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
214 Woodlawn Ave Chesterton, IN This home sits on almost 2 ACRES!!! This beautiful home situated on a wooded lot within wa...	3 beds \| 2 baths \| 2,046 sq.ft.	$320,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 5.03% Airbnb Rental Income: $1864 Traditional Rental Income: $2161 Airbnb ROI: 2.38% Traditional ROI: 5.03%
1440 Duffer Drive Chesterton, IN Welcome to 1440 Duffer Dr, Chesterton, IN - a beautifully maintained 3-bedroom, 3-bath hom...	3 beds \| 3 baths \| 3,640 sq.ft.	$370,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.72% Airbnb Rental Income: $1864 Traditional Rental Income: $2448 Airbnb ROI: 1.6% Traditional ROI: 4.72%
2011 Timberwood Ln Chesterton, IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 2 baths \| 2,476 sq.ft.	$539,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.78% Airbnb Rental Income: $3402 Traditional Rental Income: $3030 Airbnb ROI: 3.02% Traditional ROI: 3.78%
1609 Melanie Lane Chesterton, IN This beautifully maintained 3-bedroom, 3-bath townhome offers comfort, style, and scenic v...	3 beds \| 3 baths \| 1,954 sq.ft.	$399,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.87% Airbnb Rental Income: $1864 Traditional Rental Income: $2364 Airbnb ROI: 1.2% Traditional ROI: 3.87%
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%
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: 2.5% Traditional cash on cash: 2.92% Airbnb Rental Income: $3402 Traditional Rental Income: $2891 Airbnb ROI: 2.5% Traditional ROI: 2.92%
2310 Redwood Lane Chesterton, IN New construction ranch home with a full basement-ready for your enjoyment June 2025! The n...	3 beds \| 2 baths \| 1,590 sq.ft.	$439,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 2.75% Airbnb Rental Income: $1864 Traditional Rental Income: $2171 Airbnb ROI: 0.79% Traditional ROI: 2.75%
2121 Tupelo Lane Chesterton, IN Move-in ready, maintenance-free main-floor condo with a 1-car garage! A bright, open-conce...	2 beds \| 1 baths \| 1,228 sq.ft.	$167,500	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.86% Airbnb Rental Income: $1587 Traditional Rental Income: $1499 Airbnb ROI: 2.58% Traditional ROI: 4.86%
2230 Redwood Ln Chesterton, IN The Astoria in Easton Park! Welcome to luxury living in this stunning proposed two-story h...	4 beds \| 2 baths \| 2,281 sq.ft.	$599,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.18% Airbnb Rental Income: $3402 Traditional Rental Income: $2932 Airbnb ROI: 2.67% Traditional ROI: 3.18%
474 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,820 sq.ft.	$485,431	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.55% Airbnb Rental Income: $1864 Traditional Rental Income: $2559 Airbnb ROI: 0.91% Traditional ROI: 3.55%
496 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,676 sq.ft.	$486,002	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.18% Airbnb Rental Income: $1864 Traditional Rental Income: $2395 Airbnb ROI: 0.91% Traditional ROI: 3.18%
1700 Littler Dr Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 9 baths \| 17,178 sq.ft.	$2,950,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.31% Airbnb Rental Income: $2553 Traditional Rental Income: $6257 Airbnb ROI: -1.89% Traditional ROI: -0.31%
468 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,676 sq.ft.	$419,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.07% Airbnb Rental Income: $1864 Traditional Rental Income: $2432 Airbnb ROI: 1.35% Traditional ROI: 4.07%
1544 Colonial Drive Chesterton, IN Fantastic 2 story home in the sought after Villages of Sand Creek. Located in Duneland Sch...	4 beds \| 4 baths \| 2,950 sq.ft.	$419,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.23% Airbnb Rental Income: $3402 Traditional Rental Income: $3380 Airbnb ROI: 4.36% Traditional ROI: 6.23%
476 Magnolia Lane Chesterton, IN You've found your own personal hideaway! Nestled on a picturesque pond lot with no neighbo...	3 beds \| 2 baths \| 1,790 sq.ft.	$487,700	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.46% Airbnb Rental Income: $1864 Traditional Rental Income: $2531 Airbnb ROI: 0.9% Traditional ROI: 3.46%
2335 Legend Circle E Chesterton, IN Maintenance Free Living on the trail in Coffee Creek! This tastefully updated townhome off...	5 beds \| 4 baths \| 2,648 sq.ft.	$535,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.73% Airbnb Rental Income: $2553 Traditional Rental Income: $3082 Airbnb ROI: 1.44% Traditional ROI: 3.73%
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%
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: 0.4% Traditional cash on cash: 3.03% Airbnb Rental Income: $1864 Traditional Rental Income: $2830 Airbnb ROI: 0.4% Traditional ROI: 3.03%
1329 N 375 E Chesterton, IN Nestled on 5 private acres, this spacious ranch offers four bedrooms (potentially five) pl...	4 beds \| 3 baths \| 2,872 sq.ft.	$549,999	Airbnb cash on cash: 3.31% Traditional cash on cash: 3.94% Airbnb Rental Income: $3402 Traditional Rental Income: $2968 Airbnb ROI: 3.31% Traditional ROI: 3.94%
1198 N Babcock Rd Chesterton, IN Escape to your own 1.7-acre private retreat just minutes from Lake Michigan and the Indian...	2 beds \| 1 baths \| 1,860 sq.ft.	$249,500	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.99% Airbnb Rental Income: $1587 Traditional Rental Income: $1780 Airbnb ROI: 2.45% Traditional ROI: 4.99%
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%
810 Ashwood Lane Chesterton, IN Introducing the expanded Michelle floor plan-now offering 2 master suites-perfect for rela...	5 beds \| 4 baths \| 2,554 sq.ft.	$622,600	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.44% Airbnb Rental Income: $2553 Traditional Rental Income: $3162 Airbnb ROI: 1.33% Traditional ROI: 3.44%
1411 W Beam Street Chesterton, IN Remodeled 3-bedroom, 2-bath home on a beautiful 1-acre lot, tucked away on a quiet no-thro...	3 beds \| 2 baths \| 1,652 sq.ft.	$269,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 6.4% Airbnb Rental Income: $1864 Traditional Rental Income: $2166 Airbnb ROI: 3.25% Traditional ROI: 6.4%
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%
1642 Commodore Ln Chesterton, IN 1642 Commodore Ln, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 1,745 sq.ft.	$339,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 3.05% Airbnb Rental Income: $1864 Traditional Rental Income: $1661 Airbnb ROI: 2.12% Traditional ROI: 3.05%
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%
1346 Essex Dr Chesterton, IN 1346 Essex Dr, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 2,167 sq.ft.	$349,900	Airbnb cash on cash: 2.01% Traditional cash on cash: 4.34% Airbnb Rental Income: $1864 Traditional Rental Income: $2131 Airbnb ROI: 2.01% Traditional ROI: 4.34%
103 Summertree Dr Chesterton, IN 103 Summertree Dr, Chesterton, IN 46304 \| Townhouse	3 beds \| 2 baths \| 1,561 sq.ft.	$250,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 5.33% Airbnb Rental Income: $1864 Traditional Rental Income: $2000 Airbnb ROI: 2.64% Traditional ROI: 5.33%
474 E 1200 N Chesterton, IN 474 E 1200 N, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 3,538 sq.ft.	$1,100,000	Airbnb cash on cash: -0.6% Traditional cash on cash: -0.15% Airbnb Rental Income: $1864 Traditional Rental Income: $1823 Airbnb ROI: -0.6% Traditional ROI: -0.15%
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.	$645,400	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%

