Airbnb Properties for Sale in Chesterton, IN

Looking for a vacation rental investment in Chesterton, IN with high ROI ?

Explore a range of newly added short-term rental homes in Chesterton, IN. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chesterton, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$439,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.53% Airbnb Rental Income: $3816 Traditional Rental Income: $2794 Airbnb ROI: 5.01% Traditional ROI: 4.53%
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: 3.1% Traditional cash on cash: 2.93% Airbnb Rental Income: $3816 Traditional Rental Income: $2891 Airbnb ROI: 3.1% Traditional ROI: 2.93%
2230 Redwood Lane Chesterton, IN The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offeri...	4 beds \| 3 baths \| 2,281 sq.ft.	$620,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 3.03% Airbnb Rental Income: $3816 Traditional Rental Income: $2932 Airbnb ROI: 3.13% Traditional ROI: 3.03%
706 Idlewild Lane Chesterton, IN Welcome to Easton Park! The popular Michael floor plan offers all of the spaces that you n...	4 beds \| 3 baths \| 2,472 sq.ft.	$580,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.41% Airbnb Rental Income: $3816 Traditional Rental Income: $2419 Airbnb ROI: 3.47% Traditional ROI: 2.41%
810 Ashwood Lane Chesterton, IN Introducing the expanded Michelle floor plan-now offering 2 master suites-perfect for rela...	5 beds \| 4 baths \| 2,554 sq.ft.	$622,600	Airbnb cash on cash: 4.57% Traditional cash on cash: 3.44% Airbnb Rental Income: $4814 Traditional Rental Income: $3162 Airbnb ROI: 4.57% Traditional ROI: 3.44%
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: 3.97% Traditional cash on cash: 2.37% Airbnb Rental Income: $3816 Traditional Rental Income: $2201 Airbnb ROI: 3.97% Traditional ROI: 2.37%
1040 Preserve Lane Chesterton, IN Located in The Preserve in Chesterton, this thoughtfully upgraded home offers comfort, eff...	4 beds \| 3 baths \| 2,312 sq.ft.	$459,900	Airbnb cash on cash: 5.07% Traditional cash on cash: 4.77% Airbnb Rental Income: $3816 Traditional Rental Income: $2862 Airbnb ROI: 5.07% Traditional ROI: 4.77%
708 Idlewild Lane Chesterton, IN Hurry now to choose your own selections on the show-stopping Allison floor plan that inclu...	4 beds \| 3 baths \| 2,415 sq.ft.	$569,900	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.23% Airbnb Rental Income: $3816 Traditional Rental Income: $2819 Airbnb ROI: 3.56% Traditional ROI: 3.23%
1412 Essex Drive Chesterton, IN Freshly updated Split-level located just outside Chicago & minutes from Lake Michigan. Set...	4 beds \| 2 baths \| 1,788 sq.ft.	$319,000	Airbnb cash on cash: 7.67% Traditional cash on cash: 5.17% Airbnb Rental Income: $3816 Traditional Rental Income: $2242 Airbnb ROI: 7.67% Traditional ROI: 5.17%
1429 Delos Marr Avenue Chesterton, IN Step into a home that feels straight out of a magazine, where every detail has been though...	4 beds \| 3 baths \| 2,439 sq.ft.	$489,900	Airbnb cash on cash: 4.18% Traditional cash on cash: 3.82% Airbnb Rental Income: $3816 Traditional Rental Income: $2826 Airbnb ROI: 4.18% Traditional ROI: 3.82%
1938 Cory Lane Chesterton, IN If you've been looking for a home that offers more space than expected with a functional, ...	4 beds \| 3 baths \| 2,418 sq.ft.	$389,900	Airbnb cash on cash: 5.96% Traditional cash on cash: 4.13% Airbnb Rental Income: $3816 Traditional Rental Income: $2323 Airbnb ROI: 5.96% Traditional ROI: 4.13%
85 Hepburn Way Chesterton, IN Welcome to 85 Hepburn Wayâthis beautifully maintained 4-bedroom, 2.5-bath home offers th...	4 beds \| 3 baths \| 2,080 sq.ft.	$369,500	Airbnb cash on cash: 6.7% Traditional cash on cash: 4.86% Airbnb Rental Income: $3816 Traditional Rental Income: $2353 Airbnb ROI: 6.7% Traditional ROI: 4.86%
769 S Calumet Road Chesterton, IN Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 ...	4 beds \| 2 baths \| 2,242 sq.ft.	$349,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 4.72% Airbnb Rental Income: $3816 Traditional Rental Income: $2445 Airbnb ROI: 6.39% Traditional ROI: 4.72%
1167 Kinner Drive Chesterton, IN Beautifully maintained home situated on a large corner lot with gorgeous landscaping and f...	4 beds \| 3 baths \| 2,015 sq.ft.	$414,900	Airbnb cash on cash: 5.75% Traditional cash on cash: 4.84% Airbnb Rental Income: $3816 Traditional Rental Income: $2638 Airbnb ROI: 5.75% Traditional ROI: 4.84%

