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%
1171 Weaver Way Chesterton, IN This stunning 2019 ranch in the exclusive Village in Burns Harbor delivers everything on y...	3 beds \| 2 baths \| 1,524 sq.ft.	$335,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 1.94% Airbnb Rental Income: $1864 Traditional Rental Income: $1319 Airbnb ROI: 2.09% Traditional ROI: 1.94%
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%
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.	$370,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.72% Airbnb Rental Income: $1864 Traditional Rental Income: $2448 Airbnb ROI: 1.6% Traditional ROI: 4.72%
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.	$542,000	Airbnb cash on cash: 3% Traditional cash on cash: 3.76% Airbnb Rental Income: $3402 Traditional Rental Income: $3030 Airbnb ROI: 3% Traditional ROI: 3.76%
696 Admiral Dr Chesterton, IN Welcome home to 696 Admiral Drive! This well-maintained and tastefully updated home in Por...	3 beds \| 2 baths \| 2,058 sq.ft.	$365,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 5.1% Airbnb Rental Income: $1864 Traditional Rental Income: $2507 Airbnb ROI: 1.76% Traditional ROI: 5.1%
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: 1.2% Traditional cash on cash: 3.87% Airbnb Rental Income: $1864 Traditional Rental Income: $2364 Airbnb ROI: 1.2% Traditional ROI: 3.87%
326 Clifford Way Chesterton, IN Beautifully updated 4 bedroom 4 bathroom 2 story with finished basement built in 2018. 9 ...	4 beds \| 3 baths \| 2,376 sq.ft.	$347,426	Airbnb cash on cash: 5.76% Traditional cash on cash: 6.85% Airbnb Rental Income: $3402 Traditional Rental Income: $3004 Airbnb ROI: 5.76% Traditional ROI: 6.85%
2215 Easton Park Drive Chesterton, IN Construction beginning September-completion February 2026! Introducing The Carmela floor p...	4 beds \| 3 baths \| 2,241 sq.ft.	$529,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.94% Airbnb Rental Income: $3402 Traditional Rental Income: $2480 Airbnb ROI: 3.27% Traditional ROI: 2.94%
1615 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now complete! The open concept...	3 beds \| 3 baths \| 1,954 sq.ft.	$369,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 5.76% Airbnb Rental Income: $1864 Traditional Rental Income: $2758 Airbnb ROI: 1.75% Traditional ROI: 5.76%
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%
1163 Tanya St Chesterton, IN Located in a Quiet and Desirable Community Close to the National Lakeshore- with NO HOMEOW...	3 beds \| 2 baths \| 1,219 sq.ft.	$310,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 3.84% Airbnb Rental Income: $1864 Traditional Rental Income: $1730 Airbnb ROI: 2.59% Traditional ROI: 3.84%
801 Idlewild Lane Chesterton, IN Brand New & Move-In Ready! No Waiting, No Unfinished Details! Welcome to this beautifully ...	4 beds \| 3 baths \| 2,271 sq.ft.	$624,900	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.92% Airbnb Rental Income: $3402 Traditional Rental Income: $2891 Airbnb ROI: 2.5% Traditional ROI: 2.92%
2310 Redwood Lane Chesterton, IN New construction ranch home with a full basement-ready for your enjoyment June 2025! The n...	3 beds \| 2 baths \| 1,590 sq.ft.	$439,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 2.75% Airbnb Rental Income: $1864 Traditional Rental Income: $2171 Airbnb ROI: 0.79% Traditional ROI: 2.75%
1617 Melanie Ln Chesterton, IN Only 3 homes left in this golf-course community! Now complete! This is the last unit ava...	3 beds \| 3 baths \| 1,954 sq.ft.	$375,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 5.39% Airbnb Rental Income: $1864 Traditional Rental Income: $2934 Airbnb ROI: 0.93% Traditional ROI: 5.39%
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.	$170,500	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.76% Airbnb Rental Income: $1587 Traditional Rental Income: $1499 Airbnb ROI: 2.52% Traditional ROI: 4.76%
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: 2.8% Airbnb Rental Income: $3402 Traditional Rental Income: $2932 Airbnb ROI: 2.33% Traditional ROI: 2.8%
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%
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 new...	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.	$278,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 3.5% Airbnb Rental Income: $1864 Traditional Rental Income: $1820 Airbnb ROI: 1.77% Traditional ROI: 3.5%
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 r...	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: 4.98% Airbnb Rental Income: $3402 Traditional Rental Income: $2708 Airbnb ROI: 4.82% Traditional ROI: 4.98%
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: 4.28% Traditional cash on cash: 6.13% Airbnb Rental Income: $3402 Traditional Rental Income: $3380 Airbnb ROI: 4.28% Traditional ROI: 6.13%
1239 Fox Hollow Drive Chesterton, IN NEW PRICE Motivated Sellers!! Bring your offers on this Move-in Ready Townhouse. Discove...	3 beds \| 3 baths \| 1,727 sq.ft.	$259,900	Airbnb cash on cash: 2.17% Traditional cash on cash: 5.88% Airbnb Rental Income: $1864 Traditional Rental Income: $2273 Airbnb ROI: 2.17% Traditional ROI: 5.88%
476 Magnolia Lane Chesterton, IN You've found your own personal hideaway! Nestled on a picturesque pond lot with no neighbo...	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%
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.	$200,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 10.43% Airbnb Rental Income: $1864 Traditional Rental Income: $2322 Airbnb ROI: 5.38% Traditional ROI: 10.43%
422 Jefferson Avenue Chesterton, IN Old-World Charm Meets Modern Comfort in a Prime Location! Step back in time while enjoying...	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 off...	5 beds \| 4 baths \| 2,648 sq.ft.	$535,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.73% Airbnb Rental Income: $2553 Traditional Rental Income: $3082 Airbnb ROI: 1.44% Traditional ROI: 3.73%
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.	$318,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.79% Airbnb Rental Income: $3402 Traditional Rental Income: $2255 Airbnb ROI: 7.1% Traditional ROI: 5.79%
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%
319 Michigami Trail Chesterton, IN Move right in and start enjoying Chesterton living! This spacious three-bedroom ranch offe...	3 beds \| 1 baths \| 1,433 sq.ft.	$224,900	Airbnb cash on cash: 4.09% Traditional cash on cash: 5.59% Airbnb Rental Income: $1864 Traditional Rental Income: $1683 Airbnb ROI: 4.09% Traditional ROI: 5.59%
1329 N 375 E Chesterton, IN Nestled on 5 private acres, this spacious ranch offers four bedrooms (potentially five) pl...	4 beds \| 3 baths \| 2,872 sq.ft.	$559,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.85% Airbnb Rental Income: $3402 Traditional Rental Income: $2968 Airbnb ROI: 3.23% Traditional ROI: 3.85%
1034 N 350 E Chesterton, IN Welcome to this beautifully updated bi-level home on a private 1-acre lot in Jackson Towns...	3 beds \| 3 baths \| 2,636 sq.ft.	$425,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 5.02% Airbnb Rental Income: $1864 Traditional Rental Income: $2727 Airbnb ROI: 1.6% Traditional ROI: 5.02%

