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
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.	$294,999	Airbnb cash on cash: 8.18% Traditional cash on cash: 6.16% Airbnb Rental Income: $3649 Traditional Rental Income: $2291 Airbnb ROI: 8.18% Traditional ROI: 6.16%
2515 Springdale Street Chesterton, IN Welcome to your potential dream home in Chesterton, Indiana, where convenience meets comfo...	3 beds \| 2 baths \| 1,612 sq.ft.	$315,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 5.96% Airbnb Rental Income: $3649 Traditional Rental Income: $2388 Airbnb ROI: 7.53% Traditional ROI: 5.96%
1058 Mission Hills Court Chesterton, IN Welcome home to this immaculate three-bedroom, three-bathroom end-unit condo in a highly s...	3 beds \| 3 baths \| 2,059 sq.ft.	$349,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 4.22% Airbnb Rental Income: $3649 Traditional Rental Income: $2659 Airbnb ROI: 4.81% Traditional ROI: 4.22%
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.	$424,900	Airbnb cash on cash: 5.03% Traditional cash on cash: 5% Airbnb Rental Income: $3649 Traditional Rental Income: $2840 Airbnb ROI: 5.03% Traditional ROI: 5%
1010 Preserve Lane Chesterton, IN This one is a steal! Built for a customer but financing fell. Their loss is your gain. 1...	5 beds \| 4 baths \| 4,245 sq.ft.	$709,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $3624 Airbnb ROI: N/A Traditional ROI: 4.28%
1503 Snead Avenue Chesterton, IN Quality and style are abundant in this spectacular home situated on the golf course in the...	5 beds \| 6 baths \| 5,720 sq.ft.	$998,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $5893 Airbnb ROI: N/A Traditional ROI: 4.12%
991 N 250 E Chesterton, IN Step into a world where tranquility meets comfort in this stunning country residence. Surr...	5 beds \| 3 baths \| 3,248 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.81% Airbnb Rental Income: $null Traditional Rental Income: $2836 Airbnb ROI: N/A Traditional ROI: 7.81%
339 E Burdick Road Chesterton, IN WELCOME HOME! Charming home on 3 acres in Jackson Township. This one owner, well-maintaine...	3 beds \| 2 baths \| 1,344 sq.ft.	$355,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 3.95% Airbnb Rental Income: $3649 Traditional Rental Income: $1948 Airbnb ROI: 6.66% Traditional ROI: 3.95%
801 Teakwood Lane Chesterton, IN Construction complete January 2025! The popular Michael floor plan offers all of the space...	4 beds \| 3 baths \| 2,443 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $2784 Airbnb ROI: N/A Traditional ROI: 3.36%
409 Sand Creek Drive N Chesterton, IN Welcome to this maintenance-free condo in the heart of Chesterton, Indiana! This beautiful...	2 beds \| 3 baths \| 2,184 sq.ft.	$249,999	Airbnb cash on cash: 5.53% Traditional cash on cash: 8.24% Airbnb Rental Income: $2528 Traditional Rental Income: $2558 Airbnb ROI: 5.53% Traditional ROI: 8.24%
1873 Crocker Street Chesterton, IN This new to the studs home is ready for its new owners. Everything was professionally ren...	4 beds \| 2 baths \| 2,000 sq.ft.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.75% Airbnb Rental Income: $null Traditional Rental Income: $2377 Airbnb ROI: N/A Traditional ROI: 6.75%
1524 Duffer Drive Chesterton, IN Welcome home to this tastefully updated house in Golfview Subdivision! This bi-level home ...	4 beds \| 2 baths \| 2,192 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.48% Airbnb Rental Income: $null Traditional Rental Income: $2394 Airbnb ROI: N/A Traditional ROI: 5.48%
1613 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now in construction! Completi...	3 beds \| 3 baths \| 1,954 sq.ft.	$439,900	Airbnb cash on cash: 4.79% Traditional cash on cash: 4.42% Airbnb Rental Income: $3649 Traditional Rental Income: $2699 Airbnb ROI: 4.79% Traditional ROI: 4.42%
975 N 250 E Chesterton, IN Nestled on a picturesque 1.8-acre wooded lot, this charming and updated country farmhouse ...	5 beds \| 3 baths \| 3,828 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 5.62%
1615 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now in construction! Completi...	3 beds \| 3 baths \| 1,954 sq.ft.	$429,900	Airbnb cash on cash: 4.95% Traditional cash on cash: 4.71% Airbnb Rental Income: $3649 Traditional Rental Income: $2758 Airbnb ROI: 4.95% Traditional ROI: 4.71%
621 Village Point Chesterton, IN Stunning, completely MAINTENANCE-FREE townhouse that backs up to Coffee Creek Watershed Pr...	3 beds \| 3 baths \| 1,809 sq.ft.	$424,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.77% Airbnb Rental Income: $3649 Traditional Rental Income: $2389 Airbnb ROI: 4.93% Traditional ROI: 3.77%
495 Redwood 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.	$449,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.47% Airbnb Rental Income: $3649 Traditional Rental Income: $2351 Airbnb ROI: 4.66% Traditional ROI: 3.47%
2005 Timberwood Lane Chesterton, IN Welcome Home! This gorgeous new construction home is all you could ever want. Stunning kit...	4 beds \| 3 baths \| 2,481 sq.ft.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $2857 Airbnb ROI: N/A Traditional ROI: 2.55%
1716 Armour Court Chesterton, IN Discover this stunning custom-built home in the highly sought-after Sand Creek community! ...	4 beds \| 4 baths \| 4,620 sq.ft.	$1,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $3769 Airbnb ROI: N/A Traditional ROI: 0.91%
1151 Burns Boulevard Chesterton, IN Welcome to your dream home in this charming subdivision located in Burns Harbor! Sitting i...	4 beds \| 4 baths \| 2,445 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.63% Airbnb Rental Income: $null Traditional Rental Income: $3085 Airbnb ROI: N/A Traditional ROI: 6.63%
2001 Union Avenue Chesterton, IN Experience serene living in Chesterton, IN with this spacious 3,964 sq ft two-story home, ...	5 beds \| 4 baths \| 3,198 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.37% Airbnb Rental Income: $null Traditional Rental Income: $3999 Airbnb ROI: N/A Traditional ROI: 5.37%
405 Sunnybrooke Court Chesterton, IN Nestled in lush woodlands, discover this one-of-a-kind architect designed sanctuary offeri...	4 beds \| 4 baths \| 4,088 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $3632 Airbnb ROI: N/A Traditional ROI: 3.3%
1420 Maximilian Drive Chesterton, IN You will not want to miss this fantastic bi-level featuring 5 bedrooms, and 3 full baths. ...	5 beds \| 3 baths \| 2,672 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.41% Airbnb Rental Income: $null Traditional Rental Income: $2870 Airbnb ROI: N/A Traditional ROI: 5.41%
1702 Broadway Avenue Chesterton, IN Welcome to this charming bi-level home, perfectly nestled on a large corner lot in the hea...	3 beds \| 2 baths \| 1,606 sq.ft.	$252,000	Airbnb cash on cash: 9.79% Traditional cash on cash: 6.04% Airbnb Rental Income: $3649 Traditional Rental Income: $1961 Airbnb ROI: 9.79% Traditional ROI: 6.04%
326 S 11th Street Chesterton, IN This delightful older home is ready for a new owner to make it their own. The kitchen cabi...	2 beds \| 1 baths \| 1,468 sq.ft.	$190,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 5.36% Airbnb Rental Income: $2528 Traditional Rental Income: $1575 Airbnb ROI: 7.26% Traditional ROI: 5.36%
2017 Spruce Lane Chesterton, IN Hurry now to catch one of the last available homes in Chesterton's Easton Park Phase I! Th...	4 beds \| 3 baths \| 2,521 sq.ft.	$519,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 4.17%
1051 Laurel Creek Drive Chesterton, IN ALL BRICK RANCH IN TAMARACK! Extremely sought after, once in a blue moon opportunity to o...	3 beds \| 2 baths \| 2,460 sq.ft.	$529,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.88% Airbnb Rental Income: $3649 Traditional Rental Income: $2482 Airbnb ROI: 3.63% Traditional ROI: 2.88%

