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.

Condos for Sale in Chesterton, IN

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

Showing 1 Condo 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
2128 Dogwood Lane Chesterton, IN Completely remodeled 3-bedroom, 2-bath condo in the heart of Chesterton--offering modern f...	3 beds \| 2 baths \| 1,338 sq.ft.	$189,999	Airbnb cash on cash: 3.6% Traditional cash on cash: 4.97% Airbnb Rental Income: $1936 Traditional Rental Income: $1673 Airbnb ROI: 3.6% Traditional ROI: 4.97%
Other Investment Properties for Sale in Chesterton
380 Sandpiper Drive Chesterton , IN Welcome home to this beautifully updated two-story residence offering 4 bedrooms, 4 bathro...	4 beds \| 4 baths \| 4,801 sq.ft.	$565,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 4.64% Airbnb Rental Income: $3846 Traditional Rental Income: $3607 Airbnb ROI: 3.52% Traditional ROI: 4.64%
612 S Jackson Boulevard Chesterton , IN Located less than 1 hour from Chicago this All Brick Ranch will be the perfect place to ca...	3 beds \| 2 baths \| 1,305 sq.ft.	$289,900	Airbnb cash on cash: 3% Traditional cash on cash: 3.9% Airbnb Rental Income: $1936 Traditional Rental Income: $1672 Airbnb ROI: 3% Traditional ROI: 3.9%
1452 Gossett Mill Avenue Chesterton , IN Take a look at this beautifully maintained two-story home located just minutes away from t...	4 beds \| 3 baths \| 2,031 sq.ft.	$434,900	Airbnb cash on cash: 5.14% Traditional cash on cash: 4.6% Airbnb Rental Income: $3846 Traditional Rental Income: $2794 Airbnb ROI: 5.14% Traditional ROI: 4.6%
1591 Hogan Avenue Chesterton , IN Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updat...	4 beds \| 4 baths \| 2,878 sq.ft.	$649,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 2.86% Airbnb Rental Income: $3846 Traditional Rental Income: $3155 Airbnb ROI: 2.63% Traditional ROI: 2.86%
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.	$1,299,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.91% Airbnb Rental Income: $3846 Traditional Rental Income: $4919 Airbnb ROI: 0.34% Traditional ROI: 1.91%
117 Washington Avenue Chesterton , IN Welcome home to this beautifully maintained ranch in the heart of Chesterton! NEW ROOF! Of...	3 beds \| 3 baths \| 2,109 sq.ft.	$364,999	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.61% Airbnb Rental Income: $1936 Traditional Rental Income: $1656 Airbnb ROI: 1.94% Traditional ROI: 2.61%
3451 Fairway Drive Chesterton , IN Welcome home to this beautifully maintained 3-bedroom, 2-bath ranch in a convenient Cheste...	3 beds \| 3 baths \| 2,525 sq.ft.	$375,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.71% Airbnb Rental Income: $1936 Traditional Rental Income: $2535 Airbnb ROI: 1.55% Traditional ROI: 4.71%
1261 Redbud Drive Chesterton , IN Welcome to this beautifully maintained 4-bedroom, 2.5-bath home situated on over half an a...	4 beds \| 3 baths \| 1,976 sq.ft.	$389,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 4.78% Airbnb Rental Income: $3846 Traditional Rental Income: $2462 Airbnb ROI: 6.29% Traditional ROI: 4.78%
1245 Kilarney Road Chesterton , IN Highly desirable Sand Creek property!!!! Presenting this custom built, 5 bedroom, 4.5 bath...	5 beds \| 5 baths \| 5,102 sq.ft.	$979,999	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.38% Airbnb Rental Income: $4345 Traditional Rental Income: $5040 Airbnb ROI: 1.61% Traditional ROI: 3.38%
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: 0.56% Traditional cash on cash: 2.9% Airbnb Rental Income: $1936 Traditional Rental Income: $2666 Airbnb ROI: 0.56% Traditional ROI: 2.9%
1717 Crocker Street Chesterton , IN Move-in ready with built-in upside, this fully remodeled 11/2-story home offers three bedr...	3 beds \| 2 baths \| 2,400 sq.ft.	$249,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.66% Airbnb Rental Income: $1936 Traditional Rental Income: $1406 Airbnb ROI: 3.73% Traditional ROI: 3.66%
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: 3.14% Traditional cash on cash: 2.93% Airbnb Rental Income: $3846 Traditional Rental Income: $2891 Airbnb ROI: 3.14% 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.	$599,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.19% Airbnb Rental Income: $3846 Traditional Rental Income: $2932 Airbnb ROI: 3.34% Traditional ROI: 3.19%
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: 3.52% Traditional cash on cash: 2.41% Airbnb Rental Income: $3846 Traditional Rental Income: $2419 Airbnb ROI: 3.52% Traditional ROI: 2.41%

Your search for investment property begins and ends here

Condos for Sale in Chesterton, IN

2128 Dogwood Lane

Chesterton, IN

3 beds | 2 baths | 1,338 sq.ft.

$189,999

Airbnb cash on cash: 3.6%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $1936

Traditional Rental Income: $1673

Airbnb ROI: 3.6%

Traditional ROI: 4.97%

Other Investment Properties for Sale in Chesterton

Chesterton , IN

4 beds | 4 baths | 4,801 sq.ft.

$565,000

Airbnb cash on cash: 3.52%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $3846

Traditional Rental Income: $3607

Airbnb ROI: 3.52%

Traditional ROI: 4.64%

Chesterton , IN

3 beds | 2 baths | 1,305 sq.ft.

$289,900

Airbnb cash on cash: 3%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1936

Traditional Rental Income: $1672

Airbnb ROI: 3%

Traditional ROI: 3.9%

Chesterton , IN

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

$434,900

Airbnb cash on cash: 5.14%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $3846

Traditional Rental Income: $2794

Airbnb ROI: 5.14%

Traditional ROI: 4.6%

Chesterton , IN

4 beds | 4 baths | 2,878 sq.ft.

$649,900

Airbnb cash on cash: 2.63%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $3846

Traditional Rental Income: $3155

Airbnb ROI: 2.63%

Traditional ROI: 2.86%

Chesterton , IN

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

$1,299,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $3846

Traditional Rental Income: $4919

Airbnb ROI: 0.34%

Traditional ROI: 1.91%

Chesterton , IN

3 beds | 3 baths | 2,109 sq.ft.

$364,999

Airbnb cash on cash: 1.94%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1936

Traditional Rental Income: $1656

Airbnb ROI: 1.94%

Traditional ROI: 2.61%

Chesterton , IN

3 beds | 3 baths | 2,525 sq.ft.

$375,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $1936

Traditional Rental Income: $2535

Airbnb ROI: 1.55%

Traditional ROI: 4.71%

Chesterton , IN

4 beds | 3 baths | 1,976 sq.ft.

$389,900

Airbnb cash on cash: 6.29%

Traditional cash on cash: 4.78%