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: 1.35% Traditional cash on cash: 1.87% Airbnb Rental Income: $3402 Traditional Rental Income: $3087 Airbnb ROI: 1.35% Traditional ROI: 1.87%
997 N 250 E Chesterton, IN Discover peaceful country living just minutes from everything Chesterton has to offer! Thi...	3 beds \| 3 baths \| 2,610 sq.ft.	$510,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.78% Airbnb Rental Income: $1864 Traditional Rental Income: $2725 Airbnb ROI: 0.93% Traditional ROI: 3.78%
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: 2.82% Traditional cash on cash: 6.16% Airbnb Rental Income: $1864 Traditional Rental Income: $2291 Airbnb ROI: 2.82% 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.	$444,900	Airbnb cash on cash: 4.19% Traditional cash on cash: 4.54% Airbnb Rental Income: $3402 Traditional Rental Income: $2794 Airbnb ROI: 4.19% Traditional ROI: 4.54%
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: 2.32% Traditional cash on cash: 4.17% Airbnb Rental Income: $1864 Traditional Rental Income: $1919 Airbnb ROI: 2.32% Traditional ROI: 4.17%
1440 Duffer Drive Chesterton, IN Welcome to 1440 Duffer Dr, Chesterton, IN - a beautifully maintained 3-bedroom, 3-bath hom...	3 beds \| 3 baths \| 3,640 sq.ft.	$375,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 1.43% Airbnb Rental Income: $1864 Traditional Rental Income: $1319 Airbnb ROI: 1.56% Traditional ROI: 1.43%
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.	$499,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.11% Airbnb Rental Income: $1864 Traditional Rental Income: $2551 Airbnb ROI: -0.43% Traditional ROI: 2.11%
2011 Timberwood Lane Chesterton, IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 3 baths \| 2,476 sq.ft.	$544,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 3.74% Airbnb Rental Income: $3402 Traditional Rental Income: $3030 Airbnb ROI: 2.99% Traditional ROI: 3.74%
1609 Melanie Lane Chesterton, IN This beautifully maintained 3-bedroom, 3-bath townhome offers comfort, style, and scenic v...	3 beds \| 3 baths \| 1,954 sq.ft.	$399,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.59% Airbnb Rental Income: $1864 Traditional Rental Income: $2364 Airbnb ROI: 1.92% Traditional ROI: 4.59%
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.	$389,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.38% Airbnb Rental Income: $1864 Traditional Rental Income: $2758 Airbnb ROI: 1.57% Traditional ROI: 5.38%
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: 1.24% Traditional cash on cash: 2.5% Airbnb Rental Income: $1864 Traditional Rental Income: $1861 Airbnb ROI: 1.24% Traditional ROI: 2.5%
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.	$629,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 2.89% Airbnb Rental Income: $3402 Traditional Rental Income: $2891 Airbnb ROI: 2.47% Traditional ROI: 2.89%
2116 Redwood Lane Chesterton, IN Available now! Stunning 4BR, 2.5BA home in Chesterton's desirable Easton Park. Immaculate ...	4 beds \| 3 baths \| 2,445 sq.ft.	$499,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.94% Airbnb Rental Income: $3402 Traditional Rental Income: $2946 Airbnb ROI: 3.3% Traditional ROI: 3.94%
2121 Tupelo Lane Chesterton, IN Move-in ready, maintenance-free main-floor condo with a 1-car garage! A bright, open-conce...	2 beds \| 1 baths \| 1,228 sq.ft.	$174,900	Airbnb cash on cash: 4.38% Traditional cash on cash: 6.57% Airbnb Rental Income: $1587 Traditional Rental Income: $1499 Airbnb ROI: 4.38% 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: 2.33% Traditional cash on cash: 2.81% Airbnb Rental Income: $3402 Traditional Rental Income: $2932 Airbnb ROI: 2.33% 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: 0.91% Traditional cash on cash: 3.55% Airbnb Rental Income: $1864 Traditional Rental Income: $2559 Airbnb ROI: 0.91% 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: 3.29% Traditional cash on cash: 9.99% Airbnb Rental Income: $1864 Traditional Rental Income: $3009 Airbnb ROI: 3.29% Traditional ROI: 9.99%
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.	$429,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 6.07% Airbnb Rental Income: $3402 Traditional Rental Income: $3291 Airbnb ROI: 4.47% Traditional ROI: 6.07%
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: 0.91% Traditional cash on cash: 3.18% Airbnb Rental Income: $1864 Traditional Rental Income: $2395 Airbnb ROI: 0.91% Traditional ROI: 3.18%
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.	$419,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 3.97% Airbnb Rental Income: $1864 Traditional Rental Income: $2400 Airbnb ROI: 1.34% Traditional ROI: 3.97%
399 Conestoga Drive Chesterton, IN This charming 3-bedroom, 2-bathroom home in the conveniently located Olde Towne Subdivisio...	3 beds \| 2 baths \| 1,046 sq.ft.	$289,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.45% Airbnb Rental Income: $1864 Traditional Rental Income: $1820 Airbnb ROI: 1.78% Traditional ROI: 3.45%
