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
2221 Easton Park Dr Chesterton, IN Hurry now to make your own selections! The ever-popular Melanie floor plan offers all of t...	4 beds \| 2 baths \| 2,348 sq.ft.	$549,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.06% Airbnb Rental Income: $3402 Traditional Rental Income: $2630 Airbnb ROI: 3.09% Traditional ROI: 3.06%
1226 Dogwood Drive Chesterton, IN Extensive Updates Throughout! This home has been beautifully remodeled with numerous recen...	4 beds \| 2 baths \| 1,827 sq.ft.	$318,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.79% Airbnb Rental Income: $3402 Traditional Rental Income: $2255 Airbnb ROI: 7.1% Traditional ROI: 5.79%
525 S Calumet Rd Chesterton, IN Donât miss your opportunity to view this charming four-bedroom, two-full-bath home locat...	4 beds \| 2 baths \| 1,924 sq.ft.	$322,500	Airbnb cash on cash: 6.51% Traditional cash on cash: 5.48% Airbnb Rental Income: $3402 Traditional Rental Income: $2334 Airbnb ROI: 6.51% Traditional ROI: 5.48%
319 Michigami Trail Chesterton, IN Move right in and enjoy easy, everyday living in this spacious three-bedroom ranch in Ches...	3 beds \| 1 baths \| 1,433 sq.ft.	$219,900	Airbnb cash on cash: 4.2% Traditional cash on cash: 3.8% Airbnb Rental Income: $1864 Traditional Rental Income: $1280 Airbnb ROI: 4.2% Traditional ROI: 3.8%
1290 Old Porter Rd Chesterton, IN 1290 Old Porter Rd, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 1 baths \| 1,716 sq.ft.	$270,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.36% Airbnb Rental Income: $1864 Traditional Rental Income: $1164 Airbnb ROI: 3.15% Traditional ROI: 2.36%
1198 Old Porter Rd Chesterton, IN 1198 Old Porter Rd, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,976 sq.ft.	$289,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 5.51% Airbnb Rental Income: $3402 Traditional Rental Income: $2094 Airbnb ROI: 7.53% Traditional ROI: 5.51%
315 Franklin St Chesterton, IN 315 Franklin St, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,900 sq.ft.	$450,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.4% Airbnb Rental Income: $3402 Traditional Rental Income: $1882 Airbnb ROI: 4.22% Traditional ROI: 2.4%
2215 Easton Park Drive Chesterton, IN Construction beginning September-completion February 2026! Introducing The Carmela floor p...	4 beds \| 3 baths \| 2,241 sq.ft.	$529,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.37% Airbnb Rental Income: $3402 Traditional Rental Income: $2201 Airbnb ROI: 3.27% Traditional ROI: 2.37%
2519 Pradera Trl Chesterton, IN 2519 Pradera Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,134 sq.ft.	$699,900	Airbnb cash on cash: 2.38% Traditional cash on cash: 1.58% Airbnb Rental Income: $3402 Traditional Rental Income: $2166 Airbnb ROI: 2.38% Traditional ROI: 1.58%
860 Quail Ridge Cir Chesterton, IN 860 Quail Ridge Cir, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$150,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 0.8% Airbnb Rental Income: $1335 Traditional Rental Income: $472 Airbnb ROI: 3.95% Traditional ROI: 0.8%
108 Indian Boundary Rd Chesterton, IN 108 Indian Boundary Rd, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$95,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 5.11% Airbnb Rental Income: $1335 Traditional Rental Income: $736 Airbnb ROI: 7.13% Traditional ROI: 5.11%
1475 Snead Ave Chesterton, IN 1475 Snead Ave, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$85,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 0.35% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 5.88% Traditional ROI: 0.35%
1600-1602 Melanie Ln Chesterton, IN 1600-1602 Melanie Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$139,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 0.69% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 2.16% Traditional ROI: 0.69%
1270 Monterey Dr Chesterton, IN 1270 Monterey Dr, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$125,000	Airbnb cash on cash: 3.47% Traditional cash on cash: -0.33% Airbnb Rental Income: $1335 Traditional Rental Income: $466 Airbnb ROI: 3.47% Traditional ROI: -0.33%
1800 Bramble Trce Chesterton, IN 1800 Bramble Trce, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$79,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.98% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 6.51% Traditional ROI: 3.98%
1441 Nelson Dr Chesterton, IN 1441 Nelson Dr, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$279,999	Airbnb cash on cash: 0.57% Traditional cash on cash: -1.18% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 0.57% Traditional ROI: -1.18%
0 Michael Dr. Lot 134 Chesterton, IN 0 Michael Dr. Lot 134, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$99,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 4.75% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 6.79% Traditional ROI: 4.75%