Vacation Rentals in Chesterton

There are 15 vacation rental properties available for sale in the city of Chesterton . The median list price of Airbnb properties available for sale in Chesterton is $459,900 and the average price per square foot is $157. The cash on cash return on vacation rentals in Chesterton is 2.00%. The average monthly short term rental income in Chesterton is $3,816.

Chesterton, IN Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 15 Airbnb properties available for sale in Chesterton.

In 2026, the best neighborhood to buy short term rental property is Chesterton.

In May 2026, the average Airbnb occupancy rate in Chesterton is 26%.

Airbnb data on vacation rentals in Chesterton, IN is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chesterton, IN market insights, guest information and booking details, seasonality trends and historical Chesterton, IN Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chesterton, IN

1452 Gossett Mill Avenue

Chesterton, IN

4 beds | 3 baths | 2,031 sq.ft.

$439,900

Airbnb cash on cash: 5.01%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3816

Traditional Rental Income: $2794

Airbnb ROI: 5.01%

Traditional ROI: 4.53%

801 Idlewild Lane

Chesterton, IN

4 beds | 3 baths | 2,271 sq.ft.

$624,900

Airbnb cash on cash: 3.1%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $3816

Traditional Rental Income: $2891

Airbnb ROI: 3.1%

Traditional ROI: 2.93%

2230 Redwood Lane

Chesterton, IN

4 beds | 3 baths | 2,281 sq.ft.

$620,000

Airbnb cash on cash: 3.13%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3816

Traditional Rental Income: $2932

Airbnb ROI: 3.13%

Traditional ROI: 3.03%

706 Idlewild Lane

Chesterton, IN

4 beds | 3 baths | 2,472 sq.ft.

$580,000

Airbnb cash on cash: 3.47%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $3816

Traditional Rental Income: $2419

Airbnb ROI: 3.47%

Traditional ROI: 2.41%

810 Ashwood Lane

Chesterton, IN

5 beds | 4 baths | 2,554 sq.ft.

$622,600

Airbnb cash on cash: 4.57%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $4814

Traditional Rental Income: $3162

Airbnb ROI: 4.57%

Traditional ROI: 3.44%

2215 Easton Park Drive

Chesterton, IN

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

$529,900

Airbnb cash on cash: 3.97%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $3816

Traditional Rental Income: $2201

Airbnb ROI: 3.97%

Traditional ROI: 2.37%

1040 Preserve Lane

Chesterton, IN

4 beds | 3 baths | 2,312 sq.ft.

$459,900

Airbnb cash on cash: 5.07%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $3816

Traditional Rental Income: $2862

Airbnb ROI: 5.07%

Traditional ROI: 4.77%

708 Idlewild Lane

Chesterton, IN

4 beds | 3 baths | 2,415 sq.ft.

$569,900

Airbnb cash on cash: 3.56%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $3816

Traditional Rental Income: $2819

Airbnb ROI: 3.56%