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.

Multi Family for Sale in Chesterton, IN

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

Showing 3 Multi Family 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
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%
2091 Texas Street Chesterton, IN Lovingly cared for half-duplex on a desirable corner lot, just steps from nearby parks and...	3 beds \| 2 baths \| 1,626 sq.ft.	$279,900	Airbnb cash on cash: 3.48% Traditional cash on cash: 5.47% Airbnb Rental Income: $1908 Traditional Rental Income: $1927 Airbnb ROI: 3.48% Traditional ROI: 5.47%
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: 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%

Your search for investment property begins and ends here

Multi Family for Sale in Chesterton, IN

103-117 Jeffrey Street

Chesterton, IN

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

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%

2091 Texas Street

Chesterton, IN

3 beds | 2 baths | 1,626 sq.ft.

$279,900

Airbnb cash on cash: 3.48%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $1908

Traditional Rental Income: $1927

Airbnb ROI: 3.48%

Traditional ROI: 5.47%

Other Investment Properties for Sale in Chesterton

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%

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%

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%

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%

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%

Chesterton , IN

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

$519,900