Real Estate investment in Chesterton, IN

There are 92 properties for sale in the city of Chesterton . The median list price in Chesterton is $339,900 and the average price per square foot is $207. In January 2026, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $1,761.

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

There are 92 investment properties available for sale in Chesterton.

In 2026, 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 $1,761.

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%

1171 Weaver Way

Chesterton, IN

3 beds | 2 baths | 1,524 sq.ft.

$335,000

Airbnb cash on cash: 2.09%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $1864

Traditional Rental Income: $1319

Airbnb ROI: 2.09%

Traditional ROI: 1.94%

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%

1440 Duffer Drive

Chesterton, IN

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

$370,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1864

Traditional Rental Income: $2448

Airbnb ROI: 1.6%

Traditional ROI: 4.72%

2011 Timberwood Lane

Chesterton, IN

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

$542,000

Airbnb cash on cash: 3%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3402

Traditional Rental Income: $3030

Airbnb ROI: 3%

Traditional ROI: 3.76%

696 Admiral Dr

Chesterton, IN

3 beds | 2 baths | 2,058 sq.ft.

$365,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $1864

Traditional Rental Income: $2507

Airbnb ROI: 1.76%

Traditional ROI: 5.1%

1609 Melanie Lane

Chesterton, IN

3 beds | 3 baths | 1,954 sq.ft.

$399,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1864

Traditional Rental Income: $2364

Airbnb ROI: 1.2%

Traditional ROI: 3.87%

326 Clifford Way

Chesterton, IN

4 beds | 3 baths | 2,376 sq.ft.

$347,426

Airbnb cash on cash: 5.76%

Traditional cash on cash: 6.85%

Airbnb Rental Income: $3402

Traditional Rental Income: $3004

Airbnb ROI: 5.76%