Real Estate Investment Properties for Sale in Chesterton, IN

Looking for investment property in Chesterton, IN with high ROI ?

Explore a variety of short-term homes & houses in Chesterton, IN. Invest wisely with VRBO & Chesterton, IN Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chesterton, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1116 N 350 E Chesterton, IN Welcome to this one-of-a-kind estate nestled on 10 serene acres in highly desirable Jackso...	4 beds \| 3 baths \| 4,546 sq.ft.	$925,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.87% Airbnb Rental Income: $2926 Traditional Rental Income: $3087 Airbnb ROI: 0.89% Traditional ROI: 1.87%
327 S 18th Street Chesterton, IN Discover your dream home in Chesterton, just minutes from the scenic Indiana Dunes! This e...	3 beds \| 2 baths \| 1,680 sq.ft.	$294,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 6.16% Airbnb Rental Income: $1908 Traditional Rental Income: $2291 Airbnb ROI: 2.95% Traditional ROI: 6.16%
1452 Gossett Mill Avenue Chesterton, IN Welcome to this beautiful 2-story home in Chesterton, IN! Built in 2017, this 4 bedroom, 3...	4 beds \| 3 baths \| 2,031 sq.ft.	$459,999	Airbnb cash on cash: 3.1% Traditional cash on cash: 4.36% Airbnb Rental Income: $2926 Traditional Rental Income: $2794 Airbnb ROI: 3.1% Traditional ROI: 4.36%
2121 Dogwood Lane Chesterton, IN Welcome to your dream home at 2121 Dogwood Lane, Chesterton, IN 46304! HOA includes water,...	3 beds \| 2 baths \| 1,368 sq.ft.	$195,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 9.79% Airbnb Rental Income: $1908 Traditional Rental Income: $2165 Airbnb ROI: 5.67% Traditional ROI: 9.79%
1887 Jacob Lane Chesterton, IN Welcome to 1887 Jacob Ln., a move-in ready home providing full main floor living where com...	3 beds \| 2 baths \| 1,443 sq.ft.	$319,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 4.2% Airbnb Rental Income: $1908 Traditional Rental Income: $1919 Airbnb ROI: 2.48% Traditional ROI: 4.2%
2009 Timberwood Lane Chesterton, IN Motivated Seller Come view this open concept ranch located in the highly sought after ...	3 beds \| 2 baths \| 1,827 sq.ft.	$519,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.99% Airbnb Rental Income: $1908 Traditional Rental Income: $2551 Airbnb ROI: -0.37% Traditional ROI: 1.99%
2011 Timberwood Lane Chesterton, IN Step inside to discover light-toned engineered hardwood floors and upscale details through...	4 beds \| 3 baths \| 2,476 sq.ft.	$549,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.7% Airbnb Rental Income: $2926 Traditional Rental Income: $3030 Airbnb ROI: 2.18% Traditional ROI: 3.7%
412 S 15th Street Chesterton, IN Welcome to a home that truly has it all -- modern updates, timeless charm, and space for e...	5 beds \| 3 baths \| 2,894 sq.ft.	$425,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 4.76% Airbnb Rental Income: $2747 Traditional Rental Income: $2554 Airbnb ROI: 3.62% Traditional ROI: 4.76%
1615 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now complete! The open concep...	3 beds \| 3 baths \| 1,954 sq.ft.	$409,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 5.03% Airbnb Rental Income: $1908 Traditional Rental Income: $2758 Airbnb ROI: 1.5% Traditional ROI: 5.03%
506 W Morgan Avenue Chesterton, IN Completely remodeled top to bottom Cape Cod! As you walk through the new front door you'll...	3 beds \| 2 baths \| 2,304 sq.ft.	$419,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.5% Airbnb Rental Income: $1908 Traditional Rental Income: $1861 Airbnb ROI: 1.34% Traditional ROI: 2.5%
326 S 11th Street Chesterton, IN This charming home in the heart of walkable downtown Chesterton is brimming with potential...	3 beds \| 1 baths \| 1,640 sq.ft.	$165,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 6.1% Airbnb Rental Income: $1908 Traditional Rental Income: $1575 Airbnb ROI: 4.99% Traditional ROI: 6.1%
801 Idlewild Lane Chesterton, IN Home Completed-Ready to Move-in! Experience exceptional craftsmanship and modern elegance ...	4 beds \| 3 baths \| 2,271 sq.ft.	$634,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.85% Airbnb Rental Income: $2926 Traditional Rental Income: $2891 Airbnb ROI: 1.77% Traditional ROI: 2.85%
