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

separator

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: 4.14% Traditional cash on cash: 5.26% Airbnb Rental Income: $1864 Traditional Rental Income: $1629 Airbnb ROI: 4.14% 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: 4.12% Traditional cash on cash: 4.47% Airbnb Rental Income: $3402 Traditional Rental Income: $2794 Airbnb ROI: 4.12% Traditional ROI: 4.47%
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%
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: 1.6% Traditional cash on cash: 4.68% Airbnb Rental Income: $1864 Traditional Rental Income: $2577 Airbnb ROI: 1.6% 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: 3.02% Traditional cash on cash: 3.78% Airbnb Rental Income: $3402 Traditional Rental Income: $3030 Airbnb ROI: 3.02% Traditional ROI: 3.78%
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: 3.09% Traditional cash on cash: 3.06% Airbnb Rental Income: $3402 Traditional Rental Income: $2630 Airbnb ROI: 3.09% Traditional ROI: 3.06%
1163 Burns Boulevard Chesterton, IN Welcome to this charming half duplex in the Village of Burns Harbor, located within the hi...	4 beds \| 3 baths \| 2,594 sq.ft.	$315,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 6.66% Airbnb Rental Income: $3402 Traditional Rental Income: $2589 Airbnb ROI: 6.85% Traditional ROI: 6.66%
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: 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 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: 2.67% Traditional cash on cash: 3.18% Airbnb Rental Income: $3402 Traditional Rental Income: $2932 Airbnb ROI: 2.67% Traditional ROI: 3.18%
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: 4.59% Traditional cash on cash: 6.23% Airbnb Rental Income: $3402 Traditional Rental Income: $3291 Airbnb ROI: 4.59% 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: 2.83% Traditional cash on cash: 2.41% Airbnb Rental Income: $3402 Traditional Rental Income: $2419 Airbnb ROI: 2.83% 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: -2.05% Traditional cash on cash: -0.19% Airbnb Rental Income: $2553 Traditional Rental Income: $6257 Airbnb ROI: -2.05% Traditional ROI: -0.19%
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%
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%
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 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.	$249,500	Airbnb cash on cash: 2.73% Traditional cash on cash: 5.47% Airbnb Rental Income: $1587 Traditional Rental Income: $1780 Airbnb ROI: 2.73% Traditional ROI: 5.47%
525 S Calumet Road Chesterton, IN Charming four-bedroom, two-full-bath home located in Chesterton, Indiana! From the moment ...	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%
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%
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: 2.71% Traditional cash on cash: 4.59% Airbnb Rental Income: $1864 Traditional Rental Income: $1911 Airbnb ROI: 2.71% 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: 0.91% Traditional cash on cash: 3.15% Airbnb Rental Income: $1864 Traditional Rental Income: $2394 Airbnb ROI: 0.91% 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: 2.54% Traditional cash on cash: 4.88% Airbnb Rental Income: $1864 Traditional Rental Income: $2023 Airbnb ROI: 2.54% 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: 3.9% Traditional cash on cash: 4.54% Airbnb Rental Income: $1864 Traditional Rental Income: $1521 Airbnb ROI: 3.9% 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: 2.79% Traditional cash on cash: 4.13% Airbnb Rental Income: $1864 Traditional Rental Income: $1763 Airbnb ROI: 2.79% 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: -0.01% Traditional cash on cash: 3.24% Airbnb Rental Income: $2553 Traditional Rental Income: $4936 Airbnb ROI: -0.01% 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: -0.46% Traditional cash on cash: 3.8% Airbnb Rental Income: $2553 Traditional Rental Income: $7051 Airbnb ROI: -0.46% 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.	$265,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.83% Airbnb Rental Income: $1864 Traditional Rental Income: $1432 Airbnb ROI: 3.56% Traditional ROI: 3.83%
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: 3.27% Traditional cash on cash: 3.43% Airbnb Rental Income: $3402 Traditional Rental Income: $2725 Airbnb ROI: 3.27% Traditional ROI: 3.43%
2016 Laura Lane Chesterton, IN Rare opportunity to own a spacious 5-bedroom, 2.5-bath condominium offering exceptional li...	5 beds \| 3 baths \| 2,100 sq.ft.	$239,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 7.8% Airbnb Rental Income: $2553 Traditional Rental Income: $2697 Airbnb ROI: 4.46% Traditional ROI: 7.8%
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: 0.59% Traditional cash on cash: 2.3% Airbnb Rental Income: $1864 Traditional Rental Income: $2098 Airbnb ROI: 0.59% 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: 0.59% Traditional cash on cash: 3.21% Airbnb Rental Income: $2553 Traditional Rental Income: $4969 Airbnb ROI: 0.59% Traditional ROI: 3.21%
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: 0.59% Traditional cash on cash: 2.4% Airbnb Rental Income: $1864 Traditional Rental Income: $2794 Airbnb ROI: 0.59% 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.	$459,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 6.11% Airbnb Rental Income: $3402 Traditional Rental Income: $3518 Airbnb ROI: 4.08% Traditional ROI: 6.11%
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: 2.21% Traditional cash on cash: 4.49% Airbnb Rental Income: $1864 Traditional Rental Income: $2060 Airbnb ROI: 2.21% Traditional ROI: 4.49%

Real Estate investment in Chesterton, IN

There are 41 properties for sale in the city of Chesterton . The median list price in Chesterton is $419,999 and the average price per square foot is $167. In April 2026, the average monthly cash on cash return in Chesterton is 4.00%. The average monthly rental income in Chesterton is $2,490.

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

There are 41 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 $2,490.

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: 4.14%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1864

Traditional Rental Income: $1629

Airbnb ROI: 4.14%

Traditional ROI: 5.26%

1452 Gossett Mill Avenue

Chesterton, IN

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

$444,900

Airbnb cash on cash: 4.12%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $3402

Traditional Rental Income: $2794

Airbnb ROI: 4.12%

Traditional ROI: 4.47%

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%

897 Jane Avenue

Chesterton, IN

3 beds | 3 baths | 2,488 sq.ft.

$419,900

Airbnb cash on cash: 1.6%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1864

Traditional Rental Income: $2577

Airbnb ROI: 1.6%

Traditional ROI: 4.68%

2011 Timberwood Lane

Chesterton, IN

4 beds | 3 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%

2221 Easton Park Drive

Chesterton, IN

4 beds | 3 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%

1163 Burns Boulevard

Chesterton, IN

4 beds | 3 baths | 2,594 sq.ft.

$315,000

Airbnb cash on cash: 6.85%

Traditional cash on cash: 6.66%

Airbnb Rental Income: $3402

Traditional Rental Income: $2589

Airbnb ROI: 6.85%

Traditional ROI: 6.66%

801 Idlewild Lane

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%