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.

Condos for Sale in Chesterton, IN

Search for Condo for Sale in Chesterton, Indiana. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 4 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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.	$167,500	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.86% Airbnb Rental Income: $1587 Traditional Rental Income: $1499 Airbnb ROI: 2.58% Traditional ROI: 4.86%
2023 Hawthorne Ln Chesterton, IN 2023 Hawthorne Ln, Chesterton, IN 46304 \| Condo/Coop	2 beds \| 1 baths \| 1,227 sq.ft.	$162,500	Airbnb cash on cash: 1.72% Traditional cash on cash: 0.87% Airbnb Rental Income: $1587 Traditional Rental Income: $1001 Airbnb ROI: 1.72% Traditional ROI: 0.87%
Other Investment Properties for Sale in Chesterton
214 Woodlawn Ave Chesterton , IN This home sits on almost 2 ACRES!!! This beautiful home situated on a wooded lot within wa...	3 beds \| 2 baths \| 2,046 sq.ft.	$320,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 5.03% Airbnb Rental Income: $1864 Traditional Rental Income: $2161 Airbnb ROI: 2.38% Traditional ROI: 5.03%
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 Ln Chesterton , IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 2 baths \| 2,476 sq.ft.	$539,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.78% Airbnb Rental Income: $3402 Traditional Rental Income: $3030 Airbnb ROI: 3.02% Traditional ROI: 3.78%
2221 Easton Park Dr Chesterton , IN Hurry now to make your own selections! The ever-popular Melanie floor plan offers all of t...	4 beds \| 2 baths \| 2,348 sq.ft.	$549,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.06% Airbnb Rental Income: $3402 Traditional Rental Income: $2630 Airbnb ROI: 3.09% Traditional ROI: 3.06%
801 Idlewild Ln 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%
2230 Redwood Ln Chesterton , IN The Astoria in Easton Park! Welcome to luxury living in this stunning proposed two-story h...	4 beds \| 2 baths \| 2,281 sq.ft.	$599,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.18% Airbnb Rental Income: $3402 Traditional Rental Income: $2932 Airbnb ROI: 2.67% Traditional ROI: 3.18%
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%
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%
1700 Littler Dr Chesterton , IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 9 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.	$419,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.23% Airbnb Rental Income: $3402 Traditional Rental Income: $3380 Airbnb ROI: 4.36% Traditional ROI: 6.23%
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%

Your search for investment property begins and ends here

Condos for Sale in Chesterton, IN

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%

2121 Tupelo Lane

Chesterton, IN

2 beds | 1 baths | 1,228 sq.ft.

$167,500

Airbnb cash on cash: 2.58%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1587

Traditional Rental Income: $1499

Airbnb ROI: 2.58%

Traditional ROI: 4.86%

2023 Hawthorne Ln

Chesterton, IN

2 beds | 1 baths | 1,227 sq.ft.

$162,500

Airbnb cash on cash: 1.72%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $1587

Traditional Rental Income: $1001

Airbnb ROI: 1.72%

Traditional ROI: 0.87%

Other Investment Properties for Sale in Chesterton

Chesterton , IN

3 beds | 2 baths | 2,046 sq.ft.

$320,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $1864

Traditional Rental Income: $2161

Airbnb ROI: 2.38%

Traditional ROI: 5.03%

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%

Chesterton , IN

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

$539,900

Airbnb cash on cash: 3.02%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3402

Traditional Rental Income: $3030

Airbnb ROI: 3.02%

Traditional ROI: 3.78%

Chesterton , IN

4 beds | 2 baths | 2,348 sq.ft.

$549,900

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3402

Traditional Rental Income: $2630

Airbnb ROI: 3.09%

Traditional ROI: 3.06%

Chesterton , IN

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%

Chesterton , IN

3 beds | 2 baths | 1,590 sq.ft.

$439,900