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 44 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
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.	$439,900	Airbnb cash on cash: 4.87% Traditional cash on cash: 4.53% Airbnb Rental Income: $3748 Traditional Rental Income: $2794 Airbnb ROI: 4.87% Traditional ROI: 4.53%
1419 Snead Avenue Chesterton, IN This is more than a home--it's a lifestyle. Located in one of the most desirable locations...	4 beds \| 5 baths \| 6,259 sq.ft.	$1,350,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 1.8% Airbnb Rental Income: $3748 Traditional Rental Income: $4919 Airbnb ROI: 0.22% Traditional ROI: 1.8%
1123 Waverly Road Chesterton, IN Updated 2 Story 3 Bedroom 2 Bath Home located minutes from the Indiana Dunes National Lake...	3 beds \| 2 baths \| 2,184 sq.ft.	$351,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.12% Airbnb Rental Income: $1724 Traditional Rental Income: $2402 Airbnb ROI: 1.62% Traditional ROI: 5.12%
656 S 4th Street Chesterton, IN Motivated seller! Completely remodeled home in a desirable location! Location is one of th...	3 beds \| 2 baths \| 1,542 sq.ft.	$335,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 3.5% Airbnb Rental Income: $1724 Traditional Rental Income: $1625 Airbnb ROI: 2.3% Traditional ROI: 3.5%
1215 Bostwick Avenue Chesterton, IN Like new and absolutely stunning, this beautifully designed ranch home in the heart of Che...	3 beds \| 3 baths \| 2,822 sq.ft.	$569,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.9% Airbnb Rental Income: $1724 Traditional Rental Income: $2666 Airbnb ROI: 0.23% Traditional ROI: 2.9%
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: 3% Traditional cash on cash: 2.93% Airbnb Rental Income: $3748 Traditional Rental Income: $2891 Airbnb ROI: 3% Traditional ROI: 2.93%
2230 Redwood Lane Chesterton, IN The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offeri...	4 beds \| 3 baths \| 2,281 sq.ft.	$620,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.03% Airbnb Rental Income: $3748 Traditional Rental Income: $2932 Airbnb ROI: 3.03% Traditional ROI: 3.03%
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: 3.37% Traditional cash on cash: 2.41% Airbnb Rental Income: $3748 Traditional Rental Income: $2419 Airbnb ROI: 3.37% 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: -1.4% Traditional cash on cash: -0.19% Airbnb Rental Income: $4345 Traditional Rental Income: $6257 Airbnb ROI: -1.4% Traditional ROI: -0.19%
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: 0.19% Traditional cash on cash: 3.03% Airbnb Rental Income: $1724 Traditional Rental Income: $2830 Airbnb ROI: 0.19% 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: 5.9% Traditional cash on cash: 6.01% Airbnb Rental Income: $2336 Traditional Rental Income: $1780 Airbnb ROI: 5.9% 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: 3.9% Traditional cash on cash: 3.44% Airbnb Rental Income: $4345 Traditional Rental Income: $3162 Airbnb ROI: 3.9% Traditional ROI: 3.44%
507 S 20th Street Chesterton, IN Welcome to this beautifully maintained, one-owner 3-bedroom, 2-bath home offering 1,652 sq...	3 beds \| 2 baths \| 1,652 sq.ft.	$309,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 4.59% Airbnb Rental Income: $1724 Traditional Rental Income: $1911 Airbnb ROI: 2.31% Traditional ROI: 4.59%
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: 0.66% Traditional cash on cash: 3.15% Airbnb Rental Income: $1724 Traditional Rental Income: $2394 Airbnb ROI: 0.66% Traditional ROI: 3.15%
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.	$974,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.31% Airbnb Rental Income: $4345 Traditional Rental Income: $4936 Airbnb ROI: 1.65% Traditional ROI: 3.31%
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: 0.78% Traditional cash on cash: 3.8% Airbnb Rental Income: $4345 Traditional Rental Income: $7051 Airbnb ROI: 0.78% 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.	$249,900	Airbnb cash on cash: 3.33% Traditional cash on cash: 4.11% Airbnb Rental Income: $1724 Traditional Rental Income: $1432 Airbnb ROI: 3.33% Traditional ROI: 4.11%
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.	$1,240,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.22% Airbnb Rental Income: $4345 Traditional Rental Income: $4969 Airbnb ROI: 1.89% Traditional ROI: 3.22%
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.	$849,500	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.4% Airbnb Rental Income: $1724 Traditional Rental Income: $2794 Airbnb ROI: 0.45% 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.	$436,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 6.48% Airbnb Rental Income: $3748 Traditional Rental Income: $3518 Airbnb ROI: 5.05% Traditional ROI: 6.48%
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: 1.83% Traditional cash on cash: 4.49% Airbnb Rental Income: $1724 Traditional Rental Income: $2060 Airbnb ROI: 1.83% Traditional ROI: 4.49%