2116 Redwood Lane Chesterton, IN Available Now! Welcome to 2116 Redwood Lane, located in one of Chesterton's most desirable...	4 beds \| 3 baths \| 2,445 sq.ft.	$525,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.7% Airbnb Rental Income: $2926 Traditional Rental Income: $2946 Airbnb ROI: 2.28% Traditional ROI: 3.7%
1501 Maximilian Drive Chesterton, IN This fully functioning well-kept 4 bedroom, 3 Full bathroom beautiful home sits next to a ...	4 beds \| 3 baths \| 2,118 sq.ft.	$394,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 4.91% Airbnb Rental Income: $2926 Traditional Rental Income: $2611 Airbnb ROI: 3.93% Traditional ROI: 4.91%
2121 Tupelo Lane Chesterton, IN WANTED: NEW HOMEOWNERS! This maintenance-free 2-bedroom, 1-bath main floor condo with a 1-...	2 beds \| 1 baths \| 1,228 sq.ft.	$174,900	Airbnb cash on cash: 5.47% Traditional cash on cash: 6.57% Airbnb Rental Income: $1805 Traditional Rental Income: $1499 Airbnb ROI: 5.47% Traditional ROI: 6.57%
2230 Redwood Lane Chesterton, IN Proposed Construction - The Astoria in Easton Park!Welcome to luxury living in this stunni...	4 beds \| 3 baths \| 2,281 sq.ft.	$649,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.81% Airbnb Rental Income: $2926 Traditional Rental Income: $2932 Airbnb ROI: 1.68% Traditional ROI: 2.81%
474 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,820 sq.ft.	$485,431	Airbnb cash on cash: 1% Traditional cash on cash: 3.55% Airbnb Rental Income: $1908 Traditional Rental Income: $2559 Airbnb ROI: 1% Traditional ROI: 3.55%
509 E Burdick Road Chesterton, IN Discover a unique opportunity in Chesterton! Nestled on over 2 acres with a large pond, th...	3 beds \| 3 baths \| 2,204 sq.ft.	$260,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 9.99% Airbnb Rental Income: $1908 Traditional Rental Income: $3009 Airbnb ROI: 3.44% Traditional ROI: 9.99%
103-117 Jeffrey Street Chesterton, IN INCREDIBLE investment opportunity less than 1 hour from Chicago. Take a look at these full...	8 beds \| 8 baths \| N/A	$660,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.89% Airbnb Rental Income: $1908 Traditional Rental Income: $3093 Airbnb ROI: -0.86% Traditional ROI: 1.89%
112-116,106 Jeffrey Street Chesterton, IN 3 unit investment opportunity less than 1 hour from Chicago. Take a look at these fully re...	6 beds \| 6 baths \| N/A	$495,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 4.51% Airbnb Rental Income: $1908 Traditional Rental Income: $3215 Airbnb ROI: 0.59% Traditional ROI: 4.51%
2131 Pepperbush Avenue Chesterton, IN Desirable Westwood Manor Subdivision in Chesterton!Located in the award-winning Duneland S...	4 beds \| 4 baths \| 2,992 sq.ft.	$439,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 5.91% Airbnb Rental Income: $2926 Traditional Rental Income: $3291 Airbnb ROI: 3.38% Traditional ROI: 5.91%
496 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,676 sq.ft.	$486,002	Airbnb cash on cash: 0.99% Traditional cash on cash: 3.18% Airbnb Rental Income: $1908 Traditional Rental Income: $2395 Airbnb ROI: 0.99% Traditional ROI: 3.18%
608 S 21St Street Chesterton, IN Located just minutes from downtown Chesterton and the shores of Lake Michigan, this 2-bedr...	2 beds \| 1 baths \| 1,073 sq.ft.	$210,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.43% Airbnb Rental Income: $1805 Traditional Rental Income: $1290 Airbnb ROI: 3.56% Traditional ROI: 3.43%
499 Magnolia Lane Chesterton, IN New construction ranch home with a full basement-ready for your instant enjoyment! The ne...	3 beds \| 2 baths \| 1,590 sq.ft.	$439,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.71% Airbnb Rental Income: $1908 Traditional Rental Income: $2400 Airbnb ROI: 1.29% Traditional ROI: 3.71%
706 Idlewild Lane Chesterton, IN Nestled on an expansive homesite, this fabulous ranch home offers everything you've dreame...	3 beds \| 2 baths \| 1,800 sq.ft.	$542,650	Airbnb cash on cash: 0.7% Traditional cash on cash: 2.71% Airbnb Rental Income: $1908 Traditional Rental Income: $2419 Airbnb ROI: 0.7% Traditional ROI: 2.71%
