $360,510

  Last Listing Agent Debra Lightfoot McColly Real Estate

  3431 Drivers Way, Chesterton, IN 46304
• 

  

  /15

  Est $174,363

  Not Listed For Sale

  1102 Saratoga Ln, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft
  • Built 1979

  1102 Saratoga Ln, Chesterton, IN 46304

  Last Sold Summary

  • 132 Days On Market
• 

  

  /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.

  

  Paul Boyter

  McColly Real Estate

  (317) 542-3806

  23 Karner Blue Ct, Chesterton, IN 46034
• 

  

  /20

  Starting at $1,275 Per Month

  • 1 - 2 Beds

  2135 Dickinson Rd, Chesterton, IN 46304

  The Enclave is a luxurious apartment community nestled in Coffee Creek Center. Our rental properties include one bedroom and two bedroom floor plans. Select floor plans come with garages. Please view the floor plan page on ForRent.com to see what is offered. Experience outstanding amenities and remarkable features paired with all Coffee Creek Center's advantages. Welcome to a place where nature,

  The Enclave

  (219) 217-0500

  

  2135 Dickinson Rd, 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 $436,023

  Last Listing Agent Jennifer Miga McColly Real Estate

  4221 Burlwood Dr, Chesterton, IN 46304
• 

  

  /23

  Est $328,563

  Not Listed For Sale

  1023 Chestnut Blvd, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 2,356 Sq Ft
  • Built 1979

  1023 Chestnut Blvd, Chesterton, IN 46304

  Last Sold Summary

  • 0 Days On Market
• 

  

  /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

  

  Paul Boyter

  McColly Real Estate

  (219) 946-4328

  150 16th St, Chesterton, IN 46304
• 

  

  /18

  $1,800 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,666 Sq Ft
  • House for Rent

  1205 Saratoga Ln, Chesterton, IN 46304

  This maintenance free, 2-story condo unit with its 2+ bedrooms has over 1600 sqft of living space. Main floor primary bdrm has attached 3/4 bath with views of the front fenced courtyard. Center hall shared bath with main floor 2nd bedroom also is within steps away from the main level laundry room and open vaulted living room with adjacent dine-in kitchen. The upper level loft space can also be

  Patty Raffin McColly Real Estate

  1205 Saratoga Ln, Chesterton, IN 46304
• 

  

  /23

  $389,900

  Sold Jul 28, 2025

  361 Watertower Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,859 Sq Ft
  • Built 1990

  Last Sold Summary

  • $210/SF
  • 4 Days On Market

  Current Estimated Value $388,259

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  361 Watertower Dr, Chesterton, IN 46304
• 

  

  /35

  Est $393,434

  Not Listed For Sale

  367 Kingsmill Dr, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft
  • Built 1997

  367 Kingsmill Dr, Chesterton, IN 46304

  Last Sold Summary

  • 33 Days On Market
• 

  

  /35

  $679,000

  • 4 Beds
  • 2.5 Baths
  • 2,409 Sq Ft

  18 Blue Grass Way, Chesterton, IN 46304

  Welcome to The Preserve, where nature is your neighbor. Situated at the end of a quiet cul-de-sac and bordered by woods on two sides, this exceptional quality-built 4-bedroom, 3-bathroom two-story home offers privacy, luxury, and outstanding outdoor living. The beautifully landscaped backyard is designed for entertaining and recreation, featuring an in-ground pool with an automatic retractable

  

  Paul Boyter

  McColly Real Estate

  (219) 912-8043

  18 Blue Grass Way, Chesterton, IN 46304
• 

  

  /9

  $1,475 Per Month

  • 3 Beds
  • 1 Bath
  • 1,131 Sq Ft
  • House for Rent

  430 Woodlawn Ave, Porter, IN 46304

  This 1,131 square foot home would be a good starter home for your family! This home complete with washer/dryer hookups, central air, and a detached garage. Apply today to get the process started of making this home yours! You can schedule a self-tour of the home via our website, This home is MOVE IN READY. We are looking for applicants who are ready for move in as soon as possible.

