Chesterton, IN Homes

• 

  

  

  /46

  $599,000

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

  1650 Hogan Ave, Chesterton, IN 46304

  Located 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 ceiling, brand-new carpet,

  

  Paul Boyter

  McColly Real Estate

  (219) 342-2742

  1650 Hogan Ave, Chesterton, IN 46304
• Explore Chesterton

• 

  

  

  /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
• 

  

  

  /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 $443,821

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  544 Windridge Dr, Chesterton, IN 46304
• 

  

  

  /25

  Est $254,000 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

  • 1% Above List Price
  • $143/SF
  • 4 Days On Market

  • Last Sold Price $251,000
  • Apr 28, 2025

  Last Listing Agent Patty Raffin McColly Real Estate
• 

  

  

  /53

  $319,000

  • 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
• 

  

  /13

  Starting at $1,150 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
• 

  

  /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 $1,112,926

  Last Listing Agent Stefanie Neal BHHS Indiana Realty

  1458 Spyglass Cir, Chesterton, IN 46304
• 

  

  /26

  Est $602,380 Not Listed For Sale

  479 E 1100 N, Chesterton, IN 46304

  • 3 Beds
  • 3 Baths
  • 3,262 Sq Ft
  • Built 2000

  479 E 1100 N, Chesterton, IN 46304

  Last Sold Summary

  • $184/SF
  • 5 Days On Market

  • Last Sold Price $600,000
  • Apr 29, 2025

  Last Listing Agent Judy Fischer Century 21 Affiliated
• 

  

  /24

  $419,999 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,992 Sq Ft

  2131 Pepperbush Ave, Chesterton, IN 46304

  Move-In Ready in Westwood Manor - Chesterton's desired Subdivision! Nestled in the award-winning Duneland School District, this beautifully maintained home is ready for you to move in and enjoy. Boasting 4 bedrooms, 4 bathrooms, a loft office area, and a finished basement with a versatile flex room that could serve as a 5th bedroom, office, or game room, this home offers space for every need. The

  

  Jason Moon

  Trueblood Real Estate, LLC

  (219) 348-8090

  2131 Pepperbush Ave, Chesterton, IN 46304
• 

  

  /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
• 

  

  /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 $349,473

  Century Complete St. Andrews

  70 Fairmont Dr, Chesterton, IN 46304
• 

  

  /29

  Est $403,767 Not Listed For Sale

  524 Windridge Dr, Chesterton, IN 46304

  • 4 Beds
  • 3 Baths
  • 2,565 Sq Ft
  • Built 1997

  524 Windridge Dr, Chesterton, IN 46304

  Last Sold Summary

  • 3% Above List Price
  • $152/SF
  • 45 Days On Market

  • Last Sold Price $391,000
  • May 01, 2025

  Last Listing Agent Heather Alexander @properties/Christie's Intl RE
• 

  

  /49

  $2,500,000 Pending

  • 5 Beds
  • 9.5 Baths
  • 17,178 Sq Ft

  1700 Littler Dr, Chesterton, IN 46304

  Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, craftsmanship, and prestige define this extraordinary 5-bedroom, 10-bathroom estate, located just one hour from Chicago in the exclusive Sand Creek community. Designed and built in 2003 by renowned interior designer and architect David Julian, this custom masterpiece offers breathtaking golf course views of

  

  John Reagan

  @properties/Christie's Intl RE

  (219) 259-5914

  1700 Littler 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 $353,070

  Last Listing Agent Debra Lightfoot McColly Real Estate

  3431 Drivers Way, Chesterton, IN 46304
• 

  

  /11

  Est $330,236 Not Listed For Sale

  693 Admiral Dr, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1996

  693 Admiral Dr, Chesterton, IN 46304

  Last Sold Summary

  • 8% Above List Price
  • $157/SF
  • 85 Days On Market

  • Last Sold Price $305,000
  • Apr 25, 2025

  Last Listing Agent Mike Berrier Listing Leaders
• 

  

  /12

  $58,000

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

  47 Karner Blue Ct, Chesterton, IN 46034

  Phase 3 is now open and ready for building. Lot 86 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) 751-5447

  47 Karner Blue Ct, Chesterton, IN 46034
• 

  

  /19

  $1,800 Per Month

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  2105 Dogwood Ln, Chesterton, IN 46304

  Property Id: 2501544Welcome to this newly updated 3 bedroom, 3 bathroom condo in Chesterton, Indiana! This 1,500 Square foot 2-Story condo has a private entrance, new carpet, updated bathrooms, new washer & dryer and a private 1 car garage. It is located in the award winning Duneland school district, very close to Dogwood Park and to the charming and historic downtown with great