472 Magnolia Lane Chesterton, IN Now building Easton Park Villa Homes Phase 2! The newest phase of Easton Park is a quiet ...	3 beds \| 2 baths \| 1,710 sq.ft.	$429,900	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.96% Airbnb Rental Income: $1908 Traditional Rental Income: $2451 Airbnb ROI: 1.36% Traditional ROI: 3.96%
3525 Drivers Way Chesterton, IN Beautiful home on a 0.25 acre corner lot in the Golfview Estates neighborhood! Enjoy your ...	4 beds \| 3 baths \| 2,633 sq.ft.	$399,999	Airbnb cash on cash: 3.65% Traditional cash on cash: 4.91% Airbnb Rental Income: $2926 Traditional Rental Income: $2722 Airbnb ROI: 3.65% Traditional ROI: 4.91%
808 Waverly Road Chesterton, IN The 1916 brick Craftsman home is an exquisite blend of historical charm and modern comfort...	5 beds \| 3 baths \| 3,993 sq.ft.	$535,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.54% Airbnb Rental Income: $2747 Traditional Rental Income: $3264 Airbnb ROI: 2.21% Traditional ROI: 4.54%
542 Dunewood Drive Chesterton, IN Splendid location, just steps from Baily Elementary and Chesterton Middle School in your b...	4 beds \| 3 baths \| 1,721 sq.ft.	$299,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 6.24% Airbnb Rental Income: $2926 Traditional Rental Income: $2375 Airbnb ROI: 5.8% Traditional ROI: 6.24%
604 Oakwood Drive Chesterton, IN Quick Possession! This charming two story home will not disappoint you as you are welcome...	3 beds \| 3 baths \| 2,820 sq.ft.	$439,900	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.77% Airbnb Rental Income: $1908 Traditional Rental Income: $2708 Airbnb ROI: 1.6% Traditional ROI: 4.77%
1700 Littler Drive Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek EstateSophistication, cra...	5 beds \| 10 baths \| 17,178 sq.ft.	$2,950,000	Airbnb cash on cash: -1.83% Traditional cash on cash: -0.31% Airbnb Rental Income: $2747 Traditional Rental Income: $6257 Airbnb ROI: -1.83% Traditional ROI: -0.31%
1125 N 350 E Chesterton, IN PRICE IMPROVEMENT!!! Welcome to this sprawling one owner ranch, perfectly situated on 2 a...	4 beds \| 4 baths \| 3,264 sq.ft.	$439,900	Airbnb cash on cash: 3.57% Traditional cash on cash: 7.11% Airbnb Rental Income: $2926 Traditional Rental Income: $3707 Airbnb ROI: 3.57% Traditional ROI: 7.11%
468 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,676 sq.ft.	$419,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 4.07% Airbnb Rental Income: $1908 Traditional Rental Income: $2432 Airbnb ROI: 1.44% Traditional ROI: 4.07%
1550 Hogan Ave Chesterton, IN Welcome to this exquisite Sand Creek home, where sophisticated design meets cozy comfort. ...	4 beds \| 3 baths \| 3,397 sq.ft.	$614,900	Airbnb cash on cash: 1.83% Traditional cash on cash: 3.03% Airbnb Rental Income: $2926 Traditional Rental Income: $2939 Airbnb ROI: 1.83% Traditional ROI: 3.03%
2382 Dakota Street Chesterton, IN Completely rebuilt in 2012, this stunning 3-bedroom ranch home offers the perfect blend of...	3 beds \| 3 baths \| 3,108 sq.ft.	$380,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 5.61% Airbnb Rental Income: $1908 Traditional Rental Income: $2857 Airbnb ROI: 1.53% Traditional ROI: 5.61%
1544 Colonial Drive Chesterton, IN Fantastic 2 story home in the sought after Villages of Sand Creek. Located in Duneland Sch...	4 beds \| 4 baths \| 2,950 sq.ft.	$430,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 6.21% Airbnb Rental Income: $2926 Traditional Rental Income: $3380 Airbnb ROI: 3.4% Traditional ROI: 6.21%
1730 S 11th Street Chesterton, IN FULLY UPDATED RANCH-STYLE HOME ON FULL BASEMENT! stone home on half an acre features 3 bed...	3 beds \| 1 baths \| 1,580 sq.ft.	$299,999	Airbnb cash on cash: 2.88% Traditional cash on cash: 3.62% Airbnb Rental Income: $1908 Traditional Rental Income: $1612 Airbnb ROI: 2.88% Traditional ROI: 3.62%
1239 Fox Hollow Drive Chesterton, IN PRICE IMPROVEMENT This Spacious Well Maintained 3 bedroom, 2.5 bath, Open Concept Town...	3 beds \| 3 baths \| 1,727 sq.ft.	$279,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 6.32% Airbnb Rental Income: $1908 Traditional Rental Income: $2273 Airbnb ROI: 3.02% Traditional ROI: 6.32%

