View 507 S 20th Street Chesterton, IN MLS# 833228
$324,900
3

Beds

2.0

Baths

1,652

Sq.Ft.

507 S 20th Street

Chesterton, IN

GNIAR
Courtesy of LISTING LEADERS
View 214 Woodlawn Avenue Chesterton, IN MLS# 834230
  • Recently Listed
1 of 58
$320,000
3

Beds

2.0

Baths

2,046

Sq.Ft.

214 Woodlawn Avenue

Chesterton, IN

GNIAR
Courtesy of KELLER WILLIAMS REALTY - LAF
View 1226 Dogwood Drive Chesterton, IN MLS# 830004
$318,900
4

Beds

2.0

Baths

1,827

Sq.Ft.

1226 Dogwood Drive

Chesterton, IN

GNIAR
Courtesy of LISTING LEADERS
The time to sell is now! THE TIME TO SELL IS NOW!
View 322 Sherman Avenue Chesterton, IN MLS# 832285
$315,000
4

Beds

3.1

Baths

2,250

Sq.Ft.

322 Sherman Avenue

Chesterton, IN

GNIAR
Courtesy of E & V INDIANAPOLIS, LLC
View 2375 Indian Boundary Road Chesterton, IN MLS# 832507
$309,900
2

Beds

2.0

Baths

2,049

Sq.Ft.

2375 Indian Boundary Road

Chesterton, IN

GNIAR
Courtesy of @PROPERTIES/CHRISTIE'S INTL RE
View 1325 Indian Boundary Road Chesterton, IN MLS# 814947
$299,900
2

Beds

1.0

Baths

1,692

Sq.Ft.

1325 Indian Boundary Road

Chesterton, IN

GNIAR
Courtesy of MCCOLLY REAL ESTATE
View 1749 Green Meadow Lane Chesterton, IN MLS# 833024
$299,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

1749 Green Meadow Lane

Chesterton, IN

GNIAR
Courtesy of MCCOLLY REAL ESTATE
View 1541 Fox Point Drive Chesterton, IN MLS# 833927
  • Recently Listed
1 of 30
$299,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

1541 Fox Point Drive

Chesterton, IN

GNIAR
Courtesy of BLACKROCK REAL ESTATE SERVICES
View 351 Us Hwy 20 Road Chesterton, IN MLS# 833933
  • Recently Listed
1 of 33
$299,000
4

Beds

1.1

Baths

1,560

Sq.Ft.

351 Us Hwy 20 Road

Chesterton, IN

GNIAR
Courtesy of VIA REALTY
View 511 E Morgan Avenue Chesterton, IN MLS# 831224
$295,000
4

Beds

2.0

Baths

2,375

Sq.Ft.

511 E Morgan Avenue

Chesterton, IN

GNIAR
Courtesy of NEW CHAPTER REAL ESTATE
View 1183 Harbor Way Chesterton, IN MLS# 829884
  • New Construction with Virtual Tour
1 of 20
OPEN HOUSE: Friday 2/27 10:00 AM - 4:00 PM
$294,900
3

Beds

2.0

Baths

1,354

Sq.Ft.

1183 Harbor Way

Chesterton, IN

GNIAR
Courtesy of WHITE HAT REALTY GROUP, LLC
View 1181 Harbor Way Chesterton, IN MLS# 829992
  • New Construction
1 of 21
OPEN HOUSE: Friday 2/27 10:00 AM - 4:00 PM
$294,900
3

Beds

2.0

Baths

1,354

Sq.Ft.

1181 Harbor Way

Chesterton, IN

GNIAR
Courtesy of WHITE HAT REALTY GROUP, LLC
View 1807 W Porter Avenue Chesterton, IN MLS# 830778
$285,000
3

Beds

2.0

Baths

2,080

Sq.Ft.

1807 W Porter Avenue

Chesterton, IN

GNIAR
Courtesy of WHITE HAT REALTY GROUP, LLC
View 647 N Calumet Road Chesterton, IN MLS# 832382
$285,000
4

Beds

2.0

Baths

2,076

Sq.Ft.

647 N Calumet Road

Chesterton, IN

GNIAR
Courtesy of MCCOLLY REAL ESTATE
View 1441 Nelson Drive Chesterton, IN MLS# 819854
$279,999
Studio

Beds

0.0

Baths

1441 Nelson Drive

Chesterton, IN

GNIAR
Courtesy of SERAMUR PROPERTIES, LLC
View 225 Dogwood Drive Chesterton, IN MLS# 833379
$274,900
3

Beds

2.0

Baths

1,316

Sq.Ft.

225 Dogwood Drive

Chesterton, IN

GNIAR
Courtesy of BETTER HOMES AND GARDENS REAL
View 1290 Old Porter Road Chesterton, IN MLS# 823814
$270,000
3

Beds

1.1

Baths

1,716

Sq.Ft.

1290 Old Porter Road

Chesterton, IN

GNIAR
Courtesy of MCCOLLY REAL ESTATE
View 1198 N Babcock Road Chesterton, IN MLS# 830986
$270,000
2

Beds

1.0

Baths

1,860

Sq.Ft.

1198 N Babcock Road

Chesterton, IN

GNIAR
Courtesy of LISTING LEADERS
View 1178 Harbor Way Chesterton, IN MLS# 829716
  • New Construction
1 of 6
OPEN HOUSE: Friday 2/27 10:00 AM - 4:00 PM
$269,900
2

Beds

1.0

Baths

1,010

Sq.Ft.

1178 Harbor Way

Chesterton, IN

GNIAR
Courtesy of WHITE HAT REALTY GROUP, LLC
View 1411 W Beam Street Chesterton, IN MLS# 832379
$269,900
3

Beds

2.0

Baths

1,652

Sq.Ft.

1411 W Beam Street

Chesterton, IN

GNIAR
Courtesy of KELLER WILLIAMS PREFERRED REAL

About Chesterton

Listings in Chesterton, IN

141

Estimated median home price

$362,500
Chesterton IN Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chesterton, Indiana real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chesterton, IN.

Homes for Sale by Price in Chesterton, IN

Price Count
$0 - 100K 18
$100K - 200K 13
$200K - 300K 22
$300K - 400K 31
$400K - 500K 20
$500K - 600K 14
$600K - 700K 9
$700K - 800K 2
$800K - 900K 3
$900K - 1M 3
$1M - Max 6

Homes for Sale by Type in Chesterton, IN

Property Type Count
Single Family 85
Townhouse 9
Condo 5
Commercial 5
Rental 6
Lots and Land 33
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 2/23/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Greater Northwest Indiana Multiple Listing Service. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be reproduced or redistribute. Its sole purpose is to be used for no other purpose than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 2/24/2026.