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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$320,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 5.03% Airbnb Rental Income: $1864 Traditional Rental Income: $2161 Airbnb ROI: 2.38% Traditional ROI: 5.03%
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%
2011 Timberwood Ln Chesterton, IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 2 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 Dr Chesterton, IN Hurry now to make your own selections! The ever-popular Melanie floor plan offers all of t...	4 beds \| 2 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%
801 Idlewild Ln 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%
2230 Redwood Ln Chesterton, IN The Astoria in Easton Park! Welcome to luxury living in this stunning proposed two-story h...	4 beds \| 2 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%
474 Magnolia Lane Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,820 sq.ft.	$485,431	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.55% Airbnb Rental Income: $1864 Traditional Rental Income: $2559 Airbnb ROI: 0.91% Traditional ROI: 3.55%
496 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.	$486,002	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.18% Airbnb Rental Income: $1864 Traditional Rental Income: $2395 Airbnb ROI: 0.91% Traditional ROI: 3.18%
1700 Littler Dr Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 9 baths \| 17,178 sq.ft.	$2,950,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.31% Airbnb Rental Income: $2553 Traditional Rental Income: $6257 Airbnb ROI: -1.89% Traditional ROI: -0.31%
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%
1544 Colonial Drive Chesterton, IN Fantastic 2 story home in the sought after Villages of Sand Creek. Located in Duneland Sch...	4 beds \| 4 baths \| 2,950 sq.ft.	$419,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.23% Airbnb Rental Income: $3402 Traditional Rental Income: $3380 Airbnb ROI: 4.36% Traditional ROI: 6.23%
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%
1226 Dogwood Drive Chesterton, IN Extensive Updates Throughout! This home has been beautifully remodeled with numerous recen...	4 beds \| 2 baths \| 1,827 sq.ft.	$318,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.79% Airbnb Rental Income: $3402 Traditional Rental Income: $2255 Airbnb ROI: 7.1% Traditional ROI: 5.79%
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 Rd 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: 2.45% Traditional cash on cash: 4.99% Airbnb Rental Income: $1587 Traditional Rental Income: $1780 Airbnb ROI: 2.45% Traditional ROI: 4.99%
525 S Calumet Rd Chesterton, IN Donât miss your opportunity to view this charming four-bedroom, two-full-bath home locat...	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%
1411 W Beam Street Chesterton, IN Remodeled 3-bedroom, 2-bath home on a beautiful 1-acre lot, tucked away on a quiet no-thro...	3 beds \| 2 baths \| 1,652 sq.ft.	$269,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 6.4% Airbnb Rental Income: $1864 Traditional Rental Income: $2166 Airbnb ROI: 3.25% Traditional ROI: 6.4%
319 Michigami Trail Chesterton, IN Move right in and enjoy easy, everyday living in this spacious three-bedroom ranch in Ches...	3 beds \| 1 baths \| 1,433 sq.ft.	$219,900	Airbnb cash on cash: 4.2% Traditional cash on cash: 3.8% Airbnb Rental Income: $1864 Traditional Rental Income: $1280 Airbnb ROI: 4.2% Traditional ROI: 3.8%
1642 Commodore Ln Chesterton, IN 1642 Commodore Ln, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 1,745 sq.ft.	$339,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 3.05% Airbnb Rental Income: $1864 Traditional Rental Income: $1661 Airbnb ROI: 2.12% Traditional ROI: 3.05%
1290 Old Porter Rd Chesterton, IN 1290 Old Porter Rd, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 1 baths \| 1,716 sq.ft.	$270,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.36% Airbnb Rental Income: $1864 Traditional Rental Income: $1164 Airbnb ROI: 3.15% Traditional ROI: 2.36%
1346 Essex Dr Chesterton, IN 1346 Essex Dr, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 2 baths \| 2,167 sq.ft.	$349,900	Airbnb cash on cash: 2.01% Traditional cash on cash: 4.34% Airbnb Rental Income: $1864 Traditional Rental Income: $2131 Airbnb ROI: 2.01% Traditional ROI: 4.34%
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: -0.6% Traditional cash on cash: -0.15% Airbnb Rental Income: $1864 Traditional Rental Income: $1823 Airbnb ROI: -0.6% Traditional ROI: -0.15%