Lot 132 Michael Dr Chesterton, IN Lot 132 Michael Dr, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$95,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 5.01% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 7.13% Traditional ROI: 5.01%
0 Village Pt Chesterton, IN 0 Village Pt, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$199,999	Airbnb cash on cash: 2.53% Traditional cash on cash: 1.5% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 2.53% Traditional ROI: 1.5%
0 Michael Dr. Lot 135 Chesterton, IN 0 Michael Dr. Lot 135, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$101,000	Airbnb cash on cash: 6.62% Traditional cash on cash: 4.61% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 6.62% Traditional ROI: 4.61%
0 Michael Dr. Lot 133 Chesterton, IN 0 Michael Dr. Lot 133, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$97,000	Airbnb cash on cash: 6.95% Traditional cash on cash: 4.87% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 6.95% Traditional ROI: 4.87%
1915 Toms Ct Chesterton, IN 1915 Toms Ct, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$84,999	Airbnb cash on cash: 5.8% Traditional cash on cash: 3.44% Airbnb Rental Income: $1335 Traditional Rental Income: $727 Airbnb ROI: 5.8% Traditional ROI: 3.44%
ESSEX Plan Chesterton, IN	4 beds \| 2 baths \| 2,014 sq.ft.	$383,990	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.11% Airbnb Rental Income: $3402 Traditional Rental Income: $1878 Airbnb ROI: 5.24% Traditional ROI: 3.11%
1909 Chamborde Ln Chesterton, IN 1909 Chamborde Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$220,000	Airbnb cash on cash: 1.23% Traditional cash on cash: -0.98% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 1.23% Traditional ROI: -0.98%
Tbd County Rd 1050 N Chesterton, IN Tbd County Rd 1050 N, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$374,000	Airbnb cash on cash: 0.52% Traditional cash on cash: -0.79% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 0.52% Traditional ROI: -0.79%
1920 Chamborde Ln Chesterton, IN 1920 Chamborde Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$185,000	Airbnb cash on cash: 1.8% Traditional cash on cash: -0.82% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 1.8% Traditional ROI: -0.82%
1940 Chamborde Ln Chesterton, IN 1940 Chamborde Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$185,000	Airbnb cash on cash: 1.8% Traditional cash on cash: -0.82% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 1.8% Traditional ROI: -0.82%
1910 Chamborde Ln Chesterton, IN 1910 Chamborde Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$193,000	Airbnb cash on cash: 1.65% Traditional cash on cash: -0.86% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 1.65% Traditional ROI: -0.86%
1930 Chamborde Ln Ln Chesterton, IN 1930 Chamborde Ln Ln, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: 2% Traditional cash on cash: -0.76% Airbnb Rental Income: $1335 Traditional Rental Income: $463 Airbnb ROI: 2% Traditional ROI: -0.76%
650 Bote Dr Chesterton, IN 650 Bote Dr, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$173,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 0.47% Airbnb Rental Income: $1335 Traditional Rental Income: $475 Airbnb ROI: 3.19% Traditional ROI: 0.47%
Tbd Union Ave Chesterton, IN Tbd Union Ave, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$150,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 0.79% Airbnb Rental Income: $1335 Traditional Rental Income: $470 Airbnb ROI: 3.95% Traditional ROI: 0.79%
309 Michigami Trl Chesterton, IN 309 Michigami Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,581 sq.ft.	$255,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 4.96% Airbnb Rental Income: $3402 Traditional Rental Income: $1795 Airbnb ROI: 8.37% Traditional ROI: 4.96%
2023 Hawthorne Ln Chesterton, IN 2023 Hawthorne Ln, Chesterton, IN 46304 \| Condo/Coop	2 beds \| 1 baths \| 1,227 sq.ft.	$162,500	Airbnb cash on cash: 1.72% Traditional cash on cash: 0.87% Airbnb Rental Income: $1587 Traditional Rental Income: $1001 Airbnb ROI: 1.72% Traditional ROI: 0.87%
36 Karner Blue Ct Chesterton, IN 36 Karner Blue Ct, Chesterton, IN 46304 \| Single Family Residential	4 beds \| N/A baths \| 2,393 sq.ft.	$429,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 2.49% Airbnb Rental Income: $3402 Traditional Rental Income: $1896 Airbnb ROI: 4.31% Traditional ROI: 2.49%
40 Karner Blue Ct Chesterton, IN 40 Karner Blue Ct, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,735 sq.ft.	$499,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.55% Airbnb Rental Income: $3402 Traditional Rental Income: $2634 Airbnb ROI: 3.58% Traditional ROI: 3.55%
1022 N Old State Rd 49 Chesterton, IN 1022 N Old State Rd 49, Chesterton, IN 46304 \| Other	N/A beds \| N/A baths \| N/A	$389,000	Airbnb cash on cash: 0.43% Traditional cash on cash: -0.81% Airbnb Rental Income: $1335 Traditional Rental Income: $470 Airbnb ROI: 0.43% Traditional ROI: -0.81%

