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

separator

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%
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%
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%
Other Investment Properties for Sale in Chesterton
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%
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%
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 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%
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%
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%

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%

1615 Melanie Lane

Chesterton, IN

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%

2121 Tupelo Lane

Chesterton, IN

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%

Other Investment Properties for Sale in Chesterton

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%

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%

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%

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 | 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%

Chesterton , IN

4 beds | 3 baths | 2,241 sq.ft.

$529,900