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
744 S 2nd Street Chesterton, IN Step inside a piece of Chesterton history, where more than a century of character blends b...	3 beds \| 3 baths \| 2,067 sq.ft.	$415,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 4.68% Airbnb Rental Income: $2635 Traditional Rental Income: $2534 Airbnb ROI: 3.32% Traditional ROI: 4.68%
1927 Cory Lane Chesterton, IN Quality-built home that has been beautifully maintained and is truly move-in ready! This o...	4 beds \| 3 baths \| 2,372 sq.ft.	$388,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 5.06% Airbnb Rental Income: $2636 Traditional Rental Income: $2634 Airbnb ROI: 3.34% Traditional ROI: 5.06%
1591 Hogan Avenue Chesterton, IN Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updat...	4 beds \| 4 baths \| 2,878 sq.ft.	$629,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.98% Airbnb Rental Income: $2636 Traditional Rental Income: $3155 Airbnb ROI: 1.03% Traditional ROI: 2.98%
231 E 1200 N Chesterton, IN BRING YOUR VISION AND UNLOCK THE POTENTIAL! Opportunity awaits with this 4-bedroom, 1....	4 beds \| 2 baths \| 970 sq.ft.	$234,900	Airbnb cash on cash: 5.7% Traditional cash on cash: 8.52% Airbnb Rental Income: $2636 Traditional Rental Income: $2634 Airbnb ROI: 5.7% Traditional ROI: 8.52%
762 Dunewood Drive Chesterton, IN This meticulously updated four-bedroom, three-bathroom residence is situated in a prime Ch...	4 beds \| 3 baths \| 2,380 sq.ft.	$394,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 4.89% Airbnb Rental Income: $2636 Traditional Rental Income: $2611 Airbnb ROI: 3.26% Traditional ROI: 4.89%
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.	$409,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.5% Airbnb Rental Income: $2635 Traditional Rental Income: $1861 Airbnb ROI: 2.88% Traditional ROI: 2.5%
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: 6.21% Traditional cash on cash: 3.66% Airbnb Rental Income: $2635 Traditional Rental Income: $1406 Airbnb ROI: 6.21% 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: 1.41% Traditional cash on cash: 2.93% Airbnb Rental Income: $2636 Traditional Rental Income: $2891 Airbnb ROI: 1.41% Traditional ROI: 2.93%
429-431 Woodlawn Avenue Chesterton, IN Profitable duplex located less than 1 hour from Chicago, 10min to the South Shore Train, &...	4 beds \| 4 baths \| N/A	$347,900	Airbnb cash on cash: 2.76% Traditional cash on cash: 6.24% Airbnb Rental Income: $2636 Traditional Rental Income: $3146 Airbnb ROI: 2.76% Traditional ROI: 6.24%
150-152 N 16th Street Chesterton, IN This newly completed duplex was finished in 2024. This exceptional investment property fea...	6 beds \| 6 baths \| N/A	$499,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 10.98% Airbnb Rental Income: $2635 Traditional Rental Income: $6471 Airbnb ROI: 1.43% Traditional ROI: 10.98%
1240 Ryder Road Chesterton, IN Perfectly positioned along the fairway in the gated Sand Creek community, this impressive ...	5 beds \| 6 baths \| 7,084 sq.ft.	$1,199,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 4.16% Airbnb Rental Income: $3525 Traditional Rental Income: $7051 Airbnb ROI: 0.3% Traditional ROI: 4.16%
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: 2.56% Traditional cash on cash: 3.01% Airbnb Rental Income: $2635 Traditional Rental Income: $2206 Airbnb ROI: 2.56% Traditional ROI: 3.01%
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.	$300,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 5.64% Airbnb Rental Income: $2636 Traditional Rental Income: $2445 Airbnb ROI: 4.09% Traditional ROI: 5.64%
1248 Dogwood Drive Chesterton, IN Perfectly Located Just Minutes from the Indiana Dunes National Park and Lakeshore. This Cl...	3 beds \| 2 baths \| 1,419 sq.ft.	$325,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 4.32% Airbnb Rental Income: $2635 Traditional Rental Income: $1888 Airbnb ROI: 4.71% Traditional ROI: 4.32%
