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 Take a look at this beautifully maintained two-story home located just minutes away from t...	4 beds \| 3 baths \| 2,031 sq.ft.	$434,900	Airbnb cash on cash: 5.14% Traditional cash on cash: 4.6% Airbnb Rental Income: $3846 Traditional Rental Income: $2794 Airbnb ROI: 5.14% Traditional ROI: 4.6%
1261 Redbud Drive Chesterton, IN Welcome to this beautifully maintained 4-bedroom, 2.5-bath home situated on over half an a...	4 beds \| 3 baths \| 1,976 sq.ft.	$389,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 4.78% Airbnb Rental Income: $3846 Traditional Rental Income: $2462 Airbnb ROI: 6.29% Traditional ROI: 4.78%
1717 Crocker Street Chesterton, IN Move-in ready with built-in upside, this fully remodeled 11/2-story home offers three bedr...	3 beds \| 2 baths \| 2,400 sq.ft.	$249,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.66% Airbnb Rental Income: $1936 Traditional Rental Income: $1406 Airbnb ROI: 3.73% Traditional ROI: 3.66%
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: 3.14% Traditional cash on cash: 2.93% Airbnb Rental Income: $3846 Traditional Rental Income: $2891 Airbnb ROI: 3.14% 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.	$599,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.19% Airbnb Rental Income: $3846 Traditional Rental Income: $2932 Airbnb ROI: 3.34% Traditional ROI: 3.19%
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: 3.52% Traditional cash on cash: 2.41% Airbnb Rental Income: $3846 Traditional Rental Income: $2419 Airbnb ROI: 3.52% Traditional ROI: 2.41%
378 Ballenisle Court Chesterton, IN Spacious and inviting 4-bedroom, 2.5-bath home conveniently located near the heart of Ches...	4 beds \| 3 baths \| 2,270 sq.ft.	$395,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 3.53% Airbnb Rental Income: $3846 Traditional Rental Income: $2208 Airbnb ROI: 5.71% Traditional ROI: 3.53%
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: 3.6% Traditional cash on cash: 3.23% Airbnb Rental Income: $3846 Traditional Rental Income: $2819 Airbnb ROI: 3.6% 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.	$313,900	Airbnb cash on cash: 7.89% Traditional cash on cash: 5.27% Airbnb Rental Income: $3846 Traditional Rental Income: $2242 Airbnb ROI: 7.89% Traditional ROI: 5.27%
124 Beverly Drive Chesterton, IN Welcome to this beautifully maintained 2-story home featuring 4 bedrooms and 3 baths with ...	4 beds \| 3 baths \| 2,720 sq.ft.	$440,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 3.08% Airbnb Rental Income: $3846 Traditional Rental Income: $2203 Airbnb ROI: 5.06% Traditional ROI: 3.08%
303 E Porter Avenue Chesterton, IN Welcome to this charming, updated historic home located in the highly sought-after Morgan ...	4 beds \| 3 baths \| 2,282 sq.ft.	$369,999	Airbnb cash on cash: 6.69% Traditional cash on cash: 3.78% Airbnb Rental Income: $3846 Traditional Rental Income: $2006 Airbnb ROI: 6.69% Traditional ROI: 3.78%
85 Hepburn Way Chesterton, IN Price Improvement!! Welcome to 85 Hepburn Way-this beautifully maintained 4-bedroom, 2.5-b...	4 beds \| 3 baths \| 2,080 sq.ft.	$359,900	Airbnb cash on cash: 6.98% Traditional cash on cash: 5.01% Airbnb Rental Income: $3846 Traditional Rental Income: $2353 Airbnb ROI: 6.98% Traditional ROI: 5.01%
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.	$329,900	Airbnb cash on cash: 6.89% Traditional cash on cash: 5.05% Airbnb Rental Income: $3846 Traditional Rental Income: $2445 Airbnb ROI: 6.89% Traditional ROI: 5.05%
2015 Terreno Drive Chesterton, IN Stunning 2 story home offering over 2,700 finished square feet of thoughtfully designed li...	4 beds \| 3 baths \| 2,715 sq.ft.	$644,570	Airbnb cash on cash: 2.9% Traditional cash on cash: 2% Airbnb Rental Income: $3846 Traditional Rental Income: $2479 Airbnb ROI: 2.9% Traditional ROI: 2%
590 E Oak Hill Road Chesterton, IN Step inside to discover a bright, airy open-concept layout engineered for effortless livin...	4 beds \| 2 baths \| 1,844 sq.ft.	$320,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 5.37% Airbnb Rental Income: $3846 Traditional Rental Income: $2249 Airbnb ROI: 7.92% Traditional ROI: 5.37%
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: 5.77% Traditional cash on cash: 4.8% Airbnb Rental Income: $3846 Traditional Rental Income: $2638 Airbnb ROI: 5.77% Traditional ROI: 4.8%
1168 Kinner Drive Chesterton, IN This super-maintained home showcases a variety of impressive features designed for comfort...	5 beds \| 3 baths \| 3,010 sq.ft.	$459,900	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.78% Airbnb Rental Income: $4345 Traditional Rental Income: $2550 Airbnb ROI: 5.83% Traditional ROI: 3.78%
704 S 22nd Street Chesterton, IN ONLY 10 to 15 MINUTES to LAKE MICHIGAN'S SANDY BEACHES! ENJOY PEACE, QUIET, & SERENITY fro...	3 beds \| 1 baths \| 1,008 sq.ft.	$259,900	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.63% Airbnb Rental Income: $1936 Traditional Rental Income: $1170 Airbnb ROI: 3.67% Traditional ROI: 2.63%
112 Chesterton Boulevard Chesterton, IN OH MY GOODNESS, THIS ONE HAS IT ALL!!! You know what they say: LOCATION, LOCATION, LOCATIO...	3 beds \| 1 baths \| 1,109 sq.ft.	$224,990	Airbnb cash on cash: 3.71% Traditional cash on cash: 3.64% Airbnb Rental Income: $1936 Traditional Rental Income: $1409 Airbnb ROI: 3.71% Traditional ROI: 3.64%
18 Blue Grass Way Chesterton, IN Welcome to The Preserve, where nature is your neighbor. Situated at the end of a quiet cul...	4 beds \| 3 baths \| 2,409 sq.ft.	$679,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.53% Airbnb Rental Income: $3846 Traditional Rental Income: $2401 Airbnb ROI: 2.5% Traditional ROI: 1.53%
608 W Indiana Avenue Chesterton, IN Charming, move-in ready ranch just a short walk to vibrant downtown Chesterton and the pop...	2 beds \| 1 baths \| 725 sq.ft.	$194,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.38% Airbnb Rental Income: $1435 Traditional Rental Income: $998 Airbnb ROI: 3.43% Traditional ROI: 3.38%
131 Westchester Court Chesterton, IN Welcome home to this spacious 4-bedroom, 2-bathroom home situated on nearly half an acre i...	4 beds \| 2 baths \| 2,760 sq.ft.	$340,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 5.5% Airbnb Rental Income: $3846 Traditional Rental Income: $2454 Airbnb ROI: 7.26% Traditional ROI: 5.5%
415 S 16th Street Chesterton, IN Attention Investors Great Opportunity! This charming 3-bedroom, 1-bath ranch offers comfor...	3 beds \| 1 baths \| 864 sq.ft.	$125,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 7.81% Airbnb Rental Income: $1936 Traditional Rental Income: $1262 Airbnb ROI: 9.16% Traditional ROI: 7.81%
961 Monterey Drive Chesterton, IN FORE! Welcome to this exquisite Cape Cod residence in the prestigious Estates of Sand Cree...	4 beds \| 3 baths \| 2,412 sq.ft.	$539,900	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.08% Airbnb Rental Income: $3846 Traditional Rental Income: $2662 Airbnb ROI: 3.78% Traditional ROI: 3.08%

