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
2031 Northwood Lane Chesterton, IN Step into effortless style and comfort in this standout villa located in Chesterton's hot ...	3 beds \| 2 baths \| 1,664 sq.ft.	$387,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4% Airbnb Rental Income: $2278 Traditional Rental Income: $2229 Airbnb ROI: 2.57% Traditional ROI: 4%
2119 Easton Park Drive Chesterton, IN Welcome to Easton Park. Chesterton's Newest and Most Sought After Community! Step into the...	5 beds \| 4 baths \| 3,185 sq.ft.	$509,900	Airbnb cash on cash: 2.93% Traditional cash on cash: 5.97% Airbnb Rental Income: $3277 Traditional Rental Income: $3992 Airbnb ROI: 2.93% Traditional ROI: 5.97%
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: 0.21% Traditional cash on cash: 1.87% Airbnb Rental Income: $2215 Traditional Rental Income: $3087 Airbnb ROI: 0.21% 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: 4.07% Traditional cash on cash: 6.16% Airbnb Rental Income: $2278 Traditional Rental Income: $2291 Airbnb ROI: 4.07% Traditional ROI: 6.16%
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: 3.5% Traditional cash on cash: 4.2% Airbnb Rental Income: $2278 Traditional Rental Income: $1919 Airbnb ROI: 3.5% Traditional ROI: 4.2%
2117 W Morgan Avenue Chesterton, IN Why rent when you can own? This inviting 2-story townhome offers 1,120 sq ft of comfortabl...	2 beds \| 2 baths \| 1,120 sq.ft.	$192,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 5.86% Airbnb Rental Income: $2278 Traditional Rental Income: $1545 Airbnb ROI: 6.76% Traditional ROI: 5.86%
2009 Timberwood Lane Chesterton, IN Come view this open concept ranch located in the highly sought after Easton Park subdivisi...	3 beds \| 2 baths \| 1,827 sq.ft.	$529,900	Airbnb cash on cash: 0.24% Traditional cash on cash: 1.94% Airbnb Rental Income: $2278 Traditional Rental Income: $2551 Airbnb ROI: 0.24% Traditional ROI: 1.94%
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: 1.02% Traditional cash on cash: 3.7% Airbnb Rental Income: $2215 Traditional Rental Income: $3030 Airbnb ROI: 1.02% 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.	$439,900	Airbnb cash on cash: 4.53% Traditional cash on cash: 4.56% Airbnb Rental Income: $3277 Traditional Rental Income: $2554 Airbnb ROI: 4.53% Traditional ROI: 4.56%
1073 N 100 E Chesterton, IN This 3-bedroom ranch with basement has an enclosed 240 sq ft front porch and 1.5 car detac...	3 beds \| 2 baths \| 1,156 sq.ft.	$239,900	Airbnb cash on cash: 4.73% Traditional cash on cash: 4.3% Airbnb Rental Income: $2278 Traditional Rental Income: $1612 Airbnb ROI: 4.73% Traditional ROI: 4.3%
1608 Melanie Lane Chesterton, IN Now complete and ready for move in! The open concept living spaces you'll find soaring ca...	3 beds \| 3 baths \| 1,954 sq.ft.	$409,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 5.15% Airbnb Rental Income: $2278 Traditional Rental Income: $2840 Airbnb ROI: 2.21% Traditional ROI: 5.15%
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.	$404,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 4.51% Airbnb Rental Income: $2278 Traditional Rental Income: $2364 Airbnb ROI: 2.79% Traditional ROI: 4.51%
1300 Brassie Avenue Chesterton, IN Discover your dream home in this exquisite 4 bedroom, 3 1/2 bath masterpiece located in a ...	4 beds \| 3 baths \| 3,880 sq.ft.	$719,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.19% Airbnb Rental Income: $2215 Traditional Rental Income: $2719 Airbnb ROI: 0.61% Traditional ROI: 2.19%
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: 2.3% Traditional cash on cash: 5.03% Airbnb Rental Income: $2278 Traditional Rental Income: $2758 Airbnb ROI: 2.3% Traditional ROI: 5.03%
495 Magnolia Lane Chesterton, IN Now building Easton Park Villa Homes Phase 2! Nestled amongst rolling streets, the newest...	3 beds \| 2 baths \| 1,710 sq.ft.	$439,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.59% Airbnb Rental Income: $2278 Traditional Rental Income: $2351 Airbnb ROI: 2.03% Traditional ROI: 3.59%
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.	$179,900	Airbnb cash on cash: 6.31% Traditional cash on cash: 5.53% Airbnb Rental Income: $2278 Traditional Rental Income: $1575 Airbnb ROI: 6.31% Traditional ROI: 5.53%
1471 Delos Marr Avenue Chesterton, IN Charming 4-Bedroom 2.5 Bath Home in Chesterton! Welcome to this beautifully maintained ho...	4 beds \| 3 baths \| 2,272 sq.ft.	$449,900	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.44% Airbnb Rental Income: $2215 Traditional Rental Income: $2800 Airbnb ROI: 0.72% Traditional ROI: 3.44%
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: 0.77% Traditional cash on cash: 2.85% Airbnb Rental Income: $2215 Traditional Rental Income: $2891 Airbnb ROI: 0.77% Traditional ROI: 2.85%
4120 Abercrombie Drive Chesterton, IN SELLER IS MOTIVATED AND READY TO SELL!! Nestled in the desirable Abercrombie Woods, this ...	4 beds \| 3 baths \| 3,382 sq.ft.	$459,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.94% Airbnb Rental Income: $2215 Traditional Rental Income: $2747 Airbnb ROI: 1.41% Traditional ROI: 3.94%
1583 N Derby Avenue Chesterton, IN Discover a unique opportunity with this charming property offering two homes on a peacefu...	3 beds \| 2 baths \| 1,696 sq.ft.	$329,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 5.51% Airbnb Rental Income: $2278 Traditional Rental Income: $2291 Airbnb ROI: 3.64% Traditional ROI: 5.51%
612 Idlewild Lane Chesterton, IN Now releasing Phase 2 of Chesterton's coveted Easton Park community! Ready for move in Au...	4 beds \| 3 baths \| 2,359 sq.ft.	$515,900	Airbnb cash on cash: 1.36% Traditional cash on cash: 4.01% Airbnb Rental Income: $2215 Traditional Rental Income: $2934 Airbnb ROI: 1.36% Traditional ROI: 4.01%
2116 Redwood Lane Chesterton, IN Available Now! Seller is offering up to 15,000 D in CONCESSIONS to the BUYER. Welcome to ...	4 beds \| 3 baths \| 2,445 sq.ft.	$559,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.42% Airbnb Rental Income: $2215 Traditional Rental Income: $2946 Airbnb ROI: 0.95% Traditional ROI: 3.42%
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: 2.33% Traditional cash on cash: 4.91% Airbnb Rental Income: $2215 Traditional Rental Income: $2611 Airbnb ROI: 2.33% Traditional ROI: 4.91%
2121 Tupelo Lane Chesterton, IN WANTED: NEW HOMEOWNERS! This maintenance-free 2-bedroom, 1-bath main floor condo with a 1-...	2 beds \| 1 baths \| 1,228 sq.ft.	$174,900	Airbnb cash on cash: 5.69% Traditional cash on cash: 6.57% Airbnb Rental Income: $1849 Traditional Rental Income: $1499 Airbnb ROI: 5.69% Traditional ROI: 6.57%
1619 Melanie Lane Chesterton, IN Only 3 homes left in this golf-course community! Now complete! The open concept living ...	3 beds \| 3 baths \| 1,954 sq.ft.	$429,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 5.79% Airbnb Rental Income: $2278 Traditional Rental Income: $3191 Airbnb ROI: 2.11% Traditional ROI: 5.79%
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: 0.7% Traditional cash on cash: 2.81% Airbnb Rental Income: $2215 Traditional Rental Income: $2932 Airbnb ROI: 0.7% 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: 1.67% Traditional cash on cash: 3.55% Airbnb Rental Income: $2278 Traditional Rental Income: $2559 Airbnb ROI: 1.67% Traditional ROI: 3.55%
605 Jefferson Avenue Chesterton, IN Rare Find! One Owner Home in Chesterton. Has 4 bedrooms, 1.5 bathrooms, attached garage, a...	4 beds \| 2 baths \| 1,850 sq.ft.	$200,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 10.1% Airbnb Rental Income: $2215 Traditional Rental Income: $2304 Airbnb ROI: 6.69% Traditional ROI: 10.1%
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: -0.45% Traditional cash on cash: 1.89% Airbnb Rental Income: $2215 Traditional Rental Income: $3093 Airbnb ROI: -0.45% 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: 1.14% Traditional cash on cash: 4.51% Airbnb Rental Income: $2215 Traditional Rental Income: $3215 Airbnb ROI: 1.14% Traditional ROI: 4.51%
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.	$439,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.91% Airbnb Rental Income: $2215 Traditional Rental Income: $3291 Airbnb ROI: 1.94% Traditional ROI: 5.91%

