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
380 Sandpiper Drive Chesterton, IN Welcome home to this beautifully updated two-story residence offering 4 bedrooms, 4 bathro...	4 beds \| 4 baths \| 4,801 sq.ft.	$565,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 4.64% Airbnb Rental Income: $3846 Traditional Rental Income: $3607 Airbnb ROI: 3.52% Traditional ROI: 4.64%
612 S Jackson Boulevard Chesterton, IN Located less than 1 hour from Chicago this All Brick Ranch will be the perfect place to ca...	3 beds \| 2 baths \| 1,305 sq.ft.	$289,900	Airbnb cash on cash: 3% Traditional cash on cash: 3.9% Airbnb Rental Income: $1936 Traditional Rental Income: $1672 Airbnb ROI: 3% Traditional ROI: 3.9%
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%
1591 Hogan Ave Chesterton, IN Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updat...	4 beds \| 3 baths \| 2,878 sq.ft.	$649,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 2.86% Airbnb Rental Income: $3846 Traditional Rental Income: $3155 Airbnb ROI: 2.63% Traditional ROI: 2.86%
1419 Snead Ave Chesterton, IN This is more than a home--it's a lifestyle. Located in one of the most desirable locations...	4 beds \| 4 baths \| 6,259 sq.ft.	$1,279,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.91% Airbnb Rental Income: $3846 Traditional Rental Income: $4919 Airbnb ROI: 0.34% Traditional ROI: 1.91%
117 Washington Ave Chesterton, IN Welcome home to this beautifully maintained ranch in the heart of Chesterton! NEW ROOF! Of...	3 beds \| 3 baths \| 2,109 sq.ft.	$364,999	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.61% Airbnb Rental Income: $1936 Traditional Rental Income: $1656 Airbnb ROI: 1.94% Traditional ROI: 2.61%
3451 Fairway Drive Chesterton, IN Welcome home to this beautifully maintained 3-bedroom, 2-bath ranch in a convenient Cheste...	3 beds \| 3 baths \| 2,525 sq.ft.	$375,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.71% Airbnb Rental Income: $1936 Traditional Rental Income: $2535 Airbnb ROI: 1.55% Traditional ROI: 4.71%
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%
1245 Kilarney Rd Chesterton, IN Highly desirable Sand Creek property!!!! Presenting this custom built, 5 bedroom, 4.5 bath...	5 beds \| 3 baths \| 5,102 sq.ft.	$979,999	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.38% Airbnb Rental Income: $4345 Traditional Rental Income: $5040 Airbnb ROI: 1.61% Traditional ROI: 3.38%
1215 Bostwick Ave Chesterton, IN Like new and absolutely stunning, this beautifully designed ranch home in the heart of Che...	3 beds \| 2 baths \| 2,822 sq.ft.	$569,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.9% Airbnb Rental Income: $1936 Traditional Rental Income: $2666 Airbnb ROI: 0.56% Traditional ROI: 2.9%
1717 Crocker St 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 Ln 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 Ln Chesterton, IN The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offeri...	4 beds \| 2 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%
613 Idlewild Lane Chesterton, IN You're going to love the Charlie ranch floor plan! Upon entrance you'll be in awe of the g...	3 beds \| 3 baths \| 2,208 sq.ft.	$597,377	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.03% Airbnb Rental Income: $1936 Traditional Rental Income: $2830 Airbnb ROI: 0.51% Traditional ROI: 3.03%
150-152 N 16th St Chesterton, IN This newly completed duplex was finished in 2024. This exceptional investment property fea...	6 beds \| 4 baths \| N/A	$499,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 10.98% Airbnb Rental Income: $4345 Traditional Rental Income: $6471 Airbnb ROI: 4.48% Traditional ROI: 10.98%
1749 Green Meadow Ln Chesterton, IN Nice, solid all-brick ranch on a desirable corner lot directly across from the high school...	3 beds \| 2 baths \| 1,528 sq.ft.	$299,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.24% Airbnb Rental Income: $1936 Traditional Rental Income: $1568 Airbnb ROI: 2.73% Traditional ROI: 3.24%
498 Magnolia Lane Chesterton, IN Weclome to the maintenance-free lifestyle! Nestled amongst the serene nature preserve, the...	3 beds \| 2 baths \| 1,710 sq.ft.	$492,800	Airbnb cash on cash: 1.04% Traditional cash on cash: 3.15% Airbnb Rental Income: $1936 Traditional Rental Income: $2394 Airbnb ROI: 1.04% Traditional ROI: 3.15%
1240 Ryder Rd Chesterton, IN Perfectly positioned along the fairway in the gated Sand Creek community, this impressive ...	5 beds \| 4 baths \| 7,084 sq.ft.	$1,199,900	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.16% Airbnb Rental Income: $4345 Traditional Rental Income: $7051 Airbnb ROI: 0.91% Traditional ROI: 4.16%
270 Woodlawn Ave Chesterton, IN Welcome to 270 Woodlawn Ave in Chesterton. This beautifully remodeled 3-bedroom home offer...	3 beds \| 1 baths \| 1,183 sq.ft.	$248,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 4.15% Airbnb Rental Income: $1936 Traditional Rental Income: $1432 Airbnb ROI: 4.12% Traditional ROI: 4.15%
0-2 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Experience the PAXTON model the perfect blend of space, style, a...	5 beds \| 4 baths \| 4,398 sq.ft.	$1,230,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.26% Airbnb Rental Income: $4345 Traditional Rental Income: $4969 Airbnb ROI: 1.91% Traditional ROI: 3.26%
0-1 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Introducing The Ozark Ranch, a thoughtfully designed proposed c...	3 beds \| 3 baths \| 2,446 sq.ft.	$839,500	Airbnb cash on cash: 0.69% Traditional cash on cash: 2.44% Airbnb Rental Income: $1936 Traditional Rental Income: $2794 Airbnb ROI: 0.69% Traditional ROI: 2.44%
494 Magnolia Lane Chesterton, IN Last wooded homesite in Phase 2 of the villas in Easton Park! The newest phase of Easton P...	3 beds \| 2 baths \| 1,590 sq.ft.	$464,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.01% Airbnb Rental Income: $1936 Traditional Rental Income: $2206 Airbnb ROI: 1.22% Traditional ROI: 3.01%
2017 Wildwood Ct Chesterton, IN Style & grace refined in this magnificently outfitted home in Chesterton's Easton Park. Th...	3 beds \| 2 baths \| 2,866 sq.ft.	$689,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.45% Airbnb Rental Income: $1936 Traditional Rental Income: $2946 Airbnb ROI: 0.08% Traditional ROI: 2.45%
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%
1395 Waverly Rd Chesterton, IN Set on nearly an acre and within 5 minutes of the Indiana Dunes National Lakeshore, this w...	3 beds \| 2 baths \| 2,592 sq.ft.	$345,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.47% Airbnb Rental Income: $1936 Traditional Rental Income: $2055 Airbnb ROI: 2.52% Traditional ROI: 4.47%
303 E Porter Ave Chesterton, IN Welcome to this charming, updated historic home located in the highly sought-after Morgan ...	4 beds \| 2 baths \| 2,282 sq.ft.	$368,999	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%
2128 Dogwood Lane Chesterton, IN Completely remodeled 3-bedroom, 2-bath condo in the heart of Chesterton--offering modern f...	3 beds \| 2 baths \| 1,338 sq.ft.	$189,999	Airbnb cash on cash: 3.6% Traditional cash on cash: 4.97% Airbnb Rental Income: $1936 Traditional Rental Income: $1673 Airbnb ROI: 3.6% Traditional ROI: 4.97%
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 Rd 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%
1248 Dogwood Dr Chesterton, IN Perfectly Located Just Minutes from the Indiana Dunes National Park and Lakeshore. This Cl...	3 beds \| 2 baths \| 1,419 sq.ft.	$339,900	Airbnb cash on cash: 2.64% Traditional cash on cash: 4.09% Airbnb Rental Income: $1936 Traditional Rental Income: $1888 Airbnb ROI: 2.64% Traditional ROI: 4.09%
131 N 18th Street Chesterton, IN Welcome home to this well-maintained and thoughtfully updated 3-bedroom property located i...	3 beds \| 2 baths \| 2,064 sq.ft.	$250,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 7.26% Airbnb Rental Income: $1936 Traditional Rental Income: $2170 Airbnb ROI: 4.11% Traditional ROI: 7.26%
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 Rd 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%
1340 Cantigny Court Chesterton, IN This exceptional all-brick ranch offers over 4,200 finished square feet of thoughtfully de...	3 beds \| 4 baths \| 4,274 sq.ft.	$859,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.93% Airbnb Rental Income: $1936 Traditional Rental Income: $4189 Airbnb ROI: -0.52% Traditional ROI: 2.93%
1077 Mission Hills Ct Chesterton, IN Now available in Sand Creek--currently the only townhouse on the market! Located in one of...	3 beds \| 3 baths \| 3,199 sq.ft.	$465,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.3% Airbnb Rental Income: $1936 Traditional Rental Income: $2879 Airbnb ROI: -0.04% Traditional ROI: 3.3%