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: 0.2% Traditional cash on cash: 2.93% Airbnb Rental Income: $2635 Traditional Rental Income: $4189 Airbnb ROI: 0.2% Traditional ROI: 2.93%
1077 Mission Hills Court Chesterton, IN Now available in Sand Creek--currently the only townhouse on the market! Located in one of...	3 beds \| 4 baths \| 3,199 sq.ft.	$465,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.3% Airbnb Rental Income: $2635 Traditional Rental Income: $2879 Airbnb ROI: 1.29% Traditional ROI: 3.3%
947 Sandpiper Drive Chesterton, IN This property offers the ideal combination of location, lot, and lifestyle. Located in Dun...	3 beds \| 3 baths \| 3,444 sq.ft.	$425,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 1.8% Airbnb Rental Income: $2635 Traditional Rental Income: $1634 Airbnb ROI: 2.74% Traditional ROI: 1.8%
543 Windridge Drive Chesterton, IN Light, bright and thoughtfully designed, this custom-built brick home offers over 4,000 sq...	4 beds \| 5 baths \| 3,983 sq.ft.	$699,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 5.45% Airbnb Rental Income: $2636 Traditional Rental Income: $4901 Airbnb ROI: 1.01% Traditional ROI: 5.45%
1622 Port Cove Drive Chesterton, IN Welcome to 1622 Port Cove Dr in Porter, Indiana -- a charming 3-bedroom, 3-bathroom tri-le...	3 beds \| 3 baths \| 3,484 sq.ft.	$315,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 5.63% Airbnb Rental Income: $2635 Traditional Rental Income: $2385 Airbnb ROI: 4.36% Traditional ROI: 5.63%
1035 Kilarney Road Chesterton, IN Within the gated Sand Creek community, this beautiful custom residence blends timeless arc...	4 beds \| 5 baths \| 4,299 sq.ft.	$799,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.94% Airbnb Rental Income: $2636 Traditional Rental Income: $4849 Airbnb ROI: 0.13% Traditional ROI: 3.94%
1089 N 200 W Chesterton, IN First Time on the Market! Proudly offered by its original owner, this exceptional property...	4 beds \| 4 baths \| 2,970 sq.ft.	$475,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 5.78% Airbnb Rental Income: $2636 Traditional Rental Income: $3460 Airbnb ROI: 2.51% Traditional ROI: 5.78%
801 Ashwood Lane Chesterton, IN PROPOSED CONSTRUCTION-Welcome to the Sonoma in Easton Park! This stunning custom-built, 1....	3 beds \| 3 baths \| 2,173 sq.ft.	$575,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.06% Airbnb Rental Income: $2635 Traditional Rental Income: $2839 Airbnb ROI: 2.51% Traditional ROI: 4.06%
229 E Morgan Avenue Chesterton, IN Step into a timeless masterpiece where history, craftsmanship, and tradition come together...	5 beds \| 5 baths \| 6,360 sq.ft.	$875,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 4.53% Airbnb Rental Income: $3525 Traditional Rental Income: $5198 Airbnb ROI: 1.52% Traditional ROI: 4.53%
515 S Park Drive Chesterton, IN	2 beds \| 1 baths \| 1,204 sq.ft.	$259,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.21% Airbnb Rental Income: $2210 Traditional Rental Income: $1296 Airbnb ROI: 4.67% Traditional ROI: 3.21%
1100 Saratoga Lane Chesterton, IN Maintenance-Free Living at Its Best! Welcome home to this beautifully maintained main-leve...	2 beds \| 1 baths \| 962 sq.ft.	$164,900	Airbnb cash on cash: 5.91% Traditional cash on cash: 2.57% Airbnb Rental Income: $2210 Traditional Rental Income: $1127 Airbnb ROI: 5.91% Traditional ROI: 2.57%
1036 Preserve Lane Chesterton, IN Discover the perfect blend of thoughtful design, modern comfort, and peaceful surroundings...	3 beds \| 3 baths \| 2,162 sq.ft.	$529,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 4.08% Airbnb Rental Income: $2635 Traditional Rental Income: $2710 Airbnb ROI: 2.66% Traditional ROI: 4.08%
1003 Preserve Lane Chesterton, IN Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully design...	3 beds \| 2 baths \| 1,851 sq.ft.	$519,900	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.64% Airbnb Rental Income: $2635 Traditional Rental Income: $2296 Airbnb ROI: 2.05% Traditional ROI: 2.64%