Real Estate investment in Chesterton, IN

There are 32 properties for sale in the city of Chesterton . The median list price in Chesterton is $349,900 and the average price per square foot is $154. In December 2024, the average monthly cash on cash return in Chesterton is 5.00%. The average monthly rental income in Chesterton is $2,482.

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

There are 32 investment properties available for sale in Chesterton.

In 2024, the best neighborhood to buy investment property is Chesterton.

The ROI for Short-Term is higher than the Long-Term in Chesterton with average rental income of $3,649.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

327 S 18th Street

Chesterton, IN

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

$294,999

Airbnb cash on cash: 8.18%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $3649

Traditional Rental Income: $2291

Airbnb ROI: 8.18%

Traditional ROI: 6.16%

2515 Springdale Street

Chesterton, IN

3 beds | 2 baths | 1,612 sq.ft.

$315,000

Airbnb cash on cash: 7.53%

Traditional cash on cash: 5.96%

Airbnb Rental Income: $3649

Traditional Rental Income: $2388

Airbnb ROI: 7.53%

Traditional ROI: 5.96%

1058 Mission Hills Court

Chesterton, IN

3 beds | 3 baths | 2,059 sq.ft.

$349,900

Airbnb cash on cash: 4.81%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $3649

Traditional Rental Income: $2659

Airbnb ROI: 4.81%

Traditional ROI: 4.22%

1608 Melanie Lane

Chesterton, IN

3 beds | 3 baths | 1,954 sq.ft.

$424,900

Airbnb cash on cash: 5.03%

Traditional cash on cash: 5%

Airbnb Rental Income: $3649

Traditional Rental Income: $2840

Airbnb ROI: 5.03%

Traditional ROI: 5%

1010 Preserve Lane

Chesterton, IN

5 beds | 4 baths | 4,245 sq.ft.

$709,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3624

Airbnb ROI: N/A

Traditional ROI: 4.28%

1503 Snead Avenue

Chesterton, IN

5 beds | 6 baths | 5,720 sq.ft.

$998,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.12%

Airbnb Rental Income: $null

Traditional Rental Income: $5893

Airbnb ROI: N/A

Traditional ROI: 4.12%

991 N 250 E

Chesterton, IN

5 beds | 3 baths | 3,248 sq.ft.

$329,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2836

Airbnb ROI: N/A

Traditional ROI: 7.81%

339 E Burdick Road

Chesterton, IN

3 beds | 2 baths | 1,344 sq.ft.

$355,000

Airbnb cash on cash: 6.66%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $3649

Traditional Rental Income: $1948

Airbnb ROI: 6.66%