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
305 E Jackson Street Chesterton, IN Welcome Home to this Beautifully Renovated Open-Concept Ranch, Ideally Located Within Minu...	3 beds \| 1 baths \| 1,440 sq.ft.	$250,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 5.26% Airbnb Rental Income: $1158 Traditional Rental Income: $1629 Airbnb ROI: 1.64% Traditional ROI: 5.26%
1650 Hogan Ave Chesterton, IN Chesterton Indiana's Elite subdivision, Sand Creek now has this EXCELLENTLY MAINTAINED and...	4 beds \| 3 baths \| 3,066 sq.ft.	$599,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.76% Airbnb Rental Income: $2471 Traditional Rental Income: $2539 Airbnb ROI: 1.57% Traditional ROI: 2.76%
17 E 900 N Chesterton, IN Charming cape cod home in the country is updated and has flowing floor plan. Formal dinin...	3 beds \| 3 baths \| 1,866 sq.ft.	$298,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.26% Airbnb Rental Income: $1158 Traditional Rental Income: $2093 Airbnb ROI: 0.58% Traditional ROI: 5.26%
4221 Burlwood Dr Chesterton, IN 3 Bedroom Ranch with 2 more possible in a finished basement. The kitchen is large with ple...	3 beds \| 3 baths \| 3,384 sq.ft.	$433,900	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.99% Airbnb Rental Income: $1158 Traditional Rental Income: $2310 Airbnb ROI: 0.22% Traditional ROI: 3.99%
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.	$310,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 5.25% Airbnb Rental Income: $1158 Traditional Rental Income: $2161 Airbnb ROI: 0.5% Traditional ROI: 5.25%
1452 Gossett Mill Avenue Chesterton, IN Welcome to this beautiful 2-story home in Chesterton, IN! Built in 2017, this 4 bedroom, 3...	4 beds \| 3 baths \| 2,031 sq.ft.	$444,900	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.47% Airbnb Rental Income: $2471 Traditional Rental Income: $2794 Airbnb ROI: 2.25% Traditional ROI: 4.47%
4160 Westwood Ln Chesterton, IN WOW! THIS IS THE ONE YOU'VE BEEN WAITING FOR! This IMMACULATE quad level home has been ta...	4 beds \| 3 baths \| 2,369 sq.ft.	$395,999	Airbnb cash on cash: 3.28% Traditional cash on cash: 5.03% Airbnb Rental Income: $2471 Traditional Rental Income: $2520 Airbnb ROI: 3.28% Traditional ROI: 5.03%
204 Wagner Rd Chesterton, IN Fantastic move-in ready ranch home in lovely Porter. Front of property features well-main...	3 beds \| 1 baths \| 1,260 sq.ft.	$264,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.27% Airbnb Rental Income: $1158 Traditional Rental Income: $1598 Airbnb ROI: 0.98% Traditional ROI: 4.27%
897 Jane Avenue Chesterton, IN Fully remodeled inside and out, this stunning 3-bedroom, 3-bath home sits on a beautiful 1...	3 beds \| 3 baths \| 2,488 sq.ft.	$419,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.68% Airbnb Rental Income: $1158 Traditional Rental Income: $2577 Airbnb ROI: 0.11% Traditional ROI: 4.68%
2011 Timberwood Lane Chesterton, IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 3 baths \| 2,476 sq.ft.	$539,900	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.78% Airbnb Rental Income: $2471 Traditional Rental Income: $3030 Airbnb ROI: 1.48% Traditional ROI: 3.78%
656 S 4th Street Chesterton, IN Completely remodeled home in a desirable location! Location is a key feature as this home ...	3 beds \| 2 baths \| 1,542 sq.ft.	$365,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.13% Airbnb Rental Income: $1158 Traditional Rental Income: $1625 Airbnb ROI: 0.65% Traditional ROI: 3.13%
2221 Easton Park Drive Chesterton, IN Hurry now to make your own selections! The ever-popular Melanie floor plan offers all of t...	4 beds \| 3 baths \| 2,348 sq.ft.	$549,900	Airbnb cash on cash: 1.58% Traditional cash on cash: 3.06% Airbnb Rental Income: $2471 Traditional Rental Income: $2630 Airbnb ROI: 1.58% Traditional ROI: 3.06%
1163 Burns Blvd Chesterton, IN Welcome to this charming half duplex in the Village of Burns Harbor, located within the hi...	4 beds \| 2 baths \| 2,594 sq.ft.	$315,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 6.52% Airbnb Rental Income: $2471 Traditional Rental Income: $2589 Airbnb ROI: 4.1% Traditional ROI: 6.52%
2005 Timberwood Ln Chesterton, IN Welcome Home! This gorgeous new construction home is all you could ever want. Stunning kit...	4 beds \| 2 baths \| 2,481 sq.ft.	$639,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.75% Airbnb Rental Income: $2471 Traditional Rental Income: $2857 Airbnb ROI: 1.1% Traditional ROI: 2.75%
1717 Crocker St Chesterton, IN Location, Location, Location!!! Duneland Schools and minutes away from Duneland Prairie B...	3 beds \| 2 baths \| 2,400 sq.ft.	$249,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.05% Airbnb Rental Income: $1158 Traditional Rental Income: $1406 Airbnb ROI: 1.37% Traditional ROI: 4.05%
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: 1.17% Traditional cash on cash: 2.92% Airbnb Rental Income: $2471 Traditional Rental Income: $2891 Airbnb ROI: 1.17% Traditional ROI: 2.92%
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.	$169,999	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.78% Airbnb Rental Income: $1311 Traditional Rental Income: $1499 Airbnb ROI: 1.11% Traditional ROI: 4.78%
2230 Redwood Lane Chesterton, IN UNDER CONSTRUCTION...COMPLETION DATE ESTIMATED MID APRIL 2026. The Acadia in Easton Park! ...	4 beds \| 3 baths \| 2,281 sq.ft.	$599,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.19% Airbnb Rental Income: $2471 Traditional Rental Income: $2932 Airbnb ROI: 1.3% Traditional ROI: 3.19%
2131 Pepperbush Avenue Chesterton, IN Move-In Ready in Westwood Manor - Chesterton's desired Subdivision! Nestled in the award-w...	4 beds \| 4 baths \| 2,992 sq.ft.	$419,999	Airbnb cash on cash: 2.62% Traditional cash on cash: 6.23% Airbnb Rental Income: $2471 Traditional Rental Income: $3291 Airbnb ROI: 2.62% Traditional ROI: 6.23%