1002 Preserve Lane Chesterton, IN Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully design...	3 beds \| 2 baths \| 1,894 sq.ft.	$525,500	Airbnb cash on cash: 2.01% Traditional cash on cash: 2.65% Airbnb Rental Income: $2635 Traditional Rental Income: $2322 Airbnb ROI: 2.01% Traditional ROI: 2.65%
1430 N Veden Road Chesterton, IN Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, ...	3 beds \| 2 baths \| 1,400 sq.ft.	$349,900	Airbnb cash on cash: 4.13% Traditional cash on cash: 4.26% Airbnb Rental Income: $2635 Traditional Rental Income: $2048 Airbnb ROI: 4.13% Traditional ROI: 4.26%
1063 Frontage Road Chesterton, IN Welcome to your new warm and cozy home! You'll enjoy the fireplaces, solid hardwood floors...	3 beds \| 2 baths \| 1,764 sq.ft.	$199,900	Airbnb cash on cash: 8.18% Traditional cash on cash: 4.55% Airbnb Rental Income: $2635 Traditional Rental Income: $1319 Airbnb ROI: 8.18% Traditional ROI: 4.55%
2941 Nautica Drive Chesterton, IN Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This except...	5 beds \| 5 baths \| 4,932 sq.ft.	$585,000	Airbnb cash on cash: 2.82% Traditional cash on cash: N/A Airbnb Rental Income: $3525 Traditional Rental Income: $0 Airbnb ROI: 2.82% Traditional ROI: N/A
1954 David Drive Chesterton, IN This charming 1-bedroom, 1-bath condo offers comfortable, maintenance-free living in a con...	1 beds \| 1 baths \| 780 sq.ft.	$168,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.24% Airbnb Rental Income: $1482 Traditional Rental Income: $1159 Airbnb ROI: 2.54% Traditional ROI: 3.24%
363 Ridgeview Drive Chesterton, IN This stunning custom RANCH home sits on a private 1.18 wooded acre lot in the beautiful su...	3 beds \| 4 baths \| 2,775 sq.ft.	$974,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.43% Airbnb Rental Income: $2635 Traditional Rental Income: $3153 Airbnb ROI: 0.16% Traditional ROI: 1.43%
1247 Dogwood Drive Chesterton, IN Welcome to this classic two-story home nestled in an established neighborhood surrounded b...	5 beds \| 2 baths \| 1,728 sq.ft.	$359,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 4.75% Airbnb Rental Income: $3525 Traditional Rental Income: $2196 Airbnb ROI: 6.39% Traditional ROI: 4.75%
522 Park Avenue Chesterton, IN Location, convenience, and small-town charm come together in this 3-bedroom, 1-bath ranch ...	3 beds \| 1 baths \| 1,056 sq.ft.	$255,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 3.65% Airbnb Rental Income: $2635 Traditional Rental Income: $1399 Airbnb ROI: 6.18% Traditional ROI: 3.65%
350 Brown Court Chesterton, IN Fall in love with the charm, convenience, and relaxed lifestyle this delightful 3-bedroom,...	3 beds \| 2 baths \| 1,368 sq.ft.	$280,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 5.4% Airbnb Rental Income: $2635 Traditional Rental Income: $2001 Airbnb ROI: 5.42% Traditional ROI: 5.4%
354 E 1300 N Chesterton, IN Tucked away in Chesterton is a unique property where natural beauty, history, and opportun...	4 beds \| 2 baths \| 2,244 sq.ft.	$525,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 3.79% Airbnb Rental Income: $2636 Traditional Rental Income: $2634 Airbnb ROI: 2.51% Traditional ROI: 3.79%
35 E 900 N Chesterton, IN Rural residential property on 2.37 ACRES with POLE BARN! 4 bedroom/2 bath bi-level with at...	4 beds \| 2 baths \| 2,188 sq.ft.	$306,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 6.37% Airbnb Rental Income: $2636 Traditional Rental Income: $2434 Airbnb ROI: 4.89% Traditional ROI: 6.37%
2201 W Morgan Avenue Chesterton, IN Chesterton ranch living at its best! This beautifully maintained 2006 ranch offers 1,680 s...	3 beds \| 2 baths \| 1,680 sq.ft.	$345,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 1.65% Airbnb Rental Income: $2635 Traditional Rental Income: $1319 Airbnb ROI: 3.78% Traditional ROI: 1.65%
620 S 18th Street Chesterton, IN Beautifully updated 3 bed, 2 bath ranch in the heart of charming Chesterton! This move-in ...	3 beds \| 2 baths \| 1,732 sq.ft.	$339,900	Airbnb cash on cash: 4.14% Traditional cash on cash: 4.35% Airbnb Rental Income: $2635 Traditional Rental Income: $2073 Airbnb ROI: 4.14% Traditional ROI: 4.35%

