Real Estate Investments for Sale in Chesterton, IN With High ROI

Are you looking for a vacation rental in Chesterton, IN? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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
315 Larkin Lane Chesterton, IN Better than new and just a quick walk to Downtown Chesterton! Check out this recently buil...	3 beds \| 3 baths \| 2,115 sq.ft.	$374,900	Airbnb cash on cash: 6.72% Traditional cash on cash: 4.62% Airbnb Rental Income: $4048 Traditional Rental Income: $2446 Airbnb ROI: 6.72% Traditional ROI: 4.62%
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: 9.37% Traditional cash on cash: 4.24% Airbnb Rental Income: $4048 Traditional Rental Income: $1759 Airbnb ROI: 9.37% Traditional ROI: 4.24%
1601 Melanie Lane Chesterton, IN Loaded with upgraded features, this maintenance-free condo is ready for your instant enjoy...	3 beds \| 3 baths \| 1,954 sq.ft.	$429,900	Airbnb cash on cash: 5.77% Traditional cash on cash: 4.88% Airbnb Rental Income: $4048 Traditional Rental Income: $2824 Airbnb ROI: 5.77% Traditional ROI: 4.88%
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: 5.82% Traditional cash on cash: 3.16% Airbnb Rental Income: $4048 Traditional Rental Income: $2309 Airbnb ROI: 5.82% Traditional ROI: 3.16%
1608 Melanie Lane Chesterton, IN Check out the newest building in the maintenance-free community-now in construction! The ...	3 beds \| 3 baths \| 1,954 sq.ft.	$424,900	Airbnb cash on cash: 5.86% Traditional cash on cash: 5.18% Airbnb Rental Income: $4048 Traditional Rental Income: $2912 Airbnb ROI: 5.86% Traditional ROI: 5.18%
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.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $3608 Airbnb ROI: N/A Traditional ROI: 4.11%
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.	$1,049,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $6084 Airbnb ROI: N/A Traditional ROI: 4.07%
2031 Timberwood Lane Chesterton, IN Custom Built Home!! Stunning Home in Easton Park Subdivision with Beautiful Landscaping!Th...	5 beds \| 4 baths \| 3,751 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $3715 Airbnb ROI: N/A Traditional ROI: 4.33%
991 N 250 E Chesterton, IN Experience the Best of Country LivingIndulge in the tranquility of private woods, mature f...	5 beds \| 3 baths \| 3,248 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $2813 Airbnb ROI: N/A Traditional ROI: 5.91%
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.	$369,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 2.36% Airbnb Rental Income: $4048 Traditional Rental Income: $1462 Airbnb ROI: 7.33% Traditional ROI: 2.36%
1241 Sunset Lane Chesterton, IN The best of both worlds merge in this ideal home situated in a serene, idyllic setting wit...	4 beds \| 3 baths \| 2,960 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.55% Airbnb Rental Income: $null Traditional Rental Income: $2711 Airbnb ROI: N/A Traditional ROI: 5.55%
801 Teakwood Lane Chesterton, IN Construction beginning August 2024-hurry to make your own custom selections! The popular M...	4 beds \| 3 baths \| 2,443 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $2929 Airbnb ROI: N/A Traditional ROI: 3.64%
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.	$269,999	Airbnb cash on cash: 4.19% Traditional cash on cash: 5.69% Airbnb Rental Income: $2266 Traditional Rental Income: $2081 Airbnb ROI: 4.19% Traditional ROI: 5.69%
1214 Saratoga Drive Chesterton, IN Exciting news! Due to buyer financing issue, this beautiful home is back on the market and...	2 beds \| 1 baths \| 946 sq.ft.	$159,000	Airbnb cash on cash: 8.67% Traditional cash on cash: 5.16% Airbnb Rental Income: $2266 Traditional Rental Income: $1167 Airbnb ROI: 8.67% Traditional ROI: 5.16%
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.	$284,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $1976 Airbnb ROI: N/A Traditional ROI: 4.98%
1300 Brassie Avenue Chesterton, IN Discover your dream home in this exquisite 4 bedroom, 3 1/2 bath masterpiece located in a ...	4 beds \| 3 baths \| 3,880 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 2.23%
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.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $2090 Airbnb ROI: N/A Traditional ROI: 4.23%
1613 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now in construction! The open...	3 beds \| 3 baths \| 1,954 sq.ft.	$439,900	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.4% Airbnb Rental Income: $4048 Traditional Rental Income: $2690 Airbnb ROI: 5.6% Traditional ROI: 4.4%
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: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2721 Airbnb ROI: N/A Traditional ROI: 4.98%
1615 Melanie Lane Chesterton, IN Check out our new screened-in porch in the newest building -now in construction! The open...	3 beds \| 3 baths \| 1,954 sq.ft.	$429,900	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.88% Airbnb Rental Income: $4048 Traditional Rental Income: $2421 Airbnb ROI: 5.77% Traditional ROI: 3.88%
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: 5.77% Traditional cash on cash: 3.22% Airbnb Rental Income: $4048 Traditional Rental Income: $2171 Airbnb ROI: 5.77% Traditional ROI: 3.22%
4102 Abercrombie Drive Chesterton, IN PRICE REDUCED ON THIS STUNNING 4 bedroom, 3 bath Cape Cod home located in desirable Abercr...	4 beds \| 3 baths \| 3,471 sq.ft.	$519,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $2873 Airbnb ROI: N/A Traditional ROI: 3.58%
393 Lost Tree Drive Chesterton, IN This home is in the Villages of Sand Creek subdivision. It's nestled in beautifully wooded...	4 beds \| 3 baths \| 2,415 sq.ft.	$533,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 3.9%
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: 5.45% Traditional cash on cash: 3.43% Airbnb Rental Income: $4048 Traditional Rental Income: $2334 Airbnb ROI: 5.45% Traditional ROI: 3.43%
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: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $3054 Airbnb ROI: N/A Traditional ROI: 2.86%
1700 Green Meadow Lane Chesterton, IN Come discover the blend of timeless charm and modern convenience in this bi-level home loc...	3 beds \| 2 baths \| 1,812 sq.ft.	$310,000	Airbnb cash on cash: 8.8% Traditional cash on cash: 5.14% Airbnb Rental Income: $4048 Traditional Rental Income: $2118 Airbnb ROI: 8.8% Traditional ROI: 5.14%