706 Idlewild Lane Chesterton, IN Welcome to Easton Park! The popular Michael floor plan offers all of the spaces that you n...	4 beds \| 3 baths \| 2,472 sq.ft.	$580,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 2.41% Airbnb Rental Income: $2471 Traditional Rental Income: $2419 Airbnb ROI: 1.4% Traditional ROI: 2.41%
1700 Littler Drive Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 10 baths \| 17,178 sq.ft.	$2,500,000	Airbnb cash on cash: -2.09% Traditional cash on cash: -0.19% Airbnb Rental Income: $2424 Traditional Rental Income: $6257 Airbnb ROI: -2.09% Traditional ROI: -0.19%
1125 N 350 E Chesterton, IN Don't miss this opportunity! Spacious ranch home on two acres, designed for both comfort a...	4 beds \| 4 baths \| 3,792 sq.ft.	$459,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 6.71% Airbnb Rental Income: $2471 Traditional Rental Income: $3707 Airbnb ROI: 2.44% Traditional ROI: 6.71%
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: -0.39% Traditional cash on cash: 3.46% Airbnb Rental Income: $1158 Traditional Rental Income: $2531 Airbnb ROI: -0.39% Traditional ROI: 3.46%
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: -0.65% Traditional cash on cash: 3.03% Airbnb Rental Income: $1158 Traditional Rental Income: $2830 Airbnb ROI: -0.65% Traditional ROI: 3.03%
1198 N Babcock Road 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.	$230,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 6.01% Airbnb Rental Income: $1311 Traditional Rental Income: $1780 Airbnb ROI: 1.98% Traditional ROI: 6.01%
525 S Calumet Rd Chesterton, IN Charming four-bedroom, two-full-bath home located in Chesterton, Indiana! From the moment ...	4 beds \| 2 baths \| 1,924 sq.ft.	$295,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 6.08% Airbnb Rental Income: $2471 Traditional Rental Income: $2334 Airbnb ROI: 4.41% Traditional ROI: 6.08%
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: 1.15% Traditional cash on cash: 3.44% Airbnb Rental Income: $2424 Traditional Rental Income: $3162 Airbnb ROI: 1.15% Traditional ROI: 3.44%
378 Ballenisle Ct Chesterton, IN 378 Ballenisle Ct, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,270 sq.ft.	$400,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 3.6% Airbnb Rental Income: $2471 Traditional Rental Income: $2208 Airbnb ROI: 2.7% Traditional ROI: 3.6%
1874 Catkin Cir Chesterton, IN 1874 Catkin Cir, Chesterton, IN 46304 \| Single Family Residential	5 beds \| 4 baths \| 4,698 sq.ft.	$734,999	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.63% Airbnb Rental Income: $2424 Traditional Rental Income: $3203 Airbnb ROI: 0.63% Traditional ROI: 2.63%
225 Jefferson Ave Chesterton, IN 225 Jefferson Ave, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 1,600 sq.ft.	$329,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.98% Airbnb Rental Income: $1158 Traditional Rental Income: $1589 Airbnb ROI: 0.36% Traditional ROI: 2.98%
450 E Greening Rd Chesterton, IN 450 E Greening Rd, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,494 sq.ft.	$799,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.66% Airbnb Rental Income: $2471 Traditional Rental Income: $1961 Airbnb ROI: 0.54% Traditional ROI: 0.66%
1500 Nelson Dr Chesterton, IN 1500 Nelson Dr, Chesterton, IN 46304 \| Single Family Residential	6 beds \| 4 baths \| 4,789 sq.ft.	$799,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.18% Airbnb Rental Income: $2424 Traditional Rental Income: $3278 Airbnb ROI: 0.24% Traditional ROI: 2.18%
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: -1.18% Traditional cash on cash: -0.15% Airbnb Rental Income: $1158 Traditional Rental Income: $1823 Airbnb ROI: -1.18% Traditional ROI: -0.15%
2132 Pradera Trl Chesterton, IN 2132 Pradera Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,524 sq.ft.	$564,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 2.34% Airbnb Rental Income: $2471 Traditional Rental Income: $2324 Airbnb ROI: 1.48% Traditional ROI: 2.34%
2179 W 1100 N Chesterton, IN 2179 W 1100 N, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 2,850 sq.ft.	$899,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.75% Airbnb Rental Income: $1158 Traditional Rental Income: $2275 Airbnb ROI: -1.04% Traditional ROI: 0.75%
829 Johnson St #B Chesterton, IN 829 Johnson St #B, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,758 sq.ft.	$299,995	Airbnb cash on cash: 4.45% Traditional cash on cash: 4.94% Airbnb Rental Income: $2471 Traditional Rental Income: $2009 Airbnb ROI: 4.45% Traditional ROI: 4.94%
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: 1.71% Traditional cash on cash: 2.37% Airbnb Rental Income: $2471 Traditional Rental Income: $2201 Airbnb ROI: 1.71% Traditional ROI: 2.37%
2500 Pradera Trl Chesterton, IN 2500 Pradera Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,408 sq.ft.	$619,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.84% Airbnb Rental Income: $2471 Traditional Rental Income: $2235 Airbnb ROI: 1.21% Traditional ROI: 1.84%
150-152 N 16th St Chesterton, IN 150-152 N 16th St, Chesterton, IN 46304 \| Multi Family	6 beds \| 4 baths \| N/A	$499,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 11.8% Airbnb Rental Income: $2471 Traditional Rental Income: $6471 Airbnb ROI: 1.96% Traditional ROI: 11.8%
140-142 N Jackson Blvd Chesterton, IN 140-142 N Jackson Blvd, Chesterton, IN 46304 \| Multi Family	6 beds \| 4 baths \| N/A	$525,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 11.15% Airbnb Rental Income: $2471 Traditional Rental Income: $6471 Airbnb ROI: 1.78% Traditional ROI: 11.15%