Real Estate investment in Chesterton, IN

There are 110 properties for sale in the city of Chesterton . The median list price in Chesterton is $270,000 and the average price per square foot is $155. In March 2026, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $1,788.

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

There are 110 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 $1,788.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

214 Woodlawn Ave

Chesterton, IN

3 beds | 2 baths | 2,046 sq.ft.

$320,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $1864

Traditional Rental Income: $2161

Airbnb ROI: 2.38%

Traditional ROI: 5.03%

1440 Duffer Drive

Chesterton, IN

3 beds | 3 baths | 3,640 sq.ft.

$370,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1864

Traditional Rental Income: $2448

Airbnb ROI: 1.6%

Traditional ROI: 4.72%

2011 Timberwood Ln

Chesterton, IN

4 beds | 2 baths | 2,476 sq.ft.

$539,900

Airbnb cash on cash: 3.02%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3402

Traditional Rental Income: $3030

Airbnb ROI: 3.02%

Traditional ROI: 3.78%

1609 Melanie Lane

Chesterton, IN

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

$399,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1864

Traditional Rental Income: $2364

Airbnb ROI: 1.2%

Traditional ROI: 3.87%

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%

801 Idlewild Ln

Chesterton, IN

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

$624,900

Airbnb cash on cash: 2.5%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $3402

Traditional Rental Income: $2891

Airbnb ROI: 2.5%

Traditional ROI: 2.92%

2310 Redwood Lane

Chesterton, IN

3 beds | 2 baths | 1,590 sq.ft.

$439,900

Airbnb cash on cash: 0.79%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $1864

Traditional Rental Income: $2171

Airbnb ROI: 0.79%

Traditional ROI: 2.75%

2121 Tupelo Lane

Chesterton, IN

2 beds | 1 baths | 1,228 sq.ft.

$167,500

Airbnb cash on cash: 2.58%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1587

Traditional Rental Income: $1499

Airbnb ROI: 2.58%