Real Estate investment in Chesterton, IN

There are 28 properties for sale in the city of Chesterton . The median list price in Chesterton is $424,900 and the average price per square foot is $174. In October 2024, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,446.

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

There are 28 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 $4,048.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

315 Larkin Lane

Chesterton, IN

3 beds | 3 baths | 2,115 sq.ft.

$374,900

Airbnb cash on cash: 6.72%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $4048

Traditional Rental Income: $2446

Airbnb ROI: 6.72%

Traditional ROI: 4.62%

327 S 18th Street

Chesterton, IN

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

$294,999

Airbnb cash on cash: 9.37%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $4048

Traditional Rental Income: $1759

Airbnb ROI: 9.37%

Traditional ROI: 4.24%

1601 Melanie Lane

Chesterton, IN

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

$429,900

Airbnb cash on cash: 5.77%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $4048

Traditional Rental Income: $2824

Airbnb ROI: 5.77%

Traditional ROI: 4.88%

1058 Mission Hills Court

Chesterton, IN

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

$349,900

Airbnb cash on cash: 5.82%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $4048

Traditional Rental Income: $2309

Airbnb ROI: 5.82%

Traditional ROI: 3.16%

1608 Melanie Lane

Chesterton, IN

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

$424,900

Airbnb cash on cash: 5.86%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $4048

Traditional Rental Income: $2912

Airbnb ROI: 5.86%

Traditional ROI: 5.18%

1010 Preserve Lane

Chesterton, IN

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

$729,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.11%

Airbnb Rental Income: $null

Traditional Rental Income: $3608

Airbnb ROI: N/A

Traditional ROI: 4.11%

1503 Snead Avenue

Chesterton, IN

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

$1,049,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.07%

Airbnb Rental Income: $null

Traditional Rental Income: $6084

Airbnb ROI: N/A

Traditional ROI: 4.07%

2031 Timberwood Lane

Chesterton, IN

5 beds | 4 baths | 3,751 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3715

Airbnb ROI: N/A