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: 4.94% Traditional cash on cash: 4.77% Airbnb Rental Income: $3748 Traditional Rental Income: $2862 Airbnb ROI: 4.94% 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: 0.81% Traditional cash on cash: 3.01% Airbnb Rental Income: $1724 Traditional Rental Income: $2206 Airbnb ROI: 0.81% 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.	$700,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.4% Airbnb Rental Income: $1724 Traditional Rental Income: $2946 Airbnb ROI: -0.2% Traditional ROI: 2.4%
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: 3.45% Traditional cash on cash: 3.23% Airbnb Rental Income: $3748 Traditional Rental Income: $2819 Airbnb ROI: 3.45% 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.	$313,900	Airbnb cash on cash: 7.62% Traditional cash on cash: 5.27% Airbnb Rental Income: $3748 Traditional Rental Income: $2242 Airbnb ROI: 7.62% Traditional ROI: 5.27%
1830 Tour Trace Chesterton, IN Over 5,400 sqft of impeccable updating make this FIVE Bed, FIVE bath home the ONE! This ho...	5 beds \| 5 baths \| 5,425 sq.ft.	$889,999	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.99% Airbnb Rental Income: $4345 Traditional Rental Income: $5047 Airbnb ROI: 2.04% Traditional ROI: 3.99%
1429 Delos Marr Avenue Chesterton, IN Step into a home that feels straight out of a magazine, where every detail has been though...	4 beds \| 3 baths \| 2,439 sq.ft.	$489,900	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.82% Airbnb Rental Income: $3748 Traditional Rental Income: $2826 Airbnb ROI: 4.05% Traditional ROI: 3.82%
1938 Cory Lane Chesterton, IN If you've been looking for a home that offers more space than expected with a functional, ...	4 beds \| 3 baths \| 2,418 sq.ft.	$389,900	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.13% Airbnb Rental Income: $3748 Traditional Rental Income: $2323 Airbnb ROI: 5.8% Traditional ROI: 4.13%
85 Hepburn Way Chesterton, IN Welcome to 85 Hepburn Wayâthis beautifully maintained 4-bedroom, 2.5-bath home offers th...	4 beds \| 3 baths \| 2,080 sq.ft.	$364,500	Airbnb cash on cash: 6.64% Traditional cash on cash: 4.94% Airbnb Rental Income: $3748 Traditional Rental Income: $2353 Airbnb ROI: 6.64% Traditional ROI: 4.94%
503 Oakwood Drive Chesterton, IN Don't wait on this lovely 4 bedroom well maintained home . Situated on a quiet street cent...	4 beds \| 4 baths \| 3,586 sq.ft.	$405,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 6.88% Airbnb Rental Income: $3748 Traditional Rental Income: $3496 Airbnb ROI: 5.4% Traditional ROI: 6.88%
769 S Calumet Road Chesterton, IN Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 ...	4 beds \| 2 baths \| 2,242 sq.ft.	$344,900	Airbnb cash on cash: 6.3% Traditional cash on cash: 4.79% Airbnb Rental Income: $3748 Traditional Rental Income: $2445 Airbnb ROI: 6.3% Traditional ROI: 4.79%
1062 Birch Trail Drive Chesterton, IN Welcome to Duneland Trails, where space, quality, and location come together beautifully. ...	5 beds \| 4 baths \| 3,607 sq.ft.	$475,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 6.37% Airbnb Rental Income: $4345 Traditional Rental Income: $3827 Airbnb ROI: 5.48% Traditional ROI: 6.37%
1248 Dogwood Drive Chesterton, IN Perfectly Located Just Minutes from the Indiana Dunes National Park and Lakeshore. This Cl...	3 beds \| 2 baths \| 1,419 sq.ft.	$350,000	Airbnb cash on cash: 2% Traditional cash on cash: 3.94% Airbnb Rental Income: $1724 Traditional Rental Income: $1888 Airbnb ROI: 2% Traditional ROI: 3.94%
131 N 18th Street Chesterton, IN Welcome home to this well-maintained and thoughtfully updated 3-bedroom property located i...	3 beds \| 2 baths \| 2,064 sq.ft.	$250,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 7.26% Airbnb Rental Income: $1724 Traditional Rental Income: $2170 Airbnb ROI: 3.36% Traditional ROI: 7.26%
1340 Cantigny Court Chesterton, IN Condominium convenience meets the comfort and privacy of a detached single-family home in ...	3 beds \| 4 baths \| 4,274 sq.ft.	$859,900	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.93% Airbnb Rental Income: $1724 Traditional Rental Income: $4189 Airbnb ROI: -0.74% Traditional ROI: 2.93%
1077 Mission Hills Court Chesterton, IN Now available in Sand Creek--currently the only townhouse on the market! Located in one of...	3 beds \| 4 baths \| 3,199 sq.ft.	$465,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.3% Airbnb Rental Income: $1724 Traditional Rental Income: $2879 Airbnb ROI: -0.45% Traditional ROI: 3.3%
1167 Kinner Drive Chesterton, IN Beautifully maintained home situated on a large corner lot with gorgeous landscaping and f...	4 beds \| 3 baths \| 2,015 sq.ft.	$414,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 4.8% Airbnb Rental Income: $3748 Traditional Rental Income: $2638 Airbnb ROI: 5.56% Traditional ROI: 4.8%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesterton, IN