Vacation Rentals in Chesterton

There are 25 vacation rental properties available for sale in the city of Chesterton . The median list price of Airbnb properties available for sale in Chesterton is $375,775 and the average price per square foot is $147. The cash on cash return on vacation rentals in Chesterton is 3.00%. The average monthly short term rental income in Chesterton is $1,936.

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

There are 25 Airbnb properties available for sale in Chesterton.

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

In July 2026, the average Airbnb occupancy rate in Chesterton is 30%.

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.

$434,900

Airbnb cash on cash: 5.14%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $3846

Traditional Rental Income: $2794

Airbnb ROI: 5.14%

Traditional ROI: 4.6%

1261 Redbud Drive

Chesterton, IN

4 beds | 3 baths | 1,976 sq.ft.

$389,900

Airbnb cash on cash: 6.29%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3846

Traditional Rental Income: $2462

Airbnb ROI: 6.29%

Traditional ROI: 4.78%

1717 Crocker Street

Chesterton, IN

3 beds | 2 baths | 2,400 sq.ft.

$249,000

Airbnb cash on cash: 3.73%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $1936

Traditional Rental Income: $1406

Airbnb ROI: 3.73%

Traditional ROI: 3.66%

801 Idlewild Lane

Chesterton, IN

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

$624,900

Airbnb cash on cash: 3.14%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $3846

Traditional Rental Income: $2891

Airbnb ROI: 3.14%

Traditional ROI: 2.93%

2230 Redwood Lane

Chesterton, IN

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

$599,900

Airbnb cash on cash: 3.34%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $3846

Traditional Rental Income: $2932

Airbnb ROI: 3.34%

Traditional ROI: 3.19%

706 Idlewild Lane

Chesterton, IN

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

$580,000

Airbnb cash on cash: 3.52%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $3846

Traditional Rental Income: $2419

Airbnb ROI: 3.52%

Traditional ROI: 2.41%

378 Ballenisle Court

Chesterton, IN

4 beds | 3 baths | 2,270 sq.ft.

$395,000

Airbnb cash on cash: 5.71%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $3846

Traditional Rental Income: $2208

Airbnb ROI: 5.71%

Traditional ROI: 3.53%

708 Idlewild Lane

Chesterton, IN

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

$569,900

Airbnb cash on cash: 3.6%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $3846

Traditional Rental Income: $2819

Airbnb ROI: 3.6%