Real Estate investment in Chesterton, IN

There are 137 properties for sale in the city of Chesterton . The median list price in Chesterton is $369,500 and the average price per square foot is $177. In April 2026, the average monthly cash on cash return in Chesterton is 3.00%. The average monthly rental income in Chesterton is $2,009.

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

There are 137 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 $2,009.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterton, IN

305 E Jackson Street

Chesterton, IN

3 beds | 1 baths | 1,440 sq.ft.

$250,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1158

Traditional Rental Income: $1629

Airbnb ROI: 1.64%

Traditional ROI: 5.26%

1650 Hogan Ave

Chesterton, IN

4 beds | 3 baths | 3,066 sq.ft.

$599,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2471

Traditional Rental Income: $2539

Airbnb ROI: 1.57%

Traditional ROI: 2.76%

17 E 900 N

Chesterton, IN

3 beds | 3 baths | 1,866 sq.ft.

$298,900

Airbnb cash on cash: 0.58%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1158

Traditional Rental Income: $2093

Airbnb ROI: 0.58%

Traditional ROI: 5.26%

4221 Burlwood Dr

Chesterton, IN

3 beds | 3 baths | 3,384 sq.ft.

$433,900

Airbnb cash on cash: 0.22%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $1158

Traditional Rental Income: $2310

Airbnb ROI: 0.22%

Traditional ROI: 3.99%

214 Woodlawn Ave

Chesterton, IN

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

$310,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $1158

Traditional Rental Income: $2161

Airbnb ROI: 0.5%

Traditional ROI: 5.25%

1452 Gossett Mill Avenue

Chesterton, IN

4 beds | 3 baths | 2,031 sq.ft.

$444,900

Airbnb cash on cash: 2.25%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $2471

Traditional Rental Income: $2794

Airbnb ROI: 2.25%

Traditional ROI: 4.47%

4160 Westwood Ln

Chesterton, IN

4 beds | 3 baths | 2,369 sq.ft.

$395,999

Airbnb cash on cash: 3.28%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $2471

Traditional Rental Income: $2520

Airbnb ROI: 3.28%

Traditional ROI: 5.03%

204 Wagner Rd

Chesterton, IN

3 beds | 1 baths | 1,260 sq.ft.

$264,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $1158

Traditional Rental Income: $1598

Airbnb ROI: 0.98%