Real Estate investment in Chesterton, IN

There are 111 properties for sale in the city of Chesterton . The median list price in Chesterton is $375,775 and the average price per square foot is $147. In July 2026, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,425.

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

There are 111 investment properties available for sale in Chesterton.

In 2026, 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 $2,425.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

380 Sandpiper Drive

Chesterton, IN

4 beds | 4 baths | 4,801 sq.ft.

$565,000

Airbnb cash on cash: 3.52%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $3846

Traditional Rental Income: $3607

Airbnb ROI: 3.52%

Traditional ROI: 4.64%

612 S Jackson Boulevard

Chesterton, IN

3 beds | 2 baths | 1,305 sq.ft.

$289,900

Airbnb cash on cash: 3%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1936

Traditional Rental Income: $1672

Airbnb ROI: 3%

Traditional ROI: 3.9%

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%

1591 Hogan Ave

Chesterton, IN

4 beds | 3 baths | 2,878 sq.ft.

$649,900

Airbnb cash on cash: 2.63%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $3846

Traditional Rental Income: $3155

Airbnb ROI: 2.63%

Traditional ROI: 2.86%

1419 Snead Ave

Chesterton, IN

4 beds | 4 baths | 6,259 sq.ft.

$1,279,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $3846

Traditional Rental Income: $4919

Airbnb ROI: 0.34%

Traditional ROI: 1.91%

117 Washington Ave

Chesterton, IN

3 beds | 3 baths | 2,109 sq.ft.

$364,999

Airbnb cash on cash: 1.94%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1936

Traditional Rental Income: $1656

Airbnb ROI: 1.94%

Traditional ROI: 2.61%

3451 Fairway Drive

Chesterton, IN

3 beds | 3 baths | 2,525 sq.ft.

$375,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $1936

Traditional Rental Income: $2535

Airbnb ROI: 1.55%

Traditional ROI: 4.71%

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%