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.

Single Family Homes for Sale in Chesterton, IN

Search for Single Family Residential for Sale in Chesterton, Indiana. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 42 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
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%
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%
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%
498 Magnolia Lane Chesterton, IN Weclome to the maintenance-free lifestyle! Nestled amongst the serene nature preserve, the...	3 beds \| 2 baths \| 1,710 sq.ft.	$492,800	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.15% Airbnb Rental Income: $1158 Traditional Rental Income: $2394 Airbnb ROI: -0.36% Traditional ROI: 3.15%
1541 Fox Point Drive Chesterton, IN Welcome to this three-bedroom, 1 3/4- bath tri-level home located on a corner lot in the C...	3 beds \| 2 baths \| 1,848 sq.ft.	$299,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.88% Airbnb Rental Income: $1158 Traditional Rental Income: $2023 Airbnb ROI: 0.45% Traditional ROI: 4.88%
1125 In-49 Chesterton, IN Unbeatable Location Near the Stunning Shores and Trails of the Indiana Dunes National Park...	3 beds \| 1 baths \| 1,472 sq.ft.	$259,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.54% Airbnb Rental Income: $1158 Traditional Rental Income: $1521 Airbnb ROI: 1.5% Traditional ROI: 4.54%
103 Michigan Street Chesterton, IN Step into this home at 103 Michigan Street, and be impressed with everything you see. Not ...	3 beds \| 2 baths \| 1,560 sq.ft.	$315,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 4.13% Airbnb Rental Income: $1158 Traditional Rental Income: $1763 Airbnb ROI: 0.8% Traditional ROI: 4.13%
1040 Kilarney Road Chesterton, IN Buyers won't believe the endless opportunities and space in this home! A stunning corner l...	5 beds \| 5 baths \| 7,047 sq.ft.	$989,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.24% Airbnb Rental Income: $2424 Traditional Rental Income: $4936 Airbnb ROI: -0.13% Traditional ROI: 3.24%
1240 Ryder Road Chesterton, IN Perfectly positioned along the fairway in the gated Sand Creek community, this impressive ...	5 beds \| 6 baths \| 7,084 sq.ft.	$1,289,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.8% Airbnb Rental Income: $2424 Traditional Rental Income: $7051 Airbnb ROI: -0.55% Traditional ROI: 3.8%
270 Woodlawn Avenue Chesterton, IN Welcome to 270 Woodlawn Ave in Chesterton. This beautifully remodeled 3-bedroom home offer...	3 beds \| 1 baths \| 1,183 sq.ft.	$259,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.92% Airbnb Rental Income: $1158 Traditional Rental Income: $1432 Airbnb ROI: 1.25% Traditional ROI: 3.92%
2152 Redwood Lane Chesterton, IN Construction beginning March 2026-ready for move-in late summer! Introducing The Carmela f...	4 beds \| 3 baths \| 2,241 sq.ft.	$529,900	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.43% Airbnb Rental Income: $2471 Traditional Rental Income: $2725 Airbnb ROI: 1.71% Traditional ROI: 3.43%
2316 Redwood 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.	$459,900	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.3% Airbnb Rental Income: $1158 Traditional Rental Income: $2098 Airbnb ROI: -0.77% Traditional ROI: 2.3%
0-2 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Experience the PAXTON model the perfect blend of space, style, a...	5 beds \| 5 baths \| 4,398 sq.ft.	$1,245,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.21% Airbnb Rental Income: $2424 Traditional Rental Income: $4969 Airbnb ROI: 0.49% Traditional ROI: 3.21%
1137 N 475 E Chesterton, IN 1137 N 475 E, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 4 baths \| 5,809 sq.ft.	$1,499,999	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.33% Airbnb Rental Income: $2471 Traditional Rental Income: $3122 Airbnb ROI: -0.57% Traditional ROI: 0.33%
0-1 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Introducing The Ozark Ranch, a thoughtfully designed proposed c...	3 beds \| 3 baths \| 2,446 sq.ft.	$849,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.4% Airbnb Rental Income: $1158 Traditional Rental Income: $2794 Airbnb ROI: -0.15% Traditional ROI: 2.4%
529 Windridge Drive Chesterton, IN Beautifully updated two story home tucked into a quiet cul de sac in one of Chesterton's m...	4 beds \| 4 baths \| 3,346 sq.ft.	$449,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 6.27% Airbnb Rental Income: $2471 Traditional Rental Income: $3518 Airbnb ROI: 2.35% Traditional ROI: 6.27%
1510 Ash Street Chesterton, IN Welcome to this beautifully maintained 3-bedroom, 2 full bathroom home in pristine conditi...	3 beds \| 2 baths \| 1,632 sq.ft.	$325,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 4.49% Airbnb Rental Income: $1158 Traditional Rental Income: $2060 Airbnb ROI: 0.28% Traditional ROI: 4.49%
901 Bernie Court Chesterton, IN Charming 3-bedroom, 3-bathroom home in the Duneland School District sits on a serene 1.2-a...	3 beds \| 3 baths \| 1,959 sq.ft.	$399,999	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.73% Airbnb Rental Income: $1158 Traditional Rental Income: $2483 Airbnb ROI: 0.18% Traditional ROI: 4.73%
1040 Preserve Lane Chesterton, IN Located in The Preserve in Chesterton, this thoughtfully upgraded home offers comfort, eff...	4 beds \| 3 baths \| 2,312 sq.ft.	$459,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 4.77% Airbnb Rental Income: $2471 Traditional Rental Income: $2862 Airbnb ROI: 2.47% Traditional ROI: 4.77%
494 Magnolia Lane Chesterton, IN Last wooded homesite in Phase 2 of the villas in Easton Park! The newest phase of Easton P...	3 beds \| 2 baths \| 1,590 sq.ft.	$464,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.01% Airbnb Rental Income: $1158 Traditional Rental Income: $2206 Airbnb ROI: -0.27% Traditional ROI: 3.01%
2017 Wildwood Court Chesterton, IN Style & grace refined in this magnificently outfitted home in Chesterton's Easton Park. Th...	3 beds \| 3 baths \| 2,866 sq.ft.	$714,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.33% Airbnb Rental Income: $1158 Traditional Rental Income: $2946 Airbnb ROI: -0.93% Traditional ROI: 2.33%
893 Pearson Road Chesterton, IN Set on over 3.5 acres, this beautifully maintained 3,000 square foot home offers the space...	4 beds \| 3 baths \| 2,912 sq.ft.	$499,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.89% Airbnb Rental Income: $2471 Traditional Rental Income: $2856 Airbnb ROI: 1.78% Traditional ROI: 3.89%
708 Idlewild Lane Chesterton, IN Hurry now to choose your own selections on the show-stopping Allison floor plan that inclu...	4 beds \| 3 baths \| 2,415 sq.ft.	$569,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.23% Airbnb Rental Income: $2471 Traditional Rental Income: $2819 Airbnb ROI: 1.45% Traditional ROI: 3.23%
1412 Essex Drive Chesterton, IN Freshly updated Split-level located just outside Chicago & minutes from Lake Michigan. Set...	4 beds \| 2 baths \| 1,788 sq.ft.	$329,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 4.99% Airbnb Rental Income: $2471 Traditional Rental Income: $2242 Airbnb ROI: 3.78% Traditional ROI: 4.99%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

897 Jane Avenue

Chesterton, IN

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

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

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

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%

801 Idlewild Lane

Chesterton, IN

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%

2230 Redwood Lane

Chesterton, IN

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%