Real Estate investment in Chesterton, IN

There are 52 properties for sale in the city of Chesterton . The median list price in Chesterton is $368,824 and the average price per square foot is $160. In November 2026, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,271.

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

There are 52 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 $2,271.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

744 S 2nd Street

Chesterton, IN

3 beds | 3 baths | 2,067 sq.ft.

$415,000

Airbnb cash on cash: 3.32%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $2635

Traditional Rental Income: $2534

Airbnb ROI: 3.32%

Traditional ROI: 4.68%

1927 Cory Lane

Chesterton, IN

4 beds | 3 baths | 2,372 sq.ft.

$388,000

Airbnb cash on cash: 3.34%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2636

Traditional Rental Income: $2634

Airbnb ROI: 3.34%

Traditional ROI: 5.06%

1591 Hogan Avenue

Chesterton, IN

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

$629,900

Airbnb cash on cash: 1.03%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $2636

Traditional Rental Income: $3155

Airbnb ROI: 1.03%

Traditional ROI: 2.98%

231 E 1200 N

Chesterton, IN

4 beds | 2 baths | 970 sq.ft.

$234,900

Airbnb cash on cash: 5.7%

Traditional cash on cash: 8.52%

Airbnb Rental Income: $2636

Traditional Rental Income: $2634

Airbnb ROI: 5.7%

Traditional ROI: 8.52%

762 Dunewood Drive

Chesterton, IN

4 beds | 3 baths | 2,380 sq.ft.

$394,900

Airbnb cash on cash: 3.26%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $2636

Traditional Rental Income: $2611

Airbnb ROI: 3.26%

Traditional ROI: 4.89%

506 W Morgan Avenue

Chesterton, IN

3 beds | 2 baths | 2,304 sq.ft.

$409,900

Airbnb cash on cash: 2.88%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $2635

Traditional Rental Income: $1861

Airbnb ROI: 2.88%

Traditional ROI: 2.5%

1717 Crocker Street

Chesterton, IN

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

$249,000

Airbnb cash on cash: 6.21%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2635

Traditional Rental Income: $1406

Airbnb ROI: 6.21%

Traditional ROI: 3.66%

801 Idlewild Lane

Chesterton, IN

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

$624,900

Airbnb cash on cash: 1.41%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2636

Traditional Rental Income: $2891

Airbnb ROI: 1.41%