  2105 Dogwood 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 $379,451

  Last Listing Agent Lisa Gaff White Hat Realty Group, LLC

  361 Watertower Dr, Chesterton, IN 46304
• 

  

  /23

  Est $241,509 Not Listed For Sale

  2214 Texas St, Chesterton, IN 46304

  • 2 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • Built 1997

  2214 Texas St, Chesterton, IN 46304

  Last Sold Summary

  • 1% Above List Price
  • $169/SF
  • 7 Days On Market

  • Last Sold Price $238,500
  • Apr 30, 2025

  Last Listing Agent Paul Boyter McColly Real Estate
• 

  

  /42

  $345,000

  • 3 Beds
  • 2 Baths
  • 2,115 Sq Ft

  401 S 15th St, Chesterton, IN 46304

  Move-in ready and thoughtfully updated, this all brick 3 bed/1 and 3/4 bath Chesterton home offers flexible living space and a clean, well-maintained feel throughout. The main level features a bright and inviting layout with updated finishes. The finished lower level provides additional living space. An egress window adds flexibility for guest space, home office, or potential bedroom use, and a

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 554-9798

  401 S 15th St, Chesterton, IN 46304
• 

  

  /18

  $2,200 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
• 

  

  /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
• 

  

  /145

  Est $520,310 Not Listed For Sale

  2001 Union Ave, Chesterton, IN 46304

  • 5 Beds
  • 3.5 Baths
  • 3,198 Sq Ft
  • Built 1995

  2001 Union Ave, Chesterton, IN 46304

  Last Sold Summary

  • 4% Above List Price
  • $156/SF
  • 130 Days On Market

  • Last Sold Price $499,900
  • May 02, 2025

  Last Listing Agent Jeff Albertson BHHS Executive Realty
• 

  

  /44

  $1,499,999

  • 4 Beds
  • 4.5 Baths
  • 5,809 Sq Ft

  1137 N 475 E, Chesterton, IN 46304

  Welcome to your private Northwest Indiana retreat in desirable Jackson Township--where space, luxury, and nature come together on just over 15 stunning acres. This all-brick estate offers the perfect blend of elegance and outdoor adventure, featuring 4 bedrooms and 5 bathrooms, thoughtfully designed for both everyday living and unforgettable entertaining. Inside, you'll find a generously sized

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 247-7380

  1137 N 475 E, Chesterton, IN 46304
• 

  

  /15

  $1,500

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • 1,226 Sq Ft
  • Condo for Rent

  122 Jeffrey St Unit 122JeffreySt, Chesterton, IN 46304

  Charming Updated Duplex in Chesterton Schools | 2BR/1.5BA | Recently RenovatedWelcome to 122 Jeffrey St, a beautifully updated bi-level duplex unit in a quiet Chesterton neighborhood. This 2-bedroom, 1.5-bathroom home boasts a full interior refresh, perfect for modern living.Key Features & Recent Updates: Modern Kitchen: Equipped with brand-new stainless-steel appliances,

  122 Jeffrey St Unit 122JeffreySt, 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 $512,438

  Last Listing Agent Claudia Miller Forrest Century 21 Circle

  4131 Abercrombie Dr, Chesterton, IN 46304
• 

  

  /36

  Est $443,459 Not Listed For Sale

  440 Lost Tree Dr, Chesterton, IN 46304

  • 4 Beds
  • 4 Baths
  • 3,268 Sq Ft
  • Built 2001

  440 Lost Tree Dr, Chesterton, IN 46304

  Last Sold Summary

  • 5% Above List Price
  • $129/SF
  • 45 Days On Market

  • Last Sold Price $422,500
  • Apr 25, 2025

  Last Listing Agent Jodi Gheaja Realty Executives
• 

  

  /14

  $54,000

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

  1005 Preserve Ln, Chesterton, IN 46304

  Phase 3 is now open and ready for building. Lot 93 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

  (219) 419-4506

  1005 Preserve Ln, Chesterton, IN 46304
• 

  

  /13

  $1,300 Per Month

  • 1 Bed
  • 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
• 

  

  /32

  $515,000 Sold Dec 12, 2025

  997 N 250 E, Chesterton, IN 46304

  • 3 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Above List Price
  • $197/SF
  • 2 Days On Market

  Current Estimated Value $521,177

  Last Listing Agent Kayla Jones Listing Leaders

  997 N 250 E, Chesterton, IN 46304
• 

  