1452 Gossett Mill Avenue

Chesterton, IN

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

$439,900

Airbnb cash on cash: 4.87%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3748

Traditional Rental Income: $2794

Airbnb ROI: 4.87%

Traditional ROI: 4.53%

1419 Snead Avenue

Chesterton, IN

4 beds | 5 baths | 6,259 sq.ft.

$1,350,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $3748

Traditional Rental Income: $4919

Airbnb ROI: 0.22%

Traditional ROI: 1.8%

1123 Waverly Road

Chesterton, IN

3 beds | 2 baths | 2,184 sq.ft.

$351,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1724

Traditional Rental Income: $2402

Airbnb ROI: 1.62%

Traditional ROI: 5.12%

656 S 4th Street

Chesterton, IN

3 beds | 2 baths | 1,542 sq.ft.

$335,000

Airbnb cash on cash: 2.3%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $1724

Traditional Rental Income: $1625

Airbnb ROI: 2.3%

Traditional ROI: 3.5%

1215 Bostwick Avenue

Chesterton, IN

3 beds | 3 baths | 2,822 sq.ft.

$569,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $1724

Traditional Rental Income: $2666

Airbnb ROI: 0.23%

Traditional ROI: 2.9%

801 Idlewild Lane

Chesterton, IN

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

$624,900

Airbnb cash on cash: 3%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $3748

Traditional Rental Income: $2891

Airbnb ROI: 3%

Traditional ROI: 2.93%

2230 Redwood Lane

Chesterton, IN

4 beds | 3 baths | 2,281 sq.ft.

$620,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3748

Traditional Rental Income: $2932

Airbnb ROI: 3.03%

Traditional ROI: 3.03%

706 Idlewild Lane

Chesterton, IN

4 beds | 3 baths | 2,472 sq.ft.

$580,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $3748

Traditional Rental Income: $2419

Airbnb ROI: 3.37%