  430 Woodlawn Ave, Porter, IN 46304
• 

  

  /13

  $319,991

  Sold Aug 22, 2025

  881 Argyle Ct, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 1,455 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $220/SF
  • 8 Days On Market

  Century Complete St. Andrews

  881 Argyle Ct, Chesterton, IN 46304
• 

  

  /21

  Est $303,916

  Not Listed For Sale

  447 Cherry Hills Dr, Chesterton, IN 46304

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 1997

  447 Cherry Hills Dr, Chesterton, IN 46304

  Last Sold Summary

  • 9 Days On Market
• 

  

  /30

  $249,900

  Under Contract

  • 2 Beds
  • 1 Bath
  • 2,150 Sq Ft

  220 S 7th St, Chesterton, IN 46304

  Experience the Charm of Small-Town Living with all the Conveniences of a Vibrant Community right Outside your Door. Ideally located just steps from the local YMCA and only minutes from Splash Pads, Pickleball Courts, Parks, Shopping & Dining, this Inviting Home offers the Perfect Blend of Comfort, Recreation & Connection. Well-Maintained 2-Bedroom, 1-Bath Home features a fully finished basement

  

  Annette McIntyre

  Realty Executives Premier

  (219) 271-7726

  220 S 7th St, 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
• 

  

  /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 $261,876

  Last Listing Agent John Barlow White Hat Realty Group, LLC

  204 Wagner Rd, Chesterton, IN 46304
• 

  

  /31

  Est $202,593

  Not Listed For Sale

  1920 Hale Ave, Chesterton, IN 46304

  • 3 Beds
  • 1.5 Baths
  • 1,734 Sq Ft
  • Built 1972

  1920 Hale Ave, Chesterton, IN 46304

  Last Sold Summary

  • 8 Days On Market
• 

  

  /4

  $150,000

  • Land
  • 4 Acres
  • $37,500 per Acre

  860 Quail Ridge Dr, Chesterton, IN 46304

  Welcome to the undeveloped phase of the desirable Hunters Glen Subdivision in Porter, Indiana--an excellent opportunity for builders or investors. This offering includes 8 spacious, wooded lots plus 2 additional parcels designated for roads and drainage infrastructure. Nestled in a peaceful, natural setting, this subdivision combines privacy with convenience. With easy access to I-94 and the

  

  Paul Boyter

  McColly Real Estate

  (219) 533-9620

  860 Quail Ridge Dr, Chesterton, IN 46304
• 

  

  /18

  $1,545 Per Month

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Condo for Rent

  201 Chesterton Blvd Unit Upper, Chesterton, IN 46304

  201 Chesterton Blvd Unit Upper, 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
• 

  

  /30

  Est $321,221

  Not Listed For Sale

  1371 Sunset Ln, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 1972

  1371 Sunset Ln, Chesterton, IN 46304

  Last Sold Summary

  • 5 Days On Market
• 

  

  /9

  $164,999

  $10K PRICE DROP Pending

  • Land
  • 3.38 Acres
  • $48,816 per Acre

  0-1 E 1050 N, Chesterton, IN 46304

  Discover the possibilities with this beautiful 3.38-acre parcel. Located in the highly desirable Jackson Township and within the award-winning Duneland School Corporation, this property offers the perfect opportunity to build the home of your dreams. Enjoy the space, privacy, and peaceful surroundings while still being just minutes from major highways and the amenities of Chesterton. With endless

  

  Tonia Dragon

  Better Homes and Gardens Real

  (219) 544-5939

  0-1 E 1050 N, Chesterton, IN 46304
• 

  

  /9

  $1,095 Per Month

  • 1 Bed
  • 1 Bath
  • 911 Sq Ft
  • Loft style 1BR, open floor plan! Spacious!

  1043 Scarborough Ct Unit K1, Chesterton, IN 46304

  Discover Abbey Lane Apartments LLC in Chesterton, IN — a beautifully updated loft-style community offering one-bedroom, one-bath homes with open floor plans and high ceilings. Each unit features oversized closets and a private entrance, complemented by private parking. Residents enjoy on-site amenities including a pool, tennis court, playground, fitness center, and business center amid

  1043 Scarborough Ct Unit K1, 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 $509,332

  Last Listing Agent Claudia Miller Forrest Century 21 Circle

  4131 Abercrombie Dr, Chesterton, IN 46304
• 

  

  /29

  Est $565,369

  Not Listed For Sale

  307 Parc Aux Vaches Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft
  • Built 2002

  307 Parc Aux Vaches Dr, Chesterton, IN 46304

  Last Sold Summary

  • 2 Days On Market

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