  /27

  Est $441,354 Not Listed For Sale

  371 E Us Highway 20, Chesterton, IN 46304

  • 4 Beds
  • 2.5 Baths
  • 3,234 Sq Ft
  • Built 1974

  371 E Us Highway 20, Chesterton, IN 46304

  Last Sold Summary

  • 6% Above List Price
  • $129/SF
  • 0 Days On Market

  • Last Sold Price $416,978
  • Apr 28, 2025

  Last Listing Agent Milenda Simerlein McColly Real Estate
• 

  

  /42

  $440,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,350 Sq Ft

  300 E Morgan Ave, Chesterton, IN 46304

  Step into a rare piece of Northwest Indiana history with this truly one-of-a-kind 100-year-old home located in the highly coveted Morgan Park neighborhood of Chesterton. Rich in character, timeless craftsmanship, and beautifully updated for modern living, this remarkable all-brick residence offers the perfect blend of historic charm and today's conveniences. Spanning just over 3,000 square feet,

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 695-6453

  300 E Morgan Ave, Chesterton, IN 46304
• 

  

  /26

  $2,100

  Total Monthly Price

  • 4 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Condo for Rent

  518 S Calumet Rd, Chesterton, IN 46304

  This property at 518 S Calumet Rd features 4 bedrooms and 2.5 bathrooms within a total of 1,700 square feet. The living room offers ample space for relaxation, while the dining room provides a designated area for meals. The eat-in kitchen is equipped with essential appliances, including a dishwasher and disposal, and includes a pantry for additional storage. Each bedroom is designed for comfort,

  518 S Calumet Rd, Chesterton, IN 46304
• 

  

  /22

  $327,500 Sold Nov 26, 2025

  809 Olde Towne Square, Chesterton, IN 46304

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $244/SF
  • 24 Days On Market

  Current Estimated Value $322,577

  Last Listing Agent Amanda Klimczak Realty Executives Premier

  809 Olde Towne Square, Chesterton, IN 46304
• 

  

  /15

  Est $170,663 Not Listed For Sale

  114 S 13th St, Chesterton, IN 46304

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1951

  114 S 13th St, Chesterton, IN 46304

  Last Sold Summary

  • 2% Below List Price
  • $228/SF
  • 3 Days On Market

  • Last Sold Price $175,000
  • Apr 30, 2025

  Last Listing Agent Joshua Vida Paradigm Realty Solutions, LLC
• 

  

  /23

  $285,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,561 Sq Ft

  1201 Tower Ln, Chesterton, IN 46304

  Discover the perfect blend of comfort, convenience, and coastal charm in this beautiful 1,500-square-foot townhome in the heart of Porter, Indiana--just moments from the shores of Porter Beach. This spacious 3-bedroom, 2.5-bath home offers the ideal layout for everyday living and entertaining. The huge primary suite is a true retreat, complete with a private en suite bathroom and generous closet

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 217-1857

  1201 Tower Ln, Chesterton, IN 46304
• 

  

  /14

  $2,325 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,727 Sq Ft
  • Townhouse for Rent

  1239 Fox Hollow Dr, Chesterton, IN 46304

  Maintenance free 3 bedroom/2.5 bath townhome for rent near the Indiana Dunes. All new paint and carpeting throughout. Over 1700 sq ft of living space. Primary suite has private bath and walk-in-closet. 2 car garage, new driveway, and corner lot overlooking neighborhood park. Enjoy the convenience and comfort of maintenance free living with provided lawn care and snow removal. Just minutes to

  Amy Redman Dunes Realty, LLC

  1239 Fox Hollow Dr, Chesterton, IN 46304
• 

  

  /15

  $167,000 Sold Jun 05, 2025

  1102 Saratoga Ln, Chesterton, IN 46304

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

  Last Sold Summary

  • 16% Below List Price
  • $117/SF
  • 132 Days On Market

  Current Estimated Value $174,455

  Last Listing Agent Catherine Craigin Kasl Century 21 Circle

  1102 Saratoga Ln, Chesterton, IN 46304
• 

  

  /17

  Est $284,137 Not Listed For Sale

  706 S 2nd St, Chesterton, IN 46304

  • 4 Beds
  • 1 Bath
  • 2,792 Sq Ft
  • Built 1929

  706 S 2nd St, Chesterton, IN 46304

  Last Sold Summary

  • 3% Above List Price
  • $98/SF
  • 103 Days On Market

  • Last Sold Price $275,000
  • Apr 30, 2025

  Last Listing Agent Frank Ruvoli Century 21 Circle

Showing Results 1 - 40, Page 1 of 18