1198 Old Porter Rd Chesterton, IN 1198 Old Porter Rd, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,976 sq.ft.	$289,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 5.51% Airbnb Rental Income: $3402 Traditional Rental Income: $2094 Airbnb ROI: 7.53% Traditional ROI: 5.51%
315 Franklin St Chesterton, IN 315 Franklin St, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,900 sq.ft.	$450,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.4% Airbnb Rental Income: $3402 Traditional Rental Income: $1882 Airbnb ROI: 4.22% Traditional ROI: 2.4%
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%
2519 Pradera Trl Chesterton, IN 2519 Pradera Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 2,134 sq.ft.	$645,400	Airbnb cash on cash: 2.38% Traditional cash on cash: 1.58% Airbnb Rental Income: $3402 Traditional Rental Income: $2166 Airbnb ROI: 2.38% Traditional ROI: 1.58%
ESSEX Plan Chesterton, IN	4 beds \| 2 baths \| 2,014 sq.ft.	$383,990	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.11% Airbnb Rental Income: $3402 Traditional Rental Income: $1878 Airbnb ROI: 5.24% Traditional ROI: 3.11%
103 Michigan St Chesterton, IN Step into this home at 103 Michigan Street, and be impressed with everything you see. Not ...	3 beds \| 1 baths \| 1,560 sq.ft.	$325,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.59% Airbnb Rental Income: $1864 Traditional Rental Income: $1950 Airbnb ROI: 2.67% Traditional ROI: 4.59%
2828 Lakewood Trl Chesterton, IN 2828 Lakewood Trl, Chesterton, IN 46304 \| Single Family Residential	3 beds \| 3 baths \| 4,058 sq.ft.	$925,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.37% Airbnb Rental Income: $1864 Traditional Rental Income: $2030 Airbnb ROI: -0.4% Traditional ROI: 0.37%
507 S 20th St 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: 2.53% Traditional cash on cash: 4.32% Airbnb Rental Income: $1864 Traditional Rental Income: $1911 Airbnb ROI: 2.53% Traditional ROI: 4.32%
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%
225 Dogwood Drive Chesterton, IN Well-maintained 3-bedroom, 2-bath ranch home offering approximately 1,316 finished square ...	3 beds \| 2 baths \| 1,316 sq.ft.	$274,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 5.64% Airbnb Rental Income: $1864 Traditional Rental Income: $1955 Airbnb ROI: 3.37% Traditional ROI: 5.64%
107 Franklin St Chesterton, IN 107 Franklin St, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,755 sq.ft.	$249,999	Airbnb cash on cash: 8.97% Traditional cash on cash: 5.42% Airbnb Rental Income: $3402 Traditional Rental Income: $1808 Airbnb ROI: 8.97% Traditional ROI: 5.42%
309 Michigami Trl Chesterton, IN 309 Michigami Trl, Chesterton, IN 46304 \| Single Family Residential	4 beds \| 2 baths \| 1,581 sq.ft.	$255,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 4.96% Airbnb Rental Income: $3402 Traditional Rental Income: $1795 Airbnb ROI: 8.37% Traditional ROI: 4.96%
1541 Fox Point Dr 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%
1415 N 200 E Chesterton, IN 1415 N 200 E, Chesterton, IN 46304 \| Single Family Residential	3 beds \| N/A baths \| 1,539 sq.ft.	$268,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 3.97% Airbnb Rental Income: $1864 Traditional Rental Income: $1562 Airbnb ROI: 3.19% Traditional ROI: 3.97%
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.	$268,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 4.38% Airbnb Rental Income: $1864 Traditional Rental Income: $1521 Airbnb ROI: 3.76% Traditional ROI: 4.38%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesterton, IN

214 Woodlawn Ave

Chesterton, IN

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

$320,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $1864

Traditional Rental Income: $2161

Airbnb ROI: 2.38%

Traditional ROI: 5.03%

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%

2011 Timberwood Ln

Chesterton, IN

4 beds | 2 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 Dr

Chesterton, IN

4 beds | 2 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%

801 Idlewild Ln

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%

Traditional ROI: 2.92%

2310 Redwood Lane

Chesterton, IN

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%

2230 Redwood Ln

Chesterton, IN

4 beds | 2 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%

474 Magnolia Lane

Chesterton, IN

3 beds | 2 baths | 1,820 sq.ft.

$485,431

Airbnb cash on cash: 0.91%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1864

Traditional Rental Income: $2559

Airbnb ROI: 0.91%