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: 0.63% Traditional cash on cash: 2.71% Airbnb Rental Income: $1864 Traditional Rental Income: $2419 Airbnb ROI: 0.63% 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: 1.27% Traditional cash on cash: 3.96% Airbnb Rental Income: $1864 Traditional Rental Income: $2451 Airbnb ROI: 1.27% Traditional ROI: 3.96%
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: 7.21% Traditional cash on cash: 6.24% Airbnb Rental Income: $3402 Traditional Rental Income: $2375 Airbnb ROI: 7.21% Traditional ROI: 6.24%
604 Oakwood Drive Chesterton, IN Charming 2-story home conveniently located near downtown Chesterton. The original owner ha...	4 beds \| 3 baths \| 2,820 sq.ft.	$425,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.97% Airbnb Rental Income: $3402 Traditional Rental Income: $2708 Airbnb ROI: 4.82% Traditional ROI: 4.97%
1700 Littler Drive Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 10 baths \| 17,178 sq.ft.	$2,950,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.31% Airbnb Rental Income: $2553 Traditional Rental Income: $6257 Airbnb ROI: -1.89% Traditional ROI: -0.31%
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: 1.35% Traditional cash on cash: 4.07% Airbnb Rental Income: $1864 Traditional Rental Income: $2432 Airbnb ROI: 1.35% Traditional ROI: 4.07%
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.	$425,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 6.29% Airbnb Rental Income: $3402 Traditional Rental Income: $3380 Airbnb ROI: 4.45% Traditional ROI: 6.29%
1730 S 11th Street Chesterton, IN NEW HOLIDAY PRICING! SELLER'S LOWERED THE PRICE AGAIN! JUST IN TIME FOR THE HOLIDAYS! Full...	3 beds \| 1 baths \| 1,580 sq.ft.	$289,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 3.78% Airbnb Rental Income: $1864 Traditional Rental Income: $1612 Airbnb ROI: 2.88% Traditional ROI: 3.78%
1239 Fox Hollow Drive Chesterton, IN NEW PRICE IMPROVEMENT Discover exceptional value with this spacious 3 bedroom, 2.5 bath...	3 beds \| 3 baths \| 1,727 sq.ft.	$272,900	Airbnb cash on cash: 2.97% Traditional cash on cash: 6.5% Airbnb Rental Income: $1864 Traditional Rental Income: $2273 Airbnb ROI: 2.97% Traditional ROI: 6.5%
476 Magnolia Lane Chesterton, IN You've found your own personal hideaway! Nestled on a picturesque pond lot with no neighb...	3 beds \| 2 baths \| 1,790 sq.ft.	$487,700	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.46% Airbnb Rental Income: $1864 Traditional Rental Income: $2531 Airbnb ROI: 0.9% Traditional ROI: 3.46%
1908 Catkin Circle Chesterton, IN Discover a home that checks every box: turn-key, spacious, and impeccably maintained. Welc...	3 beds \| 4 baths \| 4,764 sq.ft.	$745,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.29% Airbnb Rental Income: $1864 Traditional Rental Income: $3097 Airbnb ROI: -0.21% Traditional ROI: 2.29%
1288 N Brummitt Road Chesterton, IN Cute ranch home on a 1.25 acre corner lot in a beautiful, serene area of Chesterton just m...	3 beds \| 2 baths \| 1,765 sq.ft.	$250,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 8.19% Airbnb Rental Income: $1864 Traditional Rental Income: $2322 Airbnb ROI: 4.13% Traditional ROI: 8.19%
2513 Springdale Street Chesterton, IN Welcome to your maintenance-free oasis in the desirable Springdale neighborhood of Chester...	2 beds \| 2 baths \| 1,601 sq.ft.	$315,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 5.48% Airbnb Rental Income: $1587 Traditional Rental Income: $2244 Airbnb ROI: 1.73% Traditional ROI: 5.48%
2114 Tupelo Lane Chesterton, IN Discover Effortless Living in This Well maintained 3 Bedroom, 2 Bath Main Floor Condo- The...	3 beds \| 2 baths \| 1,318 sq.ft.	$180,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 7.58% Airbnb Rental Income: $1864 Traditional Rental Income: $1709 Airbnb ROI: 5.57% Traditional ROI: 7.58%
422 Jefferson Avenue Chesterton, IN Old-World Charm Meets Modern Comfort in a Prime Location! Step back in time while enjoyin...	2 beds \| 2 baths \| 1,506 sq.ft.	$275,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 5.14% Airbnb Rental Income: $1587 Traditional Rental Income: $1884 Airbnb ROI: 2.24% Traditional ROI: 5.14%
2335 Legend Circle E Chesterton, IN Maintenance Free Living on the trail in Coffee Creek! This tastefully updated townhome of...	5 beds \| 4 baths \| 2,648 sq.ft.	$549,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 4% Airbnb Rental Income: $2553 Traditional Rental Income: $3082 Airbnb ROI: 1.78% Traditional ROI: 4%
1226 Dogwood Drive Chesterton, IN Extensive Updates Throughout! This home has been beautifully remodeled with numerous recen...	4 beds \| 2 baths \| 1,827 sq.ft.	$324,900	Airbnb cash on cash: 6.95% Traditional cash on cash: 5.67% Airbnb Rental Income: $3402 Traditional Rental Income: $2255 Airbnb ROI: 6.95% Traditional ROI: 5.67%
613 Idlewild Lane Chesterton, IN You're going to love the Charlie ranch floor plan! Upon entrance you'll be in awe of the g...	3 beds \| 3 baths \| 2,208 sq.ft.	$597,377	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.03% Airbnb Rental Income: $1864 Traditional Rental Income: $2830 Airbnb ROI: 0.4% Traditional ROI: 3.03%