Vacation Rentals in Chesterton

There are 49 vacation rental properties available for sale in the city of Chesterton . The median list price of Airbnb properties available for sale in Chesterton is $270,000 and the average price per square foot is $155. The cash on cash return on vacation rentals in Chesterton is 3.00%. The average monthly short term rental income in Chesterton is $1,864.

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

There are 49 Airbnb properties available for sale in Chesterton.

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

In March 2026, the average Airbnb occupancy rate in Chesterton is 28%.

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

2221 Easton Park Dr

Chesterton, IN

4 beds | 2 baths | 2,348 sq.ft.

$549,900

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3402

Traditional Rental Income: $2630

Airbnb ROI: 3.09%

Traditional ROI: 3.06%

1226 Dogwood Drive

Chesterton, IN

4 beds | 2 baths | 1,827 sq.ft.

$318,900

Airbnb cash on cash: 7.1%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $3402

Traditional Rental Income: $2255

Airbnb ROI: 7.1%

Traditional ROI: 5.79%

525 S Calumet Rd

Chesterton, IN

4 beds | 2 baths | 1,924 sq.ft.

$322,500

Airbnb cash on cash: 6.51%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $3402

Traditional Rental Income: $2334

Airbnb ROI: 6.51%

Traditional ROI: 5.48%

319 Michigami Trail

Chesterton, IN

3 beds | 1 baths | 1,433 sq.ft.

$219,900

Airbnb cash on cash: 4.2%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $1864

Traditional Rental Income: $1280

Airbnb ROI: 4.2%

Traditional ROI: 3.8%

1290 Old Porter Rd

Chesterton, IN

3 beds | 1 baths | 1,716 sq.ft.

$270,000

Airbnb cash on cash: 3.15%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $1864

Traditional Rental Income: $1164

Airbnb ROI: 3.15%

Traditional ROI: 2.36%

1198 Old Porter Rd

Chesterton, IN

4 beds | 2 baths | 1,976 sq.ft.

$289,000

Airbnb cash on cash: 7.53%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $3402

Traditional Rental Income: $2094

Airbnb ROI: 7.53%

Traditional ROI: 5.51%

315 Franklin St

Chesterton, IN

4 beds | 2 baths | 1,900 sq.ft.

$450,000

Airbnb cash on cash: 4.22%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3402

Traditional Rental Income: $1882

Airbnb ROI: 4.22%

Traditional ROI: 2.4%

2215 Easton Park Drive

Chesterton, IN

4 beds | 3 baths | 2,241 sq.ft.

$529,900

Airbnb cash on cash: 3.27%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $3402

Traditional Rental Income: $2201

Airbnb ROI: 3.27%