Real Estate investment in Chesterton, IN

There are 51 properties for sale in the city of Chesterton . The median list price in Chesterton is $425,000 and the average price per square foot is $166. In October 2025, the average monthly cash on cash return in Chesterton is 5.00%. The average monthly rental income in Chesterton is $2,551.

Chesterton, IN Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 51 investment properties available for sale in Chesterton.

In 2025, the best neighborhood to buy investment property is Chesterton.

The ROI for Long-Term is higher than the Short-Term in Chesterton with average rental income of $2,551.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

1116 N 350 E

Chesterton, IN

4 beds | 3 baths | 4,546 sq.ft.

$925,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $2926

Traditional Rental Income: $3087

Airbnb ROI: 0.89%

Traditional ROI: 1.87%

327 S 18th Street

Chesterton, IN

3 beds | 2 baths | 1,680 sq.ft.

$294,900

Airbnb cash on cash: 2.95%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $1908

Traditional Rental Income: $2291

Airbnb ROI: 2.95%

Traditional ROI: 6.16%

1452 Gossett Mill Avenue

Chesterton, IN

4 beds | 3 baths | 2,031 sq.ft.

$459,999

Airbnb cash on cash: 3.1%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $2926

Traditional Rental Income: $2794

Airbnb ROI: 3.1%

Traditional ROI: 4.36%

2121 Dogwood Lane

Chesterton, IN

3 beds | 2 baths | 1,368 sq.ft.

$195,000

Airbnb cash on cash: 5.67%

Traditional cash on cash: 9.79%

Airbnb Rental Income: $1908

Traditional Rental Income: $2165

Airbnb ROI: 5.67%

Traditional ROI: 9.79%

1887 Jacob Lane

Chesterton, IN

3 beds | 2 baths | 1,443 sq.ft.

$319,900

Airbnb cash on cash: 2.48%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $1908

Traditional Rental Income: $1919

Airbnb ROI: 2.48%

Traditional ROI: 4.2%

2009 Timberwood Lane

Chesterton, IN

3 beds | 2 baths | 1,827 sq.ft.

$519,900

Airbnb cash on cash: -0.37%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $1908

Traditional Rental Income: $2551

Airbnb ROI: -0.37%

Traditional ROI: 1.99%

2011 Timberwood Lane

Chesterton, IN

4 beds | 3 baths | 2,476 sq.ft.

$549,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $2926

Traditional Rental Income: $3030

Airbnb ROI: 2.18%

Traditional ROI: 3.7%

412 S 15th Street

Chesterton, IN

5 beds | 3 baths | 2,894 sq.ft.

$425,000

Airbnb cash on cash: 3.62%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $2747

Traditional Rental Income: $2554

Airbnb ROI: 3.62%