Real Estate investment in Chesterton, IN

There are 60 properties for sale in the city of Chesterton . The median list price in Chesterton is $429,900 and the average price per square foot is $162. In September 2025, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,708.

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

There are 60 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 $2,708.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

2031 Northwood Lane

Chesterton, IN

3 beds | 2 baths | 1,664 sq.ft.

$387,500

Airbnb cash on cash: 2.57%

Traditional cash on cash: 4%

Airbnb Rental Income: $2278

Traditional Rental Income: $2229

Airbnb ROI: 2.57%

Traditional ROI: 4%

2119 Easton Park Drive

Chesterton, IN

5 beds | 4 baths | 3,185 sq.ft.

$509,900

Airbnb cash on cash: 2.93%

Traditional cash on cash: 5.97%

Airbnb Rental Income: $3277

Traditional Rental Income: $3992

Airbnb ROI: 2.93%

Traditional ROI: 5.97%

1116 N 350 E

Chesterton, IN

4 beds | 3 baths | 4,546 sq.ft.

$925,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $2215

Traditional Rental Income: $3087

Airbnb ROI: 0.21%

Traditional ROI: 1.87%

327 S 18th Street

Chesterton, IN

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

$294,900

Airbnb cash on cash: 4.07%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $2278

Traditional Rental Income: $2291

Airbnb ROI: 4.07%

Traditional ROI: 6.16%

1887 Jacob Lane

Chesterton, IN

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

$319,900

Airbnb cash on cash: 3.5%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $2278

Traditional Rental Income: $1919

Airbnb ROI: 3.5%

Traditional ROI: 4.2%

2117 W Morgan Avenue

Chesterton, IN

2 beds | 2 baths | 1,120 sq.ft.

$192,000

Airbnb cash on cash: 6.76%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $2278

Traditional Rental Income: $1545

Airbnb ROI: 6.76%

Traditional ROI: 5.86%

2009 Timberwood Lane

Chesterton, IN

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

$529,900

Airbnb cash on cash: 0.24%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $2278

Traditional Rental Income: $2551

Airbnb ROI: 0.24%

Traditional ROI: 1.94%

2011 Timberwood Lane

Chesterton, IN

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

$549,000

Airbnb cash on cash: 1.02%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $2215

Traditional Rental Income: $3030

Airbnb ROI: 1.02%