Real Estate investment in Chesterton, IN

There are 46 properties for sale in the city of Chesterton . The median list price in Chesterton is $422,450 and the average price per square foot is $169. In December 2025, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,491.

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

There are 46 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 $2,491.

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: 1.35%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $3402

Traditional Rental Income: $3087

Airbnb ROI: 1.35%

Traditional ROI: 1.87%

997 N 250 E

Chesterton, IN

3 beds | 3 baths | 2,610 sq.ft.

$510,000

Airbnb cash on cash: 0.93%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1864

Traditional Rental Income: $2725

Airbnb ROI: 0.93%

Traditional ROI: 3.78%

327 S 18th Street

Chesterton, IN

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

$294,900

Airbnb cash on cash: 2.82%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $1864

Traditional Rental Income: $2291

Airbnb ROI: 2.82%

Traditional ROI: 6.16%

1452 Gossett Mill Avenue

Chesterton, IN

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

$444,900

Airbnb cash on cash: 4.19%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $3402

Traditional Rental Income: $2794

Airbnb ROI: 4.19%

Traditional ROI: 4.54%

1887 Jacob Lane

Chesterton, IN

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

$319,900

Airbnb cash on cash: 2.32%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $1864

Traditional Rental Income: $1919

Airbnb ROI: 2.32%

Traditional ROI: 4.17%

1440 Duffer Drive

Chesterton, IN

3 beds | 3 baths | 3,640 sq.ft.

$375,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $1864

Traditional Rental Income: $1319

Airbnb ROI: 1.56%

Traditional ROI: 1.43%

2009 Timberwood Lane

Chesterton, IN

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

$499,900

Airbnb cash on cash: -0.43%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $1864

Traditional Rental Income: $2551

Airbnb ROI: -0.43%

Traditional ROI: 2.11%

2011 Timberwood Lane

Chesterton, IN

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

$544,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $3402

Traditional Rental Income: $3030

Airbnb ROI: 2.99%